Hi, I’m Jeremy, I’m glad you’re here.
No matter what you create, I’m guessing you spend a good amount of time feeling lost, hopeless, and unsure about how to get from where you are to where you want to be.
So do I. And so does everyone doing creative work.
This is the Creative Wilderness.
Every week, I publish a new article in my Creative Wayfinding newsletter about how we as creators and marketers can navigate it with more clarity and confidence.
If you’re building something that matters, but aren’t quite sure how to take the next step forward, I’d be honoured to have you join us.
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You Can Get There from Here
Though the way is far
The route appears impassable
And no map exists for where you seek to travel
Remember this.
No peak
No dream
No version of yourself
Is unattainable from where you stand today.
Though it may not be easy
Most certainly full of dangers, failed attempts, and unnamed terrors
The path exists
As does the destination.
And regardless of where you are now
Of how far
How small
How scared
You can get there from here.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
Subscribe
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To Find Clarity, Start Walking Before You Know Your Destination
It would be something of an understatement to say I’m a fan of walking.
Aside from taking at least one long walk every day, I take many of my calls while walking, read books about walking, generate all my best ideas while walking, and–as you may have noticed–like to write about walking as well.
No, I’m not a fan. I’m obsessed.
Kelly, on the other hand, isn’t quite as keen. Despite this, every so often I manage to convince her to go for a long walk together, such as the one we took last weekend.
The destination was a section of the coast just outside of town. I’d walked the rocky stretch and explored the abandoned decades-old bunkers carved into the hillside a handful of times before, but wanted to share the area with her as well. As we crossed the bridge over the river that marked the edge of town, we turned off the main road and headed up a small dirt trail that snaked its way through the tall grass in the direction of the sea.
“How did you find this path the first time you walked here?” Kelly asked.
I thought for a moment, but found that I didn’t actually have a good answer.
When I don’t know the terrain, I tend to simply start walking, following what’s often little more than a vague curiosity. At times that curiosity might be centered on a prominent landmark or geological feature. At other times, however, I choose my direction simply by chasing a patch of sunlight, a particularly alluring looking street, or an enthralling scent on the breeze. My typical mode of travel might be best described as “whimsical.” If anyone was ever going to accidentally stumble into Narnia, it surely would be me.
The first time I walked this route, my goal had been the sea. From our apartment, I could see white-capped waves crashing against the ragged shoreline further up the coast, and so, on my initial exploration had set out to find my way there.
I took the main road, crossed the bridge over the river that marked the edge of town, and then stopped, spotting a small, dirt trail snaking its way through the tall grass in the direction of the sea. I didn’t know where this path led, but I had nothing but time, and the road I was on was certainly not going to lead me to the coast. So I took the trail.
Fifteen minutes later, after a few wrong turns through an abandoned property development project and a bit of light bushwhacking, I had reached the shoreline.
This approach, of starting with little more than a vague destination, sometimes only a hunch, and then following my curiosity has served me well. It leads to unexpected discoveries, helps you understand the local geography, improves your sense of direction, and to top it off, is good for your health. This mode of travel doesn’t just apply to walking, however.
Create For The Sake Of It
This act of starting before we know where we’re going and picking up the thread on the fly mirrors the creative process exactly.
We start out with a bit of curiosity and a vague destination in mind, and, if we choose to follow that curiosity, have little choice but to do so blindly. While our end destination might not be specific when we set out, at some point, we hope, by walking long enough, we’ll pick up the thread and find it.
Which is precisely what’s happened to me in the past few weeks with this newsletter.
When I started this newsletter a little over a year ago, I had no idea where it was leading. I saw an opportunity to contribute in a format that excited me, and a curiosity and willingness to see where the path would lead.
Rather than writing to help a specific audience achieve a specific goal, I wrote what I wanted to write. More than that, each week, I wrote what I needed to hear.
This approach has kept the newsletter fun, fresh, and even a vital part of my life, and it’s been immensely gratifying to hear that it’s resonated so deeply with so many readers. At the same time, I’ve known that without being clear on who the newsletter is for and what the through-line is that ties it all together it would be hard to grow consistently. It’s hard to market something when you don’t really know what it is after all.
The word “wayfinding” first popped into my head in January and immediately resonated with me as the embodiment of what I was doing with this newsletter. That initial breakthrough then kicked off a long, slow process of gaining clarity, with more and more pieces of the puzzle coming into view over the past five months.
While I’m far from absolute clarity (can we ever actually achieve it?) on the future of this newsletter, I feel as though I can see juuuust far enough through the fog ahead to kick off this new chapter with at least some certainty about where the road leads.
To be clear, nothing about the content has changed, other than it’s going to be more focused, intentional, and sure of itself. I’d like to think it’s going to have a bit more swagger.
Whether you consider yourself a creator, marketer, entrepreneur, or mix of all the above (like me), I’m guessing you spend a good chunk of your days feeling lost (also like me). Maybe you feel a vague lack of direction. Maybe you feel completely unmoored, floating out at sea.
You may have wandered off the beaten path by accident or you may have left it intentionally in search of a better way forward. Regardless, my goal with this newsletter going forward is to help you navigate that sense of not knowing where you’re going or how to get there that comes with doing creative work. Because I’m right there with you, and we’re all in this together.
While I’m excited about this newly clarified direction, it’s clear that this is just the jumping off point. I sense a manifesto in the works along with a number of new offerings and one day, hopefully, a book.
After a year of walking blindly with only a vague sense of direction, I’ve picked up the thread. The through line, I’ve realized, that runs through this newsletter and everything that will follow is this: Practical wisdom for navigating the creative wilds.
Here’s to searching, seeking, hoping and dreaming–to me the essence of wayfinding.
Thanks for walking with me this far, it means the world.
I’m looking forward to seeing where this next leg of the journey takes us as we map it together.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
The More Intimately You Know Resistance, The Better Your Work Will Become
In 1988, Andre Agassi and Boris Becker faced off for the first time, kicking off what would become one of tennis’s great rivalries.
Agassi and Becker were two of the top players in the world, finishing the year ranked No. 3 and 4 in the world respectively. But despite Agassi’s superior ranking, in this first meeting between the two stars, it was Becker coming out on top.
“His serve was something the game had never seen before,” Agassi later recalled. On the strength of that serve, Becker would defeat Agassi in two subsequent matches in 1989, leapfrogging Agassi to take the No. 2 spot on the rankings in the process.
Frustrated, and knowing that the route to victory at any major tournament was likely to lead through Becker, Agassi got to work. He pored through footage of Becker, analyzing his playing style in search of the slightest knick in his armour. And then, after countless hours watching tape, Agassi found it.
“I started to realize he had this weird tick with his tongue,” Agassi said. “He would go into his rocking motion, and just as he was about to toss the ball, he would stick his tongue out. And it would either be right in the middle of his lip, or it’d be to the left corner of his lip.
“If he put his tongue in the middle of his lip, he was either serving up the middle or to the body. But if he put it to the side, he was going to serve out wide.”
This insight proved decisive, as Agassi went on to win ten of their next eleven matches, including one en route to the Wimbledon championship in 1992.
In the end, recalled Agassi, “the hardest part wasn’t returning the serve, but not letting him know that I knew [about the tell].”
Years after they’d both retired, Agassi shared his bit of intel with Becker over a pint at Oktoberfest. A shocked Becker replied, “I used to go home and tell my wife, ‘It’s like he reads my mind.’ Little did I know you were just reading my tongue.”
Studying Your Opponent
The practice of reviewing game tape–both of yourself and your opponent–is a given at elite-level sports. While you might not always discover a tell as obvious as Boris Becker’s, there’s a lot to be learned by studying your opponent’s style.
By knowing their style, you can anticipate their next moves. Then, you can either navigate around them or prepare yourself in advance. Get to know their style well enough and it might appear as though you’re reading their mind. Compared to facing off without that knowledge, this gives you a significant advantage when facing any opponent.
As creators, this opponent is not another person, but ourselves.
Every day, our desire to make work that matters faces off against Resistance. This Resistance might come in many forms, from impostor syndrome to perfectionism, impatience to distraction, the lure of shiny objects to the endless chatter of your inner critic as you try to do the work.
The problem when facing down Resistance is that there’s an asymmetry of knowledge. Resistance has studied our tape and knows just when and where to place the dagger for the most devastating effect. It knows exactly how to cow us, to strike fear, and to sow doubt. All the while, we might not even be aware of its existence, in the worst cases, taking its whisperings as truth. But this doesn’t have to be the case.
Much like an elite athlete, we can choose to study our Resistance, learn its style, and begin to predict its moves. When we understand its moves, we can begin to dance with Resistance, rather than be pummelled by it, turning our opponent into our partner. Resistance can be a powerful indicator that we’re onto something worth pursuing, after all, and it’s from this dance that our best work emerges. But before we can join the dance, we must first learn to read our partner.
Learning To Read Resistance
The first step in learning to read Resistance is to acknowledge its existence. This in itself can be a massive breakthrough, as it means the voice in your head undermining your every creative effort is not, in fact, the voice of truth.
While Resistance is certainly real, the things it tells us are not. Its job is to protect us and in the process of doing so, it’s willing to go to great lengths. This includes doing everything within its power to keep us from shipping our work, opening ourselves up to criticism and failure. The particular way Resistance achieves this varies for each of us. The second step of learning its style, then, is recognizing the specific tricks and vocabulary it uses against you.
Start by identifying the traps that keep you from doing (and shipping) your most important creative work. Perfectionism, procrastination, distraction, and imposter syndrome are all common shapes Resistance can take, but there are many others. If you’re serious about beating Resistance, you might even make a list of its tactics and post it beside your desk as a reminder.
With your list in place, you can keep a vigilant eye out for Resistance, spotting it before it has a chance to derail you. The going might be slow at first, but recognizing, resisting, skirting and dancing with Resistance is a muscle that can be strengthened with use.
When a notification flies across your screen and you’re tempted to set your work aside and click on it, recognize Resistance. Build the muscle by ignoring it and turning your attention back to your work.
When you feel your work isn’t ready and are tempted to tinker some more, recognize Resistance. Build the muscle by hitting “publish”. Then start on your next project.
When you feel like an imposter, like you have nothing to contribute, recognize Resistance. Build the muscle by sharing something publicly that will be useful to even just one other person.
Over time, as you learn Resistance’s style and build up the muscle of defending against it, Resistance will adapt and present new methods of sabotage. No matter, learn the new tricks, add them to your list, and continue the dance.
Resistance is an opponent we can never truly defeat. But if our goal is to create work that matters, we have no choice but to learn to dance with it.
We can choose to view each day either as a series of new opportunities for Resistance to derail us.
Or, we can choose to view each day as a series of new opportunities to strengthen our muscle to resist Resistance.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
What If Taking The Easy Route To Your Destination Is Slowing You Down?
I lifted my gaze for only a second, but that was all it took.
My foot slipped on the rain-slick rock and the next thing I knew I was going down.
I landed hard on my hip. For a long moment, I lay motionless on the ground. One second. Two seconds. Three seconds. I’d anticipated a sharp shooting of pain up my leg. Luckily, I was greeted only by a dull ache.
As I picked myself up, I realized my luck was due to the fact that I’d landed in a shallow puddle of thick mud. I’d seriously stained my pants, but had managed to avoid breaking my hip on the jagged rocks surrounding the puddle. Slowing my pace, I kept my eyes on my feet as I picked my way down the hill to the main road.
As it happens, the fall wasn’t the first time my misplaced gaze had lead me astray this morning.
An hour before my fall, I was out for a short hike up one of the hills behind my apartment. Sarandë, was ringed by a half dozen or so hills and I was determined to climb them all over the course of my 6-week stay. This hill was my second.
I call it a hike, but it was more like a scramble. The landscape was all jagged boulders and brambles, making the existence of any kind of path all but impossible. And so, rather than walking, I was trying to hop from boulder to boulder in the straightest line up the hill. This was a difficult task.
The boulders were razor-sharp. I’d already found many of them to be more than capable of slicing through skin. But they were also loose, liable to shift under the slightest misplaced step.
The hill they covered wasn’t huge, maybe a 30-minute hike up. But navigating the rocks and the spiky brambles that exploded between them required the utmost attention. As such, I kept my eyes firmly on my feet, letting them stray only far enough to find the safest, easiest next step.
Spot. Step. Plant. Balance. Repeat.
After 10 minutes of this slow, careful upward progress I stopped on a large, flat boulder to survey the remainder of the climb.
As I turned my gaze upward I immediately realized that while I had been making progress up the hill, I had been taking what was clearly a very diagonal route. As a result, I had gone further laterally than I needed and would now need to angle up and back the way I came. I reoriented myself, put my head back down, and continued upward.
Five minutes later, I stopped on another boulder. I looked up, and once again, realized that I’d gone too far–this time in the opposite direction. I was making my way up the hill, but I was letting the landscape dictate my path, always opting for the easiest way forward. The result was a drunken zig-zag of a route up to the summit.
I took a breath, reoriented myself once again, and started up once again directly toward the summit, this time stopping every few steps to check my direction in relation to the hilltop.
It was slower, harder going, with more than a few bramble snags cutting up my calves along the way. But 15 minutes later I’d reached the top, having cut a nearly direct line up the rocky hillside.
5 Ways To Climb A Hill
To me, this hillside represents the work each of us does in navigating our creative careers.
The journey is littered with obstacles, some outright dangerous, some simply inconvenient. It’s up to each of us to decide how we’ll choose how to navigate them.
In my experience, we take one of five routes up the hill.
- We make slow, meandering progress up and down the hill but never truly commit to making it to the top. Eventually, we run out of daylight or the weather shifts and we turn back and head for home.
- We keep our eyes fixed upward on our destination, paying little attention to the obstacles at our feet. We might bulldoze our way through the first few hazards, but before long we find ourselves lying in the mud with an aching hip. If we’re lucky we can pick ourselves up and continue upward with more care. If we’re not, the repeated stumbles and falls that accompany this style of travel break us, causing us to limp home, defeated.
- We start climbing but don’t have a clear idea of our destination. As a result, we settle for heading in a vague, upwards direction. It’s possible that we eventually orient ourselves or even stumble on the summit by accident. But either way, it’s a slow, inefficient journey.
- We’re clear on our destination but keep our gaze directed downwards, immediately in front of us instead of the hilltop on the horizon. Each step we take feels like the obvious, easiest choice in the moment. We fail to realize, however, that over time they lead us diagonally away from our goal. At some point we look up, see we’re off-course, and must head back in a new direction.
- We’re clear on the summit we’re aiming for and balance our gaze between our feet and our destination. Each step moves us in as direct a line as possible toward it while also taking care to maintain our footing.
We have to move slower and stop regularly to re-orient ourselves. We might take detours around particularly dangerous obstacles when necessary, but push straight through the brambles and minor inconveniences. We get scraped up in the process, but we maintain the most direct course to our destination.
This mode of travel is the most uncomfortable and feels in the moment like the slowest option. The truth, however, is it’s the fastest, most predictable path up the hill.
We can’t always see the summit from the base of the hill. More often than not it’s hidden in cloud.
In these cases, we have little choice but to start up the hill, hoping that the cloud thins as we move upward. Climb far enough and it almost always does.
Once we have a clear view of the summit, however, it’s best to balance our gaze, navigating the obstacles, keeping our footing, and fighting through the inevitable brambles while maintaining as direct a line to our destination as possible.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
The Two Tipping Points Behind Every Breakthrough Success
Back in 2015, I was a landscaper with dreams of traveling the world full-time.
I had recently discovered the wide world of podcasts and was able to listen to them at work. Naturally, I spent nine hours a day binging my way through every online business podcast I could find.
After a month or two of listening, I started experimenting with what I was learning. I built (ugly) websites, and dreamt up (bad) business ideas, all the while feeling (mostly) confident that eventually, I would land on something that would gain traction.
Despite my general optimism, however, there was a small shadow of doubt in the back of my mind. What If I never landed on something that gained traction?
Whenever it surfaced, I did my best to push the thought further back into the darkest corner of my mind.
Six months passed. The idea I was most confident in was a photography blog that had a small, readership of a hundred people or so. Eventually, I planned on creating online courses in order to generate income. I had no idea what I would teach, but at the rate the blog was growing that I wouldn’t need to make a decision for a long time.
I dreamed of reaching the tipping point. The day when my work would start to pay off and the results would pour in.
In my mind, the tipping point meant thousands of new page views and hundreds of new subscribers per month. But to be honest, I would have settled for any clear sign of traction at all. Any proof that what I was doing was working, and worth my continued investment in.
As it turns out, that proof was right around the corner, just not for my photography blog.
One day at work, I was listening to one of my favourite shows, Zero To Travel, when the host, Jason, mentioned his podcast editor in an offhand comment.
Now, I had considered podcast editing before, but my ego always kept me from taling it seriously. It felt like a waste of my skills, being the professionally trained sound engineer that I was.
Jason’s comment, however, struck something inside me in a way that resonated in a way it never had before. If my goal was to build a business that would allow me to travel, surely this was a quicker route than building an audience and creating courses.
That night, I created an UpWork profile and began scouring the site for podcast editor postings. I quickly discovered there was no shortage of people looking for editing support. Before the night was over, I had applied to them all.
Three days later, I had landed my first gig.
At $30 an episode, it wasn’t much. And yet, in landing that first client, something inside me shifted. I realized I had reached a tipping point–just not the one I had been envisioning.
I knew that if I could get one client, I could get another, and another, and another until I had enough clients to quit my job and book a plane ticket. I didn’t know how long that would take, but I knew I was now on a path where that outcome was not just possible, but inevitable.
With this realization, I learned an important lesson.
A Tale of Two Tipping Points
I know I’m not alone in waiting for the tipping point, that big break after which we can stop feeling like we’re pushing a boulder up a hill and we can start reaping the rewards of all the work we’ve put in without the continued effort.
Maybe the tipping point you imagine is a piece of content going viral, a major media feature, or your first 6-figure launch. Maybe it’s getting hired for your dream job.
Let’s call this the Tipping Point of Effort.
No matter how pragmatic an approach we might take on a day-to-day basis, I think we all harbour some fantasy about what our big break will look like and how life will be different once it arrives.
This tipping point is external and measured by tangible results. It’s marked by the point at which the same amount of effort begins to generate a greater and greater return. While it might feel like reaching this tipping point is the goal we’re ultimately working towards, it is not, in fact, the only tipping point. And it’s not the one that matters most.
Long before we arrive at the Tipping Point of Effort, we must first reach another. This other tipping point is the Tipping Point of Belief. This tipping point is internal. And while it might not be measurable, the difference it makes is significant.
The Tipping Point of Belief is the point at which we realize that we’re on to something that will work if we simply give it enough time. We likely won’t know how much time it will take to reach our end goal but we know that we’re on the right track. Once we’ve passed this tipping point we can be confident that we’ll get there as long as we keep moving forward.
This is what I experienced when I landed my first podcast editing client. I had landed my first client quickly, but I had no idea how long it would take to add the additional 5-10 clients to my roster that I would need to support myself.
I remember thinking that it might take a year or two, and I was ok with that. In fact, I was ecstatic. Once I’d passed the Tipping Point of Belief, the timeline didn’t really matter. I was happy to put in the work, no matter how long it took, knowing that in the end, it was going to get me to my goal of full-time travel.
Six months later, I had quit my job and was on a plane to Europe.
That’s the thing about reaching the internal tipping point. The work doesn’t get any easier once you’ve reached it, but the clarity and confidence that come with it make it feel like you’re now moving downhill. Overnight, you’re able to bring more focus to your work because you’re not second-guessing whether your time would be better spent elsewhere. It just so happens that another side-effect is taking more joy in your work as well.
This shift leads to better work, which builds momentum. This then speeds the arrival of the Tipping Point of Effort, where the results begin to compound.
Reaching the Tipping Point of Belief isn’t just about speeding up the process, however. It’s almost impossible to reach the Tipping Point of Effort without it.
This creates a problem for us as creators.
Most of us haven’t yet reached the Tipping Point of Belief. We don’t know for certain that we’re on the right track, and are constantly second-guessing our decisions about where we spend our time. If the Tipping Point of Belief is a necessary checkpoint on the way to the results we’re chasing, how do we get there?
How To Reach The Tipping Point of Belief
The first thing to understand is that getting past the Tipping Point of Belief doesn’t mean you’re free of doubt in every facet of your work. You’ll still face myriad choices about how to create, market, and sell the work you do on a regular basis. Without having reached the tipping point, many of these choices might feel paralyzing.
The difference, I think, is that once you have the belief that you’re on the right track, you realize that these choices don’t actually matter all that much. It’s clear to you that your decision to build your audience on Instagram or Twitter, Youtube or Podcast certainly won’t make or break your idea.
The Tipping Point of Belief is often (but not always) marked by some external validation. For me, this was landing my first podcast editing client. For that validation to mean anything, however, it has to be the result of a process.
Getting a client by fluke is little cause for belief. Getting a client as the result of a defined process, however, gives you the confidence that you can repeat the process and get the same result. Achieve this, and you know you’re on to something.
We all have different skills, traits, perspectives, and results we’re working towards. But there are three things that will help anyone get to the Tipping Point of Belief faster.
An Idea Generation Habit
The first is developing a habit of generating ideas. Not necessarily good ideas, but a lot of ideas.
Since the start of the year, I’ve added almost 1,000 ideas to my list of potential blog or newsletter topics. Of that list, I’ve only ended up writing about 83 of them.
Developing the habit of constantly generating new ideas opens up your eyes to just how much opportunity is out there. This allows you to then be much more selective about the ideas you do choose to pursue. It also gives you confidence in your ability to find solutions to the problems you’re likely to encounter in the future.
The thing that trips people up when trying to build a habit of idea generation is thinking that every idea needs to be a viable business or product. Most ideas won’t be.
What you’re looking for instead is the tiny seeds of ideas. Things that pique your curiosity, that you’d like to explore more, or little insights throughout your day.
The most effective way to kickstart this idea of noticing small ideas is to write every day. Even if it’s on Twitter or Instagram, make a commitment to share one post every day around an insight you’ve had. This commitment has a way of queuing your subconscious to keep an eye out for topics to write about. Pretty soon you’ll find yourself filling notebooks with ideas as you go about your day.
A Habit of Shipping Work
Tied closely to the idea generation habit is a habit of shipping work.
As mentioned above, the idea generation habit is most easily achieved when you’ve made a commitment to publish something–no matter how small–every day. That said, reaching the Tipping Point of Belief will likely require you to ship more ambitious projects than daily tweets.
Starting, shipping, and closing out a variety of projects helps you explore different mediums, offers, and strategies. Over time, you’ll discover which resonate most strongly with you and where your strengths and weaknesses lie.
The habit also builds confidence in your ability to make a plan, execute it, and achieve a result. When combined with an idea generation habit, and a clear direction, these two skills will make you unstoppable.
Trust & Commitment
The final requirement for reaching the Tipping Point of Belief is trust and commitment.
Reaching the tipping point is going to take time. It’s going to take having a lot of bad ideas and shipping a lot of bad work.
Trust in yourself and commitment to the process are essential to make it through this early stage when you’re most likely to be wracked with doubt and frustration.
The best way through is to keep creating, however. Keep generating new ideas, keep shipping, keep iterating, and keep trusting that eventually, the process will lead you to where you need to be.
A New Tipping Point
I’ve recently felt myself pass another Tipping Point of Belief.
The first time was marked by a single significant instance of external validation–getting my first client. This time around, the approach and transition has been more subtle.
In short, this tipping point has felt a lot more like… well, a tipping point. A slow, steady build-up of a body of work suddenly giving way to something greater. The hundreds of blog posts and newsletters I’ve written over the past year and a half beginning to organize themselves into a larger whole.
My goal, for a while has been making a living as a full-time creator. Over the past few weeks, I’ve felt that goal shift from possibility to inevitability.
I’m still foggy on many of the details, but I feel the critical mass of ideas steadily coalescing into a more clearly-defined vision.
As with last time, I don’t know how long it will take to reach the goal. Six months? One year? Two? At this point, it doesn’t much matter. It will take however long it takes, and I’m certain that as long as I stick to the process, it’s only a matter of time.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
How a Disciplined Approach to Creative Work Improves Your Odds of Success
I’ve been playing a lot of backgammon, recently.
If you’re not familiar with the game, the description, per Wikipedia is as follows:
“Backgammon is a two-player game where each player has fifteen pieces that move between twenty-four points on the board according to the roll of two dice. The objective of the game is to be first to move all fifteen checkers off the board.”
The other key element of the game worth noting is that a stack of two or more pieces is protected, blocking the opposing player from placing their own piece(s) on that point. A single piece, however, is unprotected, meaning the opposing player can place their own piece(s) on that point, sending your piece home, Sorry! style.
The thing to understand about Backgammon is that while there is certainly a level of strategy involved, the strategy can be learned quickly, at which point, two experienced players are simply playing a game of pure chance.
In cases such as this, whoever rolls higher-scoring dice over the course of the game is going to win.
Or at least, they should.
As simple as the strategy of Backgammon is to understand, there is one trap that even experienced players fall prey to.
The trap? Themselves.
You see, each dice roll presents you with a series of available moves, some of which will be risky, and some safe. In my experience, the strategy that wins most consistently is to default to the safest move, taking smart risks to leave pieces exposed only when necessary.
We can think of sticking to this strategy as the “disciplined” approach to the game.
When both players take a disciplined approach to the game, the outcome will almost certainly be determined by chance alone. While it might make for a boring game, it also provides the best odds of winning.
As a game of chance between two players, those odds are 50%, meaning that if you simply follow this strategy, you can guarantee yourself victory in half the matches you play.
The trap, however, is when one or both players get greedy, believing that they can beat the 50/50 odds and straying from the disciplined approach to the game.
This departure from discipline almost always takes the form of a ratchet, with one unnecessarily risky move being punished, now requiring a further risky move in order to make up the lost ground.
This cycle perpetuates until all semblance of discipline has been thrown out the window.
When both players fall into this style of play, games can turn into wide-open free-for-alls with multiple lead changes that are exhilarating to play and heartbreaking to lose.
If only one player opts for this style of play, however, while the other maintains their discipline… The undisciplined player is likely to have their clock cleaned.
If this is the case, why then, would an experienced player who knows the disciplined approach will give them the best chance of winning, ever abandon it?
The answer is almost always emotion.
Once emotion enters into the decision-making process, probability is no longer the only determinant of the outcome. Over the long run, this can only decrease your odds of winning.
If a disciplined game is about assessing the odds and making the most rational move available, allowing emotion to affect your decision-making can by definition only lead to more irrational moves.
Soon enough, frustration, anger, revenge, spite, hope, desperation, and more all take a turn at the wheel, driving you to make riskier and riskier moves based only loosely on any assessment of the odds.
I won’t lie, the victories earned by playing with emotion are often the sweetest. But they’re also much harder to come by.
What’s more, the lows after losing an emotion-fueled game are much lower.
When you lose a disciplined game, you can take solace in the fact that for the most part, you made the right choices and luck just wasn’t on your side this time around.
Lose a game driven by emotion, however, and you’re left to beat yourself up about all the (in hindsight) stupid mistakes you made that lead to the loss.
What this all means, is that Backgammon is not the simple game of pure chance it appears to be on the surface, but a game about mastering your emotions and playing with discipline.
The same concept applies to our creative work.
Don’t Let Emotion Drive Your Creative Decisions
Much like with Backgammon, we can choose to take either a disciplined or emotional approach to our creative work.
Unlike Backgammon, however–a closed system comprised of a limited number of available moves and outcomes, all of which controlled by the roll of two dice–the potential moves, and the odds and risks associated with our creative work are harder to calculate.
This lack of clarity makes it easier for us to rely solely on emotion to guide our decision-making.
Sure, we’ll often dress our reasoning up in stories about why our choices are the most rational or strategic, but underneath it all, emotion is in the driver’s seat. As with Backgammon, with emotion at the wheel, our chances of success drop sharply.
When it comes to navigating the terrain of our creative work, the feelings most likely to drive our decision-making are negative emotions like doubt, impatience, fear, and inadequacy, as well as positive emotions like inspiration, purpose, desire, and excitement.
Our challenge, when faced with any of these emotions, is to not let them sway us from playing a disciplined game.
Much like Backgammon, playing with emotion in our work can lead us to put ourselves in risky positions.
More often, however, emotion in our work leads to inconsistency, causing us to jump from strategy to strategy, tactic to tactic, never giving any of them enough time or attention to actually begin to work for us.
In Backgammon, the strategy of playing a disciplined game is clear: assess the odds and make the least risky move.
But what does discipline look like for creative work?
Disciplined Creative Work
The core of the disciplined approach to creative work is the same as the disciplined approach to Backgammon: Default to the moves that in the long run, give you the highest probability of success, taking a sprinkling of smart, calculated risks along the way.
This raises the question, however, what are the moves that give the highest probability of success in the long run?
There are a number of practices, habits, tasks and mindsets that fall into this category, but I want to focus on two.
Focus On the Long Game
The first is to make the decision to play the long game in the first place. Playing with discipline requires you to ride out the surges of emotion, positive and negative, that might otherwise compel you to jump from strategy to strategy at the first sign of frustration.
Think of your work as an acorn.
While it has the potential to one day grow into a towering oak, it must first be planted in fertile soil, and then be given a steady supply of sunshine and water for months before the first signs of growth become even the tiniest bit visible above the soil.
Any strategy worth pursuing will require the same patience, attention, and nourishment in order to succeed.
Adopting the long view from the beginning and helps you ride the waves of emotion and make wiser decisions, even when the first signs of growth have yet to appear
Once you’ve adopted the long view, the second practice central to disciplined creative work is to consistently ship new work.
Ship More Work
Imagine for a moment that you knew that with every podcast episode, newsletter issue, or YouTube video you published, you would get 25 new subscribers.
Knowing this, you would likely never stop publishing new content.
Now imagine you knew that you would get 2,500 new subscribers at the moment you published your 100th piece of content, but not one before that.
With this guarantee, you would likely still feel confident as you published those first 99 episodes, even without the steady signals of progress along the way.
With the guaranteed influx of subscribers after your hundredth iteration, you might even choose to speed up the process, compressing the requisite number of reps into less time in order to get the resulting subscribers more quickly.
While we like to think that growth happens in a linear fashion, it more often resembles an exponential curve, similar to the second scenario, with long periods of slow, incremental (maybe even imperceptible) growth and improvement that then–suddenly and unexpectedly–gives way to a surge of progress.
While the surge always takes time to materialize, time itself is not the factor leading to it.
We can’t simply wait it out. The only way to arrive at the surge is to ship a lot of work.
There are a few reasons why.
Shipping With Discipline Improves Your Luck
First, our early work just isn’t that all that good, at least not compared to what it will be 50, or 100, or 500, or 1,000 reps from now.
We can learn and read and study all we want, but nothing improves our work like creating, publishing, and getting real-time feedback (even if that feedback is crickets).
Secondly, each time we ship our work is an opportunity to experiment.
If we only publish 4 pieces of content a year, for example, it will be hard to draw conclusions on what’s resonating, and thus worth doubling down on, and what’s not.
Publish 100, however, and you’ve got a significant sample size from which to draw conclusions.
Finally, as with Backgammon, there is an element of luck to doing successful creative work.
In Backgammon, our opportunities to get lucky are constrained by the number of turns in the game. When it comes to our work, however, our opportunities to get lucky are constrained only by the number of times we choose to ship.
The more work we ship, the more opportunity we give luck to find us.
Playing a disciplined game helps us level the odds when it comes to our creative work.
By taking the long view and continually shipping our work, we can put ourselves in a position where it’s only a matter of time before we catch a break and we ride the surge upward.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
Fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
Don’t Confuse the Tools You Use With the Work You Do
“Shit,” I think to myself.
I reach back, feel the emptiness in my back pocket before frantically checking both my front pockets. Also empty.
My heart sinks.
Up until now, the past two hours have been one of the best hikes I’ve ever been on. That type of perfect hike that only happens when you set off with less of a destination and more of a curiosity.
For me, that curiosity was centered around a valley, visible from my apartment, that begins at the far edge of Sarandë, the Southern Albanian town in which I’m currently living, and leads… well, that’s what I wanted to find out.
As I walked through town, I chatted on the phone with one of my oldest and best friends. We caught up as I made my way past rows and rows of tightly packed apartment buildings, which gave way to more generously spaced houses as the road began to incline toward the valley. We ended the call when the houses petered out entirely, and soon after, so did the cell signal.
On my own, I continued up the trail, well-worn by centuries, if not millennia of use by sheep and goat herders making their way into town from the rolling hills and mountains that surround it.
The narrow valley eventually opened up to a wider bowl, empty, save for two tiny goat farms, each consisting of little more than a few small pens and a stone hut with a tarp roof.
At the end of the valley I continued up the sloping hill, thinking of looping back along the ridge separating my valley on the East from the town and the sea on the West.
At the top, I stopped for a snack, admiring the view of the shimmering Adriatic, the Greek Island of Corfu rising dramatically out of it, while wondering what lies beyond the ridge that lays just ahead of me to the North.
After a half hour or so I got up, consider heading back South along the ridge as I had planned, but instead turn North, my curiosity getting the better of me.
As I pick my way forward through the maze of razor sharp boulders that make up this landscape, I think to myself that this is the part of the story that I’ll look back on either as the moment the adventure truly began, or the moment of stupidity that I should have turned back.
It turns out, I don’t have to wait long to find out.
As I reach the edge I discover that it descends and then drops into a canyon that runs directly down to the sea. I pull out my phone to check Google Maps to see if I can follow the coast at the end of the canyon back into town.
It looks like I can, so I lower myself down one low cliff, and then another, take a few steps, reach for my phone again to snap a photo, and find my pocket empty.
“Shit.”
I spend the next 45 minutes scouring the area, retracing my steps, already knowing it’s gone.
The landscape is all tall grasses and pockmarked limestone, filled with thousands upon thousands of holes the perfect size for a phone to fall into and never be seen again.
The valley I’m in has likely seen more goats than people, and chances are that whatever nook the phone has found its way into it will never be seen by another human again.
As I climb up out of the valley, I head for the ridge that I perhaps should have stuck to initially. As I follow it back toward town, I think about what the lost phone is going to mean. I’m not upset or annoyed (ok, I’m mildly annoyed), so much as curious.
My data is all regularly backed up to the cloud, so nothing valuable has been lost in that regard. The biggest hassle is almost certainly going to be dealing with 2-factor authentication requests from various apps and websites. In most of those cases at least, I should be able to get alternative authentications through email… at least I hope so.
Being in Albania for the time being, it might be a while before I can get a replacement phone from my phone company, who almost certainly doesn’t ship here…
I think about the things I most commonly use my phone for, especially while away from home and my other devices, and brace myself as I start to tally up the inconveniences.
Take Your Tools Off Their Pedestal
The list of inconveniences turns out to be shorter than I had expected; note-taking, podcast listening, navigation, photos, and keeping track of time round out the list of most common uses.
As I list them off, I realize that really, all I’ve lost is a tool. A wonderful, multi-functional one, but a tool nonetheless, and one that–at least for my purposes–can be easily replaced by other, more analog tools.
It’s worth remembering that while we have access to many incredible tools that enable and streamline our creative work, our tools are biased.
The tools we use have a way of shaping how we engage with the work we use them. It’s never a bad thing to be forced to go without a well-worn tool, at least for a while, in order to determine in which direction its bias leans.
Tools (especially phones) also have a habit of streamlining and enforcing behaviours that aren’t always positive. One of the reasons I was enjoying the hike so much in the first place is that I wasn’t plugged into a podcast or audiobook. I was also outside the range of cell service, free of any pings, notifications, and the urge to check in and see what’s happening on any of the various social networks.
To me, being forced to spend more time in that state certainly isn’t a bad thing.
As I begin to descend the ridge I look to my right, taking in the sea, the forest of jagged stone, and two lonely trees springing up between the rocks, backstopped by the island of Corfu in the distance. I pull out my Nikon DSLR from my backpack, zoom in, and snap a couple of photos my phone would have been entirely incapable of taking.
I wonder if I’m going to be getting better reacquainted with my long-neglected camera now.
Don’t Confuse The Tools With The Work Itself
Walking into town I can’t help but feel a wave of gratitude. I’ve lost a bit of convenience, but when I think about what really matters to me and my work, phones, computers, and all the rest of the various tools I use merely help to facilitate the work itself.
I think about the curiosity that lead me to first take this hike in the first place, and then lead me into the canyon. I think about how before I had even lost the phone, I was already thinking of the narrative of the day’s story and my decision to choose the canyon over the ridge. I think about the insights and lessons I’ve been mulling over on my walk back home. I think about the new ideas and stories and connections this experience is seeding in my brain.
This is the work.
Curiosity, insight and storytelling don’t require a phone or any other tool in order to flourish. In fact, they often function best in the absence of tools and their biases and distractions.
I think again about what’s been lost. A 5-year old chunk of metal, plastic, and glass that was already on its way out. Some convenience, ubiquitous connection and the accompanying distraction, anxiety, and impatience.
Then I think about what’s been gained. Perspective. Some new ideas to mull over. A new challenge to approach. A story.
As I walk up the the hill toward my apartment, the sun beginning to sink behind the hills from which I’ve just walked, I can’t help but feel as though I’ve come out ahead in the day’s transaction.
A Question For You
What’s a tool you put too much value or emphasis on when it comes to your work?
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
Fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
What I Learned Publishing An Email Newsletter For A Year
Just over a year ago, I sent out the very first issue of the Listen Up Newsletter.
The subject line of that first issue was, “Focus On What Fuels You,” and was, at least in some part about coming back to writing newsletters, something I’d tried multiple times in the past, but had never been able to stick with.
While those past attempts at writing a consistent newsletter had always felt like chores, this one felt different. A year ago, starting the LU Newsletter felt like something that actually energized me, an additive force rather than a draining one.
A year later, I’m grateful that I still experience that energy when I sit down to write each issue.
The past year has brought a lot of trial, error, and learning when it comes to the newsletter, and in this issue, I want to break down some of my personal takeaways from one year and 50 issues of newsletter writing.
But before we do, let’s look at why I started it in the first place.
Why I Started A Newsletter
When I started the newsletter in April, 2020, the pandemic had recently shut the world down. Like most everyone else, I found myself stuck at home with more time to fill, especially during the weekends.
It was during the initial lockdown that I started discovering some truly fantastic email newsletters that completely changed my idea of what a newsletter could be.
These newsletters from people like Khe Hy, Jay Clouse, Ann Handley, and The DO Lectures showed me that a newsletter was not the same as email marketing. It wasn’t about simply summarizing your latest blog post or podcast episode or blasting your list.
I learned that a good newsletter could (and should) stand on its own, as a unique product, valuable in its own right. What’s more, like a podcast, if presented the right way, it’s something people would choose to subscribe to willingly without the need for a lead magnet, freebie, bribe, etc.
What I especially liked about the newsletters I read was the sense of intimacy and familiarity that was lacking from a lot of blogs, including mine. As a writer, I wanted to speak more personally and directly to a community of like-minded people, and I didn’t feel that was happening through my current blogs. A newsletter, however, felt like the perfect fit.
My motivations for starting the newsletter has always been personal first, business second, which is one of the reasons why I think I’ve been able to main the energy and excitement behind it for this long
The primary reason I started was to give me a forum to experiment with and improve my long-form writing, particularly as it related to storytelling and teaching. What I liked about that goal is that it could be worked toward and achieved even if no one ever read a single issue.
That said, I did have a number of audience-facing goals related to the newsletter as well.
Audience-Facing Goals
I saw the newsletter as becoming what I refer to as my flagship content, the primary content channel that I poured the bulk of my focus and creative energy into, and which would drive the rest of my content marketing.
Like most flagship content, my primary audience-facing goals were to grow my email list, and nurture the subscribers on it with regular insight and communication that they (hopefully) found valuable.
I’d built up an email list of around 900 people in the past, but had let my communication lapse multiple times. At the time I started the LU Newsletter, I hadn’t sent a single email to my list in over a year.
Starting a newsletter as a dedicated content channel was a way to avoid falling back into that situation again.
So with those goals in mind, let’s have a look at some of the results of publishing the newsletter weekly over the past year.
Outcomes
Writing Improvement
The biggest and most obvious benefit of writing the newsletter for a year has been the improvement of my writing.
As mentioned, this was one of my biggest goals when I started the newsletter so I’m glad to see that there has, in fact, been growth and improvement.
There have been a few issues of the newsletter in particular that stand out to me as being notable leaps forward in my writing, where everything just clicked for me. Two of the issues that stand out most as big steps forward are #10: Directing Your Energy Wisely and #43: What Pinky Toes Teach Us About Strong Foundations.
That said, after a year of writing, I’m starting to realize that my writing has a long way to go to be at the level I want it to be, and that I’m reaching the limits of how much I can improve my writing on my own. With that in mind, I plan on taking one or more writing courses over the next year to take a more active approach to continued improvement.
List Nurturing & Engagement
After the improvement of my writing, the list engagement has been the biggest positive outcome for me a year into the newsletter.
I’ve had a number of people reach out either privately or publicly on social media and say that the Listen Up Newsletter is their very favourite newsletter. As you might imagine, this means a lot to me. I’ve written before about how our goal as creators needs to be to make work that has the potential to be someone’s favourite, an idea I borrowed from Jay Acunzo.
While the growth of the newsletter has been slower than I’d hoped, the fact that it’s resonating with people and has achieved that coveted “favourite” status for at least a handful of them is a strong sign to me that I’m on the right track, and that it’s worth continuing.
Beyond the compliments and the positive feedback, I’ve also run three launches for Podcast Marketing Academy, as well as some other mini-promotions and the majority of the sales have come from the list.
There’s no way to know for certain, but given that I hadn’t sent an email in over a year before starting the newsletter, I’m guessing all of those launches would have fallen flat if not for the regular contact with my subscribers and in many cases, back and forth interaction that email allows for.
Unexpected Benefits
Aside from some of the goals and expectations I had in mind when I started the newsletter, there have been some unexpected side benefits of publishing it consistently as well.
The first has been some of the relationships I’ve both made and deepened through back and forth conversations with subscribers who’ve replied to my emails. In many cases we’ve actually ended up getting on Zoom calls to connect and chat. These connections weren’t something I anticipated when I started out, but I’m really grateful that the newsletter has facilitated them.
The second big unexpected benefit has come as a result of the curated section of each newsletter.
In each issue, I include a list of “5 Things You Might Dig” based on my own content consumption and findings each week. The unexpected byproduct of doing this section is that I now have a reason to always be on the lookout for interesting content that is helpful to the creators, marketers, and entrepreneurs in my audience. In seeking out and consuming this content myself, I’ve learned a lot when it comes to marketing, content creation, and more.
List Growth
Alright, finally we get to list growth, the goal where the least progress has been made.
As you might expect, after not having emailed my list for over a year, I experience a large drop off in subscribers when I started sending emails again. I had 50 unsubscribes from the first email alone, and over the first two months of publishing the newsletter, I dropped from a high of 1,094 subscribers down to a low of 955.
From there, the list started growing, but if I’m honest, it hasn’t grown at nearly the rate I would’ve hoped.
In the year of publishing, I’ve been able to grow it from the low point of 955 subscribers up to 1,186 where it’s currently at, a net gain of 231 over the course of a year. I hadn’t set any measurable goals around list growth when I started out, but I think I would have hoped or expected to grow the newsletter by at least 1,000 subscribers in a year of publishing.
The growth that has come has mainly been driven by speaking at virtual summits, participating in a handful of collaborative promotions, and most recently by running a free 5-day workshop related to podcast sponsorship, which was promoted by a number of affiliate partners as well.
While the results have been somewhat discouraging, as I mentioned earlier, the fact that I’m getting positive feedback and engagement from readers is a much stronger indicator for me to double down and keep going than the number of subscribers is.
Lessons Learned From A Year Of Newsletter Writing
While there’s a lot to think and sort through when it comes to what’s working and what’s not, there have been a few lessons that clearly stand out from this first year of the newsletter.
1. It’s Hard To Have More Than One Flagship Content Channel at a Time
Shortly after starting the newsletter, I also started a podcast, Build A Better Wellness Biz. The show was a fairly ambitious endeavour with high production value, and each episode of the weekly show ended up taking between 15-20 hours of my time to produce on top of the time my team put into it.
On top of that, I also maintained my practice of writing and publishing a new blog post every day. This ended up being way too much content to produce at the level I wanted it to be at, and so, after 30 episodes, I decided to end the podcast.
In the end, the newsletter felt much more aligned with the direction I wanted to be heading in, and the topics were more focused around where I thought I could bring unique insight and perspective to the world.
Going forward, while I will almost certainly experiment with adding more content channels again in the future, none of those endeavours will be as ambitious or time-consuming as Build A Better Wellness Biz. Ultimately, the one thing I want to be known for is the newsletter, so I’m going to make sure I’m allocating the time and attention to making it the best it can be, with everything else being secondary.
2. The Secret to a Successful Newsletter Is Thinking About It as a Product
This is true for all content, but I think it’s especially worth mentioning for newsletters. It’s easy for the line to blur between email marketing and a newsletter, when they are not, in fact, the same thing.
To me, each issue of a newsletter needs to be approached as a discrete product, something that your subscribers look forward to and are excited to read, much like the latest issue of a print magazine. It should be tight, cohesive, and nicely packaged.
Unlike email marketing the point of the newsletter should never be sales, but value. There should be a clear line drawn between the two types of emails.
3. I Need To Bring More Clarity to the Newsletter if I Want It To Grow More Quickly
To market anything effectively, it’s essential to be able to concisely summarize who it’s for and what it’s for. One of my current frustrations with the newsletter is that I’m not quite sure how to actually articulate this in a concise and compelling way.
The best I can come up with right now is that this is a newsletter helping creators find the clues to navigating a meaningful creative life that are hidden in plain sight. Kinda clunky but it’s the best I’ve got right now.
I feel like gaining clarity on both the topics I write about and how I talk about the newsletter is a piece that needs to fall into place before the newsletter can really start growing.
On that note, I’d love to hear how you would describe this newsletter. Feel free to hit reply to this email or even better, fill out this reader survey and let me know.
4. I Need To Create More on-Ramps to the Newsletter
Lastly, I’ve realized that while I have one or two solid lead magnets leading people to the newsletter, I need to create more diversified, high-quality on-ramps to appeal to more people.
My big focus over the next six months or so is going to be list growth. I’ve already got a number of ideas on how to create valuable free or low-cost resources to grow my list, and I’m excited to start building them.
I’ll be sharing updates both through the newsletter a well as on Twitter as to how Project List Growth is progressing, including what I’m trying, what’s working and what’s not.
Bring On Year Two
If I had any doubt a year ago about the newsletter as a long-term content medium, it’s long since dissipated. I still have just as much excitement to sit down and write each new issue and as the momentum continues to slowly build, I imagine that excitement is only going to grow.
I see this newsletter as being the compass needle of all the work I do going forward, where ideas are started, explored, and eventually developed into something bigger. I’m honoured that you’ve signed up to follow along and will do my best to keep sharing insight that you find valuable in developing your own creative work.
That said, I can’t make this newsletter the best it can be on my own.
How You Can Help
The first and most helpful thing you can do is to fill out this subscriber survey. It will only take a few of minutes and will help me understand what you like about the newsletter, what you don’t, and give me ideas on how to improve the content and your experience as a reader.
The second thing you can do is to reach out at any time. My inbox is always open, so please hit reply to any (or every) newsletter issue you enjoy and let me know what you took away. Also, feel free to reach out on Twitter.
Lastly, if you find value in the newsletter, I would be beyond grateful if you would send it to someone else who you think might enjoy it as well. I’m convinced all good things grow by word of mouth, and this newsletter will be no different.
Thank you so much for being a reader, it means the world to me. Now let’s get on to year two, shall we?
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
Fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
Leveraging Gravity
To the person seeking to move a boulder to the top of a hill, gravity is an ever-present, malevolent force to be fought with, pushed on, and toiled against.
To the person seeking to move a boulder down the hill, however, gravity is a benevolent ally that takes care of most of the work itself.
We know gravity is a constant.
What’s not a constant is how we choose to view it and how that view informs the ways in which we work with or against it.
Used wisely, simple physics provides many solutions that allow us to leverage gravity even when moving our boulders uphill.
All it takes is an awareness of the tools and environment at our disposal, and a little ingenuity.
What are the forces you’re currently working against, and how can you put them to use for you instead?
Aim For “Favourite” Status
Think for a moment about your absolute favourite creator.
Maybe they’re a podcaster, blogger, author, marketer or business. Maybe they’re something else entirely.
When you compare your favourite creator to others in the same category, it probably doesn’t take long to realize that you give your favourite special treatment.
You’re predisposed to love everything they do as soon as they release it. You sign up for every new offer the second it comes out. Most important of all, you can’t help yourself from spreading the word and telling everyone you know about how great they are, often to the point of annoying your friends and colleagues.
The other week, I signed up for a $500 course from one of my favourite creators without reading the sales email, landing page, or anything else except the subject line of the email and the “Buy Now” button text.
Yep, being someone’s favourite has its advantages.
And yet, as creators, marketers and entrepreneurs ourselves, we often align our goals with meaning a little bit to a lot of people, rather than a whole lot to a few.
We tell ourselves that the more people we initially appeal loosely to, the more people will trickle down into our inner circle, with us at the center as their favourite.
The problem is that when we’re focused on appealing to the masses at the outer reaches of our influence, we can’t possibly create anything that matters enough to any one person to become their favourite.
The answer then, both to creating work that has the potential to be one person’s favourite as well as building a broader audience, is to start with that one person for whom we can be the absolute best in the world. Every new thing we create must be made with the intent of serving that one person better than anything else currently does.
If we can create that for one person, chances are it will resonate with others, too. Our person will likely begin to spread the word and we’ll be off and running.
The reason we don’t do this, I think, is because creating for one person leaves no room for us to hide. Because if we can’t create something that is the favourite of even one person… Well, that means our work isn’t at the level it needs to be at.
Easier to assume we have a marketing problem than confront the fact that maybe our work just isn’t good enough.
And yet, we all start with work that isn’t good enough. None of us comes out of the womb creating work worthy of attention, why should we assume it’s good enough now?
In the end, the only way to know is to find that one, ideal person, and then hone and perfect and iterate on our work until they can’t help but talk about it.
Then, double down, do more of it, and let them grow our audiences for us.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
Fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
Embracing the Mentality of the Underdog Creator
The mentality of the underdog is an empowering mindset to own and embody.
The underdog expects that nothing will come easy.
That nothing will be freely given.
That everything they desire must be worked, clawed, and fought for.
The underdog owns her situation.
She doesn’t blame or begrudge, others, fate, or the system she is working to change for her hardships and the inequities forced upon her (even though they may be stacked against her).
She simply recommits to working harder, taking a new tack, approaching the challenge from a different angle. Time and time and time again until she succeeds.
The underdog knows that when so little is freely given, one of the most powerful acts is to freely give.
To share what little comes her way with those less fortunate.
For there are always those that are less fortunate.
She passes on what she has learned.
Lifts up instead of puts down.
Takes on the role of the champion, cheerleader and supporter she wishes she had when she was starting out with less than she has now.
The underdog knows that while this tactic or that might not work, if she keeps trying, experimenting, exploring every angle of her problem, eventually it will be solved.
She maintains belief.
Trust in herself.
Hope in the face of endless adversity.
That one day, it will pay off.
That her work has the power to change things in a deep and meaningful way, if only for a few people.
We could all use a bit more of the underdog mentality.
Creative Wayfinding For Ambitious Optimists.
Adolescence Is a B*tch…
I mean, let’s not beat around the bush.
It’s an awkward, uncomfortable, turbulent time of growth and exploration where we experiment, rebel, and push the boundaries as we decide who we’ll become. We make our share of mistakes and execute horrendously poor judgment along the way. With each mistake, our view of the world and our place within it becomes a little more nuanced and self-aware, but it’s a slow, painful, often embarrassing process that most of us are glad to have put behind us.
Except… We haven’t.
Sure, our bodies may have developed past the gangly, acned teenagers we once were. We’ve gained experience, worked jobs other than the McDonald’s drive-through window, and maybe even married and had kids. While we might be surrounded by the trappings of adulthood, however, adolescence exists in many areas beyond simply the social and biological.
Of particular importance to us as creators is navigating the adolescence of our work. Most of us don’t even realize it exists or that we might be in it, but until we move through it and reach maturity, we’re not going get the results we’re chasing.
The Traits Of Adolescence
In many ways, our work’s adolescence mirrors our own. When we first start creating, we’re well aware that the work we’re doing isn’t all that good. Like toddlers, we’re finding our feet, playing with the basic building blocks of our craft, and doing our best to piece them together. With some dedicated practice, our work quickly improves in both quality and originality, and before long, we may even develop the confidence to start sharing it with the world.
But while we might have outgrown childhood, there is still a significant gap to cross before we reach maturity. This gap is adolescence, and it’s where many creators get stuck, unaware that they’re suspended in a state of arrested development.
In adolescence, we can write grammatically correct essays, produce tightly edited podcasts and film videos that rival the technical quality of the biggest YouTubers. But while we’re slowly adopting the accouterments of creative adulthood, our immaturity still shines through in ways we might not realize, but others certainly do.
While our work may be technically sufficient for our medium of choice, the ideas behind the work lag behind. They’re awkward, gangly, poorly thought out, and inarticulate, if not outright incoherent. Frustrated by these gangly ideas, we spend a good deal of time remixing and repurposing what we’ve learned from others, keeping our own insights in the background, and adding little to the conversation ourselves.
As if transported back to high school, we’re hyper-aware of what everyone else is doing, measuring our work against theirs and avoiding going too far out on a limb from the norm. Though we might have new and interesting ideas, we spend most of our time creating work similar to what’s already proven to be successful for others.
We jump from fad to fad, chasing every shiny new tool and growth hack the way we might have chased the latest clothing trend. But much like the right brand of jeans didn’t instantly grant us membership into the cool clique, these hacks never deliver us the results we seek.
If we want to fulfill the potential of our work, it’s essential that we move past this stage. Luckily for us, we’ve successfully navigated adolescence once and can apply the same process to find our way through the adolescence of our work, hopefully with less awkwardness, embarrassment, and acne.
Getting Past The Growing Pains
The defining attribute of adolescence is a lack of experience. This means the surest antidote is to gain as much and as varied experience as you can.
Much like it would be ridiculous to expect a 14-year-old to commit to a university major or future career path, it’s ridiculous for us to commit to any niche, medium, format, or even topic while working through the adolescence of our work.
A productive adolescence is about experimenting broadly, keeping our options open, gathering and synthesizing information about where we have the greatest opportunity to contribute in a meaningful way. While we might be clear on the topic or niche we want to operate in, the mediums we use and the formats within those mediums should be experimented with liberally in order to find our fit.
The time will come to commit and double down, but not until we’ve thoroughly explored and experimented with the available options.
While the defining outward attribute of adolescence might be lack of experience, the internal driver of this phase is a yearning to discover who we are as individuals and find our place in the world.
In our teenage years, this meant leaving the nest and establishing our identities as separate from our parents, often rebelling outright against them. With our work, our adolescence is about moving past our teachers and mentors, developing our own unique perspectives, approaches, and styles, and building on what we’ve learned.
As we mature, we find our voice, expand our vocabularies, and develop defendable opinions. We move from passive absorbers of information to offering valuable additions to the conversation happening in our field. Yes, we’ll make various gaffes, missteps, and blunders as we start speaking up, but these are not the mistakes.
The only real mistake we can make in adolescence is not speaking up, not asserting our views, not experimenting, and exploring the world that is open to us. This process, while uncomfortable, confusing, and at times even embarrassing is the only way through to maturity.
But here’s the thing about adolescence. No matter how awkward, gangly, or uncomfortable in the moment, if we keep moving forward, it ends.
In fact, there comes a point where the growth can simply no longer be contained and the butterfly that’s slowly been developing under wraps bursts from its cocoon.
We emerge more confident, more centred, more sure of the place we and our work occupy in the world.
Adolescence might be frustrating, but it’s a natural and unavoidable phase of life, one we must all travel through. What’s more, it’s when we truly become ourselves. I think that’s something to be cherished.
Adulthood will come soon enough. But until it does, live. Explore, experiment, break the rules and rebel. Create with abandon and above all else, don’t forget to have fun with it. That’s what being young is for, after all.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
To Find Clarity, Start Walking Before You Know Your Destination
It would be something of an understatement to say I’m a fan of walking.
Aside from taking at least one long walk every day, I take many of my calls while walking, read books about walking, generate all my best ideas while walking, and–as you may have noticed–like to write about walking as well.
No, I’m not a fan. I’m obsessed.
Kelly, on the other hand, isn’t quite as keen. Despite this, every so often I manage to convince her to go for a long walk together, such as the one we took last weekend.
The destination was a section of the coast just outside of town. I’d walked the rocky stretch and explored the abandoned decades-old bunkers carved into the hillside a handful of times before, but wanted to share the area with her as well. As we crossed the bridge over the river that marked the edge of town, we turned off the main road and headed up a small dirt trail that snaked its way through the tall grass in the direction of the sea.
“How did you find this path the first time you walked here?” Kelly asked.
I thought for a moment, but found that I didn’t actually have a good answer.
When I don’t know the terrain, I tend to simply start walking, following what’s often little more than a vague curiosity. At times that curiosity might be centered on a prominent landmark or geological feature. At other times, however, I choose my direction simply by chasing a patch of sunlight, a particularly alluring looking street, or an enthralling scent on the breeze. My typical mode of travel might be best described as “whimsical.” If anyone was ever going to accidentally stumble into Narnia, it surely would be me.
The first time I walked this route, my goal had been the sea. From our apartment, I could see white-capped waves crashing against the ragged shoreline further up the coast, and so, on my initial exploration had set out to find my way there.
I took the main road, crossed the bridge over the river that marked the edge of town, and then stopped, spotting a small, dirt trail snaking its way through the tall grass in the direction of the sea. I didn’t know where this path led, but I had nothing but time, and the road I was on was certainly not going to lead me to the coast. So I took the trail.
Fifteen minutes later, after a few wrong turns through an abandoned property development project and a bit of light bushwhacking, I had reached the shoreline.
This approach, of starting with little more than a vague destination, sometimes only a hunch, and then following my curiosity has served me well. It leads to unexpected discoveries, helps you understand the local geography, improves your sense of direction, and to top it off, is good for your health. This mode of travel doesn’t just apply to walking, however.
Create For The Sake Of It
This act of starting before we know where we’re going and picking up the thread on the fly mirrors the creative process exactly.
We start out with a bit of curiosity and a vague destination in mind, and, if we choose to follow that curiosity, have little choice but to do so blindly. While our end destination might not be specific when we set out, at some point, we hope, by walking long enough, we’ll pick up the thread and find it.
Which is precisely what’s happened to me in the past few weeks with this newsletter.
When I started this newsletter a little over a year ago, I had no idea where it was leading. I saw an opportunity to contribute in a format that excited me, and a curiosity and willingness to see where the path would lead.
Rather than writing to help a specific audience achieve a specific goal, I wrote what I wanted to write. More than that, each week, I wrote what I needed to hear.
This approach has kept the newsletter fun, fresh, and even a vital part of my life, and it’s been immensely gratifying to hear that it’s resonated so deeply with so many readers. At the same time, I’ve known that without being clear on who the newsletter is for and what the through-line is that ties it all together it would be hard to grow consistently. It’s hard to market something when you don’t really know what it is after all.
The word “wayfinding” first popped into my head in January and immediately resonated with me as the embodiment of what I was doing with this newsletter. That initial breakthrough then kicked off a long, slow process of gaining clarity, with more and more pieces of the puzzle coming into view over the past five months.
While I’m far from absolute clarity (can we ever actually achieve it?) on the future of this newsletter, I feel as though I can see juuuust far enough through the fog ahead to kick off this new chapter with at least some certainty about where the road leads.
To be clear, nothing about the content has changed, other than it’s going to be more focused, intentional, and sure of itself. I’d like to think it’s going to have a bit more swagger.
Whether you consider yourself a creator, marketer, entrepreneur, or mix of all the above (like me), I’m guessing you spend a good chunk of your days feeling lost (also like me). Maybe you feel a vague lack of direction. Maybe you feel completely unmoored, floating out at sea.
You may have wandered off the beaten path by accident or you may have left it intentionally in search of a better way forward. Regardless, my goal with this newsletter going forward is to help you navigate that sense of not knowing where you’re going or how to get there that comes with doing creative work. Because I’m right there with you, and we’re all in this together.
While I’m excited about this newly clarified direction, it’s clear that this is just the jumping off point. I sense a manifesto in the works along with a number of new offerings and one day, hopefully, a book.
After a year of walking blindly with only a vague sense of direction, I’ve picked up the thread. The through line, I’ve realized, that runs through this newsletter and everything that will follow is this: Practical wisdom for navigating the creative wilds.
Here’s to searching, seeking, hoping and dreaming–to me the essence of wayfinding.
Thanks for walking with me this far, it means the world.
I’m looking forward to seeing where this next leg of the journey takes us as we map it together.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
The More Intimately You Know Resistance, The Better Your Work Will Become
In 1988, Andre Agassi and Boris Becker faced off for the first time, kicking off what would become one of tennis’s great rivalries.
Agassi and Becker were two of the top players in the world, finishing the year ranked No. 3 and 4 in the world respectively. But despite Agassi’s superior ranking, in this first meeting between the two stars, it was Becker coming out on top.
“His serve was something the game had never seen before,” Agassi later recalled. On the strength of that serve, Becker would defeat Agassi in two subsequent matches in 1989, leapfrogging Agassi to take the No. 2 spot on the rankings in the process.
Frustrated, and knowing that the route to victory at any major tournament was likely to lead through Becker, Agassi got to work. He pored through footage of Becker, analyzing his playing style in search of the slightest knick in his armour. And then, after countless hours watching tape, Agassi found it.
“I started to realize he had this weird tick with his tongue,” Agassi said. “He would go into his rocking motion, and just as he was about to toss the ball, he would stick his tongue out. And it would either be right in the middle of his lip, or it’d be to the left corner of his lip.
“If he put his tongue in the middle of his lip, he was either serving up the middle or to the body. But if he put it to the side, he was going to serve out wide.”
This insight proved decisive, as Agassi went on to win ten of their next eleven matches, including one en route to the Wimbledon championship in 1992.
In the end, recalled Agassi, “the hardest part wasn’t returning the serve, but not letting him know that I knew [about the tell].”
Years after they’d both retired, Agassi shared his bit of intel with Becker over a pint at Oktoberfest. A shocked Becker replied, “I used to go home and tell my wife, ‘It’s like he reads my mind.’ Little did I know you were just reading my tongue.”
Studying Your Opponent
The practice of reviewing game tape–both of yourself and your opponent–is a given at elite-level sports. While you might not always discover a tell as obvious as Boris Becker’s, there’s a lot to be learned by studying your opponent’s style.
By knowing their style, you can anticipate their next moves. Then, you can either navigate around them or prepare yourself in advance. Get to know their style well enough and it might appear as though you’re reading their mind. Compared to facing off without that knowledge, this gives you a significant advantage when facing any opponent.
As creators, this opponent is not another person, but ourselves.
Every day, our desire to make work that matters faces off against Resistance. This Resistance might come in many forms, from impostor syndrome to perfectionism, impatience to distraction, the lure of shiny objects to the endless chatter of your inner critic as you try to do the work.
The problem when facing down Resistance is that there’s an asymmetry of knowledge. Resistance has studied our tape and knows just when and where to place the dagger for the most devastating effect. It knows exactly how to cow us, to strike fear, and to sow doubt. All the while, we might not even be aware of its existence, in the worst cases, taking its whisperings as truth. But this doesn’t have to be the case.
Much like an elite athlete, we can choose to study our Resistance, learn its style, and begin to predict its moves. When we understand its moves, we can begin to dance with Resistance, rather than be pummelled by it, turning our opponent into our partner. Resistance can be a powerful indicator that we’re onto something worth pursuing, after all, and it’s from this dance that our best work emerges. But before we can join the dance, we must first learn to read our partner.
Learning To Read Resistance
The first step in learning to read Resistance is to acknowledge its existence. This in itself can be a massive breakthrough, as it means the voice in your head undermining your every creative effort is not, in fact, the voice of truth.
While Resistance is certainly real, the things it tells us are not. Its job is to protect us and in the process of doing so, it’s willing to go to great lengths. This includes doing everything within its power to keep us from shipping our work, opening ourselves up to criticism and failure. The particular way Resistance achieves this varies for each of us. The second step of learning its style, then, is recognizing the specific tricks and vocabulary it uses against you.
Start by identifying the traps that keep you from doing (and shipping) your most important creative work. Perfectionism, procrastination, distraction, and imposter syndrome are all common shapes Resistance can take, but there are many others. If you’re serious about beating Resistance, you might even make a list of its tactics and post it beside your desk as a reminder.
With your list in place, you can keep a vigilant eye out for Resistance, spotting it before it has a chance to derail you. The going might be slow at first, but recognizing, resisting, skirting and dancing with Resistance is a muscle that can be strengthened with use.
When a notification flies across your screen and you’re tempted to set your work aside and click on it, recognize Resistance. Build the muscle by ignoring it and turning your attention back to your work.
When you feel your work isn’t ready and are tempted to tinker some more, recognize Resistance. Build the muscle by hitting “publish”. Then start on your next project.
When you feel like an imposter, like you have nothing to contribute, recognize Resistance. Build the muscle by sharing something publicly that will be useful to even just one other person.
Over time, as you learn Resistance’s style and build up the muscle of defending against it, Resistance will adapt and present new methods of sabotage. No matter, learn the new tricks, add them to your list, and continue the dance.
Resistance is an opponent we can never truly defeat. But if our goal is to create work that matters, we have no choice but to learn to dance with it.
We can choose to view each day either as a series of new opportunities for Resistance to derail us.
Or, we can choose to view each day as a series of new opportunities to strengthen our muscle to resist Resistance.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
What If Taking The Easy Route To Your Destination Is Slowing You Down?
I lifted my gaze for only a second, but that was all it took.
My foot slipped on the rain-slick rock and the next thing I knew I was going down.
I landed hard on my hip. For a long moment, I lay motionless on the ground. One second. Two seconds. Three seconds. I’d anticipated a sharp shooting of pain up my leg. Luckily, I was greeted only by a dull ache.
As I picked myself up, I realized my luck was due to the fact that I’d landed in a shallow puddle of thick mud. I’d seriously stained my pants, but had managed to avoid breaking my hip on the jagged rocks surrounding the puddle. Slowing my pace, I kept my eyes on my feet as I picked my way down the hill to the main road.
As it happens, the fall wasn’t the first time my misplaced gaze had lead me astray this morning.
An hour before my fall, I was out for a short hike up one of the hills behind my apartment. Sarandë, was ringed by a half dozen or so hills and I was determined to climb them all over the course of my 6-week stay. This hill was my second.
I call it a hike, but it was more like a scramble. The landscape was all jagged boulders and brambles, making the existence of any kind of path all but impossible. And so, rather than walking, I was trying to hop from boulder to boulder in the straightest line up the hill. This was a difficult task.
The boulders were razor-sharp. I’d already found many of them to be more than capable of slicing through skin. But they were also loose, liable to shift under the slightest misplaced step.
The hill they covered wasn’t huge, maybe a 30-minute hike up. But navigating the rocks and the spiky brambles that exploded between them required the utmost attention. As such, I kept my eyes firmly on my feet, letting them stray only far enough to find the safest, easiest next step.
Spot. Step. Plant. Balance. Repeat.
After 10 minutes of this slow, careful upward progress I stopped on a large, flat boulder to survey the remainder of the climb.
As I turned my gaze upward I immediately realized that while I had been making progress up the hill, I had been taking what was clearly a very diagonal route. As a result, I had gone further laterally than I needed and would now need to angle up and back the way I came. I reoriented myself, put my head back down, and continued upward.
Five minutes later, I stopped on another boulder. I looked up, and once again, realized that I’d gone too far–this time in the opposite direction. I was making my way up the hill, but I was letting the landscape dictate my path, always opting for the easiest way forward. The result was a drunken zig-zag of a route up to the summit.
I took a breath, reoriented myself once again, and started up once again directly toward the summit, this time stopping every few steps to check my direction in relation to the hilltop.
It was slower, harder going, with more than a few bramble snags cutting up my calves along the way. But 15 minutes later I’d reached the top, having cut a nearly direct line up the rocky hillside.
5 Ways To Climb A Hill
To me, this hillside represents the work each of us does in navigating our creative careers.
The journey is littered with obstacles, some outright dangerous, some simply inconvenient. It’s up to each of us to decide how we’ll choose how to navigate them.
In my experience, we take one of five routes up the hill.
- We make slow, meandering progress up and down the hill but never truly commit to making it to the top. Eventually, we run out of daylight or the weather shifts and we turn back and head for home.
- We keep our eyes fixed upward on our destination, paying little attention to the obstacles at our feet. We might bulldoze our way through the first few hazards, but before long we find ourselves lying in the mud with an aching hip. If we’re lucky we can pick ourselves up and continue upward with more care. If we’re not, the repeated stumbles and falls that accompany this style of travel break us, causing us to limp home, defeated.
- We start climbing but don’t have a clear idea of our destination. As a result, we settle for heading in a vague, upwards direction. It’s possible that we eventually orient ourselves or even stumble on the summit by accident. But either way, it’s a slow, inefficient journey.
- We’re clear on our destination but keep our gaze directed downwards, immediately in front of us instead of the hilltop on the horizon. Each step we take feels like the obvious, easiest choice in the moment. We fail to realize, however, that over time they lead us diagonally away from our goal. At some point we look up, see we’re off-course, and must head back in a new direction.
- We’re clear on the summit we’re aiming for and balance our gaze between our feet and our destination. Each step moves us in as direct a line as possible toward it while also taking care to maintain our footing.
We have to move slower and stop regularly to re-orient ourselves. We might take detours around particularly dangerous obstacles when necessary, but push straight through the brambles and minor inconveniences. We get scraped up in the process, but we maintain the most direct course to our destination.
This mode of travel is the most uncomfortable and feels in the moment like the slowest option. The truth, however, is it’s the fastest, most predictable path up the hill.
We can’t always see the summit from the base of the hill. More often than not it’s hidden in cloud.
In these cases, we have little choice but to start up the hill, hoping that the cloud thins as we move upward. Climb far enough and it almost always does.
Once we have a clear view of the summit, however, it’s best to balance our gaze, navigating the obstacles, keeping our footing, and fighting through the inevitable brambles while maintaining as direct a line to our destination as possible.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
The Two Tipping Points Behind Every Breakthrough Success
Back in 2015, I was a landscaper with dreams of traveling the world full-time.
I had recently discovered the wide world of podcasts and was able to listen to them at work. Naturally, I spent nine hours a day binging my way through every online business podcast I could find.
After a month or two of listening, I started experimenting with what I was learning. I built (ugly) websites, and dreamt up (bad) business ideas, all the while feeling (mostly) confident that eventually, I would land on something that would gain traction.
Despite my general optimism, however, there was a small shadow of doubt in the back of my mind. What If I never landed on something that gained traction?
Whenever it surfaced, I did my best to push the thought further back into the darkest corner of my mind.
Six months passed. The idea I was most confident in was a photography blog that had a small, readership of a hundred people or so. Eventually, I planned on creating online courses in order to generate income. I had no idea what I would teach, but at the rate the blog was growing that I wouldn’t need to make a decision for a long time.
I dreamed of reaching the tipping point. The day when my work would start to pay off and the results would pour in.
In my mind, the tipping point meant thousands of new page views and hundreds of new subscribers per month. But to be honest, I would have settled for any clear sign of traction at all. Any proof that what I was doing was working, and worth my continued investment in.
As it turns out, that proof was right around the corner, just not for my photography blog.
One day at work, I was listening to one of my favourite shows, Zero To Travel, when the host, Jason, mentioned his podcast editor in an offhand comment.
Now, I had considered podcast editing before, but my ego always kept me from taling it seriously. It felt like a waste of my skills, being the professionally trained sound engineer that I was.
Jason’s comment, however, struck something inside me in a way that resonated in a way it never had before. If my goal was to build a business that would allow me to travel, surely this was a quicker route than building an audience and creating courses.
That night, I created an UpWork profile and began scouring the site for podcast editor postings. I quickly discovered there was no shortage of people looking for editing support. Before the night was over, I had applied to them all.
Three days later, I had landed my first gig.
At $30 an episode, it wasn’t much. And yet, in landing that first client, something inside me shifted. I realized I had reached a tipping point–just not the one I had been envisioning.
I knew that if I could get one client, I could get another, and another, and another until I had enough clients to quit my job and book a plane ticket. I didn’t know how long that would take, but I knew I was now on a path where that outcome was not just possible, but inevitable.
With this realization, I learned an important lesson.
A Tale of Two Tipping Points
I know I’m not alone in waiting for the tipping point, that big break after which we can stop feeling like we’re pushing a boulder up a hill and we can start reaping the rewards of all the work we’ve put in without the continued effort.
Maybe the tipping point you imagine is a piece of content going viral, a major media feature, or your first 6-figure launch. Maybe it’s getting hired for your dream job.
Let’s call this the Tipping Point of Effort.
No matter how pragmatic an approach we might take on a day-to-day basis, I think we all harbour some fantasy about what our big break will look like and how life will be different once it arrives.
This tipping point is external and measured by tangible results. It’s marked by the point at which the same amount of effort begins to generate a greater and greater return. While it might feel like reaching this tipping point is the goal we’re ultimately working towards, it is not, in fact, the only tipping point. And it’s not the one that matters most.
Long before we arrive at the Tipping Point of Effort, we must first reach another. This other tipping point is the Tipping Point of Belief. This tipping point is internal. And while it might not be measurable, the difference it makes is significant.
The Tipping Point of Belief is the point at which we realize that we’re on to something that will work if we simply give it enough time. We likely won’t know how much time it will take to reach our end goal but we know that we’re on the right track. Once we’ve passed this tipping point we can be confident that we’ll get there as long as we keep moving forward.
This is what I experienced when I landed my first podcast editing client. I had landed my first client quickly, but I had no idea how long it would take to add the additional 5-10 clients to my roster that I would need to support myself.
I remember thinking that it might take a year or two, and I was ok with that. In fact, I was ecstatic. Once I’d passed the Tipping Point of Belief, the timeline didn’t really matter. I was happy to put in the work, no matter how long it took, knowing that in the end, it was going to get me to my goal of full-time travel.
Six months later, I had quit my job and was on a plane to Europe.
That’s the thing about reaching the internal tipping point. The work doesn’t get any easier once you’ve reached it, but the clarity and confidence that come with it make it feel like you’re now moving downhill. Overnight, you’re able to bring more focus to your work because you’re not second-guessing whether your time would be better spent elsewhere. It just so happens that another side-effect is taking more joy in your work as well.
This shift leads to better work, which builds momentum. This then speeds the arrival of the Tipping Point of Effort, where the results begin to compound.
Reaching the Tipping Point of Belief isn’t just about speeding up the process, however. It’s almost impossible to reach the Tipping Point of Effort without it.
This creates a problem for us as creators.
Most of us haven’t yet reached the Tipping Point of Belief. We don’t know for certain that we’re on the right track, and are constantly second-guessing our decisions about where we spend our time. If the Tipping Point of Belief is a necessary checkpoint on the way to the results we’re chasing, how do we get there?
How To Reach The Tipping Point of Belief
The first thing to understand is that getting past the Tipping Point of Belief doesn’t mean you’re free of doubt in every facet of your work. You’ll still face myriad choices about how to create, market, and sell the work you do on a regular basis. Without having reached the tipping point, many of these choices might feel paralyzing.
The difference, I think, is that once you have the belief that you’re on the right track, you realize that these choices don’t actually matter all that much. It’s clear to you that your decision to build your audience on Instagram or Twitter, Youtube or Podcast certainly won’t make or break your idea.
The Tipping Point of Belief is often (but not always) marked by some external validation. For me, this was landing my first podcast editing client. For that validation to mean anything, however, it has to be the result of a process.
Getting a client by fluke is little cause for belief. Getting a client as the result of a defined process, however, gives you the confidence that you can repeat the process and get the same result. Achieve this, and you know you’re on to something.
We all have different skills, traits, perspectives, and results we’re working towards. But there are three things that will help anyone get to the Tipping Point of Belief faster.
An Idea Generation Habit
The first is developing a habit of generating ideas. Not necessarily good ideas, but a lot of ideas.
Since the start of the year, I’ve added almost 1,000 ideas to my list of potential blog or newsletter topics. Of that list, I’ve only ended up writing about 83 of them.
Developing the habit of constantly generating new ideas opens up your eyes to just how much opportunity is out there. This allows you to then be much more selective about the ideas you do choose to pursue. It also gives you confidence in your ability to find solutions to the problems you’re likely to encounter in the future.
The thing that trips people up when trying to build a habit of idea generation is thinking that every idea needs to be a viable business or product. Most ideas won’t be.
What you’re looking for instead is the tiny seeds of ideas. Things that pique your curiosity, that you’d like to explore more, or little insights throughout your day.
The most effective way to kickstart this idea of noticing small ideas is to write every day. Even if it’s on Twitter or Instagram, make a commitment to share one post every day around an insight you’ve had. This commitment has a way of queuing your subconscious to keep an eye out for topics to write about. Pretty soon you’ll find yourself filling notebooks with ideas as you go about your day.
A Habit of Shipping Work
Tied closely to the idea generation habit is a habit of shipping work.
As mentioned above, the idea generation habit is most easily achieved when you’ve made a commitment to publish something–no matter how small–every day. That said, reaching the Tipping Point of Belief will likely require you to ship more ambitious projects than daily tweets.
Starting, shipping, and closing out a variety of projects helps you explore different mediums, offers, and strategies. Over time, you’ll discover which resonate most strongly with you and where your strengths and weaknesses lie.
The habit also builds confidence in your ability to make a plan, execute it, and achieve a result. When combined with an idea generation habit, and a clear direction, these two skills will make you unstoppable.
Trust & Commitment
The final requirement for reaching the Tipping Point of Belief is trust and commitment.
Reaching the tipping point is going to take time. It’s going to take having a lot of bad ideas and shipping a lot of bad work.
Trust in yourself and commitment to the process are essential to make it through this early stage when you’re most likely to be wracked with doubt and frustration.
The best way through is to keep creating, however. Keep generating new ideas, keep shipping, keep iterating, and keep trusting that eventually, the process will lead you to where you need to be.
A New Tipping Point
I’ve recently felt myself pass another Tipping Point of Belief.
The first time was marked by a single significant instance of external validation–getting my first client. This time around, the approach and transition has been more subtle.
In short, this tipping point has felt a lot more like… well, a tipping point. A slow, steady build-up of a body of work suddenly giving way to something greater. The hundreds of blog posts and newsletters I’ve written over the past year and a half beginning to organize themselves into a larger whole.
My goal, for a while has been making a living as a full-time creator. Over the past few weeks, I’ve felt that goal shift from possibility to inevitability.
I’m still foggy on many of the details, but I feel the critical mass of ideas steadily coalescing into a more clearly-defined vision.
As with last time, I don’t know how long it will take to reach the goal. Six months? One year? Two? At this point, it doesn’t much matter. It will take however long it takes, and I’m certain that as long as I stick to the process, it’s only a matter of time.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
How a Disciplined Approach to Creative Work Improves Your Odds of Success
I’ve been playing a lot of backgammon, recently.
If you’re not familiar with the game, the description, per Wikipedia is as follows:
“Backgammon is a two-player game where each player has fifteen pieces that move between twenty-four points on the board according to the roll of two dice. The objective of the game is to be first to move all fifteen checkers off the board.”
The other key element of the game worth noting is that a stack of two or more pieces is protected, blocking the opposing player from placing their own piece(s) on that point. A single piece, however, is unprotected, meaning the opposing player can place their own piece(s) on that point, sending your piece home, Sorry! style.
The thing to understand about Backgammon is that while there is certainly a level of strategy involved, the strategy can be learned quickly, at which point, two experienced players are simply playing a game of pure chance.
In cases such as this, whoever rolls higher-scoring dice over the course of the game is going to win.
Or at least, they should.
As simple as the strategy of Backgammon is to understand, there is one trap that even experienced players fall prey to.
The trap? Themselves.
You see, each dice roll presents you with a series of available moves, some of which will be risky, and some safe. In my experience, the strategy that wins most consistently is to default to the safest move, taking smart risks to leave pieces exposed only when necessary.
We can think of sticking to this strategy as the “disciplined” approach to the game.
When both players take a disciplined approach to the game, the outcome will almost certainly be determined by chance alone. While it might make for a boring game, it also provides the best odds of winning.
As a game of chance between two players, those odds are 50%, meaning that if you simply follow this strategy, you can guarantee yourself victory in half the matches you play.
The trap, however, is when one or both players get greedy, believing that they can beat the 50/50 odds and straying from the disciplined approach to the game.
This departure from discipline almost always takes the form of a ratchet, with one unnecessarily risky move being punished, now requiring a further risky move in order to make up the lost ground.
This cycle perpetuates until all semblance of discipline has been thrown out the window.
When both players fall into this style of play, games can turn into wide-open free-for-alls with multiple lead changes that are exhilarating to play and heartbreaking to lose.
If only one player opts for this style of play, however, while the other maintains their discipline… The undisciplined player is likely to have their clock cleaned.
If this is the case, why then, would an experienced player who knows the disciplined approach will give them the best chance of winning, ever abandon it?
The answer is almost always emotion.
Once emotion enters into the decision-making process, probability is no longer the only determinant of the outcome. Over the long run, this can only decrease your odds of winning.
If a disciplined game is about assessing the odds and making the most rational move available, allowing emotion to affect your decision-making can by definition only lead to more irrational moves.
Soon enough, frustration, anger, revenge, spite, hope, desperation, and more all take a turn at the wheel, driving you to make riskier and riskier moves based only loosely on any assessment of the odds.
I won’t lie, the victories earned by playing with emotion are often the sweetest. But they’re also much harder to come by.
What’s more, the lows after losing an emotion-fueled game are much lower.
When you lose a disciplined game, you can take solace in the fact that for the most part, you made the right choices and luck just wasn’t on your side this time around.
Lose a game driven by emotion, however, and you’re left to beat yourself up about all the (in hindsight) stupid mistakes you made that lead to the loss.
What this all means, is that Backgammon is not the simple game of pure chance it appears to be on the surface, but a game about mastering your emotions and playing with discipline.
The same concept applies to our creative work.
Don’t Let Emotion Drive Your Creative Decisions
Much like with Backgammon, we can choose to take either a disciplined or emotional approach to our creative work.
Unlike Backgammon, however–a closed system comprised of a limited number of available moves and outcomes, all of which controlled by the roll of two dice–the potential moves, and the odds and risks associated with our creative work are harder to calculate.
This lack of clarity makes it easier for us to rely solely on emotion to guide our decision-making.
Sure, we’ll often dress our reasoning up in stories about why our choices are the most rational or strategic, but underneath it all, emotion is in the driver’s seat. As with Backgammon, with emotion at the wheel, our chances of success drop sharply.
When it comes to navigating the terrain of our creative work, the feelings most likely to drive our decision-making are negative emotions like doubt, impatience, fear, and inadequacy, as well as positive emotions like inspiration, purpose, desire, and excitement.
Our challenge, when faced with any of these emotions, is to not let them sway us from playing a disciplined game.
Much like Backgammon, playing with emotion in our work can lead us to put ourselves in risky positions.
More often, however, emotion in our work leads to inconsistency, causing us to jump from strategy to strategy, tactic to tactic, never giving any of them enough time or attention to actually begin to work for us.
In Backgammon, the strategy of playing a disciplined game is clear: assess the odds and make the least risky move.
But what does discipline look like for creative work?
Disciplined Creative Work
The core of the disciplined approach to creative work is the same as the disciplined approach to Backgammon: Default to the moves that in the long run, give you the highest probability of success, taking a sprinkling of smart, calculated risks along the way.
This raises the question, however, what are the moves that give the highest probability of success in the long run?
There are a number of practices, habits, tasks and mindsets that fall into this category, but I want to focus on two.
Focus On the Long Game
The first is to make the decision to play the long game in the first place. Playing with discipline requires you to ride out the surges of emotion, positive and negative, that might otherwise compel you to jump from strategy to strategy at the first sign of frustration.
Think of your work as an acorn.
While it has the potential to one day grow into a towering oak, it must first be planted in fertile soil, and then be given a steady supply of sunshine and water for months before the first signs of growth become even the tiniest bit visible above the soil.
Any strategy worth pursuing will require the same patience, attention, and nourishment in order to succeed.
Adopting the long view from the beginning and helps you ride the waves of emotion and make wiser decisions, even when the first signs of growth have yet to appear
Once you’ve adopted the long view, the second practice central to disciplined creative work is to consistently ship new work.
Ship More Work
Imagine for a moment that you knew that with every podcast episode, newsletter issue, or YouTube video you published, you would get 25 new subscribers.
Knowing this, you would likely never stop publishing new content.
Now imagine you knew that you would get 2,500 new subscribers at the moment you published your 100th piece of content, but not one before that.
With this guarantee, you would likely still feel confident as you published those first 99 episodes, even without the steady signals of progress along the way.
With the guaranteed influx of subscribers after your hundredth iteration, you might even choose to speed up the process, compressing the requisite number of reps into less time in order to get the resulting subscribers more quickly.
While we like to think that growth happens in a linear fashion, it more often resembles an exponential curve, similar to the second scenario, with long periods of slow, incremental (maybe even imperceptible) growth and improvement that then–suddenly and unexpectedly–gives way to a surge of progress.
While the surge always takes time to materialize, time itself is not the factor leading to it.
We can’t simply wait it out. The only way to arrive at the surge is to ship a lot of work.
There are a few reasons why.
Shipping With Discipline Improves Your Luck
First, our early work just isn’t that all that good, at least not compared to what it will be 50, or 100, or 500, or 1,000 reps from now.
We can learn and read and study all we want, but nothing improves our work like creating, publishing, and getting real-time feedback (even if that feedback is crickets).
Secondly, each time we ship our work is an opportunity to experiment.
If we only publish 4 pieces of content a year, for example, it will be hard to draw conclusions on what’s resonating, and thus worth doubling down on, and what’s not.
Publish 100, however, and you’ve got a significant sample size from which to draw conclusions.
Finally, as with Backgammon, there is an element of luck to doing successful creative work.
In Backgammon, our opportunities to get lucky are constrained by the number of turns in the game. When it comes to our work, however, our opportunities to get lucky are constrained only by the number of times we choose to ship.
The more work we ship, the more opportunity we give luck to find us.
Playing a disciplined game helps us level the odds when it comes to our creative work.
By taking the long view and continually shipping our work, we can put ourselves in a position where it’s only a matter of time before we catch a break and we ride the surge upward.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
Fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
Don’t Confuse the Tools You Use With the Work You Do
“Shit,” I think to myself.
I reach back, feel the emptiness in my back pocket before frantically checking both my front pockets. Also empty.
My heart sinks.
Up until now, the past two hours have been one of the best hikes I’ve ever been on. That type of perfect hike that only happens when you set off with less of a destination and more of a curiosity.
For me, that curiosity was centered around a valley, visible from my apartment, that begins at the far edge of Sarandë, the Southern Albanian town in which I’m currently living, and leads… well, that’s what I wanted to find out.
As I walked through town, I chatted on the phone with one of my oldest and best friends. We caught up as I made my way past rows and rows of tightly packed apartment buildings, which gave way to more generously spaced houses as the road began to incline toward the valley. We ended the call when the houses petered out entirely, and soon after, so did the cell signal.
On my own, I continued up the trail, well-worn by centuries, if not millennia of use by sheep and goat herders making their way into town from the rolling hills and mountains that surround it.
The narrow valley eventually opened up to a wider bowl, empty, save for two tiny goat farms, each consisting of little more than a few small pens and a stone hut with a tarp roof.
At the end of the valley I continued up the sloping hill, thinking of looping back along the ridge separating my valley on the East from the town and the sea on the West.
At the top, I stopped for a snack, admiring the view of the shimmering Adriatic, the Greek Island of Corfu rising dramatically out of it, while wondering what lies beyond the ridge that lays just ahead of me to the North.
After a half hour or so I got up, consider heading back South along the ridge as I had planned, but instead turn North, my curiosity getting the better of me.
As I pick my way forward through the maze of razor sharp boulders that make up this landscape, I think to myself that this is the part of the story that I’ll look back on either as the moment the adventure truly began, or the moment of stupidity that I should have turned back.
It turns out, I don’t have to wait long to find out.
As I reach the edge I discover that it descends and then drops into a canyon that runs directly down to the sea. I pull out my phone to check Google Maps to see if I can follow the coast at the end of the canyon back into town.
It looks like I can, so I lower myself down one low cliff, and then another, take a few steps, reach for my phone again to snap a photo, and find my pocket empty.
“Shit.”
I spend the next 45 minutes scouring the area, retracing my steps, already knowing it’s gone.
The landscape is all tall grasses and pockmarked limestone, filled with thousands upon thousands of holes the perfect size for a phone to fall into and never be seen again.
The valley I’m in has likely seen more goats than people, and chances are that whatever nook the phone has found its way into it will never be seen by another human again.
As I climb up out of the valley, I head for the ridge that I perhaps should have stuck to initially. As I follow it back toward town, I think about what the lost phone is going to mean. I’m not upset or annoyed (ok, I’m mildly annoyed), so much as curious.
My data is all regularly backed up to the cloud, so nothing valuable has been lost in that regard. The biggest hassle is almost certainly going to be dealing with 2-factor authentication requests from various apps and websites. In most of those cases at least, I should be able to get alternative authentications through email… at least I hope so.
Being in Albania for the time being, it might be a while before I can get a replacement phone from my phone company, who almost certainly doesn’t ship here…
I think about the things I most commonly use my phone for, especially while away from home and my other devices, and brace myself as I start to tally up the inconveniences.
Take Your Tools Off Their Pedestal
The list of inconveniences turns out to be shorter than I had expected; note-taking, podcast listening, navigation, photos, and keeping track of time round out the list of most common uses.
As I list them off, I realize that really, all I’ve lost is a tool. A wonderful, multi-functional one, but a tool nonetheless, and one that–at least for my purposes–can be easily replaced by other, more analog tools.
It’s worth remembering that while we have access to many incredible tools that enable and streamline our creative work, our tools are biased.
The tools we use have a way of shaping how we engage with the work we use them. It’s never a bad thing to be forced to go without a well-worn tool, at least for a while, in order to determine in which direction its bias leans.
Tools (especially phones) also have a habit of streamlining and enforcing behaviours that aren’t always positive. One of the reasons I was enjoying the hike so much in the first place is that I wasn’t plugged into a podcast or audiobook. I was also outside the range of cell service, free of any pings, notifications, and the urge to check in and see what’s happening on any of the various social networks.
To me, being forced to spend more time in that state certainly isn’t a bad thing.
As I begin to descend the ridge I look to my right, taking in the sea, the forest of jagged stone, and two lonely trees springing up between the rocks, backstopped by the island of Corfu in the distance. I pull out my Nikon DSLR from my backpack, zoom in, and snap a couple of photos my phone would have been entirely incapable of taking.
I wonder if I’m going to be getting better reacquainted with my long-neglected camera now.
Don’t Confuse The Tools With The Work Itself
Walking into town I can’t help but feel a wave of gratitude. I’ve lost a bit of convenience, but when I think about what really matters to me and my work, phones, computers, and all the rest of the various tools I use merely help to facilitate the work itself.
I think about the curiosity that lead me to first take this hike in the first place, and then lead me into the canyon. I think about how before I had even lost the phone, I was already thinking of the narrative of the day’s story and my decision to choose the canyon over the ridge. I think about the insights and lessons I’ve been mulling over on my walk back home. I think about the new ideas and stories and connections this experience is seeding in my brain.
This is the work.
Curiosity, insight and storytelling don’t require a phone or any other tool in order to flourish. In fact, they often function best in the absence of tools and their biases and distractions.
I think again about what’s been lost. A 5-year old chunk of metal, plastic, and glass that was already on its way out. Some convenience, ubiquitous connection and the accompanying distraction, anxiety, and impatience.
Then I think about what’s been gained. Perspective. Some new ideas to mull over. A new challenge to approach. A story.
As I walk up the the hill toward my apartment, the sun beginning to sink behind the hills from which I’ve just walked, I can’t help but feel as though I’ve come out ahead in the day’s transaction.
A Question For You
What’s a tool you put too much value or emphasis on when it comes to your work?
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
Fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
What I Learned Publishing An Email Newsletter For A Year
Just over a year ago, I sent out the very first issue of the Listen Up Newsletter.
The subject line of that first issue was, “Focus On What Fuels You,” and was, at least in some part about coming back to writing newsletters, something I’d tried multiple times in the past, but had never been able to stick with.
While those past attempts at writing a consistent newsletter had always felt like chores, this one felt different. A year ago, starting the LU Newsletter felt like something that actually energized me, an additive force rather than a draining one.
A year later, I’m grateful that I still experience that energy when I sit down to write each issue.
The past year has brought a lot of trial, error, and learning when it comes to the newsletter, and in this issue, I want to break down some of my personal takeaways from one year and 50 issues of newsletter writing.
But before we do, let’s look at why I started it in the first place.
Why I Started A Newsletter
When I started the newsletter in April, 2020, the pandemic had recently shut the world down. Like most everyone else, I found myself stuck at home with more time to fill, especially during the weekends.
It was during the initial lockdown that I started discovering some truly fantastic email newsletters that completely changed my idea of what a newsletter could be.
These newsletters from people like Khe Hy, Jay Clouse, Ann Handley, and The DO Lectures showed me that a newsletter was not the same as email marketing. It wasn’t about simply summarizing your latest blog post or podcast episode or blasting your list.
I learned that a good newsletter could (and should) stand on its own, as a unique product, valuable in its own right. What’s more, like a podcast, if presented the right way, it’s something people would choose to subscribe to willingly without the need for a lead magnet, freebie, bribe, etc.
What I especially liked about the newsletters I read was the sense of intimacy and familiarity that was lacking from a lot of blogs, including mine. As a writer, I wanted to speak more personally and directly to a community of like-minded people, and I didn’t feel that was happening through my current blogs. A newsletter, however, felt like the perfect fit.
My motivations for starting the newsletter has always been personal first, business second, which is one of the reasons why I think I’ve been able to main the energy and excitement behind it for this long
The primary reason I started was to give me a forum to experiment with and improve my long-form writing, particularly as it related to storytelling and teaching. What I liked about that goal is that it could be worked toward and achieved even if no one ever read a single issue.
That said, I did have a number of audience-facing goals related to the newsletter as well.
Audience-Facing Goals
I saw the newsletter as becoming what I refer to as my flagship content, the primary content channel that I poured the bulk of my focus and creative energy into, and which would drive the rest of my content marketing.
Like most flagship content, my primary audience-facing goals were to grow my email list, and nurture the subscribers on it with regular insight and communication that they (hopefully) found valuable.
I’d built up an email list of around 900 people in the past, but had let my communication lapse multiple times. At the time I started the LU Newsletter, I hadn’t sent a single email to my list in over a year.
Starting a newsletter as a dedicated content channel was a way to avoid falling back into that situation again.
So with those goals in mind, let’s have a look at some of the results of publishing the newsletter weekly over the past year.
Outcomes
Writing Improvement
The biggest and most obvious benefit of writing the newsletter for a year has been the improvement of my writing.
As mentioned, this was one of my biggest goals when I started the newsletter so I’m glad to see that there has, in fact, been growth and improvement.
There have been a few issues of the newsletter in particular that stand out to me as being notable leaps forward in my writing, where everything just clicked for me. Two of the issues that stand out most as big steps forward are #10: Directing Your Energy Wisely and #43: What Pinky Toes Teach Us About Strong Foundations.
That said, after a year of writing, I’m starting to realize that my writing has a long way to go to be at the level I want it to be, and that I’m reaching the limits of how much I can improve my writing on my own. With that in mind, I plan on taking one or more writing courses over the next year to take a more active approach to continued improvement.
List Nurturing & Engagement
After the improvement of my writing, the list engagement has been the biggest positive outcome for me a year into the newsletter.
I’ve had a number of people reach out either privately or publicly on social media and say that the Listen Up Newsletter is their very favourite newsletter. As you might imagine, this means a lot to me. I’ve written before about how our goal as creators needs to be to make work that has the potential to be someone’s favourite, an idea I borrowed from Jay Acunzo.
While the growth of the newsletter has been slower than I’d hoped, the fact that it’s resonating with people and has achieved that coveted “favourite” status for at least a handful of them is a strong sign to me that I’m on the right track, and that it’s worth continuing.
Beyond the compliments and the positive feedback, I’ve also run three launches for Podcast Marketing Academy, as well as some other mini-promotions and the majority of the sales have come from the list.
There’s no way to know for certain, but given that I hadn’t sent an email in over a year before starting the newsletter, I’m guessing all of those launches would have fallen flat if not for the regular contact with my subscribers and in many cases, back and forth interaction that email allows for.
Unexpected Benefits
Aside from some of the goals and expectations I had in mind when I started the newsletter, there have been some unexpected side benefits of publishing it consistently as well.
The first has been some of the relationships I’ve both made and deepened through back and forth conversations with subscribers who’ve replied to my emails. In many cases we’ve actually ended up getting on Zoom calls to connect and chat. These connections weren’t something I anticipated when I started out, but I’m really grateful that the newsletter has facilitated them.
The second big unexpected benefit has come as a result of the curated section of each newsletter.
In each issue, I include a list of “5 Things You Might Dig” based on my own content consumption and findings each week. The unexpected byproduct of doing this section is that I now have a reason to always be on the lookout for interesting content that is helpful to the creators, marketers, and entrepreneurs in my audience. In seeking out and consuming this content myself, I’ve learned a lot when it comes to marketing, content creation, and more.
List Growth
Alright, finally we get to list growth, the goal where the least progress has been made.
As you might expect, after not having emailed my list for over a year, I experience a large drop off in subscribers when I started sending emails again. I had 50 unsubscribes from the first email alone, and over the first two months of publishing the newsletter, I dropped from a high of 1,094 subscribers down to a low of 955.
From there, the list started growing, but if I’m honest, it hasn’t grown at nearly the rate I would’ve hoped.
In the year of publishing, I’ve been able to grow it from the low point of 955 subscribers up to 1,186 where it’s currently at, a net gain of 231 over the course of a year. I hadn’t set any measurable goals around list growth when I started out, but I think I would have hoped or expected to grow the newsletter by at least 1,000 subscribers in a year of publishing.
The growth that has come has mainly been driven by speaking at virtual summits, participating in a handful of collaborative promotions, and most recently by running a free 5-day workshop related to podcast sponsorship, which was promoted by a number of affiliate partners as well.
While the results have been somewhat discouraging, as I mentioned earlier, the fact that I’m getting positive feedback and engagement from readers is a much stronger indicator for me to double down and keep going than the number of subscribers is.
Lessons Learned From A Year Of Newsletter Writing
While there’s a lot to think and sort through when it comes to what’s working and what’s not, there have been a few lessons that clearly stand out from this first year of the newsletter.
1. It’s Hard To Have More Than One Flagship Content Channel at a Time
Shortly after starting the newsletter, I also started a podcast, Build A Better Wellness Biz. The show was a fairly ambitious endeavour with high production value, and each episode of the weekly show ended up taking between 15-20 hours of my time to produce on top of the time my team put into it.
On top of that, I also maintained my practice of writing and publishing a new blog post every day. This ended up being way too much content to produce at the level I wanted it to be at, and so, after 30 episodes, I decided to end the podcast.
In the end, the newsletter felt much more aligned with the direction I wanted to be heading in, and the topics were more focused around where I thought I could bring unique insight and perspective to the world.
Going forward, while I will almost certainly experiment with adding more content channels again in the future, none of those endeavours will be as ambitious or time-consuming as Build A Better Wellness Biz. Ultimately, the one thing I want to be known for is the newsletter, so I’m going to make sure I’m allocating the time and attention to making it the best it can be, with everything else being secondary.
2. The Secret to a Successful Newsletter Is Thinking About It as a Product
This is true for all content, but I think it’s especially worth mentioning for newsletters. It’s easy for the line to blur between email marketing and a newsletter, when they are not, in fact, the same thing.
To me, each issue of a newsletter needs to be approached as a discrete product, something that your subscribers look forward to and are excited to read, much like the latest issue of a print magazine. It should be tight, cohesive, and nicely packaged.
Unlike email marketing the point of the newsletter should never be sales, but value. There should be a clear line drawn between the two types of emails.
3. I Need To Bring More Clarity to the Newsletter if I Want It To Grow More Quickly
To market anything effectively, it’s essential to be able to concisely summarize who it’s for and what it’s for. One of my current frustrations with the newsletter is that I’m not quite sure how to actually articulate this in a concise and compelling way.
The best I can come up with right now is that this is a newsletter helping creators find the clues to navigating a meaningful creative life that are hidden in plain sight. Kinda clunky but it’s the best I’ve got right now.
I feel like gaining clarity on both the topics I write about and how I talk about the newsletter is a piece that needs to fall into place before the newsletter can really start growing.
On that note, I’d love to hear how you would describe this newsletter. Feel free to hit reply to this email or even better, fill out this reader survey and let me know.
4. I Need To Create More on-Ramps to the Newsletter
Lastly, I’ve realized that while I have one or two solid lead magnets leading people to the newsletter, I need to create more diversified, high-quality on-ramps to appeal to more people.
My big focus over the next six months or so is going to be list growth. I’ve already got a number of ideas on how to create valuable free or low-cost resources to grow my list, and I’m excited to start building them.
I’ll be sharing updates both through the newsletter a well as on Twitter as to how Project List Growth is progressing, including what I’m trying, what’s working and what’s not.
Bring On Year Two
If I had any doubt a year ago about the newsletter as a long-term content medium, it’s long since dissipated. I still have just as much excitement to sit down and write each new issue and as the momentum continues to slowly build, I imagine that excitement is only going to grow.
I see this newsletter as being the compass needle of all the work I do going forward, where ideas are started, explored, and eventually developed into something bigger. I’m honoured that you’ve signed up to follow along and will do my best to keep sharing insight that you find valuable in developing your own creative work.
That said, I can’t make this newsletter the best it can be on my own.
How You Can Help
The first and most helpful thing you can do is to fill out this subscriber survey. It will only take a few of minutes and will help me understand what you like about the newsletter, what you don’t, and give me ideas on how to improve the content and your experience as a reader.
The second thing you can do is to reach out at any time. My inbox is always open, so please hit reply to any (or every) newsletter issue you enjoy and let me know what you took away. Also, feel free to reach out on Twitter.
Lastly, if you find value in the newsletter, I would be beyond grateful if you would send it to someone else who you think might enjoy it as well. I’m convinced all good things grow by word of mouth, and this newsletter will be no different.
Thank you so much for being a reader, it means the world to me. Now let’s get on to year two, shall we?
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
Fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
Leveraging Gravity
To the person seeking to move a boulder to the top of a hill, gravity is an ever-present, malevolent force to be fought with, pushed on, and toiled against.
To the person seeking to move a boulder down the hill, however, gravity is a benevolent ally that takes care of most of the work itself.
We know gravity is a constant.
What’s not a constant is how we choose to view it and how that view informs the ways in which we work with or against it.
Used wisely, simple physics provides many solutions that allow us to leverage gravity even when moving our boulders uphill.
All it takes is an awareness of the tools and environment at our disposal, and a little ingenuity.
What are the forces you’re currently working against, and how can you put them to use for you instead?
Aim For “Favourite” Status
Think for a moment about your absolute favourite creator.
Maybe they’re a podcaster, blogger, author, marketer or business. Maybe they’re something else entirely.
When you compare your favourite creator to others in the same category, it probably doesn’t take long to realize that you give your favourite special treatment.
You’re predisposed to love everything they do as soon as they release it. You sign up for every new offer the second it comes out. Most important of all, you can’t help yourself from spreading the word and telling everyone you know about how great they are, often to the point of annoying your friends and colleagues.
The other week, I signed up for a $500 course from one of my favourite creators without reading the sales email, landing page, or anything else except the subject line of the email and the “Buy Now” button text.
Yep, being someone’s favourite has its advantages.
And yet, as creators, marketers and entrepreneurs ourselves, we often align our goals with meaning a little bit to a lot of people, rather than a whole lot to a few.
We tell ourselves that the more people we initially appeal loosely to, the more people will trickle down into our inner circle, with us at the center as their favourite.
The problem is that when we’re focused on appealing to the masses at the outer reaches of our influence, we can’t possibly create anything that matters enough to any one person to become their favourite.
The answer then, both to creating work that has the potential to be one person’s favourite as well as building a broader audience, is to start with that one person for whom we can be the absolute best in the world. Every new thing we create must be made with the intent of serving that one person better than anything else currently does.
If we can create that for one person, chances are it will resonate with others, too. Our person will likely begin to spread the word and we’ll be off and running.
The reason we don’t do this, I think, is because creating for one person leaves no room for us to hide. Because if we can’t create something that is the favourite of even one person… Well, that means our work isn’t at the level it needs to be at.
Easier to assume we have a marketing problem than confront the fact that maybe our work just isn’t good enough.
And yet, we all start with work that isn’t good enough. None of us comes out of the womb creating work worthy of attention, why should we assume it’s good enough now?
In the end, the only way to know is to find that one, ideal person, and then hone and perfect and iterate on our work until they can’t help but talk about it.
Then, double down, do more of it, and let them grow our audiences for us.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
Fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
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Hi, I'm Jeremy, I'm glad you're here.
No matter what you create, I'm guessing you spend a good amount of time feeling lost, hopeless, and unsure about how to get from where you are to where you want to be.
So do I. And so does everyone doing creative work.
This is the Creative Wilderness.
Every week, I publish a new article in my Creative Wayfinding newsletter about how we as creators and marketers can navigate it with more clarity and confidence.
If you're building something that matters, but aren't quite sure how to take the next step forward, I'd be honoured to have you join us.