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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The Magic of Zero-Expectation Creative Work
This week, my partner, Kelly, and I celebrated our 5-year anniversary.
Like every relationship, ours has had its share of ebbs and flows, ups and downs. By and large, however, the challenges and conflicts we’ve faced have been few and far between and our daily experience of the relationship is one of joy, possibility, and ease.
To be honest, the level of ease continues to surprise and mystify us.
In fact, we spend a good amount of time trying to decipher the reason behind it.
So far, we’ve come up with a pretty solid list.
For starters, we genuinely like each other, and are fascinated by each other’s work (she works at a startup and is also in the process of launching her own startup).
It also surely helps that we don’t have kids.
But in further reflecting over our anniversary dinner, this week, we had a new revelation, which is this:
Neither of us seems to have any expectation of what this relationship should be.
We’re in the relationship because we recognize the value of being in it now, in the moment, in the day-to-day experience of it, not because of where we hope it will lead or what we hope it will become.
Instead of working toward some pre-defined archetypal (most likely mythical) idea of relationship—and life—we appear to be content to simply be… and see what emerges from that being.
What emerges, it seems, is a greater sense of possibility than would—or perhaps even could—exist with a set of expectations governing and constraining the relationship.
This zero-expectation mindset is a useful one to cultivate in our creative work and businesses as well.
As in any relationship, the experience and results we get from our relationship with our work are beyond our control.
At best, we can influence those outcomes based on what we personally bring to the relationship. But after we’ve shown up consistently with our best work, all we can do is let go and hope our energy, effort, and intention are reciprocated.
Introducing expectation to the mix sets us up for regular (and often severe) disappointment.
In more than 10 years of creative work, I can’t think of a single project or endeavour that has ever met my (usually secretly held) expectations, let alone exceeded them.
Early in my career, those shortfalls were crushing.
As I’ve relaxed or let go of my expectations around my desired results (and more often the timelines of achieving those results), however, the outcomes of any endeavour hold less significance.
Good or bad, thrilling or disappointing, every outcome is simply a way station on the way to some further destination that is currently hidden from view, somewhere beyond the horizon.
Which brings us to the second pitfall of expectation:
Expectation is a destination that is inherently limited by your existing map of the world.
That map doesn’t include the vast territory that will open up as you gain new knowledge, acquire new skills, and meet new people.
Nor does it take into account how the world—and you—will change over that span.
Said differently, expectation is the death of possibility.
And in a world ripe with always emerging possibilities, it’s a poor stance to take if we want to be in a position to take advantage of them.
Instead, in our relationship with our work, as in our relationship with others, the most productive stance we can take is to show up generously, consistently, with firm boundaries but without expectation, and be open to what life brings us.
We don’t have to like what life brings us, often enough we won’t.
But keep showing up in this way long enough and life has a way of reciprocating.
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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Why Perspective Is an Underrated Creative Superpower (And How You Can Develop It)
There’s an old Indian parable about 5 blind men who encounter an elephant for the first time.
Curious to know exactly what an elephant is, they approach it and attempt to describe it by touch.
The first man grabs the trunk and says, “Ah, an elephant is thick and round like a snake.”
The second, wrapping his arms around a leg responds, “No, an elephant is a pillar, like a tree trunk.”
The third, pressing against the elephant’s side disagrees further, “What are you talking about? An elephant is clearly a kind of wall.”
The fourth, grabbing onto an ear says, “No, no, no, an elephant surely is thin and flexible like a fan.”
The fifth, grabbing ahold of the tail says, “You’re all wrong, an elephant is obviously a kind of rope.”
The parable is about perspective and the value of being able to see the larger picture beyond our own limited experience.
Of all the traits necessary to build a successful career as a creator, I think this type of perspective is one of the most essential. And yet one we often overlook it, spending little–if any–time developing it.
The Importance of Perspective
We each have our own perspective, of course. But like the blind men in the parable, it’s incomplete.
This incomplete perspective is at the root of many of our creative frustrations.
Lack of perspective leads us to misjudge the importance of various aspects of our work, wasting time perfecting things that won’t make a difference while ignoring the things that will. It opens the door to self-centeredness and entitlement, thinking we deserve more than we’ve received, and paves the way for many avoidable mistakes.
A complete perspective on the other hand lubricates almost every aspect of our creative journey.
Perspective allows us to see clearly how our work fits into the world. It opens our eyes to needs and opportunities we would otherwise miss. It centers us and keeps us grounded, as it imparts a clear sense of both how far we’ve come and how far we still have yet to go. Maybe most importantly, a complete perspective allows us to respond appropriately and productively to the unexpected situations we encounter along our way.
A rich and nuanced perspective allows us to rise above the fog that engulfs so much of our creative work and accurately assess the landscape we inhabit.
Despite the host of benefits, however, we rarely think about our perspective as something to be honed and developed.
Seeking Out Perspective
I think the lack of attention given to developing our perspective is due to the fact that we generally think of perspective as something we gain passively as we go through life.
And we do.
But we can also actively seek out and expand it.
Seeking out perspective, it turns out, has a lot of overlap with seeking out Expansive Experiences. While gaining perspective might not come with the visceral physical effects that often accompany Expansive Experiences, both of these concepts are rooted in the idea of understanding our (and our work’s) place in the larger world.
The best way to gain perspective, then, is to learn broadly about the world outside our tiny sliver of experience.
This is easily achieved by reading books, taking courses, and consuming content on topics we’re interested in, but which might be entirely disconnected from the work we do.
These resources are available in abundance, and many of us already aspire to be more well-rounded people with broader, richer perspectives.
Despite this desire, we tend not to prioritize this type of growth and learning as it rarely feels as though it will lead to tangible results, such as better work, better clients, more money, and forward progress. Further specializing in our core skills on the other hand feels like a surer path to concrete–and perhaps more immediate–outcomes.
In the short run, this is probably true.
In the long run, however, the equation flips.
This is because as we enrich and broaden our perspective we realize that almost everything ties back into our work, intersecting, connecting, and influencing it in some way or another.
What’s more, it’s these oblique and abstract influences that make us and our work stand out.
A rich perspective allows us to stumble across interesting ideas elsewhere and see how they could be applied to our craft. This gives us an unfair advantage over everyone else in our space who is pulling their ideas from the same stale pool of books, podcasts, and newsletters.
If we want our creative output to stand out, our creative input has to stand out as well.
More interesting work, however, is just one of the benefits of a rich and full perspective.
Perspective is in Short Supply
Whether you’re a business owner, service provider, creator, artist, or all of the above, it’s important to realize that there’s no shortage of ultra-specialized, ultra-skilled people in any niche.
We can join the chase, and over time become highly skilled & specialized ourselves. But sooner or later we reach a point of diminishing returns with the specialized knowledge and skills we acquire.
What there is a shortage of, however, in every niche imaginable, is people who are solidly skilled, but also have a rich and full perspective. This combination is infinitely more valuable than specialized skill alone.
Perspective allows us to more easily adapt to a rapidly changing world, where any one of our primary skills might be outmoded in 5-year’s time. It also allows us to more clearly look ahead, and anticipate, prepare, and retool for what’s coming down the pike.
Perhaps most importantly, perspective imparts resiliency.
It puts both our successes and failures in context, it helps us see when to persevere with a project and when to move on, and it keeps us grounded as we weather the ups, downs, twists, and turns of a creative life.
In short, perspective is a creative superpower.
But it’s one that must continually be sought out, earned, and added to.
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.
Some Limits Aren’t Meant to Be Pushed (And Should Actually Be Avoided)
If you’ve spent much time in the worlds of entrepreneurship and personal development, you’ve probably heard your fair share about the value of finding and pushing the edges of your limits.
The idea is that the further we push our limits, the greater our capabilities, and the more we’re capable of doing. This is the whole idea behind Marathon Projects, which I’ve written about before.
There’s a lot of value to this approach when it comes to finding the limits of our skills, stamina, patience, and comfort in order to expand on them and increase our level of competence.
But there are some boundaries where the value of finding them lies not in our ability to then push outward, but in our ability to avoid or stop short of them.
Our Personal Achilles’ Heels
Much as we each have a distinct set of personal superpowers that we can identify and lean into in order to create our most effective work, we also each have a unique set of personal weaknesses.
These weaknesses, left unidentified and unchecked are the things that get (and keep) us stuck.
The challenge is that they’re rarely spectacular, obvious or dramatic.
Instead, our Achilles’ Heels are often small and subtle traits and habits that slowly but surely undermine our ability to create and ship meaningful work from the inside if we put ourselves in situations that allow them to.
Steven Pressfield’s idea of Resistance is certainly one of these Achilles’ Heels we must learn to identify and dance with.
But it’s not the only one.
Other Achilles’ Heels might include temptations we find ourselves unable to resist, situations in which things never seem to work out, types of people we don’t work well with, projects that are a bad fit for our skills or disposition, and many more.
Being aware of our Achilles’ Heels and knowing where the boundaries lie allows us to avoid situations in which we’re likely to fail.
If you know that you have a highly addictive personality, for example, it’s probably best to avoid alcohol, drugs, sugar, and other potentially addictive substances.
I discovered one of my Achilles’ Heel’s last year when I started–and subsequently ended–my Build A Better Wellness Biz podcast.
For Me, The Type of Motivation Matters
In the end, the root of the problem for me was the fact that the podcast was all strategy and no heart.
While I enjoyed connecting with my guests and the modest audience I built, a show about building a better wellness business wasn’t the show I was dying to make. It was a means to an end. It was a way to double down on the accidental niche of wellness practitioners that I’d grown into through referrals, and better serve them while attracting more like-minded people.
Given enough time, I’m certain the strategy would have worked.
What I learned, however, is that for me to be able to stick with a project like this long enough for it to be successful (ie. multiple years) I need to deeply care about every aspect of it, from the audience to the content, to the creation itself.
When I was thinking about ending the show, I found myself comparing my experience creating the podcast with my experience creating this newsletter.
It was immediately clear that one ticked all the boxes, and the other didn’t.
Now, when considering new projects, I’m very cognizant of this personal Achilles’ Heel when evaluating whether the project is a good fit for me and has a chance of being successful. This knowledge helps me steer clear of ideas that might be good ideas, but which I don’t have the necessary drive to follow through on.
It’s worth noting that in many cases it’s entirely possible to expand the boundaries of our Achilles’ Heels and improve our resistance to them. If you find yourself with one that you simply can’t avoid and will otherwise lead to a lifetime of difficulty and defeat, this is probably a good idea.
Typically, however, our energy is better spent improving and expanding on our existing strengths.
Identifying Your Absolute Limits
The second type of boundaries worth knowing–so that we can avoid them–are Absolute Limits.
These limits are rooted in the limited availability of time, energy and attention, and are the most rigid of our boundaries. Attempting to push past them frequently leads to shoddy work, taking unethical shortcuts, burnout, and any number of other negative outcomes.
The limits of the time, energy, and attention each of us has will vary, as will our responses to pushing past them.
For me, I know that one of my Absolute limits relates to the relative importance of the projects I take on related to each other, and the hierarchy they exist within.
As it turns out, it was again the Build A Better Wellness Biz podcast that made me aware of this limit.
Maintaining a Project Hierarchy
Running a podcast production company, I naturally wanted to make sure the podcast to be a showcase of our team’s (and my own) capabilities. As such, I opted for an ambitious format with music queues and interstitial narration breaking up the interviews.
The show sounded great, and I was really proud of what I had created.
But the format also meant that each episode took ~20 hours to produce from start to finish.
This might have been manageable if I was producing a monthly show, but I had opted to release the show weekly. In addition, I was publishing this weekly newsletter, which took another 10 hours a week to create.
For a few months, I tried to find a way to do both projects well, batching segments of the production and finding clever ways to automate or streamline the process.
Before long, however, I could feel myself veering toward burnout.
I realized that the problem stemmed from trying to produce two “flagship” content platforms. These are platforms that take significant time, energy, and attention from you as a creator and can’t easily be outsourced. With a large enough team and budget, this is certainly possible, but as a solo creator, doing more than one flagship content platform well is difficult, if not impossible.
To me, my newsletter is my most sacred thing I work on and I realized that I needed to protect the time and energy that goes into creating it.
At the time, that meant shutting the podcast down.
But it also means that going forward, I’m aware that any additional content I create needs to be limited in scope, and play a secondary role to the newsletter.
In practice, this means limiting additional shows or newsletters to short-run seasonal endeavours without strict publishing commitments. Perhaps a 10-episode season here, a 20 issue evergreen newsletter there. It also means eliminating as much friction as possible from the production of these projects.
Backing Away from Your Limits
We spend a lot of time and energy working to level ourselves up.
We’re constantly improving our skills, gaining knowledge, growing our networks, and expanding our boundaries in order to become more successful creators.
Much of what holds us back as creators, however, is an unawareness of which boundaries are best to simply avoid. So much of our wasted time is due to putting ourselves in situations and taking on projects that simply aren’t a good fit for us.
An awareness of our Achilles’ Heels and Absolute limits allows us to avoid these projects that are doomed to fail. In their place, we can then pick projects that fit into our core competencies, and approach them in a way that gives them the focus they need to be successful.
Continual growth and improvement are still an essential part of building a successful creative career.
But I can’t help but think that the fastest way to improve our results is by putting ourselves in situations we’re already likely to succeed in and avoiding those where we’re not.
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.
Your World Is Shrinking. Here’s How It Hurts Your Creative Work (And How to Push Back)
When was the last time you sat around a campfire and looked up at the stars?
For me, it was a few weeks ago when some friends invited Kelly and me over to their place for dinner and a backyard fire.
At the time, we’d recently arrived back in Canada after being stuck in Europe throughout COVID and were freshly removed from our mandatory two-week quarantine. Suffice it to say the freedom of getting outside of the house was still very much a novelty, perhaps even a luxury.
But as I sat by the fire, leaned back, and looked up at the expanse of space above, I experienced something more profound. A powerful reminder of one of the essential ingredients of doing meaningful creative work.
Staring up at the stars always has a way of making you realize how small you really are. But as I looked up that night, I realized how unnecessarily small I’d allowed my world to become over the previous weeks.
Sure, the quarantine accounted for some of the shrinking of my world.
But there was more to it than that.
I was in the middle of a big project. And as the project ramped up in the weeks preceding the quarantine, I’d stopped going for my daily walks, stopped writing every day, and stopped reading fiction, stopped engaging with my community on Twitter.
It was an exciting project that I enjoyed working on. But as I shut off the outside world to focus solely on my work, my world shrunk down until the only thing it contained was the project itself.
Pushing Back on a Constantly Shrinking World
Over the past year, most of us have had our worlds shrink in one way or another.
Yours may have shrunk to the size of your neighbourhood, home, office, bedroom, or computer. But while global pandemics are certainly one reason for world shrinkage, they’re not the only one.
In fact, the natural state of our worlds is to shrink in on themselves.
The weight of our routines, schedules, and obligations exerts a sort of gravity on our lives and worlds, constantly pulling them in on themselves.
Without intentional effort to push back on this gravity, our lives soon shrink down to the size of our office, our local coffee shop, the route we take every day to and from work, and the same 5 restaurants we always go to… or more likely order in from.
Part of the problem is this shrinkage is subtle.
We don’t realize the shrinking is happening until we have an expansive experience like the one I had around the fire that opens us up to what we’ve been missing out on. It’s not all negative either. As our worlds shrink, they become more predictable, giving us a sense of order, safety, and control.
But that sense of security comes at a price.
Because as our worlds shrink, they become increasingly inhospitable to creative projects and original ideas.
How a Small World Hurts Us Creatively
Great creative work doesn’t exist in a vacuum.
It requires an awareness of–and interaction with–the world in which it exists, and is born of a broad and diverse set of influences. As our world becomes smaller, our awareness, perspective, and influences shrink down and our work suffers.
New ideas are the first to go.
Coming up with a steady stream of new ideas requires regular interaction with a broad set of influences. The larger your world, the more unique and interesting your inputs are likely to be and as a result, the more unique and interesting the ideas that emerge from their collisions and permutations.
The smaller our world, the more limited our set of influences, and the more likely we are to have generic, uninteresting, unoriginal ideas.
We also lose perspective on our projects.
As the boundaries of our worlds shrink, their contents take up more relative space within them, and with it, more significance… at least to us. We forget that while our work might now make up our entire world, it occupies only a tiny fraction (if any) of anyone else’s.
This is a dangerous place to operate from as a creator…
For one that makes it hard to make and market anything effectively.
Creating and marketing successful creative work requires a constant process of interaction and iteration. When our world shrinks down, our intended audience often gets shut out and we end up creating blindly. With no feedback to keep us moving in the right direction and our work suffers.
Secondly, we tend to overemphasize the importance of our work itself, leading to perfectionism and unnecessary pressure on ourselves and the project to perform.
Without perspective it feels like this project might be our one and only shot and that if we blow it, we’re doomed to failure.
Needless to say, this isn’t a productive mindset from which to do our best creative work, which most often comes from a place of ease and flow.
Make Space for Expansive Experiences
As creators seeking to do meaningful work, this means that one of the most essential activities of our creative process needs to be a constant pushing back on the boundaries of our worlds.
If small worlds lead to small, generic, mediocre work, then it only makes sense that we should seek to make our worlds as big as possible while still shipping regular work.
The way we push back on the boundaries of our world is through expansive experiences.
These might be experiences that make you feel small and realize your place in the universe. This might include sitting around a campfire, staring up at the stars, traveling abroad, or looking out over a landscape from a mountain top.
But we can also have expansive experiences closer to home.
Reading fiction might be one of the most expansive experiences available to us. As George R.R. Martin quipped, “A reader lives a thousand lives before he dies . . . The man who never reads lives only one.”
Fiction allows us to experience different viewpoints and perspectives which in turn develop our sense of empathy, which is critical to successful creative work and marketing.
Non-fiction too can be expansive.
Expansive non-fiction is not likely to be found in reading the same business and marketing books that everyone else is gobbling up, but by identifying your curiosities and following them. I’m rarely more creatively inspired than when I’m reading non-fiction books about the natural world, for example.
Outside of books, we can work to intentionally add more variety and novelty to our day-to-day lives.
We can start by unplugging from our phones and paying attention to the world around us.
We can walk more, taking a slightly different route each time. We can shop at different grocery stores, eat at different restaurants, and explore our cities and surrounding areas.
By tapping into our curiosity we can build a habit of seeking out the novel, the unique and the foreign, and in doing so, grow into a constant state of expansion, rather than reduction.
Pushing back on the boundaries of your world isn’t always easy.
Expansive experiences are by their nature more difficult or uncomfortable than their alternatives.
They make us feel small. And make us realize how little we know about the world, about others, and about ourselves. And yet, it’s this very not knowing that further fuels our curiosity, and with it our creativity.
All great creative work is an exploration after all.
But before you can embark on an exploration, you must first find a slice of unknown, uncharted territory to explore.
It exists. But it’s up to you to expand the boundaries of your world to encompass it.
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.
What if There Are No Right Answers?
We spend so much of our time seeking out the right answers to our problems.
“What’s the right way to grow my audience?”
“What’s the right content to create for my podcast?”
“What’s the right price to charge for my offer?”
The problem is that “right” implies a singular answer.
And when we’re fixated on finding only the single very best answer to our question, we become paralyzed, unwilling to commit until we know that our effort will not be wasted.
What if instead, we accepted that there are no right answers, only questions to be explored.
By taking up the role of explorer, we open ourselves up to stumbling across answers to our questions we would have otherwise never found.
Maybe the thing that ends up working best for us, only works for us, but is the thing that ends up making our work singular.
What a shame if by settling for someone else’s right answer, we never landed on the thing that would truly set our work apart.
Spend less time seeking answers and more time exploring the questions.
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.
What to Do When You’re Gripping the Stick Too Tight
I’ve never been great at tennis.
But in the past month, I’ve played more than at any other time in my life. As you might expect, over that span, my game has improved.
In one recent game, I found myself consistently hitting shots I’d never been able to hit before.
My serves were on fire. I was able to hit both forehand and backhand shots with speed, topspin, and accuracy. I hit drop shot after drop shot that left my friend Jordon sprinting up to the net to no avail. The game felt effortless like I didn’t have to think about making the shots, I just had to swing, the ball and racket understanding my intention and complying.
Through the first two sets, Jordon and I both played with this kind of loose, easy confidence, winning one each and setting up a winner-take-all third set.
But with the added stakes, something changed.
From the very first point, I was timid. and began overthinking every one of my shots. Where I had been swinging from a place of ease, fluidity, and confidence, I now found myself tensing up. The feeling of effortlessness had dissipated, each shot now requiring focused, concerted effort.
The result wasn’t pretty.
Shot after shot after shot went long, wide, or into the net.
We hear about this type of tension affecting a player’s game at even the highest levels of sport.
With the game, medal, or championship on the line, even the best players are prone to abandon the ease and flow that got them there, tense up, and choke.
In Canada, we refer to this phenomenon as “gripping the stick too tight” as it commonly occurs in hockey players who get into a rut and can’t even seem to put the puck into an empty net when presented with the opportunity.
Of course, it being Canada, we need a hockey analogy for everything.
But the problem of gripping the stick too tight also shows up in creative work.
Just think of the safe sophomore album that fails to meet the expectations set by a breakthrough debut, the sequel that flops, or the sales call with a potential high-end client that you botch.
We often find ourselves gripping the stick a little tighter as our audience grows, bringing with it more attention and scrutiny. Or, we may experience it as we feel ourselves approaching a major milestone in our creative careers. Regardless of the trigger, when the stakes feel high, we begin second guess ourselves and our work, slipping into analysis paralysis and perfectionism, and grinding our creative process to a halt.
Ironically in these cases, it’s the very fact that we’re moving closer to our goals that makes it harder to actually achieve them.
The problem is rooted in loss aversion, the fact that humans are psychologically wired to prefer to avoid losses rather than acquire equivalent gains.
When we’re first starting out and we have nothing to lose. We feel confident experimenting, creating freely and easily, testing the limits of what we can create, and exploring broadly in search of the work that will resonate both with us and our audience.
As we acquire an audience, however, and the attention on us grows, we retreat.
We find ourselves playing not to lose instead of doing what is needed and extending ourselves further than we have yet, pushing through and reaching for the win.
The answer, when we’re gripping the stick too tight is twofold.
First, we need to use the anonymity we have in our early days to its fullest.
When we have nothing to lose, we need to act like it and create anything and everything that we feel called to create, without worry of what anyone else will think. At this stage, chances are no one’s watching anyway, and if they do, they almost certainly don’t care.
Secondly, when we start to have some success, we need to dial down the pressure we put on ourselves.
Creative work is supposed to be fun. It’s supposed to come from a place of ease and flow and intuition, not tension and analysis.
Like my recreational tennis match with a friend, when we take a step back, the stakes are almost never as high as we make them out to be. Big breaks rarely exist, meaning that although we might feel as though we’re on the precipice of our one and only opportunity to achieve our goals, we’ll have plenty more in the future.
What got us to this point was our ability to swing freely and easily, to disengage our mind and let instinct and muscle memory take the wheel.
What will get us to the next level is to continue swinging effortlessly.
Perhaps even more effortlessly than we have yet.
• • •
I ended up winning my tennis match.
It wasn’t because I was able to get back into the flow I had experienced during the first two sets. Rather, under the pressure of the (pseudo-) stakes, Jordon had tensed up as much as I had. He just happened to have a few more misfires than I did.
There was one bright spot in that final set, however.
A lone shot where I was able to get into position, push my timidness aside, plant my feet, and swing freely.
For just a moment, the feeling of ease returned. The racket connected and the ball exploded back across the court in a tight arc, landing just inside the far corner for a point.
While I wasn’t able to make a shot like that again, it was a reminder that no matter how tightly we’re gripping the stick, (or in my case, the racket) that ease, flow, and instinct is still somewhere inside us, waiting to be tapped into.
We just need to relax, recenter ourselves, and swing.
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.
False Assumptions Are Keeping You Stuck. It’s Your Job to Find & Fix Them
Every new project begins with a series of assumptions and guesses.
These guesses might relate to our audience, offering, content, messaging, marketing strategy, and any of a near endless list of other variables.
If we’ve done our homework and talked with our audience, many of these guesses will be at least somewhat educated.
Many, however, will not.
Some of these uninformed assumptions are based on an incomplete understanding of the challenge at hand. Some are based on what we would like to believe is true. And some are simply pulled from the ether. When we don’t know what we don’t know we have to start somewhere after all.
If we’re lucky, some of the guesses and assumptions we’ve made will be correct.
But no matter how lucky, prepared, or well-researched we are, many of our assumptions will always turn out to be just plain wrong. It’s these false assumptions that often get–and keep–us stuck.
In these cases, it feels like we’re looking at a math equation where all the variables seem to be laid out correctly but we continue to get the wrong answer no matter how many times we run it. We blame the formula for being broken, without realizing we’ve made a false assumption about the value of one of the variables when constructing it.
Unaddressed, these false assumptions lead us to beat our heads against the wall for weeks, months, and even years as we try and muscle our way through a problem that can’t be muscled through.
If we want to move forward, our job as creators, is twofold.
- Identify the areas of our work in which we’ve made guesses or assumptions.
- Find out where we’re wrong.
If there’s one assumption that’s helpful, it’s that we’ve guessed wrong about a great many things related to making and marketing our work.
No one gets it all right the first time.
The most successful creators are simply those who have tested their assumptions enough times to eventually stumble their way into the right answer. Which means achieving great work is more about humility and perseverance than any kind of elusive creative genius.
To me, that’s an encouraging thought.
While true genius might be reserved for a select few, humility and perseverance are readily available to all of us.
But first, we need to admit all that we don’t know, and question honestly the decisions and assumptions we’ve built our work on.
Only then can we begin to correct them.
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.
Fast, Easy, or Effective Marketing: Pick Any Two
Fast. Cheap. High-Quality.
You might have heard that when you’re looking to hire someone for a given job, you can choose any two of these three options.
It turns out that the same type of choice exists when choosing how to market ourselves, although the variables have changed slightly.
When it comes to how we choose to pursue growth, we’re presented with the options of Fast, Easy, and Effective.
While the options have changed, the rule of only being able to have two out of three remains the same.
When we aim for the fast and easy route, we generally find our marketing to be entirely ineffective.
Of course, there’s no point in pursuing ineffective marketing, so our choice then comes down to whether we want to put in a lot of work quickly, or take the easier route over the long run.
A fast but difficult approach might involve organizing a virtual summit, doing a podcast guesting tour, or some other endeavour involving an intense period of research, outreach, and preparation.
A slow but easy approach may involve creating consistent content over the span of multiple years at a cadence that works for you.
Of course, you’re welcome to take both approaches, opting for slow and easy with the occasional larger endeavour thrown in to speed things up.
It isn’t important which approach you take. Sooner or later, both with get you where you’re looking to go.
What is important is understanding the choice you’ve made and calibrating your expectations accordingly.
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.
You Don’t Need to Make a Moonshot to Be Successful
It often feels like the only acceptable version of success to aspire to is to aim a high as humanly possible.
And so we dream of selling out arena tours across every continent, writing the NYT bestselling book, or changing the lives of a million people through our work.
What we often forget in our quest for big success however, is that it’s not the only version of success.
We don’t need to be famous to make a living or an impact.
In fact, it’s often easier to achieve both when we set our sights a little lower. To the more attainable, more immediate.
When we lower our gaze, we realize the opportunities that are right in front of us, ripe for the picking.
The path to big success is filled with gatekeepers to persuade, walls to climb and moats (filled with crocodiles, no less) to swim across.
Sure, it’s an adventure, if that’s what you’re after. But is that the adventure you really want?
Attainable success on the other hand is freely available to anyone simply willing to show up and do the work.
Don’t be fooled, the work is required, and it’s not easy.
The irony is that so many twist themselves in knots, attempting to scale the walls, swim the moats, and persuade the gatekeepers, all in an attempt to avoid doing the work that would surely deliver results if only they could settle down and focus.
The opportunities for joy, impact, and meaning are already in front of you.
Take them.
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 Reach the Next Level, You Have to Let Some Fires Burn
I’m someone who thrives on order.
I like a regular routine, I build systems for everything, and am most satisfied when everything has (and is in) its proper place.
It’s no surprise that this internal drive for order extends to most aspects of my work.
Every task has either a “due” or a “do” date, projects have target completion dates with regularly scheduled reviews to assess their status, and I put significant effort into staying on top of my inbox. I typically try to respond to emails within a day and if an issue comes up with a client, I drop everything to set things right immediately.
In many ways, this level of order has served me well.
When I ask for feedback from clients, my responsiveness is referenced regularly as one of the things they love about working with me and my team. My projects make regular progress forward thanks to the systems and timelines I’ve set around them. When the occasional fires flare up, I’m able to put them out immediately.
This order gives me a sense of control over my world.
And yet lately, I’m beginning to wonder whether this quest for order is holding me back.
Let The Fires Burn
I remember reading a blog post a while back about building and growing a bootstrapped SaaS product as a solo founder.
The author shared that in his experience, the biggest impediment to founders scaling their products to the point of being sustainable businesses was their own reluctance to let fires burn.
Before launching, a founder is able to devote 100% of their time to developing the idea and building out the product.
Once the product is built and launched, however, they suddenly find themselves having to handle support requests, fix bugs, market the product, do sales, and all the other maintenance related to running a business.
For a while, this maintenance might be manageable.
The problem is that the ongoing maintenance often leaves no time to continue building and improving the product, which is the only way the business will attract new users and reach a level where it can sustain itself.
Faced with this challenge, the founders that succeed in the long term are those that get comfortable with letting some (maybe even many) fires burn in order to focus on the things that really matter when it comes to achieving the bigger picture goals for the business.
In the short term, however, this will almost certainly mean bugs with the product, unanswered support tickets, unhappy customers, and a loss of users.
Choosing Important > Urgent
When I think about this idea in the context of my own life, this scares me.
I want to be known as reliable, responsive, and trustworthy. I want to hit the deadlines I set for myself and others. I want to stay on top of every project, task, question, comment, and request that crosses my path.
Essentially, I want to maintain a sense of order and control over my life.
I think we all do.
And yet, to do the things that matter most well, we often need to neglect the things that matter less. To abandon our pursuit of order–at least for a time–in pursuit of progress.
The truth is there are a never-ending number of fires waiting to flare up and demand our attention.
Knowing this, we face a choice.
We can attempt to run around, putting each of them out in a desperate attempt to maintain the current state of balance and order. Or we can choose to get comfortable letting them burn, embracing some disorder–maybe even some chaos–in some parts of our lives in order to commit fully to the work that only we can do.
Sometimes we need to let the fires burn to pave the way for new growth.
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.
Downtime: Bad for Software, Essential for Creativity
When it comes to software or a service we provide, downtime is something to be avoided at all costs.
We don’t need to look further than the Fastly and Akamai internet service outages that occurred within the past few months to see the negative effects. These unrelated internet hosting issues combined to take down the websites and mobile apps from many of the world’s largest brands including Hulu, New York Times, CNN, Twitch, Reddit, Spotify, Vimeo, Amazon, Chase, and many more.
Despite being only 49 minutes long, the downtime caused by the Fastly outage alone has been estimated at $32 million in lost revenue.
Downtime causes the gears of every system built using our platform to grind to a halt, costing us (and our customers) money, and inviting a flurry of angry support emails.
When necessary, we can schedule downtime in advance in order to mitigate its negative effects, but this type of downtime is certainly not something we want to invite more of into our lives than is absolutely necessary.
And so we do everything within our power to maintain peak productivity.
When it comes to our creativity, however, downtime is essential.
Rather than grinding to a halt, downtime greases the gears of our creative system, allowing us time and space to process the seeds of ideas that have been planted but haven’t yet started to grow.
Downtime is when unexpected connections are made, sparking new ideas and spotting opportunities.
Downtime feels unproductive, as though it’s not helping us move forward towards completing our projects and achieving our goals. And yet, without regular downtime, we burn out… of ideas, energy, motivation, inspiration, and everything else that is essential to being “productive.”
Much like a software product, creative downtime is best scheduled in.
Unlike software, however, it should be scheduled more often than we think is necessary, even daily, if possible.
How we spend that downtime is up to each of us to decide. Walking, reading, journaling, drawing, exercising, or puttering around are all good options. If it works for you, simply stare at a blank wall and let boredom (or your creative mind) take over.
What matters is that we regularly and intentionally create the time and space to refuel, recharge, and let our best ideas rise to the surface, unsuppressed by the never-ending busyness that otherwise occupies our attention.
The important entries in our calendars and items on our to-do list will take care of themselves, whether or not we make space for them. The seeds of ideas in the back of our minds, and undiscovered connections waiting to happen, however, won’t.
Creativity thrives on downtime. Schedule it more often.
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.
Creative Wayfinding For Ambitious Optimists.
How to Identify Your Keys to Victory (And How They’ll Accelerate Your Creative Success)
As so often happens when picking up a new hobby, as I’ve gotten into playing tennis this year, I’ve also been watching a lot of tennis YouTube.
Lately, I’ve been binging through compilation videos of each of the “Big 3” of modern tennis: Roger Federer, Rafael Nadal, and Novak Djokovic, each of whom (depending on who you ask) might be considered the Greatest Of All Time when it comes to men’s tennis.
What’s struck me in watching each of these men play hours of tennis, is that while they’ve all ended up with near-identical career win-totals and legacies, the style of play they’ve each used to get there has been unique.
Federer, for example, beats opponents with his touch, finesse, and what seems to be an ability to read their minds and anticipate shots.
Nadal, on the other hand, wins by never giving up on a point, chasing down balls that should be impossible to catch, and then ripping otherworldly winning shots from ridiculous angles.
Djokovic, finally, simply wears his opponents down with his complete mix of power, precision, consistency, and pure athleticism.
Watching the differing styles of these three greats reminds me of a standard segment at the start of many sports broadcasts, the Keys To Victory.
In the segment, the commentators will outline the specific things each team or player needs to do in order to win.
Of course, the easy answer for most sports is to score more points than their opponents. But as with the Big 3 of tennis, every team or athlete has a unique game plan and style of play that will best allow them to win consistently.
Some highly skilled teams (like my hockey team, the Edmonton Oilers) might win by going all out on the offensive and scoring five or six or seven goals… even if they give up four in the process.
Others might win by playing a tight, disciplined, defensive game and then capitalizing on opponent mistakes.
Depending on the makeup of the team, or the physical, mental, and emotional makeup of the player, the Keys To Victory will differ.
The same is true for us as creators.
While we might not be aiming for the title “Greatest Of All Time” in our fields, each of us is working toward the same goal of building a successful (whatever that means to each of us) and sustainable creative career.
As with athletes and sports teams, while our end destinations may be similar, our personal Keys to Victory, which make up the shortest, most enjoyable, and most effective path to getting there differ for each of us.
Identifying Your Keys to Victory
Our personal Keys to Victory are typically processes-oriented activities that are dictated by many factors including our specific goals, skills, disposition, worldview, experience, values, and more.
More specifically, our Keys are based on how each of these traits intersects with and is interpreted by the audience we seek to serve.
You might be an exceptional writer, for example. But if your target audience isn’t interested in written content, creating an exquisite blog or newsletter is hardly one of your Keys to Victory.
In my experience, the best way to identify your personal Keys is to draw a simple graph and plot the activities that contribute to your work across two axes.
1. Other People’s Response
Before you draw your graph, set a timer for 5 minutes and brain dump a list of every audience-facing activity you’ve ever engaged in.
A short list of some of my personal activities might include:
- Live video teaching & facilitation
- Community organization & management
- Blogging
- Newsletter writing
- Podcasting
- YouTube video creation
- 1:1 connection calls
Once your list is complete, plot each of those activities on the x-axis of the graph.
The far right edge of the graph represents activities that get an exceptional public response and the far left side is for the activities in which you get no–or perhaps even a negative–response.
Keep in mind that these placements are relative to your own experience, you’re not measuring your results against anyone else’s. A positive response for you might mean just two people reached out with positive feedback.
With that in mind, spread your activities out along the x-axis according to their response relative to one another, with at least one activity near each of the far right and far left edges.
2. Your Response
One of my favourite quotes about winning as a creator is from Khe Hy, the creator of Rad Reads who says, “It’s impossible to compete with someone who genuinely cares, and is having fun.”
Success at any strategy will require us to be consistent with it for years at a time. It’s much easier to be consistent with something we actually enjoy than something that drains us every time we sit down to do it.
With that in mind, the next step to completing your graph is to measure the activities you’ve listed based on your own response to it.
For each activity, ask yourself:
- Do I enjoy love doing this or dread it?
- Does it give me energy or drain it?
- Do I have fun with it or is it a slog?
Based on your responses, move each activity on your graph vertically.
Tasks that are a net positive to you personally (ie. those that are fun, energy-giving, etc) should be placed in the upper half of the graph. Net negative tasks (ie. those that drain your energy, you dread doing, etc) should be placed in the lower half.
A completed graph of my own keys to victory would look something like this:
Interpreting Your Graph
With your activities plotted, you’ll find each of the activities you’ve listed falls into one of four quadrants.
Keys to Victory (Top-Right)
The top right quadrant of your completed graph should clearly show your Keys to Victory.
These are the activities that you both enjoy doing, and that get the most positive reaction from others and should be leaned into every chance you get.
As you can see from my graph, there’s a cluster of activities all related to live presentation or facilitation, either over video or audio. This is a good sign that I should be seeking out more opportunities that allow me to present live.
Pit of Despair (Bottom-Left)
Opposite the Keys to Victory, in the bottom left quadrant is the Pit of Despair, which should be avoided at all costs. Not only do these tasks not bring you any enjoyment, but they don’t garner any kind of positive response from your audience either.
Both the Pit of Despair and the Keys to Victory are pretty straightforward, the remaining quadrants, however, are where things get a bit more nuanced.
Watch & Develop (Top-Left)
The top left quadrant consists of activities you enjoy but your audience doesn’t really care about.
These can still be valuable creative outlets for you personally, and it’s entirely possible that you just haven’t put the reps in to start seeing real results. Often, over time, these activities can move to the right as you improve on them.
Regardless, it’s helpful to see plainly the tasks that aren’t currently adding up to tangible results so you can allocate your time accordingly.
Handle with Care (Bottom-Right)
The bottom right quadrant is perhaps the most interesting.
These are activities that get a good response from your audience but which you don’t necessarily enjoy doing yourself.
If you have a healthy selection of activities in your Keys to Victory quadrant, you might choose to ignore the activities in this quadrant altogether. If you don’t have many Keys to Victory, however, these activities can be useful short-term pursuits to help you grow your audience and get results.
Be warned, however: The fact that you’ve placed these activities in this quadrant means that they are inherently unsustainable.
You might choose to build a short-term strategy around any of them, but avoid any strategy that will require you to commit to it for the long term. This is a recipe for frustration, burnout, and resentment*, hence the title of this quadrant.
*Who me? No, I’m not speaking from experience at all…
Your Keys to Victory Are Fluid & Evolving
Regardless of how many Keys to Victory you’ve identified, remember that this graph is not the be-all, end-all.
While many of your Keys to Victory may continue to be effective throughout your life, others will change positions on your graph as your goals, target audiences, and interests change.
Correspondingly, you’ll also identify many new Keys to Victory as you grow, improve your skills, take on new projects, and evolve as a person.
The best (and perhaps only) way to identify new Keys to Victory is to try things out and see what sticks, both for your audience and for yourself. This is an essential phase in the life cycle of a creator and is where most would-be creators give up.
In the first few years, the most effective use of our time might just be experimenting with every type of tactic, strategy, and activity we can think of in order to give ourselves some baseline data with which to work.
Most of the things we try won’t work all that well for us.
The good news is we only really need to find a few things that do.
If you’re struggling to identify your Keys to Victory, push yourself to get outside your comfort zone and start experimenting with new methods of creating and promoting your work. Identifying your Keys is a numbers game.
Outward & Inward Facing Keys to Victory
It’s worth noting that while many of the Keys to Victory you identify will be outward-facing activities that involve (or are at least visible to) your audience, others may be strictly internal.
These Keys are the habits and activities that contribute to the outward-facing work, but aren’t in themselves visible.
Some of my personal inward-facing Keys to Victory are my daily walks, the content I choose to consume, the people I surround myself with, scheduling in time for reflection, and the systems I use to capture, organize and structure my ideas.
While they might not be outwardly visible, and may not always feel “productive”, I know from experience that each of them has a direct impact on every project I work on, and the work suffers when I neglect them.
If you’re a nerd like me, you might choose to draw up a second graph of these internal Keys to Victory.
Follow Your Game Plan
In most sports, the team or player that wins is often the one who’s able to dictate the style of game being played, forcing their opponent off of their preferred style of play.
Whether it’s Resistance, shiny objects, new tools, tactics, or strategies, we too face a world that is relentlessly attempting to pull us into playing the type of game it wants to play, rather than the one that best serves us.
Having a defined game plan, however, built around our specific Keys to Victory allows us to resist that temptation, block out the distractions, and focus on what we know works for us.
Knowing our Keys to Victory gives us confidence as we move through the fog that so often engulfs our creative work, that if we keep following the path we’ve defined, we’ll get where we’re seeking to go.
And more likely, somewhere unexpected, but even better.
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.
Why Perspective Is an Underrated Creative Superpower (And How You Can Develop It)
There’s an old Indian parable about 5 blind men who encounter an elephant for the first time.
Curious to know exactly what an elephant is, they approach it and attempt to describe it by touch.
The first man grabs the trunk and says, “Ah, an elephant is thick and round like a snake.”
The second, wrapping his arms around a leg responds, “No, an elephant is a pillar, like a tree trunk.”
The third, pressing against the elephant’s side disagrees further, “What are you talking about? An elephant is clearly a kind of wall.”
The fourth, grabbing onto an ear says, “No, no, no, an elephant surely is thin and flexible like a fan.”
The fifth, grabbing ahold of the tail says, “You’re all wrong, an elephant is obviously a kind of rope.”
The parable is about perspective and the value of being able to see the larger picture beyond our own limited experience.
Of all the traits necessary to build a successful career as a creator, I think this type of perspective is one of the most essential. And yet one we often overlook it, spending little–if any–time developing it.
The Importance of Perspective
We each have our own perspective, of course. But like the blind men in the parable, it’s incomplete.
This incomplete perspective is at the root of many of our creative frustrations.
Lack of perspective leads us to misjudge the importance of various aspects of our work, wasting time perfecting things that won’t make a difference while ignoring the things that will. It opens the door to self-centeredness and entitlement, thinking we deserve more than we’ve received, and paves the way for many avoidable mistakes.
A complete perspective on the other hand lubricates almost every aspect of our creative journey.
Perspective allows us to see clearly how our work fits into the world. It opens our eyes to needs and opportunities we would otherwise miss. It centers us and keeps us grounded, as it imparts a clear sense of both how far we’ve come and how far we still have yet to go. Maybe most importantly, a complete perspective allows us to respond appropriately and productively to the unexpected situations we encounter along our way.
A rich and nuanced perspective allows us to rise above the fog that engulfs so much of our creative work and accurately assess the landscape we inhabit.
Despite the host of benefits, however, we rarely think about our perspective as something to be honed and developed.
Seeking Out Perspective
I think the lack of attention given to developing our perspective is due to the fact that we generally think of perspective as something we gain passively as we go through life.
And we do.
But we can also actively seek out and expand it.
Seeking out perspective, it turns out, has a lot of overlap with seeking out Expansive Experiences. While gaining perspective might not come with the visceral physical effects that often accompany Expansive Experiences, both of these concepts are rooted in the idea of understanding our (and our work’s) place in the larger world.
The best way to gain perspective, then, is to learn broadly about the world outside our tiny sliver of experience.
This is easily achieved by reading books, taking courses, and consuming content on topics we’re interested in, but which might be entirely disconnected from the work we do.
These resources are available in abundance, and many of us already aspire to be more well-rounded people with broader, richer perspectives.
Despite this desire, we tend not to prioritize this type of growth and learning as it rarely feels as though it will lead to tangible results, such as better work, better clients, more money, and forward progress. Further specializing in our core skills on the other hand feels like a surer path to concrete–and perhaps more immediate–outcomes.
In the short run, this is probably true.
In the long run, however, the equation flips.
This is because as we enrich and broaden our perspective we realize that almost everything ties back into our work, intersecting, connecting, and influencing it in some way or another.
What’s more, it’s these oblique and abstract influences that make us and our work stand out.
A rich perspective allows us to stumble across interesting ideas elsewhere and see how they could be applied to our craft. This gives us an unfair advantage over everyone else in our space who is pulling their ideas from the same stale pool of books, podcasts, and newsletters.
If we want our creative output to stand out, our creative input has to stand out as well.
More interesting work, however, is just one of the benefits of a rich and full perspective.
Perspective is in Short Supply
Whether you’re a business owner, service provider, creator, artist, or all of the above, it’s important to realize that there’s no shortage of ultra-specialized, ultra-skilled people in any niche.
We can join the chase, and over time become highly skilled & specialized ourselves. But sooner or later we reach a point of diminishing returns with the specialized knowledge and skills we acquire.
What there is a shortage of, however, in every niche imaginable, is people who are solidly skilled, but also have a rich and full perspective. This combination is infinitely more valuable than specialized skill alone.
Perspective allows us to more easily adapt to a rapidly changing world, where any one of our primary skills might be outmoded in 5-year’s time. It also allows us to more clearly look ahead, and anticipate, prepare, and retool for what’s coming down the pike.
Perhaps most importantly, perspective imparts resiliency.
It puts both our successes and failures in context, it helps us see when to persevere with a project and when to move on, and it keeps us grounded as we weather the ups, downs, twists, and turns of a creative life.
In short, perspective is a creative superpower.
But it’s one that must continually be sought out, earned, and added to.
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.
Some Limits Aren’t Meant to Be Pushed (And Should Actually Be Avoided)
If you’ve spent much time in the worlds of entrepreneurship and personal development, you’ve probably heard your fair share about the value of finding and pushing the edges of your limits.
The idea is that the further we push our limits, the greater our capabilities, and the more we’re capable of doing. This is the whole idea behind Marathon Projects, which I’ve written about before.
There’s a lot of value to this approach when it comes to finding the limits of our skills, stamina, patience, and comfort in order to expand on them and increase our level of competence.
But there are some boundaries where the value of finding them lies not in our ability to then push outward, but in our ability to avoid or stop short of them.
Our Personal Achilles’ Heels
Much as we each have a distinct set of personal superpowers that we can identify and lean into in order to create our most effective work, we also each have a unique set of personal weaknesses.
These weaknesses, left unidentified and unchecked are the things that get (and keep) us stuck.
The challenge is that they’re rarely spectacular, obvious or dramatic.
Instead, our Achilles’ Heels are often small and subtle traits and habits that slowly but surely undermine our ability to create and ship meaningful work from the inside if we put ourselves in situations that allow them to.
Steven Pressfield’s idea of Resistance is certainly one of these Achilles’ Heels we must learn to identify and dance with.
But it’s not the only one.
Other Achilles’ Heels might include temptations we find ourselves unable to resist, situations in which things never seem to work out, types of people we don’t work well with, projects that are a bad fit for our skills or disposition, and many more.
Being aware of our Achilles’ Heels and knowing where the boundaries lie allows us to avoid situations in which we’re likely to fail.
If you know that you have a highly addictive personality, for example, it’s probably best to avoid alcohol, drugs, sugar, and other potentially addictive substances.
I discovered one of my Achilles’ Heel’s last year when I started–and subsequently ended–my Build A Better Wellness Biz podcast.
For Me, The Type of Motivation Matters
In the end, the root of the problem for me was the fact that the podcast was all strategy and no heart.
While I enjoyed connecting with my guests and the modest audience I built, a show about building a better wellness business wasn’t the show I was dying to make. It was a means to an end. It was a way to double down on the accidental niche of wellness practitioners that I’d grown into through referrals, and better serve them while attracting more like-minded people.
Given enough time, I’m certain the strategy would have worked.
What I learned, however, is that for me to be able to stick with a project like this long enough for it to be successful (ie. multiple years) I need to deeply care about every aspect of it, from the audience to the content, to the creation itself.
When I was thinking about ending the show, I found myself comparing my experience creating the podcast with my experience creating this newsletter.
It was immediately clear that one ticked all the boxes, and the other didn’t.
Now, when considering new projects, I’m very cognizant of this personal Achilles’ Heel when evaluating whether the project is a good fit for me and has a chance of being successful. This knowledge helps me steer clear of ideas that might be good ideas, but which I don’t have the necessary drive to follow through on.
It’s worth noting that in many cases it’s entirely possible to expand the boundaries of our Achilles’ Heels and improve our resistance to them. If you find yourself with one that you simply can’t avoid and will otherwise lead to a lifetime of difficulty and defeat, this is probably a good idea.
Typically, however, our energy is better spent improving and expanding on our existing strengths.
Identifying Your Absolute Limits
The second type of boundaries worth knowing–so that we can avoid them–are Absolute Limits.
These limits are rooted in the limited availability of time, energy and attention, and are the most rigid of our boundaries. Attempting to push past them frequently leads to shoddy work, taking unethical shortcuts, burnout, and any number of other negative outcomes.
The limits of the time, energy, and attention each of us has will vary, as will our responses to pushing past them.
For me, I know that one of my Absolute limits relates to the relative importance of the projects I take on related to each other, and the hierarchy they exist within.
As it turns out, it was again the Build A Better Wellness Biz podcast that made me aware of this limit.
Maintaining a Project Hierarchy
Running a podcast production company, I naturally wanted to make sure the podcast to be a showcase of our team’s (and my own) capabilities. As such, I opted for an ambitious format with music queues and interstitial narration breaking up the interviews.
The show sounded great, and I was really proud of what I had created.
But the format also meant that each episode took ~20 hours to produce from start to finish.
This might have been manageable if I was producing a monthly show, but I had opted to release the show weekly. In addition, I was publishing this weekly newsletter, which took another 10 hours a week to create.
For a few months, I tried to find a way to do both projects well, batching segments of the production and finding clever ways to automate or streamline the process.
Before long, however, I could feel myself veering toward burnout.
I realized that the problem stemmed from trying to produce two “flagship” content platforms. These are platforms that take significant time, energy, and attention from you as a creator and can’t easily be outsourced. With a large enough team and budget, this is certainly possible, but as a solo creator, doing more than one flagship content platform well is difficult, if not impossible.
To me, my newsletter is my most sacred thing I work on and I realized that I needed to protect the time and energy that goes into creating it.
At the time, that meant shutting the podcast down.
But it also means that going forward, I’m aware that any additional content I create needs to be limited in scope, and play a secondary role to the newsletter.
In practice, this means limiting additional shows or newsletters to short-run seasonal endeavours without strict publishing commitments. Perhaps a 10-episode season here, a 20 issue evergreen newsletter there. It also means eliminating as much friction as possible from the production of these projects.
Backing Away from Your Limits
We spend a lot of time and energy working to level ourselves up.
We’re constantly improving our skills, gaining knowledge, growing our networks, and expanding our boundaries in order to become more successful creators.
Much of what holds us back as creators, however, is an unawareness of which boundaries are best to simply avoid. So much of our wasted time is due to putting ourselves in situations and taking on projects that simply aren’t a good fit for us.
An awareness of our Achilles’ Heels and Absolute limits allows us to avoid these projects that are doomed to fail. In their place, we can then pick projects that fit into our core competencies, and approach them in a way that gives them the focus they need to be successful.
Continual growth and improvement are still an essential part of building a successful creative career.
But I can’t help but think that the fastest way to improve our results is by putting ourselves in situations we’re already likely to succeed in and avoiding those where we’re not.
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.
Your World Is Shrinking. Here’s How It Hurts Your Creative Work (And How to Push Back)
When was the last time you sat around a campfire and looked up at the stars?
For me, it was a few weeks ago when some friends invited Kelly and me over to their place for dinner and a backyard fire.
At the time, we’d recently arrived back in Canada after being stuck in Europe throughout COVID and were freshly removed from our mandatory two-week quarantine. Suffice it to say the freedom of getting outside of the house was still very much a novelty, perhaps even a luxury.
But as I sat by the fire, leaned back, and looked up at the expanse of space above, I experienced something more profound. A powerful reminder of one of the essential ingredients of doing meaningful creative work.
Staring up at the stars always has a way of making you realize how small you really are. But as I looked up that night, I realized how unnecessarily small I’d allowed my world to become over the previous weeks.
Sure, the quarantine accounted for some of the shrinking of my world.
But there was more to it than that.
I was in the middle of a big project. And as the project ramped up in the weeks preceding the quarantine, I’d stopped going for my daily walks, stopped writing every day, and stopped reading fiction, stopped engaging with my community on Twitter.
It was an exciting project that I enjoyed working on. But as I shut off the outside world to focus solely on my work, my world shrunk down until the only thing it contained was the project itself.
Pushing Back on a Constantly Shrinking World
Over the past year, most of us have had our worlds shrink in one way or another.
Yours may have shrunk to the size of your neighbourhood, home, office, bedroom, or computer. But while global pandemics are certainly one reason for world shrinkage, they’re not the only one.
In fact, the natural state of our worlds is to shrink in on themselves.
The weight of our routines, schedules, and obligations exerts a sort of gravity on our lives and worlds, constantly pulling them in on themselves.
Without intentional effort to push back on this gravity, our lives soon shrink down to the size of our office, our local coffee shop, the route we take every day to and from work, and the same 5 restaurants we always go to… or more likely order in from.
Part of the problem is this shrinkage is subtle.
We don’t realize the shrinking is happening until we have an expansive experience like the one I had around the fire that opens us up to what we’ve been missing out on. It’s not all negative either. As our worlds shrink, they become more predictable, giving us a sense of order, safety, and control.
But that sense of security comes at a price.
Because as our worlds shrink, they become increasingly inhospitable to creative projects and original ideas.
How a Small World Hurts Us Creatively
Great creative work doesn’t exist in a vacuum.
It requires an awareness of–and interaction with–the world in which it exists, and is born of a broad and diverse set of influences. As our world becomes smaller, our awareness, perspective, and influences shrink down and our work suffers.
New ideas are the first to go.
Coming up with a steady stream of new ideas requires regular interaction with a broad set of influences. The larger your world, the more unique and interesting your inputs are likely to be and as a result, the more unique and interesting the ideas that emerge from their collisions and permutations.
The smaller our world, the more limited our set of influences, and the more likely we are to have generic, uninteresting, unoriginal ideas.
We also lose perspective on our projects.
As the boundaries of our worlds shrink, their contents take up more relative space within them, and with it, more significance… at least to us. We forget that while our work might now make up our entire world, it occupies only a tiny fraction (if any) of anyone else’s.
This is a dangerous place to operate from as a creator…
For one that makes it hard to make and market anything effectively.
Creating and marketing successful creative work requires a constant process of interaction and iteration. When our world shrinks down, our intended audience often gets shut out and we end up creating blindly. With no feedback to keep us moving in the right direction and our work suffers.
Secondly, we tend to overemphasize the importance of our work itself, leading to perfectionism and unnecessary pressure on ourselves and the project to perform.
Without perspective it feels like this project might be our one and only shot and that if we blow it, we’re doomed to failure.
Needless to say, this isn’t a productive mindset from which to do our best creative work, which most often comes from a place of ease and flow.
Make Space for Expansive Experiences
As creators seeking to do meaningful work, this means that one of the most essential activities of our creative process needs to be a constant pushing back on the boundaries of our worlds.
If small worlds lead to small, generic, mediocre work, then it only makes sense that we should seek to make our worlds as big as possible while still shipping regular work.
The way we push back on the boundaries of our world is through expansive experiences.
These might be experiences that make you feel small and realize your place in the universe. This might include sitting around a campfire, staring up at the stars, traveling abroad, or looking out over a landscape from a mountain top.
But we can also have expansive experiences closer to home.
Reading fiction might be one of the most expansive experiences available to us. As George R.R. Martin quipped, “A reader lives a thousand lives before he dies . . . The man who never reads lives only one.”
Fiction allows us to experience different viewpoints and perspectives which in turn develop our sense of empathy, which is critical to successful creative work and marketing.
Non-fiction too can be expansive.
Expansive non-fiction is not likely to be found in reading the same business and marketing books that everyone else is gobbling up, but by identifying your curiosities and following them. I’m rarely more creatively inspired than when I’m reading non-fiction books about the natural world, for example.
Outside of books, we can work to intentionally add more variety and novelty to our day-to-day lives.
We can start by unplugging from our phones and paying attention to the world around us.
We can walk more, taking a slightly different route each time. We can shop at different grocery stores, eat at different restaurants, and explore our cities and surrounding areas.
By tapping into our curiosity we can build a habit of seeking out the novel, the unique and the foreign, and in doing so, grow into a constant state of expansion, rather than reduction.
Pushing back on the boundaries of your world isn’t always easy.
Expansive experiences are by their nature more difficult or uncomfortable than their alternatives.
They make us feel small. And make us realize how little we know about the world, about others, and about ourselves. And yet, it’s this very not knowing that further fuels our curiosity, and with it our creativity.
All great creative work is an exploration after all.
But before you can embark on an exploration, you must first find a slice of unknown, uncharted territory to explore.
It exists. But it’s up to you to expand the boundaries of your world to encompass it.
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.
What if There Are No Right Answers?
We spend so much of our time seeking out the right answers to our problems.
“What’s the right way to grow my audience?”
“What’s the right content to create for my podcast?”
“What’s the right price to charge for my offer?”
The problem is that “right” implies a singular answer.
And when we’re fixated on finding only the single very best answer to our question, we become paralyzed, unwilling to commit until we know that our effort will not be wasted.
What if instead, we accepted that there are no right answers, only questions to be explored.
By taking up the role of explorer, we open ourselves up to stumbling across answers to our questions we would have otherwise never found.
Maybe the thing that ends up working best for us, only works for us, but is the thing that ends up making our work singular.
What a shame if by settling for someone else’s right answer, we never landed on the thing that would truly set our work apart.
Spend less time seeking answers and more time exploring the questions.
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.
What to Do When You’re Gripping the Stick Too Tight
I’ve never been great at tennis.
But in the past month, I’ve played more than at any other time in my life. As you might expect, over that span, my game has improved.
In one recent game, I found myself consistently hitting shots I’d never been able to hit before.
My serves were on fire. I was able to hit both forehand and backhand shots with speed, topspin, and accuracy. I hit drop shot after drop shot that left my friend Jordon sprinting up to the net to no avail. The game felt effortless like I didn’t have to think about making the shots, I just had to swing, the ball and racket understanding my intention and complying.
Through the first two sets, Jordon and I both played with this kind of loose, easy confidence, winning one each and setting up a winner-take-all third set.
But with the added stakes, something changed.
From the very first point, I was timid. and began overthinking every one of my shots. Where I had been swinging from a place of ease, fluidity, and confidence, I now found myself tensing up. The feeling of effortlessness had dissipated, each shot now requiring focused, concerted effort.
The result wasn’t pretty.
Shot after shot after shot went long, wide, or into the net.
We hear about this type of tension affecting a player’s game at even the highest levels of sport.
With the game, medal, or championship on the line, even the best players are prone to abandon the ease and flow that got them there, tense up, and choke.
In Canada, we refer to this phenomenon as “gripping the stick too tight” as it commonly occurs in hockey players who get into a rut and can’t even seem to put the puck into an empty net when presented with the opportunity.
Of course, it being Canada, we need a hockey analogy for everything.
But the problem of gripping the stick too tight also shows up in creative work.
Just think of the safe sophomore album that fails to meet the expectations set by a breakthrough debut, the sequel that flops, or the sales call with a potential high-end client that you botch.
We often find ourselves gripping the stick a little tighter as our audience grows, bringing with it more attention and scrutiny. Or, we may experience it as we feel ourselves approaching a major milestone in our creative careers. Regardless of the trigger, when the stakes feel high, we begin second guess ourselves and our work, slipping into analysis paralysis and perfectionism, and grinding our creative process to a halt.
Ironically in these cases, it’s the very fact that we’re moving closer to our goals that makes it harder to actually achieve them.
The problem is rooted in loss aversion, the fact that humans are psychologically wired to prefer to avoid losses rather than acquire equivalent gains.
When we’re first starting out and we have nothing to lose. We feel confident experimenting, creating freely and easily, testing the limits of what we can create, and exploring broadly in search of the work that will resonate both with us and our audience.
As we acquire an audience, however, and the attention on us grows, we retreat.
We find ourselves playing not to lose instead of doing what is needed and extending ourselves further than we have yet, pushing through and reaching for the win.
The answer, when we’re gripping the stick too tight is twofold.
First, we need to use the anonymity we have in our early days to its fullest.
When we have nothing to lose, we need to act like it and create anything and everything that we feel called to create, without worry of what anyone else will think. At this stage, chances are no one’s watching anyway, and if they do, they almost certainly don’t care.
Secondly, when we start to have some success, we need to dial down the pressure we put on ourselves.
Creative work is supposed to be fun. It’s supposed to come from a place of ease and flow and intuition, not tension and analysis.
Like my recreational tennis match with a friend, when we take a step back, the stakes are almost never as high as we make them out to be. Big breaks rarely exist, meaning that although we might feel as though we’re on the precipice of our one and only opportunity to achieve our goals, we’ll have plenty more in the future.
What got us to this point was our ability to swing freely and easily, to disengage our mind and let instinct and muscle memory take the wheel.
What will get us to the next level is to continue swinging effortlessly.
Perhaps even more effortlessly than we have yet.
• • •
I ended up winning my tennis match.
It wasn’t because I was able to get back into the flow I had experienced during the first two sets. Rather, under the pressure of the (pseudo-) stakes, Jordon had tensed up as much as I had. He just happened to have a few more misfires than I did.
There was one bright spot in that final set, however.
A lone shot where I was able to get into position, push my timidness aside, plant my feet, and swing freely.
For just a moment, the feeling of ease returned. The racket connected and the ball exploded back across the court in a tight arc, landing just inside the far corner for a point.
While I wasn’t able to make a shot like that again, it was a reminder that no matter how tightly we’re gripping the stick, (or in my case, the racket) that ease, flow, and instinct is still somewhere inside us, waiting to be tapped into.
We just need to relax, recenter ourselves, and swing.
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.
False Assumptions Are Keeping You Stuck. It’s Your Job to Find & Fix Them
Every new project begins with a series of assumptions and guesses.
These guesses might relate to our audience, offering, content, messaging, marketing strategy, and any of a near endless list of other variables.
If we’ve done our homework and talked with our audience, many of these guesses will be at least somewhat educated.
Many, however, will not.
Some of these uninformed assumptions are based on an incomplete understanding of the challenge at hand. Some are based on what we would like to believe is true. And some are simply pulled from the ether. When we don’t know what we don’t know we have to start somewhere after all.
If we’re lucky, some of the guesses and assumptions we’ve made will be correct.
But no matter how lucky, prepared, or well-researched we are, many of our assumptions will always turn out to be just plain wrong. It’s these false assumptions that often get–and keep–us stuck.
In these cases, it feels like we’re looking at a math equation where all the variables seem to be laid out correctly but we continue to get the wrong answer no matter how many times we run it. We blame the formula for being broken, without realizing we’ve made a false assumption about the value of one of the variables when constructing it.
Unaddressed, these false assumptions lead us to beat our heads against the wall for weeks, months, and even years as we try and muscle our way through a problem that can’t be muscled through.
If we want to move forward, our job as creators, is twofold.
- Identify the areas of our work in which we’ve made guesses or assumptions.
- Find out where we’re wrong.
If there’s one assumption that’s helpful, it’s that we’ve guessed wrong about a great many things related to making and marketing our work.
No one gets it all right the first time.
The most successful creators are simply those who have tested their assumptions enough times to eventually stumble their way into the right answer. Which means achieving great work is more about humility and perseverance than any kind of elusive creative genius.
To me, that’s an encouraging thought.
While true genius might be reserved for a select few, humility and perseverance are readily available to all of us.
But first, we need to admit all that we don’t know, and question honestly the decisions and assumptions we’ve built our work on.
Only then can we begin to correct them.
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.
Fast, Easy, or Effective Marketing: Pick Any Two
Fast. Cheap. High-Quality.
You might have heard that when you’re looking to hire someone for a given job, you can choose any two of these three options.
It turns out that the same type of choice exists when choosing how to market ourselves, although the variables have changed slightly.
When it comes to how we choose to pursue growth, we’re presented with the options of Fast, Easy, and Effective.
While the options have changed, the rule of only being able to have two out of three remains the same.
When we aim for the fast and easy route, we generally find our marketing to be entirely ineffective.
Of course, there’s no point in pursuing ineffective marketing, so our choice then comes down to whether we want to put in a lot of work quickly, or take the easier route over the long run.
A fast but difficult approach might involve organizing a virtual summit, doing a podcast guesting tour, or some other endeavour involving an intense period of research, outreach, and preparation.
A slow but easy approach may involve creating consistent content over the span of multiple years at a cadence that works for you.
Of course, you’re welcome to take both approaches, opting for slow and easy with the occasional larger endeavour thrown in to speed things up.
It isn’t important which approach you take. Sooner or later, both with get you where you’re looking to go.
What is important is understanding the choice you’ve made and calibrating your expectations accordingly.
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.
You Don’t Need to Make a Moonshot to Be Successful
It often feels like the only acceptable version of success to aspire to is to aim a high as humanly possible.
And so we dream of selling out arena tours across every continent, writing the NYT bestselling book, or changing the lives of a million people through our work.
What we often forget in our quest for big success however, is that it’s not the only version of success.
We don’t need to be famous to make a living or an impact.
In fact, it’s often easier to achieve both when we set our sights a little lower. To the more attainable, more immediate.
When we lower our gaze, we realize the opportunities that are right in front of us, ripe for the picking.
The path to big success is filled with gatekeepers to persuade, walls to climb and moats (filled with crocodiles, no less) to swim across.
Sure, it’s an adventure, if that’s what you’re after. But is that the adventure you really want?
Attainable success on the other hand is freely available to anyone simply willing to show up and do the work.
Don’t be fooled, the work is required, and it’s not easy.
The irony is that so many twist themselves in knots, attempting to scale the walls, swim the moats, and persuade the gatekeepers, all in an attempt to avoid doing the work that would surely deliver results if only they could settle down and focus.
The opportunities for joy, impact, and meaning are already in front of you.
Take them.
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 Reach the Next Level, You Have to Let Some Fires Burn
I’m someone who thrives on order.
I like a regular routine, I build systems for everything, and am most satisfied when everything has (and is in) its proper place.
It’s no surprise that this internal drive for order extends to most aspects of my work.
Every task has either a “due” or a “do” date, projects have target completion dates with regularly scheduled reviews to assess their status, and I put significant effort into staying on top of my inbox. I typically try to respond to emails within a day and if an issue comes up with a client, I drop everything to set things right immediately.
In many ways, this level of order has served me well.
When I ask for feedback from clients, my responsiveness is referenced regularly as one of the things they love about working with me and my team. My projects make regular progress forward thanks to the systems and timelines I’ve set around them. When the occasional fires flare up, I’m able to put them out immediately.
This order gives me a sense of control over my world.
And yet lately, I’m beginning to wonder whether this quest for order is holding me back.
Let The Fires Burn
I remember reading a blog post a while back about building and growing a bootstrapped SaaS product as a solo founder.
The author shared that in his experience, the biggest impediment to founders scaling their products to the point of being sustainable businesses was their own reluctance to let fires burn.
Before launching, a founder is able to devote 100% of their time to developing the idea and building out the product.
Once the product is built and launched, however, they suddenly find themselves having to handle support requests, fix bugs, market the product, do sales, and all the other maintenance related to running a business.
For a while, this maintenance might be manageable.
The problem is that the ongoing maintenance often leaves no time to continue building and improving the product, which is the only way the business will attract new users and reach a level where it can sustain itself.
Faced with this challenge, the founders that succeed in the long term are those that get comfortable with letting some (maybe even many) fires burn in order to focus on the things that really matter when it comes to achieving the bigger picture goals for the business.
In the short term, however, this will almost certainly mean bugs with the product, unanswered support tickets, unhappy customers, and a loss of users.
Choosing Important > Urgent
When I think about this idea in the context of my own life, this scares me.
I want to be known as reliable, responsive, and trustworthy. I want to hit the deadlines I set for myself and others. I want to stay on top of every project, task, question, comment, and request that crosses my path.
Essentially, I want to maintain a sense of order and control over my life.
I think we all do.
And yet, to do the things that matter most well, we often need to neglect the things that matter less. To abandon our pursuit of order–at least for a time–in pursuit of progress.
The truth is there are a never-ending number of fires waiting to flare up and demand our attention.
Knowing this, we face a choice.
We can attempt to run around, putting each of them out in a desperate attempt to maintain the current state of balance and order. Or we can choose to get comfortable letting them burn, embracing some disorder–maybe even some chaos–in some parts of our lives in order to commit fully to the work that only we can do.
Sometimes we need to let the fires burn to pave the way for new growth.
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.
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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.