For the first 10 years of my creative endeavours, I lived in nearly a constant state of frustration that things weren’t progressing as fast as I wanted them to.

On any given day, the focal point of that frustration may have been related to income, audience growth, skill development, or more likely, all of the above… plus a dozen other areas where progress felt painfully slow.

Of course, we all want things to happen faster than they often seem to be happening in the moment.

Indeed, no matter how quickly things are actually moving, we seem to feel that they could always still be going faster.

This is especially frustrating when things don’t seem to be moving at all.

It’s no wonder why we feel this way.

The reason so many of us embark on our creative journey in the first place is to escape some dissatisfaction with our current circumstances.

Perhaps we feel stifled, uninspired, or worried that we’re wasting our potential doing work that doesn’t use our skills or unique perspectives. Perhaps we feel as though we don’t fit into our current community, circumstance, or culture. Or perhaps we’re simply curious about what lies beyond the boundaries of the standard-issue life we’ve been sold as “normal” and desirable.

Whatever our reasoning, many of us are looking to use our creative work as a vehicle to get somewhere we perceive to be better.

It’s only natural, then that we should want to be in that better place as soon as possible.

The truth, however, is that progress related to creative work is not linear.

Instead, creative progress is a lag effect. In other words, it requires us to put in a significant amount of upfront work before seeing even the smallest of results.

Said differently still: Creative progress takes time.

In the middle of one of my bouts of frustration about my own speed of progress, I decided to start journaling about all the things that take time when it comes to developing a sustainable creative platform.

The resulting list provided a stark reminder that of course creative progress takes a long time. Presented with an itemized list of all the components of creative work that take time to develop, it becomes obvious why progress feels so slow, especially at the start.

There’s just a lot to work through!

Hopefully, the following list provides you the same type of reassurance and frame of reference it’s provided me to help you reset your expectations around the timeline of your work.

Things That Take Time

• Finding clarity
• Building up the confidence to make a leap
• Nursing yourself and your ego back to health when your leaps fail (they will) and getting yourself back out there (this can take a lifetime if you let it. So don’t.)
• Releasing the handbrake that’s keeping your voice in check (no, you don’t need to find your voice, you need to release it)
• Recognizing and then overcoming all the many limiting beliefs about yourself that are keeping you stuck
• Developing your skills to the point where they’re actually capable of getting the job done
• Completing the necessary reading, learning, and apprenticeship to be seen as a serious contributor to your space
• Getting to intimately know your ideal audience members
• Building your network of support, accountability, partners, collaborators
• Developing an interesting and unique point of view
• Getting clear on what the hell you’re actually creating (there’s probably a deeper thread that runs through your work than what’s visible on the surface)
• Once you do, learning how to talk about what you do in a way that’s compelling to others
• Understanding where your work and perspective uniquely fits in your niche, industry, and the world
• Starting and quitting dozens of different blogs, podcasts, newsletters, Youtube channels, social accounts, projects, and more that weren’t quite the right fit for either you or your audience
• Developing offers that suck and don’t sell
• Going back to the drawing board to develop better offers that do
• Creating a whole lot of shitty content
• Creating a whole lot of mediocre content
• Creating even a small amount of good or even great content (and finding that this content takes way more time to create… but the positive results are obvious)
• Developing a sustainable distribution system for your content to get it seen by more people
• Learning how to market yourself and your work
• Finding and learning the tools that will help you make and market your work
• Running regular experiments and analyzing the results
• Running more experiments and analyzing those results
• Continuing to run & analyze more experiments… (you basically do this til the end of time)
• Pivoting when it all goes to shit
• Pivoting when you realize you don’t want what you used to want and having to go back to the top of this list
• Pivoting when you realize you’ve been playing small and that you have more to offer but it will require you to expose yourself in a way that is terrifying, uncertain, and vulnerable
• Getting the timing right (this might mean sitting on your idea for years)
• Learning to navigate and leverage your personal and creative patterns, habits, strengths, and weaknesses
• Learning the limits of your capabilities
• Learning the limits of your knowledge
• Learning who you really are
• Learning to trust yourself.

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.

Within minutes of leaving my front door for a walk, it’s almost inevitable that I’ll have stooped down to pick up something off the ground.

Most often it’s a small, interesting (at least to me) stone or pebble–when I’m walking along the coast my pockets will end up literally overflowing with such stones–but any vaguely spherical object will do, including various forms of nuts, seeds, fruits, or other naturally occurring orbs.

While in Texas a couple of months ago, I picked up a collection of acorns that are now apparently accompanying me around the world.

Acorns are wonderful metaphors for the value of patience, persistence and how great things can grow from small beginnings, and I keep them on my desk as a reminder.

This isn’t an article about acorns, however.

See the picking up of the object, in this case, an acorn, is only the starting point. Once I have it in my hand, it’s only a matter of time before I begin tossing it to myself.

Toss. Catch. Toss. Catch.

I’ll start with low tosses and easy catches, all the while continuing to walk, but as I become more comfortable with the size and weight of the object, understanding how it arcs through the air in the current conditions, I’ll begin to throw higher.

Soon, I’ll attempt throwing it over tree branches, through gaps in the foliage, throwing higher and higher as my confidence increases.

Toss. Catch. Toss. Catch. Toss. Bounce. Drop. Stoop. Retrieve. Toss. Catch.

I originally thought this habit was some kind of boyish male compulsion born of a love of sports and competition.

How many groups of guys have I been around, who, when pulled over at a road trip rest stop for example, within five minutes have, without speaking or explicit organization, found a target at which to collectively throw rocks in tacit competition?

But the more I thought about it, the more I realized there was something else going on and that this habit had further reaching implications than the simple tossing and catching of an acorn might initially suggest.

In the end, I realized that this tossing and catching was a small, subtle form of confidence building, that, silly as though it may seem, extended into the rest of my life, including my creative work.

Confidence Is Fluid

We often think of confidence as being domain-specific.

We might be confident in our ability to prepare a delicious meal, for example, without having any confidence in being able to run a 10k race.

The truth, however, is that confidence is more transferrable than we often think and can bleed over from one domain to another.

This is especially true of pursuits that share some common denominator.

Take sports for example.

While you might be a novice soccer player, if you’ve been playing hockey your whole life you likely have a level of confidence and comfort in your physical abilities, an understanding of the how team sports work, and your ability to to pick up the nuances of the game fairly quickly.

Confidence is especially fluid and transferable when the activities in question fall under a domain we hold as a core part of our identity.

In the example above, if we see ourselves as athletes we’re likely to have confidence in our ability to understand and excel at any type of athletic endeavour, regardless of whether or not we have any current experience with it.

This type of identity-based confidence is a powerful tool to acquire.

If we hold the idea of being “creative” as being a core part of our identity for example, and have confidence in it, we’re far more likely to excel at any (and perhaps all) creative pursuits we encounter.

But what if we don’t yet have confidence in our abilities as a creator?

Is it possible to transfer confidence over from somewhere else?

Finding Your Common Denominator

It turns out that confidence built up in one area is, in fact, transferrable to pursuits in unrelated domains.

The trick is we just need to work a little harder to find the common denominator tying them together.

I’ve written before about how there’s a lot we can learn as creators from the word game Wordle, for example.

By most definitions, Wordle and creative work fall into entirely unrelated domains.

One is a short, sweet, fun diversion that takes 5-10 minutes a day while the other is the work that many of us pour our hearts, souls, fears, and hopes into for years, decades, or even a lifetime with the goal of earning a living and creating an impact off of it.

And yet, when we shift our categorizations of each of these pursuits from “game” and “work” to the common denominator of “puzzle” all of a sudden the link between the two becomes a whole lot clearer.

With the link now established, the confidence that comes from competence in one area almost naturally begins to flow into the other.

I’ve experienced this exact boost in puzzle and problem-solving confidence in my creative work by regularly playing games like Wordle, crosswords, learning how to solve a Rubik’s Cube, board games, card games, and more.

When you find the link and then approach two pursuits as fundamentally the same thing, the gains made in either of them apply to the other.

Which brings us back to tossing and catching acorns.

Confidence is a Common Denominator Unto Itself

As I walked and tossed and caught and dropped and tossed and thought about the possible common denominators between tossing and catching and any other more… shall we say, useful pursuits, I cycled through possibilities.

The obvious one was the physicality of the activity.

The accuracy and timing required of the toss and the hand-eye coordination required of the catch both feel fairly broadly applicable to other physical activities.

Then I pushed a level deeper and thought about so much of creative work is essentially tossing an idea up to our audience and hoping they catch it. At the same time, we ourselves are constantly trying to catch the subtle cues our audience and the market are sending our way in order to inform our work.

Toss. Catch. Toss. Miss. Stoop. Retrieve. Toss. Catch. Toss. Catch.

It’s a tenuous connection, I’ll admit, when it comes to how much creative confidence can possibly be built by tossing acorns over tree branches.

And yet, it provides an interesting lens to think about the process of doing creative work.

The unexpected gusts of wind, caroms off tree branches from poorly aimed tosses, and simple misjudgments that might cause us to miss catching an acorn all exist in some form or another in creative work.

As do the ways in which we might account for and manage these potential disruptions.

As too does the thrill in our gut of aiming an ambitious toss and pulling out the catch on the far side of its arc.

Perhaps the more fundamental form of confidence we gain stand to gain from tossing and catching, however, is the belief in ourselves to envision an action and have it work out successfully.

Whether it’s tossing and catching an acorn or planning and executing a product launch, establishing a vision and following through on it is how confidence builds.

The more ambitious the toss we’re able to snag, the more confidence we gain for the next one.

That’s not to say every toss we make will be perfect, or that we’ll make every catch. But as long as we keep tossing, we find that the confidence gained from a successful toss and catch is greater than the amount lost by missing.

And in the end, in my experience, at least, confidence built up in any area of our lives is additive.

Even if we can’t make a direct connection about how confidence built up in one area might flow into and serve us in another area of our lives, our overall, master level of confidence in ourselves is informed by all the domain-specific confidence we possess.

And in the end, that master level of confidence has a way of finding its way into every single thing we do.

Confidence is confidence.

Which means any chance we have to increase it–be it tossing up an acorn or an idea–is worth taking.

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.

Think about the board game, Monopoly for a minute.

Chances are if you play it 10 different times with 10 different people you’ll get 10 different variations on the rules.

Some of the variations are minor, such as changing the amount of cash each player starts with, randomly dealing out a selection of starting properties, or taxing certain board spaces.

Others are drastic alterations to the core mechanics of the game, such as adding custom rules that apply to specific dice rolls, and new opportunities (or requirements) for landing on a certain spot on the board.

It’s not that the rules of Monopoly are fluid by nature.

The official rules for the game are firmly defined, set in stone–or at least in the paper print-out that comes in the box.

And yet despite these standardized, codified rules, so often, we, as the people playing the game find ways to reinterpret, bend, break, subtract from or add to the rules in a way that makes the game more fun for us.

Having fun, of course, is the whole point behind playing a game in the first place, so if we stumble across (or engineer) a way to play that makes it more fun for all involved, why not ditch the official rulebook and adopt the House Rules.

What we need to realize as creators is that we too have the ability to create our own house rules.

We might read about a dozen different frameworks and strategies for growing our audiences or creating better work.

Each of these frameworks is likely solid, and probably even works wonders for some people.

But no matter how granular and detailed their instructions, by no means is any framework or strategy hard and fast.

If the process doesn’t work for us, whether related to the results we’re receiving or the experience we’re having while following it, we have the option to create our own House Rules.

That might mean choosing to ignore or change a few selected instructions. Or it might mean ditching the rulebook altogether, keeping the board and the playing pieces but inventing an entirely new way of using them.

In the end, as long as we stumble on something that works for us, what else really matters?

The first step is to understand that playing by (and inventing) House Rules is even an option.

The second step is to start experimenting, finding out what we can do to have more fun with our work and create a better experience for ourselves and those we engage with.

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.

Last week in the newsletter, you might have noticed that I switched things up a bit.

While the subject matter was more or less the same as my usual–how to navigate the Creative Wilderness–the format was different, in that, I opted for a poem rather than my typical weekly essay.

I wasn’t entirely satisfied with the finished version of the poem I sent.

And yet, within a few hours of publishing the newsletter, I was surprised to see a number of emails from readers hitting my inbox, telling me how much they appreciated the poem, as well as a couple of shares on social media.

Compared to the average newsletter, this was a significant positive response.

It also meant that two of my five most resonant newsletter issues featured poems instead of essays.

So what’s going on here?

Do people like you who read this newsletter prefer poetry to essays?

Somehow, I didn’t think so.

Curious, I looked back at the issues that had received the most positive feedback from readers and discovered a through-line between them.

What surprised me, however, was that the common thread wasn’t related to a specific topic or format of the writing, but to my personal experience and approach to creating them.

It turns out, there’s a lesson here for all of us seeking to create work that resonates more deeply with our audiences.

But first, back to the poem.

Poetry Is Hard

This wasn’t the first time I’d included a poem in the newsletter.

Issue #35 is not only one of my very favourite issues of this newsletter, but the poem I wrote for it is one of the things I’m most proud to have ever created.

Ever.

It’s also the issue I received the greatest positive response for to date.

And yet despite the precedent and the positive feedback, I was nervous all week as I wrote the poem and prepped the newsletter.

The reason?

Writing poetry is hard.

Compared to an essay, poetry has a less-forgiving structure.

Each line (and perhaps word) needs to earn its place and flow from and into those around it. These factors, combined with rhythm and pacing, can undermine a poem with otherwise interesting content if not executed well.

While I’ve written several dozen poems in my life (most of them of the teenage angst variety), I’m certainly no expert.

From the moment I sit down to write a poem, it feels as though its future is in doubt, like I may give up on it halfway through when it feels too hard to complete.

Unlike the average essay I write, writing poetry stretches me in an uncomfortable way.

And it’s this stretching that turned out to be the through-line in my own most resonant work.

Stretching Past Your Natural Resting State

Much like our muscles naturally come to rest in a state of comfortable relaxation, so too does our creative work.

In both cases, in order to experience any positive benefits, we need to actively and intentionally stretch.

Whether it’s writing a blog post, producing a podcast, or rolling out a new product, or service, when we’re entirely comfortable with the work we’re doing, chances are, it’s not that interesting.

This is because that feeling of safety can only really exist when we know going in that we’re not saying something that our audience might take issue with, push back on, on fail to understand.

When you think about it, the only way to have that kind of confidence before you hit publish is to (consciously or unconsciously) be rehashing an existing, broadly accepted idea.

No stretch.

No risk.

No resonance.

If we want to create work that truly resonates with others, that hooks them and keeps them coming back to see what we’ll do next, we need to stretch past the edge of our comfort zone and into discomfort.

I think David Bowie said it best:

If you feel safe in the area you’re working in, you’re not working in the right area. Always go a little further into the water than you feel you’re capable of being in. Go a little bit out of your depth. And when you don’t feel that your feet are quite touching the bottom, you’re just about in the right place to do something exciting.

– David Bowie

So what does this type of stretching look (or more accurately, feel) like?

The Challenge Zone

We’ve talked before in this newsletter about the value of Marathon Projects.

These ambitious, time-bound projects go above and beyond our typical creative output and stretch us to improve our skills and conception of what we’re capable of achieving.

Marathon Projects, along with micro-challenges we might impose on our daily or weekly creative output (eg. write a 1,000 word blog post in only 30 minutes or record a podcast working the word “chicken” in every 5 minutes…) are certainly one type of stretch.

These stretches push us out of our safe, resting mode and into what I think of as the Challenge Zone.

Work done in the Challenge Zone engages our creative muscles, tests our skills and capabilities, and expands our conception of what we’re able to achieve.

This type of stretch is important in developing our creative skills and building confidence in ourselves.

But to create deeply resonant work, we need to perform a deeper kind of stretch, extending ourselves past the Challenge Zone, and into the Discomfort Zone.

The Discomfort Zone

The Discomfort Zone is what Bowie was talking about in regards to wading out into the water to the point where your feet can’t quite touch the bottom.

In practical terms, the gap between our feet and the seabed is doubt.

And while it might seem like inviting doubt into our work is the last thing we would want to do, the presence of doubt is a clear indication that we’re doing something interesting.

In my experience, there are two ways to stretch into this level of discomfort.

1. Stretching Into Vulnerability

On the last Creative Wayfinding Friday Fireside call a few weeks ago, we got talking about the work that had been best received by our audiences.

Without fail, every single person on the call shared that the work that seemed to resonate most with their audiences was not the work that contained the most information (ie. the work that should have been most “helpful”), but the work where they themselves had gotten uncomfortably vulnerable.

As the conversation progressed, however, it became clear that while all of us on the call were aware of this correlation between vulnerability and resonance, few, if any of us made this type of vulnerability a regular part of our work.

This is because, when done right, it stretches us in an uncomfortable way.

It’s easier and safer to instead default to information-sharing, which, while potentially helpful, offers little opportunity for genuine emotional connection.

The connection that comes from this kind of uncomfortable vulnerability is an important ingredient for creating work that resonates deeply. But there’s a balance to be found somewhere between surface-level, faux-vulnerability, and oversharing.

In my experience, vulnerability that resonates needs to:

1. Be relevant to the topic at hand, and
2. Make you nervous to share

This type of stretch into vulnerability can work wonders for developing and strengthening your relationship with your existing audiences, turning casual engages into superfans.

But there’s another type of stretch into discomfort that is necessary if we want to become true leaders and innovators in our niches and community.

2. Stretching Into the Unknown

If there’s one thing that keeps us as creators stuck, it’s our default setting of producing content and work that’s more or less the same as what everyone else around us is creating.

We cover the same topics in the same formats, perhaps with a little personal flair thrown in here and there. On the whole, however, the work we create is a different recipe for the same dish many others are creating.

What separates the thought-leaders of any niche, however, is their willingness to explore new topics and start conversations that aren’t already happening.

Creating this type of work requires a major stretch into discomfort.

This type of work isn’t about simply sitting down and recording our existing knowledge. Instead, it’s about exploring and attempting to get our head around something new, finding a thread to pull on, and unraveling it to see where it leads.

Work that fits this category is more about the thinking than the writing, recording, or tangible creating, and consists of extensive detours, backtracking, deletions, edits, and amendments.

In short, this type of stretching is frustrating, time-consuming, uncertain work.

And this is exactly what keeps us from pursuing it.

I personally have a list of 20 or so of these ideas that I’ve been sitting on in some cases for more than a year.

These are ideas that I’m excited to write about, but feel too big and too important to start on just yet. If I’m going to commit to fleshing out these ideas, I know I’m going to need time, space, and focus that never feels readily available.

And so, for the most part, they sit on the shelf gathering dust.

The irony is I have a sense that all of these topics would be among my most resonant work if I were able to publish them, with potential to be shared and circulated within the creator community. This was the case with my article on the unasked questions guiding your creative work, the one big idea I’ve been able to develop so far, and one of my most popular articles to date.

Shipping work that stretches us into the unknown terrain of big, unexplored ideas requires extensive grappling with Resistance, impostor syndrome, and perfectionism, as it never feels ready to publish.

An inherent trait of this type of work is that we don’t have our heads around it yet. As such, the wording feels clunky, the ideas don’t feel cohesive, and we feel self-conscious about publishing such an unrefined mess.

And yet, once again, the discomfort at the thought of publishing is exactly the right place to be.

On the same recent Friday Fireside call, CW reader Sam Harris brought up the point that if the idea is novel and interesting, it doesn’t actually need to be perfectly articulated and fully developed in order to benefit our audiences.

In fact, when we’re stuck trying to tie all the loose ends of an idea like this together, it often helps to share it before it’s complete.

If all goes well, it will start a conversation that may open us up to additional perspectives and ideas we’d never have otherwise considered.

While time-consuming and frustrating, the potential upside of stretching into the unknown is significant.

Novel, relevant, big ideas are infinitely more likely to be shared throughout our niches than generic “how-tos”, listicles, and other safe, generic content that lies firmly within our comfort zones.

As We Stretch, So Do Our Audiences

Few of the big wins in life come from playing it safe, pursuing the same as usual, or perpetuating the status quo.

But pushing our boundaries and stretching into discomfort doesn’t need to mean grand gestures and wildly ambitious projects with a sprawling scope.

Instead, we can choose to stretch ourselves juuuuuuust a little bit into discomfort with each blog post, podcast, product, and anything else we create.

For you, it might be taking on a topic that’s been nagging at you but which you don’t quite feel ready to share publicly.

Maybe it’s asking every podcast guest at least one question that makes you as the host uncomfortable to ask.

Or maybe it’s leaning into vulnerability and sharing your own stories and experience more deeply and honestly than you have yet.

The most successful creators consistently create work that stretches their audience to think and perceive the world differently.

We might try to convince ourselves we can create this type of work without extending ourselves beyond our comfort zones.

But the truth is we have to lead by example, stretching into discomfort, and then inviting our audiences to join us.

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.

For most of this year, my weekly review has been one of my most effective, enlightening, and enjoyable creative practices.

I started doing weekly reviews at the beginning of this year after being convinced of the benefits by Khe Hy and August Bradley, two creators and thinkers I admire who rave about the practice.

The idea is that doing a short review at the end of the week allows you to:

1. Reflect on the past week, identify what worked & what didn’t and tie up or reschedule any loose ends.
2. Prep for the week ahead by setting an intention, a few goals, and planning out your schedule so you can hit the ground running on Monday morning.

While it took me a few weeks to set up my weekly review template and find my rhythm, once I did, the benefits were as advertised.

The review gave a satisfying kind of closure to each week and allowed me to go into each week with a strong sense of focus about where my effort will be most impactful or required. Projects flowed more smoothly, I got more important work done, and I felt clear on how everything I was doing contributed to my big-picture, long-term goals.

In short, the weekly reviews acted as a kind of lubricant that made everything I did run more efficiently.

Despite all the benefits, however, this week marks three months since I completed my last weekly review.

The reason is a kind of all-or-nothing perfectionism I refer to as Grandiose Ideation, which not only derailed my weekly reviews but regularly derails many of our creative practices, habits, and projects.

Fortunately for us, there’s a simple mindset shift that can help us avoid this fate.

But before we get to it, let’s take a closer look at the root of the problem.

Falling Prey to Grandiose Ideation

The start of a new practice or project is perhaps the most exciting and energetic phase of its lifecycle.

We’re buzzing with ideas, itching to dive in, and have the benefit of more than a few blind spots to the potential challenges and pitfalls along the way.

It’s also where we’re most prone to Grandiose Ideation.

In our enthusiasm about our new endeavour, we scope out a grand plan, including a robust feature set, slick design, and (perhaps wildly) ambitious goals.

For me and my weekly reviews, this meant building out a robust template for the review which would get me thinking deeply about what I had accomplished the past week, what I wanted to achieve in the week ahead, and how it all fit together with my big-picture goals.

The structure I’d laid out worked wonderfully. But there was a problem.

Every week, the review took me 1-2 hours to complete.

According to both Khe and August, one of the characteristics of a successful weekly review is that it takes no more than 30 minutes to complete. Any longer than this, and the friction to doing it becomes too great, and you’ll ultimately drop off.

Despite being aware of the potential friction I was adding to the process, however, I couldn’t help but lay out a grand vision for my weekly reviews.

At first, I didn’t see this as a problem.

I actually enjoyed the hour or two I spent every Friday afternoon doing the review and found it incredibly valuable. As the months progressed, however, my Friday afternoon reviews began to regularly get pushed to Saturday mornings.

Then they got pushed to Sunday mornings.

Then Sunday nights. Then Monday mornings. Then I started missing a week here and there.

Until finally, they got pushed off my schedule altogether.

Even as I began slipping, I resisted trimming down and streamlining the process of the review.

“If I’m going to do it, I’m going to do it fully,” I thought to myself.

And in one sense, this is an admiral commitment to make to any project.

But it’s also one of the core reasons we end up failing and giving up on promising projects.

Dealing with The Dip

Our enthusiasm for any practice or project wanes when we hit The Dip, the point at which the fun fades and we’re faced with the reality that there’s a long slog ahead if we want to see the project or practice through to our desired results.

At this point, we realize that the project will likely never live up to our initial lofty ambitions, and rather than scaling it back, we often decide to shelve it.

If I can’t do it fully, I might as well not do it at all.

Grandiose ideation is a classic disruptor of projects and potential products. But it also wreaks havoc on less well-defined practices and habits.

“If I’m going to start running, I’m going to run 5 miles, three times a week,” we might think. Or, “If I’m going to be active on social media I’m going to post 5 times on Twitter, twice on LinkedIn, once on Instagram… oh, and 10 IG stories every day.”

Or perhaps even, “I’m going to do a weekly review that will include recapping every possible thing I might ever want to look back on in the future and plan for every contingency in the coming week…”

All of these lofty commitments, while noble in intent, have the unintended effect of planting the seeds for failure before we even start.

Clearly defined projects and products that succumb to Death by Grandiose Ideation are often the most painful or disappointing. This is because they likely have a timeline attached to them along with a very clear end result. Never mind that both may be wildly optimistic…

But while an abandoned project might be disappointing, it’s the long-term habits and practices we abandon that ultimately have the greater negative impact on our success.

This is because while the positive results of an ongoing practice may be subtle and ill-defined, they tend to compound over time, adding up to greater and greater impact, even if we’re not entirely aware of it.

But while practices and habits have incredible potential for positive impact, they’re are also much easier to abandon than time-bound projects with a clear beginning and end.

Most healthy practices don’t deliver an immediate dopamine hit for doing them. They take effort, the positive results are likely to be in the far future, and often end up feeling like a burden, with few tangible results in return for the time and effort we put in.

For this reason, Grandiose Ideation is especially disruptive to ongoing practices.

We’re already predisposed to abandoning them when things start getting tough. Heaping on greater scope and expectation before we even begin only stands to increase the gap between our vision and reality, leading to almost immediate disillusionment once we get into the practice.

Fortunately, when we’re aware of Grandiose Ideation and how it sets us up for failure, we can dance with (and around) it.

Shrink Your Ambitions to Improve Your Results

When it comes to a defined, user-facing product, the answer to Grandiose Ideation is to start by identifying and building a Minimum Viable Product, or MVP.

The MVP is the smallest version of the core product that the target group of customers will (hopefully) be willing to pay for. If it’s successful and people buy it, the product has been validated and you can expand on it from there. If it fails, you haven’t wasted that much time and you can move on to the next idea.

But what about when the subject of our Grandiose Ideation isn’t a defined product with users to help us validate it?

What if, instead, it’s a habit, or practice, perhaps one that no one else will ever engage with beyond us ourselves?

For these cases, it’s worth thinking not about the Minimum Viable Product, but the Minimum Effective Effort (MEE).

Minimum Effective Effort

For any task, habit, or practice, the Minimum Effective Effort is the least amount of effort required to achieve a meaningful result.

In short, it’s the perfect counterbalance to Grandiose Ideation.

At the start of a new pursuit, when the excitement is flowing we have a way of viewing it with tunnel vision, looking only at the very best-case, absolutely most-effective version of the practice and ignoring everything else.

My weekly review template was a perfect example of this. The most effective (and least possible to do consistently) version of a review.

Knowing we’re in this stage and prone to Grandiose Ideation, it’s worth taking a moment to stop, take a breath, and ask what the MEE for this activity would be.

When we identify the lower floor of the “effective” range of activities, we immediately become aware of a whole spectrum of alternative effective versions of the practice to choose from. It makes plain the fact that while our grandiose version of the pursuit might be the most effective version, it’s far from the only effective version.

Knowing this, we’re able to take a more nuanced, measured approach to the activity, committing to an amount of effort we’ll actually be capable of sustaining over the long term.

Part of Grandiose Ideation is the fact that we tend to drastically overestimate the bandwidth we’ll be able to dedicate to a long-term, ongoing project or practice.

Sure, we’re excited at the start and have the energy and time in to creating a weekly podcast that takes 15 hours per episode to produce. But will we have that same energy and bandwidth six months from now when we’re firmly in The Dip?

Maybe. But usually not.

In my experience, it’s much easier to scale up a practice, increasing our effort once we’ve got our feet under us and as more bandwidth becomes available than it is to scale down when we’re floundering.

While identifying and pursuing the MEE is about scaling back our effort, however, it’s worth underlining the point that the Minimum Effective Effort is not the same as the minimum possible effort.

For a given pursuit, the MEE may actually require a substantial amount of effort in order to be effective.

Training for a marathon comes to mind as an example, where the minimum effective effort would require us to go for long runs multiple times per week over a long period of time.

The goal when identifying the MEE, then, is not to do the least amount of work possible, but the least amount of work that will get us a meaningful result.

This means that the first step to finding the MEE for a given pursuit is to identify what a meaningful outcome would be for the task at hand.

Identifying Your Minimum Meaningful Outcome

As it turns out, goal-setting is another area in which we’re often prone to Grandiose Ideation. As such, it’s worth thinking about the closely-related idea of the Minimum Meaningful Outcome.

Let’s look at an example.

If your goal is to grow your newsletter subscribers, for example, adding 1,000 new subscribers every month would certainly be a meaningful outcome.

But if you’re starting from zero or kickstarting a stagnant newsletter, perhaps the Minimum Meaningful Outcome is 25 new subscribers per month. Or maybe it’s simply net-positive growth.

The Minimum Meaningful Outcome for a given pursuit is something we each need to decide for ourselves, given our goals, experience, and current situation.

If it helps (read: if you’re a nerd like me), we can plot the range of acceptable outcomes on a graph.

Once we have an idea of the range of potential meaningful outcomes defined for ourselves, we can start to take a more informed view of what it might take to achieve them.

Usually, this will require some guesswork and is something we won’t truly know until we actually begin the practice and start getting some feedback. But we can make an educated guess based on research and talking with others who’ve pursued similar goals to ours.

When it comes to growing a newsletter, for example, we can ask people we know with newsletters about their process.

How much time do they spend writing, researching, engaging on social media, and more?

What kind of results are they getting from that effort?

Once we have this information, we can map it over our existing graph.

The required effort to achieve a given result is indicated here by the yellow line, and we can think of the Minimum Effective Effort as the point where the effort curve intersects with our Minimum Meaningful Outcome.

Note that I’ve drawn the effort curve as an s-curve based on my experience that usually, the relationship between effort and result follows a non-linear pattern.

At the start of many pursuits, we need to put in a decent amount of effort before seeing any result at all. As we continue, the return on our effort begins to compound, requiring less effort for greater results and perhaps approaching exponential growth, before finally tapering off when we reach a point of diminishing returns.

Putting the Minimum Effective Effort to Work

Viewed on a graph, we can clearly see the effort we stand to save ourselves by starting with the MEE versus falling prey to grandiose ideation.

But you don’t need to draw out a graph for every new practice or project you’re considering.

Instead, before you commit to a new project, no matter how promising it might be, stop, take a breath, and ask yourself:

1. What is the Minimum Meaningful Outcome for this project?
2. What would it take to achieve that?
3. Is there any reason I need to do more than that immediately?

These questions can help you ground yourself before jumping into a project or practice that is ultimately doomed to failure by excessive and unnecessary scope.

In almost every case, it’s the project that gets completed or the practice that is done consistently that gets results. Achieving these feats, however, often requires us to scale back our initial expectations.

Once the habit has been built, or the MVP has been made, we can always add to it from there.

In my experience, however, we often find (with some irony) that the Minimum Meaningful Outcome is, in fact, enough.

That’s what I’m hoping to find as I reboot my weekly review this week.

Having gone three months without it, it’s clear to me which aspects of it I miss most, which were nice to haves, and which were pure fluff. As I reimagine the practice, I’m building it entirely around the MEE version of it.

A year from now, there may be things I look back on and wish I had included. But at least I’ll have been doing it consistently for that year.

It’s worth dreaming big and aiming high.

But don’t forget that while your biggest, most elaborate creative ideas might be the most effective solutions for the problems they seek to solve, they’re not the only ones.

And they’re certainly not the best starting point.

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.

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
• Twitter
• Facebook
• Instagram
• LinkedIn

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.