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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6 Lessons From Crosswords On Solving Sticky Creative Puzzles
As I write this, I’m working on a 10-day streak of solving the New York Times daily crossword.
Crosswords for me are both the perfect way to unwind and relax while also engaging my brain in an activity that feels challenging and productive.
Solving them requires a blend of logic, abstract thinking, cultural knowledge, and willingness to experiment, traits that, when you think about it, have a lot of overlap with those required to do successful creative work.
And while crosswords are certainly a useful way to flex our creative muscles in a different way than normal, where they really shine is in what they can teach us about solving sticky problems.
Solving sticky problems is a pretty good working definition of what creative work is at its core. In fact, our lives as creators consist of little more than attempting to solve sticky problems, either for ourselves, or our audiences.
- How do we get attention in a noisy world?
- How can we make a sustainable living doing creative work that matters?
- How do we rally and empower our audiences to challenge the status quo in our communities, industries, and the world?
All of these (and many, many more) are the problems we spend our days working to solve.
Which means the better we get at problem-solving as a skill, the greater our success and our impact in all our creative endeavours.
And while problem-solving, like most skills, is something we can only really improve with practice, there’s a lot we can learn from crossword solving that we can then apply to that practice.
1. The Clues Are Right in Front of You (You Just Need to Know How to Look at Them)
A typical crossword puzzle consists of three basic components.
- The 15×15 grid
- The clues
- You, the solver
The premise of the puzzle is that these three self-contained elements should be enough to fill in the puzzle.
Our creative careers can be thought of similarly. We, of course, are the solvers and the grid is the niche or industry we’re operating within.
The clues, however, are a little less obvious.
Then again, so are many crossword clues.
In any challenging puzzle, there will be a small handful of fairly obvious clues which allow us to fill in a few squares and get started. But after that, many–if not most–of the clues are intentionally vague or misleading.
Some clues we might puzzle over for an hour or more, before finally realizing that we’ve been approaching the clue from the wrong angle altogether. When we make the required mental shift, however, the answer seems obvious and we wonder how we didn’t see it all along.
Much like crosswords, the clues to our creative work are usually staring us in the face.
The challenge for us, then, is twofold.
- Learning to spot the clues in the first place
- Making the required mental shift to interpret them in a way that is helpful
Reinterpreting The Clues Around You
We tend to spend most of our time looking externally for clues as to what our correct next step is.
We read books and blog posts and listen to podcasts, looking for the clue–or better yet the answer–to appear in flashing neon letters, “THIS IS THE WAY FORWARD!”
The irony is that the clues are there in the books and blogs and podcasts, but they’re rarely obvious.
They’re more likely to exist in the subtext than in what’s been explicitly stated. In fact, in many cases, the original creator may not even be aware they’re communicating these clues.
To spot them then, we need to dig a little bit deeper than the surface level. To inquire into the thought process behind what’s being presented.
Then we need to inquire into ourselves.
Compared to our external quests for answers, we tend to spend little time seeking out the clues within ourselves. But in my experience, within ourselves is where we’re more likely to find the most useful clues.
The better we get to know ourselves and understand how our skills, tendencies, worldviews, beliefs, Keys to Victory, and more all intersect, the clearer the next step becomes, and the better our results.
But it’s not just the clues that we hold inside ourselves.
It turns out that many of the answers we’re seeking are also hidden away in our own internal nooks and crannies.
2. You Already Know the Answers
In almost every challenging crossword, I reach a point where I’m completely and utterly stumped.
Sometimes there are only a handful of squares remaining, sometimes a whole quarter of the puzzle is blank. At this point, I’ll write the puzzle off as impossible, concede defeat and walk away, looking forward to coming back to a fresh new puzzle the next day.
Inevitably, however, a few hours later, out of some sort of masochistic compulsion, I’ll return to puzzle over it some more.
And yet, somehow, after stepping away it rarely takes much puzzling.
Almost without fail, immediately upon sitting down and running through the clues, something clicks into place. Maybe I grasp the word I’ve been trying to remember or realize there’s a different interpretation of a clue.
What fascinates me about this is that even while I was stumped, beating my head against the wall the first time through, thinking the puzzle was impossible, the answers were already buried somewhere inside of me, and I was just unable to access them for one reason or another.
Like a Chinese finger trap, it often feels like the harder I fight to come to a solution to a clue, the less likely I am to find it.
In the same way, it often takes a break, some space, and a change of scenery to solve particularly frustrating creative problems.
For smaller daily problems, simply getting up and going for a walk is often enough to knock the answers loose. For larger, more vexing problems, it might take a week-long vacation, or even setting the project aside for an indeterminate period of time so we can recuperate and come back fresh.
I most regularly experience breakthroughs over the Christmas holidays when I take time off and do a lot of journaling and reflecting, often finding the answers to the problems I’ve been wrestling with for months reflected back in my writing.
The time off and change of scenery that accompanies attending conferences has proven to be another reliable method of gaining clarity for me.
When we’re stuck, it turns out, the best thing we can do is often not to keep staring at the problem, running through the same clues again and again with a tired mind, but giving ourselves some time and space to relax, back away from the problem for a time, and let our subconscious go to work uncovering the answers we already have within us.
Often, this is all it takes for the answers we’ve been seeking to rise to the surface.
Of course, while we might have many of the answers to a given puzzle within us, there are always going to be those we have to come to by other means.
3. Solve by Triangulating
If you’ve ever done the crosswords yourself, one of the things that might have frustrated you is the obscure pop-culture references from decades, or even centuries past.
When I first started doing crosswords regularly as an early 20-something, these were the clues that always stumped me.
At the time, I imagined that crosswords were simply intended for an older audience, and that I’d have to wait another 30-40 years until I reached my prime crossword-solving years.
Now, however, I’m beginning to suspect otherwise.
In almost any crossword, there’s at least one word that, even once solved, I have no idea what it means. In late-week puzzles, there are typically a handful of these.
Initially, I thought these blindspots were simply a result of my youth, or narrow knowledge. I’m convinced now, however, that this is an intentional decision by crossword creators.
See, while era-specific answers are certainly one type of potential blindspot for solvers, most puzzles have a similar selection of niche, domain-specific answers that would be equally unknowable to the average layperson. This leads me to believe that crossword creators purposefully attempt to design puzzles that almost no one person will have all the answers to.
That doesn’t mean they’re unsolvable, however.
In fact, this is one of the things that actually makes crosswords fun.
One of the interesting results of the format of a crossword is that in theory, you could solve the puzzle by knowing only half the answers. Fill in either all the across or all of the down clues and the puzzle is complete.
What this means is that you can triangulate (or perhaps biangulate?) your way to the answers of many clues about which you are, in fact, clueless.
This is precisely the process required to solve many of the creative problems we encounter.
It often feels like the only way to arrive at the answer is to study and research our way to finding the actual answer itself. But in fact, the shorter (perhaps even immediate) route to solving many problems is to simply fill in the blanks based on the adjacent knowledge we already have.
Marketing is the most obvious field in which to practice this type of triangulation.
While each of us is at least fairly knowledgeable in our primary field of work or core topic we create around, few of us have thoroughly studied the ins and outs of marketing theory.
In fact, I’d argue that marketing is such a multifaceted field that no one person can possibly have deep knowledge in each of the sub-categories that make it up such as psychology, copywriting, design, positioning, and so on, not to mention all the technology-specific applications of marketing.
And yet, if we’re going to get our work out in front of the people we seek to serve, we’re going to have to market it.
Which means we’re going to have to do our best to fill in the gaps and make educated guesses based on our existing knowledge.
There’s no way we can study long enough to know the answer to every possible problem we encounter.
But we don’t need them.
More often than not, our foundational knowledge and experience are enough to get us to a place where we can make an educated guess about those blank squares in front of us, and take the next step forward with confidence, slow and incremental as that progress may be.
4. One Square At a Time
During my first run through the clues of a challenging puzzle, I might be able to fill in less than 10% of the puzzle’s squares. The second pass, in many cases, may only result in one or two more answers.
Of course, challenging puzzles are not meant to be solved in just a couple passes, but when the initial cycles through the clues yield so little progress, it doesn’t leave you feeling great about your prospects of completion.
What fascinates me, however, is that while each pass through the clues may only fill in a few additional squares, those few squares are often juuuuuust enough to get us the next few squares.
Occasionally, we might fill in a long, 10-letter word that opens up the board. But most often our progress is made by filling in a square here, a square there, bit by bit until the puzzle is complete.
In the same way, few of the creative problems we struggle with have grand solutions we can simply plug in and be done with.
Instead, our problems will be solved by wearing away at them, bit by bit.
Much like moving through a dense patch of fog, each little bit of progress, irrelevant though it may seem, often illuminates juuuuuuust enough of the way ahead to make the next tiny bit of progress.
As we continue to circle back on the problems we’re grappling with, we find that over time, the little bits of knowledge, perspective, or clarity we’ve picked up elsewhere allow us to more clearly identify the structure of the problem at hand, until at some point, the answer becomes obvious.
Two of the things I marvel at the most when it comes to this approach to solving crosswords are:
- Just how big a difference one letter can often make
- How arriving at the answer to a clue in one corner of the puzzle often has its root in solving a clue in the far opposite corner, slowly but surely snaking your way across the puzzle.
The lesson is that we never know where the answers will come from.
Everything connects up in one way or another, and sometimes, even the smallest bit of progress in one area can lead to a breakthrough in another.
5. Sooner or Later, You Need to Leap
Even following all of the puzzle-strategies strategies listed above, we still often reach a point where we are well and truly stuck.
We’ve spent hours on the puzzle, taken breaks and come back, and triangulated our way to a semi-completed stalemate. I typically reach this point at least once a week, usually on one of the difficult weekend puzzles.
At this point, it feels as though we’ve exhausted our options and have no choice but to concede defeat.
And yet, we have one strategy left at our disposal, that we often overlook.
To take a leap and start making some (educated) guesses.
The wonderful thing about being well and truly stuck is that we have nothing to lose by taking a leap and penciling our best guesses into the empty squares. If none of our guesses stick? Well, we were about to give up anyway. But if we guess right on even one clue, it may be enough to solve the rest of the puzzle.
Despite the asymmetrical positive rewards of guessing, we often overlook it as a valid strategy.
In creative work, this guessing often occupies the gap between researching how to do something and actually doing it.
You can read a dozen books and listen to many more podcasts on how to successfully launch a product. But no amount of research will be able to fill in all the blanks for you to launch your specific product to your specific audience.
Those answers don’t exist out there. At least not yet.
Which means if you want to find them, sooner or later, you’ll have to make some educated guesses, and leap.
Chances are, your first guess might not be entirely correct. This is where a lot of creators get frustrated and give up.
As with crosswords, however, when it comes to creative work, our first guess is never the be-all, end-all. We have the opportunity to erase any of our guesses and pencil in something new, trying new solutions and seeing what opportunities they open up.
6. How Long Are You Willing to Stare at the Problem?
There’s one last piece to this puzzle-solving puzzle, and it’s best articulated Albert Einstein, who, refuting his own reputation said, “It’s not that I’m so smart, it’s just that I stay with problems longer.”
In fact, in perhaps the ultimate display of sticking with a problem, Einstein spent more than 30 years working on and puzzling over the problem of relativity.
This ability to stick with problems, it turns out, might be the most essential skill in solving sticky creative problems.
In crosswords, this ability to stick with the problem plays out in two ways, both of which map over to creative equivalents.
1. Sticking with the Individual Clue
When I’m first going through a puzzle, I’ll breeze through the clues, filling in the answers I know immediately and skipping the ones I have to exert any brainpower on whatsoever.
On a Monday puzzle, I might be able to solve the whole puzzle this way in a matter of minutes.
But in a late-week puzzle, there’s not much low-hanging fruit, meaning before long, a change in tactics is required.
At this point, I’ll continue to cycle through the clues sequentially, spending a bit more time puzzling over each. But at some point, there comes a time when the only way to solve a clue is to stop cycling and simply sit with the single clue, puzzling over its various possible interpretations and possible answers.
There’s something about this pausing and puzzling that is inherently uncomfortable.
Cycling through the clues provides a feeling of motion, momentum, and optimism.
Pausing and puzzling, however… It just makes you feel stuck.
The irony is that sitting with this feeling of being stuck is often the only way to get unstuck, both in regard to a tricky crossword clue and a tricky creative problem.
I can’t count the number of times I’ve breezed over a problem I’ve faced in my creative work because the answer wasn’t immediately obvious, telling myself I’d come back to it later and letting promising projects languish in the meantime.
Often, in fact, almost always, when I finally did come back to the problem, it took little more than 5 or 10 minutes of focused thought directed squarely at the specific problem to come up with an answer and kick-start the project.
Sometimes, cycling through the problems in front of us and filling in as many of the easy answers as quickly as possible is the best strategy.
But sooner or later, we reach a point with every project where the only way to move the project forward is to stop cycling, and focus our attention on the one problem that’s grinding everything to a halt .
Over time, conditioning ourselves to stick with problems trains us to take on more ambitious projects in the future.
This is because as we work our way through problems that had initially stumped us, we build up our confidence that we can work our way through future problems that might look difficult (or even impossible) when viewed at first approach.
This type of confidence is invaluable in creative work.
2. Sticking with the Puzzle
The second form of sticking with the problem applies to the puzzle as a whole.
With Sunday crosswords, in particular, I often find myself stuck around 30 or 45 minutes into working on the puzzle.
The average time for me to complete a Sunday puzzle however is probably between 2 and 2.5 hours.
This ratio between the time-to-frustration and the time-to-success (let’s call it roughly a 1:4 ratio) feels about right to me when applied to creative work as well.
Most successful creators I know were creating things online in one form or another for at least 5 years before things really started to click.
And yet, for most new creators, frustration often sets in between the 1-2 year mark.
This is the point at which we’ve tried a bunch of stuff, done a lot of research, educated ourselves (or so we think), and feel like things should be getting easier.
When it doesn’t, many creators give up.
What we can learn from both Einstein and crossword puzzles, however, is that perhaps our single biggest asset as creators is our ability to stick with the puzzle in front of us well past the point at which we become frustrated with it.
Keep in mind that at the macro level, the puzzle we’re working on is not tied to a particular project, niche, or medium.
Instead, the macro project we’re each trying to solve is building a meaningful, fulfilling life.
If doing creative work is an essential part of such a life for us, it’s worth remembering that there are many outlets for and expressions of our creativity.
You might be podcasting (and frustrated) now only to find out a year from now that the thing that clicks for you is a YouTube channel.
Or, you might be struggling to build a digital product business only to find in the future that what really lights you up the most is working 1:1 with people.
Sticking with the creative puzzle is about pushing through the frustration and continuing to cycle through all the clues presented to us, reframing them in our minds to find new possible answers which we’ve never before considered.
You Get to Choose the Puzzle to Solve
Viewing creative work as a puzzle is perhaps the most helpful lens available to us.
It implies frustration, the ability to think abstractly and solve non-obvious problems. It also implies that there is, in fact, a solution.
Unlike the crossword, however, that answer—and the clues that lead to it—aren’t the same for every player.
This is both a blessing and a curse
It means we might not immediately know when we’ve arrived at the end of the puzzle.
But it also means that perhaps we get to choose what solving the puzzle looks like. Which means if we choose, we can construct and solve a puzzle that plays to our natural strengths.
That’s not to say it will be quick or easy.
Any puzzle worth solving will certainly require us to walk away in frustration more than once.
But if we’re working on the right puzzle, we’ll find ourselves continually drawn back to spend more time staring at the problems in front of us until something shifts, unlocks, and the next step becomes apparent.
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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Ideas & Broken Bones
Getting a new idea off the ground is a lot like healing from a broken bone.
New ideas are typically made up of two (or more) disparate ideas that have never been connected and must now be grafted together.
We set them in place, and at first glance, they might look complete. But apply even the smallest amount of pressure and instantly, they splinter back into their component parts.
In order to fuse properly, new ideas must be given support, encased in a protective cast, and given time for the connections to strengthen into something that can support weight.
Over time, the ideas will fuse to become one, the seams between the original building blocks no longer obvious. At this point, the cast can be removed, but while the core of the idea is whole, the muscles supporting it must now be tested and trained, building up strength and confidence over time.
As with a broken bone, new ideas are fragile and must be given the proper time, care, and support in order to one day bear weight.
Don’t rush the process.
Push the Domino
We often hold back on taking action because we’re uncertain of the effect it will have.
Sure, we have an idea that might work, but what if it doesn’t give us the result we were looking for?
What if, in hindsight, we realize that we would have been better off taking that other action instead? Or the other action besides that?
One of the core traits of successful creators is an eagerness to topple the first domino and simply see what happens.
Rather than get hung up on the blank page or the empty canvas, they commit easily to writing the first line, to making the first brush stroke.
They understand that it’s impossible to ruin their work before it’s begun, and that the only way to uncover the potential of the seed of the idea in their head is by getting it out of their head and playing with it in a more physical form.
The creative process is equal parts practice & preparation, and then relinquishing control and letting an idea take you where it wants to go.
If it leads to a dead-end, or somewhere you’re unwilling to follow, leave it, and move on to the next one. There are more than enough ideas to waste your time chasing those going nowhere.
Detach yourself of the expectation of making the best or right next move. It’s impossible to ever know for certain.
Simply choose a domino, give it a push, and see what happens.
Seeking to Understand
When we set out to create something meaningful for any group of people, no matter how big or small, the first step is always understanding.
Who are they? What are their specific challenges, backstories, and circumstances? Why haven’t the other solutions available been effective for or adopted by them?
When we understand, we can draw up an informed blueprint outlining the best way to solve the problem.
Then, we get to work, follow the plan, and build it.
The trap we often fall into is that we don’t fully understand before we start building. Or more likely we think we understand, but our understanding turns out to be only surface-level.
No matter how embedded in a given community, our own personal understanding of the challenges facing it and the opportunities available is almost never enough.
Sure it might increase our odds of making a lucky guess, but if we truly want to understand how to create the best possible solution to the problem, we need to go deeper than our own experience and delve into the experience of others who might not experience the problem the same way we do.
Understanding rarely goes out of its way to seek us out, which means it’s up to us to do the hard work of seeking ourselves.
Spotting The Potential For Interesting
Five years ago, when I first started editing and producing podcasts, I didn’t plan on sticking with it for long.
I was a huge fan of the medium, but I certainly didn’t plan on building a team around my production business, writing about it in-depth, and dedicating the majority of my waking hours to thinking about it.
No, initially, it was just a means to an end. A way to start an online business that would allow me to travel and work from anywhere in the world, while giving my real passion a chance to incubate and grow into what I was certain would become my real business.
That passion was photography.
In the end, the photography business never got off the ground, mainly because the podcasting one did, leaving me too little time to actually put the work into growing the business side of my photography work.
And while photography has become a much smaller part of my life than I once thought it would, it’s still one of the great teachers to me on how to approach creative work with patience and intention.
Recognizing The Potential For Interesting
After two years of neglecting the practice almost entirely, lately, I’ve been making an effort to bring my camera out with me more often, mainly by bringing it along for each of my morning walks through Belgrade.
One crisp but sunny morning this week, I was walking through the grassy park abutting St Mark’s, a striking Serbian Orthodox church, built of huge tan blocks of stone sandwiched between angular rows of red mortar. The design is both simple and spectacular and is one of the most recognizable landmarks of the city.
As I make my way to exit the park, I watch as one of the old, Yugoslavian-era tram cars parked pulls up just inside the park, coming to a stop beside the large walkway leading up to the church’s entrance.
These old trams come in a variety of colours, most commonly dull hues of red, green, and yellow, all of which are mixed with a significant amount of rust. And despite their dated, utilitarian design, there’s something quaint about them that I’m always drawn to.
With this rusty red car, in particular, and the scene it’s set in, parked as it is in the foreground of this spectacular old church with similarly coloured adornment, something catches my eye.
I can’t tell exactly what it is. Some kind of subtle symmetry between these two objects perhaps? Analogy? Juxtaposition? Whatever’s going on, it’s interesting.
And so I start exploring the perimeter of the park, trying to line up a photo that captures this curious relationship between church and tram in a compelling way.
After a few minutes of hunting for the perfect angle, however, the tramcar pulls away, leaving me empty-empty handed.
Sometimes, more often than not, in fact, that’s simply the way it goes, especially when it comes to street photography.
Work With What You Have
As opposed to portraiture in a well-controlled studio, with street photography, you as the photographer have little to no control over any of the variables at play.
The lighting and arrangement of the elements comprising your shot are often fixed by your environment. In many cases, your subject itself is liable to walk (or in my case slowly lurch) out of your frame if you wait too long to snap the shutter.
What you have, and what you must learn to rely on, is your awareness, perspective, and ability to get creative with how you position yourself.
With so little control, you learn that great photos are not made by carefully curating and arranging the elements you’re working with, taking a number of test shots, and adjusting the lighting and placement as you go.
Instead, great photos are made by developing a keen ability to recognize the component parts of a potentially interesting image, and then getting yourself into a position to bring them all together in a novel way.
You might see the potential for interesting down the street, two objects or people that play off of and speak to each other visually in some way. And while the potential for an interesting shot may certainly exist, there’s no way of knowing if an interesting photo itself is actually possible until you walk over and get yourself into position.
As with the tram and the church, more often than not, the potential for interesting does not, in fact, add up to an interesting shot. The framing doesn’t work, the lighting has changed, or your subject has moved on.
But you’ll almost never create any interesting photos if you don’t first learn to spot the potential for interesting, and explore it thoroughly when it comes across your field of view.
And once you’re able to spot that potential, there’s another way of using that knowledge to your advantage.
Use Your Position To Your Advantage
When you develop a keen awareness of the potential for interesting, rather than spotting that potential from afar and chasing it down the street, you can position yourself in a spot that already has one or more interesting raw materials, and simply wait to see what comes across your frame.
Sometimes you end up waiting a long time. But wait long enough and you find that something interesting is almost always bound to happen. When it does, you’re already in position to simply click the shutter.
Sometimes you wait for a specific subject to enter the scene to complete the photo. More often than not, however, the interesting thing that enters your frame and makes the image special is not what you were expecting it to be. In fact, it’s often something you would never have dreamed up.
What great street photographers and creators of all kinds know is that more important than any of the technical skills, gear, or editing, is their ability to recognize the potential for interesting, position themselves in the heart of it, and then wait for the scene to unfold before them.
A question for you this week: Instead of chasing interesting, how can you position yourself in a way that it will come to you?
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
Fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
The Things No One Tells You
No matter the goal we’ve set for ourselves, there are always going to be challenges, hardships, and hard-learned lessons of which we are completely unaware until we’re staring them in the face.
These are the things we wish someone had told us to help us prepare, whether mentally, physically, financially, or most likely, emotionally.
In the moment, we can’t believe the oversight. How could everyone who’s walked this road before us failed to mention the part where it drops away off a cliff edge into the sea?
And so we must choose to either forge ahead or turn back, in either case, furious with having to face this challenge unprepared.
It’s only if and when we make it to the other side of the chasm that we realize the truth.
That maybe we were told but we weren’t listening.
Maybe we didn’t want to listen.
Maybe we didn’t know how to listen.
Maybe we didn’t know what we were supposed to listen for.
Most of all, we realize that on every journey, there are things that can only be experienced to be understood.
That there are rites of passage we must all go through, alone and unprepared.
That our destination is as much a singular place as it is the route we choose to get there.
And most of all, who we become along the way.
No One Wants Anything From You
As creators, we tend to waste a lot of time early in our careers trying to make work we think others want from us.
The truth, however, is that nobody wants anything from us. In fact, they don’t care about us at all.
As Steven Pressfield writes, “Nobody wants to read your shit.”
But while the chances are that no one wants anything from us, there are some creators from whom a given audience actually does want something specific.
The irony is that these are creators who have bucked the notion of catering to expectations, basing their work on a perceived desire, and created something with a singular voice. Work that no one else can create.
We don’t want a new band we’ve never heard of to make music that sounds like our favorite band.
We want our favourite band to make more new music.
Realizing that there are no expectations of us frees us to stop chasing the latest trend and simply create what comes naturally.
With enough time and persistence, we may be lucky enough to develop our own singular voice and an audience that wants it and only it.
But until then–in fact especially then–better to ignore the expectations and desires of others, and create what only you can create.
Realistic Expectations
Part of the problem building a creative career feels so hard is that we’re often working off of faulty assumptions and unrealistic expectations.
We think that we can buckle down and in 6 months to a year from now be living that 6-figure online business dream life.
What if we knew going in that it was going to take 5-10 years to build something sustainable?
Something we were truly proud to put our name on.
Something that has the weight and momentum to create real change.
Would we still have started?
I think we would have.
But I think we’d have done it differently.
If we knew we weren’t supposed to have all the answers out of the starting gate, maybe we would have started by experimenting, trying a dozen different things and seeing what stuck.
If we knew that overnight success was a myth, maybe we’d have buckled down, picked a strategy, and opted for the consistent, boring actions that lead to real progress.
If we knew our work was supposed to suck at the start, maybe we wouldn’t have waited so long to ship it, knowing that it was never going to be the work to make or break us.
Maybe we would have had an easier time publishing the shitty stuff until it improved. First to mediocre, then solid, and then maybe even great.
If we knew our first big success would only be the first of many hills to climb, maybe we’d have lowered the pedestal we put it on and made it easier to attain.
If we knew attention without trust was meaningless, maybe we’d have spent more time engaging with the people already in our circle and less time trying to bring new people in.
If we knew the greatest thing we could offer was our unique perspective, maybe we wouldn’t have wasted so much time trying to emulate the style and content of everyone else.
Maybe we would have committed to the initial loneliness of creating singular work, knowing that if we could just get those first ten raving fans, they would bring in the next hundred themselves.
The good news is that we know these things now, and it’s not too late to recalibrate our expectations.
2 Types of Motivators
Anger, fear, scarcity, FOMO, loss aversion, loneliness, shame and guilt.
Negative emotions like these can be powerful motivators in driving our customers to take the action we want them to take.
In fact, they’re some of the most common buttons marketers push in order to motivate buyers who are on the fence.
But they’re not the only motivators we have available to us.
Hope, desire, love, trust, affinity, joy, excitement, curiosity, pride, belonging, possibility.
These are powerful motivators as well.
Instead of aiming to show our customers how small and weak they are without us, these motivators call on them to step up, to reach for their potential, to be and become their best selves.
Rather than denigration, this type of marketing is about actualization.
And not just for our customers, but for us as well.
Whether or not we realize it, sooner or later we all end up eating our own dog food.
Marketing built on negative motivators influences our own work as well. Under its influence, we begin looking to cut corners, compromise on our integrity, and create work that lacks depth, meaning, and impact. As long as it sells, who cares?
Marketing built on positive motivators, on possibility and potential, however, does the opposite. It motivates us to be our best selves. To create our best work, to be generous and empathetic in our marketing, and to take a view that honours what’s best for our customers, communities and ourselves in the long run.
This type of marketing is generative. A call to adventure. An invitation to step into what could be.
We get to decide which type of motivation we use in our marketing.
Game-Changing Content
For every piece of content you create, it’s a good idea to have one person in mind for whom that content will be a game-changer.
Whether it’s a podcast, blog post, YouTube video, or any other content piece, be clear on the one specific problem you’re addressing for one specific person. This allows you to break down and explain the idea in a way that you know will benefit that person in a meaningful way.
Too often, we get caught up in our desire for scale, chasing views, downloads, and subscribers, and forget the point of content creation in the first place: To create something useful for others.
In search of scale, we often neglect impact, focusing more on distribution than on substance.
What we fail to realize is that content that spreads and reaches a larger audience, does so because individual consumers talk about it.
Sure, effective distribution can help hasten the spread of a remarkable piece of content, but it needs to be remarkable first for it to continue to spread.
Creating content with the intent of changing things for just one person helps keep you from pandering. From watering down. From creating what you think you’re supposed to create over what you know would be helpful.
It grants you the focus to create the best piece of content you’re able to on your given topic.
Creating for an aspirational audience of thousands makes defining a singular goal for your content nearly impossible.
Creating for one, however, allows you to begin with the end in mind. It gives you clarity on where your audience is starting from and where you need to get them to by the end of the content in question.
It removes the guesswork and allows you to simply fill in the blanks, paving the path to understanding brick by brick.
And if you can pave a path that can get one person to their destination, it’s only a matter of time before they share it with another person, and another, and another, and another.
All content that spreads starts with one person for whom it resonated so deeply that they couldn’t help but pass it on.
So who’s your next person and what’s the problem you can solve for them?
Marketing Is Inherently Inefficient
When it comes to our marketing, we’re often in search of a formula that will consistently and reliably deliver the results we’re looking for.
Input x and receive y.
Whether it’s ad spend, conversion rate or any other metric we choose to track, what we’re striving for with our marketing is often efficiency.
This is a worthy objective, no point in doing or spending more than you need when a few small tweaks here or there could improve your results.
The problem is that effective marketing over the long run–while it might be made up of a number of well-oiled components–is always a highly inefficient process.
For every marketing tool or technique we’re able to optimize fully, we’ve likely had to test and tweak our way through a handful of others that couldn’t pass muster.
There’s no perfect template or formula for effective marketing. No way to connect the dots with perfect efficiency.
Marketing that’s wildly successful for someone else, their personality, style, content, and audience might not work for us. And even when we land on a strategy that works in the moment, it’s surely only a matter of time before its returns begin to decline.
When our only metric is maximum efficiency, we’re incentivized to ignore all the inefficient exploration and experimentation that is required to sustain our marketing over the long haul.
Our job then, as marketers and creators is to constantly seek out new ways to connect and build relationships with our ideal audience members. To test and tweak and experiment our way through often-unproven, even seemly irrational strategies in search of the ones that might unexpectedly work for us.
There’s no reason any of us can’t stumble on on a new strategy.
Marketing, like science, is filled with discoveries made by common folk like us.
What’s more, we already have our starting point.
If we’ve done our homework, we know our audience as well as they know themselves.
We know what they read, listen to, consume, and where they hang out online.
We know where they’re looking to go, the challenges in their path, and the solutions we’re best positioned to deliver.
With the map already filled in, we only need to get creative in making a connection. Capturing their attention just long enough for them to realize that we’re exactly what they’ve been looking for.
With this as our goal, it’s not hard to see that there are dozens, maybe even hundreds of ways to capture that attention.
Which means all we have to do is start experimenting, doubling down on what works and rejecting what doesn’t.
Creative Wayfinding For Ambitious Optimists.
Embracing the Mentality of the Underdog Creator
The mentality of the underdog is an empowering mindset to own and embody.
The underdog expects that nothing will come easy.
That nothing will be freely given.
That everything they desire must be worked, clawed, and fought for.
The underdog owns her situation.
She doesn’t blame or begrudge, others, fate, or the system she is working to change for her hardships and the inequities forced upon her (even though they may be stacked against her).
She simply recommits to working harder, taking a new tack, approaching the challenge from a different angle. Time and time and time again until she succeeds.
The underdog knows that when so little is freely given, one of the most powerful acts is to freely give.
To share what little comes her way with those less fortunate.
For there are always those that are less fortunate.
She passes on what she has learned.
Lifts up instead of puts down.
Takes on the role of the champion, cheerleader and supporter she wishes she had when she was starting out with less than she has now.
The underdog knows that while this tactic or that might not work, if she keeps trying, experimenting, exploring every angle of her problem, eventually it will be solved.
She maintains belief.
Trust in herself.
Hope in the face of endless adversity.
That one day, it will pay off.
That her work has the power to change things in a deep and meaningful way, if only for a few people.
We could all use a bit more of the underdog mentality.
Ideas & Broken Bones
Getting a new idea off the ground is a lot like healing from a broken bone.
New ideas are typically made up of two (or more) disparate ideas that have never been connected and must now be grafted together.
We set them in place, and at first glance, they might look complete. But apply even the smallest amount of pressure and instantly, they splinter back into their component parts.
In order to fuse properly, new ideas must be given support, encased in a protective cast, and given time for the connections to strengthen into something that can support weight.
Over time, the ideas will fuse to become one, the seams between the original building blocks no longer obvious. At this point, the cast can be removed, but while the core of the idea is whole, the muscles supporting it must now be tested and trained, building up strength and confidence over time.
As with a broken bone, new ideas are fragile and must be given the proper time, care, and support in order to one day bear weight.
Don’t rush the process.
Push the Domino
We often hold back on taking action because we’re uncertain of the effect it will have.
Sure, we have an idea that might work, but what if it doesn’t give us the result we were looking for?
What if, in hindsight, we realize that we would have been better off taking that other action instead? Or the other action besides that?
One of the core traits of successful creators is an eagerness to topple the first domino and simply see what happens.
Rather than get hung up on the blank page or the empty canvas, they commit easily to writing the first line, to making the first brush stroke.
They understand that it’s impossible to ruin their work before it’s begun, and that the only way to uncover the potential of the seed of the idea in their head is by getting it out of their head and playing with it in a more physical form.
The creative process is equal parts practice & preparation, and then relinquishing control and letting an idea take you where it wants to go.
If it leads to a dead-end, or somewhere you’re unwilling to follow, leave it, and move on to the next one. There are more than enough ideas to waste your time chasing those going nowhere.
Detach yourself of the expectation of making the best or right next move. It’s impossible to ever know for certain.
Simply choose a domino, give it a push, and see what happens.
Seeking to Understand
When we set out to create something meaningful for any group of people, no matter how big or small, the first step is always understanding.
Who are they? What are their specific challenges, backstories, and circumstances? Why haven’t the other solutions available been effective for or adopted by them?
When we understand, we can draw up an informed blueprint outlining the best way to solve the problem.
Then, we get to work, follow the plan, and build it.
The trap we often fall into is that we don’t fully understand before we start building. Or more likely we think we understand, but our understanding turns out to be only surface-level.
No matter how embedded in a given community, our own personal understanding of the challenges facing it and the opportunities available is almost never enough.
Sure it might increase our odds of making a lucky guess, but if we truly want to understand how to create the best possible solution to the problem, we need to go deeper than our own experience and delve into the experience of others who might not experience the problem the same way we do.
Understanding rarely goes out of its way to seek us out, which means it’s up to us to do the hard work of seeking ourselves.
Spotting The Potential For Interesting
Five years ago, when I first started editing and producing podcasts, I didn’t plan on sticking with it for long.
I was a huge fan of the medium, but I certainly didn’t plan on building a team around my production business, writing about it in-depth, and dedicating the majority of my waking hours to thinking about it.
No, initially, it was just a means to an end. A way to start an online business that would allow me to travel and work from anywhere in the world, while giving my real passion a chance to incubate and grow into what I was certain would become my real business.
That passion was photography.
In the end, the photography business never got off the ground, mainly because the podcasting one did, leaving me too little time to actually put the work into growing the business side of my photography work.
And while photography has become a much smaller part of my life than I once thought it would, it’s still one of the great teachers to me on how to approach creative work with patience and intention.
Recognizing The Potential For Interesting
After two years of neglecting the practice almost entirely, lately, I’ve been making an effort to bring my camera out with me more often, mainly by bringing it along for each of my morning walks through Belgrade.
One crisp but sunny morning this week, I was walking through the grassy park abutting St Mark’s, a striking Serbian Orthodox church, built of huge tan blocks of stone sandwiched between angular rows of red mortar. The design is both simple and spectacular and is one of the most recognizable landmarks of the city.
As I make my way to exit the park, I watch as one of the old, Yugoslavian-era tram cars parked pulls up just inside the park, coming to a stop beside the large walkway leading up to the church’s entrance.
These old trams come in a variety of colours, most commonly dull hues of red, green, and yellow, all of which are mixed with a significant amount of rust. And despite their dated, utilitarian design, there’s something quaint about them that I’m always drawn to.
With this rusty red car, in particular, and the scene it’s set in, parked as it is in the foreground of this spectacular old church with similarly coloured adornment, something catches my eye.
I can’t tell exactly what it is. Some kind of subtle symmetry between these two objects perhaps? Analogy? Juxtaposition? Whatever’s going on, it’s interesting.
And so I start exploring the perimeter of the park, trying to line up a photo that captures this curious relationship between church and tram in a compelling way.
After a few minutes of hunting for the perfect angle, however, the tramcar pulls away, leaving me empty-empty handed.
Sometimes, more often than not, in fact, that’s simply the way it goes, especially when it comes to street photography.
Work With What You Have
As opposed to portraiture in a well-controlled studio, with street photography, you as the photographer have little to no control over any of the variables at play.
The lighting and arrangement of the elements comprising your shot are often fixed by your environment. In many cases, your subject itself is liable to walk (or in my case slowly lurch) out of your frame if you wait too long to snap the shutter.
What you have, and what you must learn to rely on, is your awareness, perspective, and ability to get creative with how you position yourself.
With so little control, you learn that great photos are not made by carefully curating and arranging the elements you’re working with, taking a number of test shots, and adjusting the lighting and placement as you go.
Instead, great photos are made by developing a keen ability to recognize the component parts of a potentially interesting image, and then getting yourself into a position to bring them all together in a novel way.
You might see the potential for interesting down the street, two objects or people that play off of and speak to each other visually in some way. And while the potential for an interesting shot may certainly exist, there’s no way of knowing if an interesting photo itself is actually possible until you walk over and get yourself into position.
As with the tram and the church, more often than not, the potential for interesting does not, in fact, add up to an interesting shot. The framing doesn’t work, the lighting has changed, or your subject has moved on.
But you’ll almost never create any interesting photos if you don’t first learn to spot the potential for interesting, and explore it thoroughly when it comes across your field of view.
And once you’re able to spot that potential, there’s another way of using that knowledge to your advantage.
Use Your Position To Your Advantage
When you develop a keen awareness of the potential for interesting, rather than spotting that potential from afar and chasing it down the street, you can position yourself in a spot that already has one or more interesting raw materials, and simply wait to see what comes across your frame.
Sometimes you end up waiting a long time. But wait long enough and you find that something interesting is almost always bound to happen. When it does, you’re already in position to simply click the shutter.
Sometimes you wait for a specific subject to enter the scene to complete the photo. More often than not, however, the interesting thing that enters your frame and makes the image special is not what you were expecting it to be. In fact, it’s often something you would never have dreamed up.
What great street photographers and creators of all kinds know is that more important than any of the technical skills, gear, or editing, is their ability to recognize the potential for interesting, position themselves in the heart of it, and then wait for the scene to unfold before them.
A question for you this week: Instead of chasing interesting, how can you position yourself in a way that it will come to you?
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Listen Up Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
Fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilderness of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
The Things No One Tells You
No matter the goal we’ve set for ourselves, there are always going to be challenges, hardships, and hard-learned lessons of which we are completely unaware until we’re staring them in the face.
These are the things we wish someone had told us to help us prepare, whether mentally, physically, financially, or most likely, emotionally.
In the moment, we can’t believe the oversight. How could everyone who’s walked this road before us failed to mention the part where it drops away off a cliff edge into the sea?
And so we must choose to either forge ahead or turn back, in either case, furious with having to face this challenge unprepared.
It’s only if and when we make it to the other side of the chasm that we realize the truth.
That maybe we were told but we weren’t listening.
Maybe we didn’t want to listen.
Maybe we didn’t know how to listen.
Maybe we didn’t know what we were supposed to listen for.
Most of all, we realize that on every journey, there are things that can only be experienced to be understood.
That there are rites of passage we must all go through, alone and unprepared.
That our destination is as much a singular place as it is the route we choose to get there.
And most of all, who we become along the way.
No One Wants Anything From You
As creators, we tend to waste a lot of time early in our careers trying to make work we think others want from us.
The truth, however, is that nobody wants anything from us. In fact, they don’t care about us at all.
As Steven Pressfield writes, “Nobody wants to read your shit.”
But while the chances are that no one wants anything from us, there are some creators from whom a given audience actually does want something specific.
The irony is that these are creators who have bucked the notion of catering to expectations, basing their work on a perceived desire, and created something with a singular voice. Work that no one else can create.
We don’t want a new band we’ve never heard of to make music that sounds like our favorite band.
We want our favourite band to make more new music.
Realizing that there are no expectations of us frees us to stop chasing the latest trend and simply create what comes naturally.
With enough time and persistence, we may be lucky enough to develop our own singular voice and an audience that wants it and only it.
But until then–in fact especially then–better to ignore the expectations and desires of others, and create what only you can create.
Realistic Expectations
Part of the problem building a creative career feels so hard is that we’re often working off of faulty assumptions and unrealistic expectations.
We think that we can buckle down and in 6 months to a year from now be living that 6-figure online business dream life.
What if we knew going in that it was going to take 5-10 years to build something sustainable?
Something we were truly proud to put our name on.
Something that has the weight and momentum to create real change.
Would we still have started?
I think we would have.
But I think we’d have done it differently.
If we knew we weren’t supposed to have all the answers out of the starting gate, maybe we would have started by experimenting, trying a dozen different things and seeing what stuck.
If we knew that overnight success was a myth, maybe we’d have buckled down, picked a strategy, and opted for the consistent, boring actions that lead to real progress.
If we knew our work was supposed to suck at the start, maybe we wouldn’t have waited so long to ship it, knowing that it was never going to be the work to make or break us.
Maybe we would have had an easier time publishing the shitty stuff until it improved. First to mediocre, then solid, and then maybe even great.
If we knew our first big success would only be the first of many hills to climb, maybe we’d have lowered the pedestal we put it on and made it easier to attain.
If we knew attention without trust was meaningless, maybe we’d have spent more time engaging with the people already in our circle and less time trying to bring new people in.
If we knew the greatest thing we could offer was our unique perspective, maybe we wouldn’t have wasted so much time trying to emulate the style and content of everyone else.
Maybe we would have committed to the initial loneliness of creating singular work, knowing that if we could just get those first ten raving fans, they would bring in the next hundred themselves.
The good news is that we know these things now, and it’s not too late to recalibrate our expectations.
2 Types of Motivators
Anger, fear, scarcity, FOMO, loss aversion, loneliness, shame and guilt.
Negative emotions like these can be powerful motivators in driving our customers to take the action we want them to take.
In fact, they’re some of the most common buttons marketers push in order to motivate buyers who are on the fence.
But they’re not the only motivators we have available to us.
Hope, desire, love, trust, affinity, joy, excitement, curiosity, pride, belonging, possibility.
These are powerful motivators as well.
Instead of aiming to show our customers how small and weak they are without us, these motivators call on them to step up, to reach for their potential, to be and become their best selves.
Rather than denigration, this type of marketing is about actualization.
And not just for our customers, but for us as well.
Whether or not we realize it, sooner or later we all end up eating our own dog food.
Marketing built on negative motivators influences our own work as well. Under its influence, we begin looking to cut corners, compromise on our integrity, and create work that lacks depth, meaning, and impact. As long as it sells, who cares?
Marketing built on positive motivators, on possibility and potential, however, does the opposite. It motivates us to be our best selves. To create our best work, to be generous and empathetic in our marketing, and to take a view that honours what’s best for our customers, communities and ourselves in the long run.
This type of marketing is generative. A call to adventure. An invitation to step into what could be.
We get to decide which type of motivation we use in our marketing.
Game-Changing Content
For every piece of content you create, it’s a good idea to have one person in mind for whom that content will be a game-changer.
Whether it’s a podcast, blog post, YouTube video, or any other content piece, be clear on the one specific problem you’re addressing for one specific person. This allows you to break down and explain the idea in a way that you know will benefit that person in a meaningful way.
Too often, we get caught up in our desire for scale, chasing views, downloads, and subscribers, and forget the point of content creation in the first place: To create something useful for others.
In search of scale, we often neglect impact, focusing more on distribution than on substance.
What we fail to realize is that content that spreads and reaches a larger audience, does so because individual consumers talk about it.
Sure, effective distribution can help hasten the spread of a remarkable piece of content, but it needs to be remarkable first for it to continue to spread.
Creating content with the intent of changing things for just one person helps keep you from pandering. From watering down. From creating what you think you’re supposed to create over what you know would be helpful.
It grants you the focus to create the best piece of content you’re able to on your given topic.
Creating for an aspirational audience of thousands makes defining a singular goal for your content nearly impossible.
Creating for one, however, allows you to begin with the end in mind. It gives you clarity on where your audience is starting from and where you need to get them to by the end of the content in question.
It removes the guesswork and allows you to simply fill in the blanks, paving the path to understanding brick by brick.
And if you can pave a path that can get one person to their destination, it’s only a matter of time before they share it with another person, and another, and another, and another.
All content that spreads starts with one person for whom it resonated so deeply that they couldn’t help but pass it on.
So who’s your next person and what’s the problem you can solve for them?
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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.