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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