Imagine sitting at your kitchen table with a thousand puzzle pieces scattered before you.

A small island of interconnected pieces has taken shape. They were easy—the only face in the whole scene. You reach for a piece that looks like it could be part of the person’s hair. After rotating it and testing the fit a few times, you confirm it’s not the right one.

Then, angered that it didn’t work, you toss the entire table over in a furious rage. With pieces flying in every direction, you swear off jigsaw puzzles forever, convince yourself you stink at them, and remind yourself that you always knew this was how it would go. Then you slide into depression and inhale an entire can of Pringles, beating yourself up for not choosing the right piece.

Woah, you’re probably thinking, That’s not me, but whoever it is sounds like they have some serious anger management issues.

I know, it’s silly to think about getting so worked up over a simple jigsaw puzzle. Most people don’t descend into a shame spiral and immediately quit if one piece doesn’t fit. Most people just put it down and look for another one to try.

But what if the endeavor felt a little more…important?

In real life, how often do we beat ourselves up for making a wrong move? How often do we quit after the first setback? How often do we even hesitate to begin something new because we’re convinced it is beyond our capabilities, worried the journey is too arduous, or that we’ll look foolish to others if we struggle?

Maybe you’re engaged with a different kind of puzzle right now…

• Perhaps you’re trying to get a business idea off the ground
• Helping a child deal with a newly diagnosed health issue.
• Struggling to keep morale up amongst your team.
• Or maybe you’re adjusting to an overwhelmingly different work routine or environment.

Like a sea of puzzle pieces laid across your kitchen table, it probably feels pretty overwhelming. But what if you reframed your current challenge to be more like the approach you’d take in putting it together?

You know in advance what the end picture (aka “success”) is supposed to look like. 

You know that every piece you pick up isn’t going to fit perfectly the first time.

You’re not sure how long it will take, but you know that if you keep trying pieces that look like they could work, you’ll eventually complete the puzzle.

And, most importantly, you know that you are not an idiot or a terrible person simply because one thing you tried didn’t work. Especially if it’s a puzzle you’ve never encountered before.

Sure, the stakes for your challenge are higher than those surrounding the assembly of a silly jigsaw puzzle.

However.

The strategies for solving it are exactly the same.

Anger and anxiety are not going to help one bit.

That’s why I always praise the benefits of tinkering.

Tinkering—and its delightfully playful connotation—helps lower the anxiety level so we can think more clearly. It reframes our mistakes so they are not so devastating, preventing anger and shame from getting a foothold.

Tinkering is a great tool that’s a lot like putting together a jigsaw puzzle.

You try a piece that looks like it might fit. If it doesn’t, you simply look for and try another one, and another one, until you find the one that does. Then you keep going, celebrating the little wins along the way. (There’s something gratifying about the feeling when a piece clicks into place, isn’t there?)

Oh, and you don’t toss the table in a fit of rage when something doesn’t work.

So, you know that dilemma you’re mired in right now? The one that’s got you filled with frustration and self-doubt?

Yes, it’s more important than a simple jigsaw puzzle.

But treating it more like one might be the missing piece you need to solve it.

🤔 I wonder…what current challenge in your life might benefit from being looked at more like a jigsaw puzzle?

“Here goes nothing.”

It’s a phrase we often use when we’re not sure how something will turn out. In fact, since it tends to come from a sense of desperation, we use it to admit that there’s a pretty good chance of it not working. It’s our little way of softening the psychological blow of failing.

It makes me think of the pass play in football referred to as a “Hail Mary.” The team with the ball is losing, and time has nearly expired. They need a touchdown but they’re so far from the goal line that their only hope is to launch a long pass into a sea of waiting defenders. It’s a pass with a very low chance of success, but at that point, you’re out of options. 

Here. Goes. Nothing. 

However.

This isn’t a football game.

Trying things that might not work is not nothing.

It takes tremendous courage, vulnerability, and faith. Dare I say it’s the most important thing we can ever do.

Doing things that we are sure will work is safe and comfortable. Chasing guarantees is one way to go about our days, but if this is all we ever do, we will have wasted our life. This is not why we were born.

When you try something that might not work, it’s true: it might not. But in the end, many other good things will have come of it. At the very least, you will have learned something and your comfort zone will have inched a little larger.

And that’s definitely not nothing.

We recently hosted our third Wondernite. Before our first, I had no idea if it would work. I didn’t know if anyone would come. I didn’t know if I even sell one painting. There was a distinct possibility that my brother Doug would go through all twenty items up for auction and not receive one bid and I’d have the exciting opportunity to descend into a catastrophically humiliating shame spiral while sitting in the back of the room. Thankfully for all concerned parties, it turned out well enough that we are currently planning our fourth.

By the same token, we’ve also invested thousands of dollars into trade shows that did not deliver a good return on investment. They drove us deeper into debt. They bordered on soul-crushing. But the lessons we learned in the process, about marketing, positioning, pricing, and branding, were invaluable, and part of the reason Wondernite turned out to be a success.

Tinker. Play. Experiment. Try things that might not work. And when you cast off into the unknown, you can be confident in saying to yourself, “Here goes something!!!”

In my family growing up, I was always the art guy. Today, I make a living painting pictures, telling stories and writing books.

My younger brother Dan was the science guy. He now works for a cancer hospital analyzing and improving “systems,” or something structured and boring like that.

I always saw us as complete opposites, which is how I think most people see art and science.

Yes, my brother and I are different, but I was also decent at math and enjoyed doing experiments in chemistry class. Meanwhile, he had a pretty good drawing talent that went under the radar. Today he collects Pearl Jam posters because he appreciates the art.

I was so locked in to looking at the difference between us that I never noticed the connections.

Artists are thought of as free-spirited, open-ended, and subjective. Scientists are often viewed as analytical, precise, and objective.

But Science is not cold, rigid, and unfeeling. Art is not some frivolous, fluffy extra. Believe it or not, they are connected.

Curiosity and Imagination are the parents of both art and science.

The same curiosity and imagination that is present when an artist creates a new play, sculpture, or piece of music is present in the best scientists as well. We imagine space travel, and curiosity asks, “How can we make that happen?” We imagine a world without cancer, and curiosity asks, “What hasn’t been tried on this particular strain?” Curiosity asks, “How can we become more energy independent?” and our imagination gets to work on thinking up a whole bunch of possible solutions, ranging from the far-fetched to the less so. Sometimes solutions are hidden within an idea that seems completely preposterous.

This painting was inspired by my first trip to Vancouver, and by a quote often attributed to Albert Einstein: “Logic will get you from A to B. Imagination will take you everywhere.”

Imagination is often seen as a peculiar skillset of children and the pastime of daydreamers. Mildly amusing, but hardly practical for a self-respecting adult. Too often, our imaginations fade as we grow older. We stop asking questions and dreaming big. We reward the rule-followers. We search for and obediently follow the the best practices.

But in a changing world, what worked before will not get us to where we need to go. There is no roadmap. No formula. No step-by-step manual to help us succeed tomorrow.

The well-worn paths we’re used to treading now only lead us astray, to a world that no longer exists.

So what now?

We must stop looking at science and art as opposing forces.

We need to realize that we are all artists. Working in paint, charcoal, or clay is not required.

And likewise, we are all scientists. Even if we don’t wear lab coats.

If you are stuck, or have a sneaking suspicion that things could be better in your life, your relationships, or your organization…you are right.

The way forward is to imagine a better reality, the future we wish to create. And then we tinker our way there, by trying things that might not work and using what we learn to guide our next steps — even small stapes — forward.

Imagination. It’s not just a plaything for children.

Dust yours off. It can take you to some pretty amazing places.

We just wrapped up Escape Adulthood Summit #6. I’m definitely tired, but also overflowing with joy from being around such awesome people that renew my hope in humanity.

As Kim and I pulled away from the barn in the big yellow rental truck, she said, “Even if we never get to do another one, no regrets.”

She was referring to a discussion we had back in 2011, on a chilly night in a cozy cabin in Alaska. We talked about regrets that night, and asked, “If we only had one more year together, is there anything we’d regret?”

The only thing that came up was the “live event.” For years, we dreamed about hosting an in-person conference for Adultitis Fighters. We had experience organizing events and attending retreats. What we didn’t have was the certainty that anyone would come to ours.

We doubted whether or not we’d even get one person to sign up. Long story short, we did. Every single Summit has sold out so far. And every one has been special in its own way.

At the beginning, I had a pretty good idea of what failure looked like. But this time was the first time I thought about what things would look like if we hadn’t even tried.

Most of us, when considering the prospect of pursuing something new – a new project, place to live, degree, career, or relationship – we make a list of pros and cons. Oftentimes, the doubts carry more weight and the cons win the day.

That discussion in Alaska felt very personal, and maybe even a bit selfish. It was about our dreams, our doubts, our regrets. I never considered how much our decision would affect other people. As we drove away in the big yellow truck last Tuesday night, I envisioned a scenario in which we had allowed our doubts to keep us from trying that first one. Suddenly, all the good things that have come from six Escape Adulthood Summits – all the friendships formed, relationships repaired, memories made, light bulbs lit, laughs shared and lives changed – vanish in an instant like smoke in the wind. All the grateful eyes and smiling faces of the hundreds of people who’ve attended disappear from my memory. It’s a sad and terrible thought, enough to bring me to tears.

I am proud that we didn’t give in to the doubts. Mostly because I know how often I have.

Then I think of all the first-timers who attended, and who certainly had doubts about what they were getting themselves into. There is a lot of mystery to each Summit, because there’s nothing quite like it and we have a lot of surprises we keep secret. I hope they are happy they pushed past the doubts, and realize how much of an impact their presence had on the lives of the people they encountered.

Paying no mind to the doubts in our head is a hard thing. But we must.

“Doubt kills more dreams than failure ever will.” – Karim Seddiki

What’s something that you’d regret not giving a shot? Is doubt the thing holding you back? Instead of listing all the reasons it might not work, dream up a vision of what it looks like if it does.

Your courage has consequences that impact more lives than your own.