The Art of Figuring Shit Out (A Trainable Skill Supporting Thriving over Surviving)

The Soulpreneur Series Free Issue No. 31

Most people aren’t struggling with change.

They’re struggling by resisting change.

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The world moves—fast (literally and metaphorically).

Change is one of the few constants — right along with time.

New industries emerge. Old ones collapse.

Algorithms shift. Business models expire.

Jobs are created. Jobs are lost.

What worked last year is already outdated.

Sometimes, what worked last month, last week… is now outdated.

And yet, most people—and many institutions—cling to the past.

• They follow playbooks written for an old game.

• They wait for permission, validation, certainty.

• They react instead of adapt.

The most valuable skill today isn’t what you know.

It’s often your ability, flexibility, and persistency to move forward without knowing.

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Death Clocks (& CEO of My Time)

A powerful anecdote I heard last week is still sitting with me:

Many people die at about 25 years old but don’t get buried until they’re in their 70s.

It’s often attributed to Benjamin Franklin, but no real evidence exists that he wrote it somewhere.

In the past, I’ve written about this similarly — in relation to a powerful website highlighting a “Death Clock.”

Put in some details, and get an estimate of your estimated life span.

• In other words, how much time do I have left?

I find it an immensely motivating concept. However, I'm also in my fifth decade of circling the sun.

This is a big part of why I left a secure, six-figure, decade-plus career in the corporate public sector (in early 2022) to start building my own creative enterprises.

CEO of my time and energy.

Becoming an entrepreneur (as opposed to a wantrepreneur).

When I walked I had no clients lined up. No contracts. No significant financial runway. (I borrowed from my future pension and, for some things, leaned on credit cards.)

I had a deep drive that I’d figure shit out.

And, you know what?

This April will be 3 years independent. I’ve figured shit out this far along.

So much so my wife Lisa made a similar choice in June 2023.

She became CEO of her time and energy — starting and building a private counselling practice and her own creative enterprises.

We both subscribe to The Art of the Figure-out-able

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Think. Adapt. Create.

These three skills separate those who thrive from those who don’t.

They aren’t talents. They aren’t gifts.

They are disciplines—trainable, repeatable, essential.

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1. Master the Art of the Figure-Out-Able (Adaptation)

Most people assume they need perfect conditions before they can begin.

They wait until they have more knowledge, more money, more time.

They don’t realize clarity comes from action, not just thinking.

• Plans don’t survive reality. Act, adjust, refine—fast.

• Every problem has echoes of a past solution. Look for patterns.

• Stop waiting for instructions. Ask: “How can I solve this with what I have?”

The universe doesn’t reward the best ideas. It opens up possibilities for people who execute before they feel ready.

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2. Turn Setbacks into Springboards (Resilience)

Most people treat obstacles as dead ends.

They see failure as proof they should stop.

But resilience is built in the aftermath—not the moment itself. Here’s some shifts to try:

• How can I turn this failure into fuel? Setbacks are tuition. Learn from them.

• What if I measured progress by scars, not streaks? The best lessons don’t show up as wins—yet.

• Where is discomfort pointing me next? Resilience isn’t just about bouncing back — it’s about bouncing forward.

The world is full of opportunity and potential for those who endure, learn, and keep moving forward.

This is why I regularly say “be consistent” is Bullshit.

At its roots, ‘consistent’ means to stand in place. Instead:

Be Persistent!

Per- means forward.

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3. Break the Mental Autopilot (Creativity)

Most people assume creativity is a flash of brilliance (but that’s largely Bullshit).

Creativity isn’t magic.

It’s the result of thinking differently. Its root meaning also means “to grow.”

• Want to be more creative?

Then, support and facilitate more space for creative things to grow.

Don’t wait for the perfect conditions — the writing course, the studio, the perfect quiet, etc.

• Teach a flawed version of something first. You’ll understand it better by fixing it in real-time.

• Study what almost worked (and why). Failures at the edge of success reveal a lot. Outright disasters reveal a whole world of opportunity.

• Destroy your best ideas and rebuild them differently. What remains after you strip them down?

Creativity isn’t about inspiration or perfection. It’s about exploration. Persistency.

• Thinking and Unthinking

• Learning and Unlearning

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Tangible Ways to Hone These Skills

If you want to thrive in uncertainty, you must train for it.

Here are three ways to try that:

1. The 30-Day Experiment

Yes — these have become cliché. But damn it, they can also work marvellously.

Choose one thing outside your comfort zone and commit to it for 30 days.

It can be a skill, a habit, or a practice.

At the end, reflect:

• What did I learn?

• What surprised me?

• What should I do more of? (the gurus call it: “doubling down”)

For example, I’ve just completed a 30-day walking challenge.

I quietly committed to doing it. Yesterday was day 40 in a row—and over that time, I’ve walked over 200 km.

This included while I was travelling (in St. Louis, MO) and through the coldest weather of the year (one day here at home was -25C 🥶)

One of the best parts of this little challenge?

• The clarity of thought it brings me. The creativity-fuel it provides.

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2. The ‘What If…’ Reframe

The next time you hit a creativity or business challenge, try not to ask: “Why me?”

Try Asking: What if this is happening for me?

How would the challenge look different if it was actually an opportunity?

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3. The Reverse Engineer Method

Instead of consuming content passively, break it down.

Pick a book, article, or podcast. Ask:

• Why did the author structure it this way?

• What assumptions are they making?

• How could I improve or challenge their argument or approach?

Most people don’t have a creativity problem.

They have a thinking problem.

They follow the set path instead of questioning the terrain.

They cling to the known instead of exploring the unknown.

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But here’s the reality…

Default thinking often leads to a default life.

Challenge. Upgrade. Strengthen. Re-fresh-en

If you want to stay ahead or at least feel more alive… stay fresh.

Train and build these skills daily by:

• Challenging your defaults.

• Upgrading your patterns.

• Strengthening your tolerance for uncertainty.

The reality of today’s world isn’t knowing…

It’s figuring things out—again and again and again. Over and over and over…

Imagine if businesses were built around selling ignorance—not pretending to know.

Or a business built on mastering The Art of Figuring Shit Out.

This is a buildable mindset. It’s also a practice.

And it’s one you can train.

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What do you think?

Do you have practices related to The Art of Figuring Shit Out?

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Box Cutter Co. | The Soulpreneur Series