What If the Point Was Just to See What We’re Capable Of?

In defense of being a ‘jack of all trades’

“For me, wandering isn’t aimlessness. It’s testing the edges of what I might be capable of.”

Turkish coffee, a simit, and a window onto Istanbul’s version of multitasking: me reflecting, them hustling.

First, some world-building. I’m writing this from my hotel in Istanbul, set in the strangely charming streets of Beyoğlu’s red-light-district equivalent. Yep, it’s blatant prostitution at every corner and, somehow, it still feels romantic.

If you’re European, you probably get this. If you’re American, probably not.

The funny part is, I’m perched at my window above it all; me doing my Turkish coffee thing, them doing their…commerce thing. We see each other. No judgment either way. Just two parallel morning routines running on different currencies.

And in a strange way, that’s exactly the headspace I’m in right now: perched between past and future, watching life happen on both sides of the glass. Neighborhoods like this, much like airports, are liminal spaces: You’re not here, not there, just caught in the in-between.

Which is kind of how this next chapter of my life feels.

On paper, it’s my excuse to finally dip my wick into all the things I’ve been fascinated with for years but never gave myself permission to pursue. Tailoring. Leather goods. Curating experiences around coffee and mocktails. Expanding into wellness and regenerative tourism.

All of it designed to support small family businesses across Southeast Asia.

Yes, I still coach. Someone has to help CEOs be slightly less unbearable to their teams, their families, hell, to all humankind. And I do love that work. I just don’t always love the part where I spend an hour explaining empathy to a man who thinks dropping a Slack emoji counts as emotional labor.

But as powerful as coaching is, it’s mostly invisible. The breakthroughs live in people’s heads and get measured in KPIs and quarterly decks no one actually reads.

Lately, I’ve wanted to try my hand at things that don’t vanish the second PowerPoint crashes or Webex freezes mid-sentence. Things you can eat, wear, spill on your shirt, or trip over on your kitchen counter.

Things that, unlike a CEO’s self-awareness, actually exist in the real world. And underneath all that is the real itch:

The endless question of what I’m capable of.

My life has always followed the same pattern. First, I get really good at something. Then I prove it works. And then, instead of doubling down like a sane person, I wander off to see what else I can do.

Society often calls that flakiness. I call it being consistent with my inner eight-year-old because if we’re being completely honest, kids are the flakiest of us all. They go from wanting to be astronauts to magicians to paleontologists before lunch.

And that’s the point. Childhood is about trying on possibilities.

Nobody grows up dreaming of ‘strategic roadmaps’ or ‘powerpoint decks.’ No kid lies awake at night thinking about quarterly earnings calls or AI optimization. There are no Ray Dalio dolls. No Goldman Sachs playsets or Elon Musk posters taped above bunk beds.

At least I hope not. If so, we need to call child protective services immediately because that’s weird as f%$k.

We dream about space travel, saving the world, and starting a dinosaur park. Not market share or valuations. In short:

We’re explorers, not settlers.

And yet somewhere along the way, we’re told that narrowing ourselves down to one thing, forever, is the mature move. Stick to your lane. Specialize. Build expertise until your LinkedIn headline makes people yawn with admiration.

But what if that’s the real flakiness? What if doubling down on a story someone else wrote for you is just a very adult way of settling…or worse, quitting on yourself? For me, wandering isn’t aimlessness.

It’s testing the edges of what I might be capable of.

It’s still kid logic, really…just scaled up to adult stakes. Except instead of building a time machine, I build ventures. Instead of a fort, I’m tinkering with the dreams of small business owners with visions of a better future.

Different playground, same curiosity.

The Myth of One True Calling

I think we’ve been sold the idea that a “real” career is a single arc: pick a path, commit to it, climb until you can see the view. Anything else? Just a hobby. Just a passion project. Cute, but not serious.

At some point, we’re all told we can no longer play the child’s game. We need to start ticking the boxes. Hitting the milestones. Collecting the promotions. “Grow up,” they say. Honestly, is there a less inspiring rallying cry in the English language? Grow up. Yay.

Here’s the kicker though: even the clichés got mangled along the way. You’ve heard “Jack of all trades, master of none,” right? It’s always delivered like a diagnosis, an Achilles’ heel you’re supposed to apologize for at networking events.

But the original phrase didn’t stop there. The full line is: “Jack of all trades, master of none, is still always better than a master of one.” Better. Always better. That last part got lopped off somewhere between the Industrial Revolution and the modern job description.

Can you picture it? An Industrial Revolution HR brochure, circa 1840?

Congratulations! You’ve been selected for a promising career in button-making. Here’s what to expect:

• You’ll be making one button, in exactly the same way, every day, for the next 40 years.

• Thinking about tailoring jackets? Or designing boots? Stop that. Curiosity is a workplace hazard.

• Please refrain from asking what else you might be capable of. It distracts from the button.

• And remember: mastery is producing the same output on repeat until you can no longer feel your hands. Passion is what you do on Sundays (as long as it doesn’t interfere with Monday’s quota).

Thank you for your service to progress and efficiency. We look forward to ignoring your other talents.

Was it a conspiracy to keep us in tidy lanes? A management ploy to build reliable worker bees? Or maybe just a collective allergy to nuance. Either way, we’ve turned what was once a compliment into a cautionary tale.

The truth is, most of us aren’t restless because we’re broken. We’re restless because we’re alive. Because even if society pretends otherwise, we know deep down that the human experience was never meant to be one long climb up the same mountain.

We want to see how many different peaks we can scale, how many valleys we can stumble through, how many ridiculous detours we can take along the way. And if that makes me a Jack of all trades, then fine.

I’ll take the whole phrase, thank you very much.

Not the watered-down, productivity-optimized, corporate-friendly version. The messy, hopeful, contradictory version. The one that admits maybe the point isn’t mastery at all. Maybe the point is to keep finding out what else you can do.

Ideally before you’ve convinced your friends to buy Ray Dalio action figures for their kids. Or Goldman Sachs playsets. Or Elon Musk posters taped above bunk beds. Seriously, can’t you tell I’m both obsessed and a little gutted by these images?

The Permission to Try Again

I’ve seen people climb one mountain faithfully for decades. They get the view, the money, the title. Some of them genuinely seem happy. I’ve also seen people with those very same things look completely hollow.

Like they finally reached the summit only to find a Starbucks and Wi-Fi waiting for them, and thought: Oh, this is it?

Either way, it’s not failure. But it is proof that success on paper isn’t the same as satisfaction in your bones. Which is why I’ve started giving myself permission to try again. And again. And again.

What I’ve learned in my 45 years is that trying something new isn’t weakness. It isn’t flakiness. It’s actually a weird form of discipline. Because it means letting go of the ego boost of being “the guy who’s great at X” to step back into being a beginner.

That’s not easy. Believe me, my nervous system files a complaint every time.

It also means accepting the risk that people won’t get it. They’ll tilt their heads, squint, and ask, “Wait, you’re doing what now?” And that’s when you need the patience (and maybe a talk track) to say:

“Yeah. I just want to see what I’m capable of.”

So What’s the Point?

Maybe the point isn’t to find our one thing. Maybe the point is to find out how many things we’re capable of before the credits roll.

To test the edges of ourselves.

Not just for the joy of proving we can, but for the value it creates along the way. For the businesses that grow. For the people who benefit. For the moments of satisfaction that show up in unexpected places.

Because at the end of the day, I’d rather be accused of trying too much than regretting I tried too little. Being the guy who tried too many things rather than the one who quietly decided he’d already done enough.

And as I finish this from my hotel window in Istanbul…me with my coffee, them with their commerce…I can’t help but laugh at the parallel. We’re all just out here running experiments with the time we’ve been given.

Different currencies, different trades, same restless need to see what we’re capable of before the lights go out.

All this to say, I’m working on it.