When I was seven, I decided to test the structural integrity of a porcelain bathroom sink by using it as a starting block for a standing long jump. My father had warned me three minutes earlier that the sink was for hands, not feet. But I was seven, and in my mind, the laws of physics were merely suggestions for people without my level of ambition.
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I fucked around. I jumped. The porcelain shattered with a sound like a gunshot, and I found out exactly how many stitches it takes to close a gash in a shin.
That was my first real lesson in feedback loops. I didn’t need a lecture on material science or a fucking performance review. I just needed a bandage and the sudden realization that my dad was right.
In the corporate world, we spend decades unlearning this. We’re taught to mitigate and hedge until the possibility of shattering the sink is zero. We become experts at the Fuck Around phase (the ideation, the strategy decks, the alignment meetings) without ever dealing with the Finding Out part. But since I quit my job to build GUTSY, I’ve realized that avoiding the “find out” is just career stagnation with better branding. If you aren’t breaking the sink occasionally, you aren’t actually moving.
The Corporate Insulation Layer
When you’re an operator in a large organization, you live in a padded cell. It’s comfortable and beige and it’s killing your edge. You’re insulated from the raw consequences of your own ignorance by layers of middle management and annual budgets. You can champion a flawed strategy, watch it stall in Q3, and still receive a direct deposit on the last day of the month.
In that environment, you’re fucking around on someone else’s balance sheet. Finding out is a Tuesday morning post-mortem you can tune out while checking your email. The stakes are fake. The feedback is delayed. The learning never sticks.
This safety doesn’t protect you. It just makes you soft. It makes you think learning happens in a webinar rather than in the wreckage of a failed experiment. It makes you confuse risk mitigation with competence.
The Pivot to Pure Friction
Since leaving, I’ve replaced the padded cell with a series of high-velocity collisions with reality.
I started posting short-form content on Instagram. If you want to find out how little the world cares about your “perfectly curated brand voice,” post a reel you spent four hours editing and watch it get destroyed by a blurry video of a cat. Instagram is a brutal laboratory for humility. You fuck around with transitions and hooks and you find out (within seconds) exactly how boring you actually are to a stranger scrolling in an airport lounge.
Then there’s this Substack. Writing here is an exercise in public vulnerability with no safety net. There’s no corporate communications team to sanitize my thoughts or align them with brand guidelines. It’s just me and the very real possibility of being wrong in front of thousands of people. Every essay is a test. Every publish button is a small act of professional self-immolation.
But the most aggressive form of finding out has been my consulting work. I’ve spent the last few months diving into industries where I had zero prior context: real estate, jewelry, CPG. In a past life, I would have spent six weeks “onboarding” and reading industry reports before I dared to open my mouth. Now, I just dive in. I ask the “stupid” questions that make experts wince. I propose the “impossible” fixes. And then I wait to find out why they won’t work.
Consulting in jewelry when you come from tech is a masterclass in getting your ass handed to you by reality. You fuck around with new business models and find out the hard truths of luxury margins, supply chain constraints, and why your brilliant idea died in 1987. You fail. You look slightly ridiculous. And then you actually understand how the industry moves.
This cycle is the only form of education that actually sticks. You can read every fucking Substack on product-led growth, but you won’t truly understand the principles until you try to sell a supplement and fail to move a single sachet. Failure strips away the theoretical fluff and leaves you with a hard piece of truth you can use to build the next version.
I’ve learned more from the wreckage of the last six months than I ever did from the successes handed to me in a cubicle. Every time I find out, I’m paying my tuition to the school of reality. And unlike my MBA, this education is actually useful.
The Point
The goal isn’t to avoid the find out phase. The goal is to move through it as quickly as possible so you can fuck around with something bigger next time.
Fucking around is the price of admission for a life that isn’t scripted by a committee. Finding out is the receipt. If you aren’t finding out at least once a week, you probably aren’t doing anything worth mentioning.
The corporate world will tell you that competence means never looking stupid. That’s horseshit. Real competence is what’s left after you’ve looked stupid enough times that you’ve actually learned something.
The tuition is high. But I’d rather pay it than spend another decade pretending that consensus equals courage.
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