IYKYK: What Owning a Business Really Feels Like

Time has a funny way of giving you perspective — especially once you’ve stepped out of the blender.

For years, owning my small business felt like living inside a whirling appliance: loud, chaotic, exhilarating, exhausting. You don’t really see how crazy it all is while you’re in it. You’re just trying not to lose a finger.

Now, nearly two years after selling my business, I finally have enough distance to look back and truly see what that life was really like.

And I’m in awe.

Owning a business is a little like Stockholm Syndrome. You convince yourself that your life is normal — maybe a little hectic — when in reality, it’s wildly abnormal. You carry pressures most people never see: other people’s livelihoods depending on your decisions, your home serving as collateral for loans and leases, and the constant low‑grade anxiety of trying to tow the endless line of taxes, rules, regulations, and compliance requirements without landing in the jackpot.

I joke about having “Entrepreneurial PTSD,” and while I’m not being dramatic, I am being honest. What we sign up for — and then somehow sustain for decades — is extraordinary.

Until you’ve owned a business, you can’t fully understand it. You can empathize, you can admire it from the outside, and you can guess at the stress — but you can’t really know it. IYKYK may be a phrase I dislike, and yet there’s no better way to describe it.

Meeting payroll. Keeping up with benefits and employment law. Hiring and firing. Creating processes from a swirling black void of nothingness. Handling HR issues you never trained for. Managing customers, vendors, bankers, landlords, accountants, and attorneys. And somehow still finding the energy to sell enough work to make all of it worthwhile.

That is the “normal” life of an entrepreneur.

Yes, corporate employees worry about reorgs. Nonprofits live with the stress of funding uncertainty. Government workers face the anxiety of political shifts. Those pressures are real — and I don’t minimize them.

From my vantage point, though, the all‑consuming, never‑off, skin‑in‑the‑game intensity of owning a business is in a category of its own.

So, to all the non‑business owners out there: be kind, be gentle, be appreciative, and be considerate of the entrepreneurs in your orbit. What they carry is heavier than it looks from the outside.

And to all the entrepreneurs — past, present, and future — I see you. I applaud you. I admire your bravery, your resilience, and your dogged determination to build something from nothing.

Keep fighting the good fight.