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Welcome to the emotional whiplash of starting a business
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Welcome to the emotional whiplash of starting a business.

Matthew Webb·3 min read·Feb 2025

Nobody warns you about the strange parts of starting a business.

The least glamorous rite of passage

Insurance, for one. Who knew you needed so much insurance? Not me. But apparently you do, so you spend an afternoon buying protection against things you sincerely hope never to use. It's the least glamorous rite of passage imaginable, and it never makes the founder highlight reel.

Then there's the messaging. I've rewritten my website at least five times. Tweaked the logo. Changed the tagline. Refined my positioning more often than I can admit. Why? Because when it's your own business it stops being a marketing task and turns personal. You want it right in a way that borders on the irrational. And here's the spoiler nobody mentions: it never feels finished. I'm already planning the next change, because what's there still isn't quite it.

The part no one prepares you for

But the real shock is the emotional whiplash.

One minute you're on top of the world, riding the high of a brilliant conversation, certain this is going to work. An hour later you're staring at a silent inbox, convinced the whole thing is quietly falling apart. Unstoppable and out of your depth, sometimes before lunch.

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The emotional swing isn't a sign you're doing it wrong. It's the tax you pay for caring this much about something you built yourself.

That reframe took me longer to reach than it should have. The lows feel like evidence. They're mostly just weather.

What I'd tell a new founder

So if you're thinking about starting your own thing, here's what I'd pass on:

  • The first weeks are the hardest: the highs are unreal and the lows are brutal. Expect both, ride them out, and trust that the amplitude settles.
  • It won't be perfect, so launch anyway: perfect is a moving target you'll never hit from the sidelines. Ship it, learn, refine in public.
  • You'll handle things you never imagined: accountants, insurance, tax returns, and a hundred small admin jobs nobody warns you about. It comes with the territory.

I'm writing this having just started my first venture, and I can already tell the journey will look nothing like I pictured. To everyone who's built something from nothing and come out the other side: I understand now what it took, and my hat is off to you. The whiplash, it turns out, is just what it feels like to be all in.

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