Get Comfortable With the Uncomfortable

Every founder I know has had the moment. The product ships, a customer says something nice, the team is humming, the bank account looks healthy, and for about a day and a half everything feels like it’s finally working. Perfect. Then a key hire quits, a customer churns, a competitor announces a big round, and you’re right back where you started, staring at a mess and wondering why you decided to do this in the first place.

Here’s what nobody tells you at the beginning. Perfection might be real, but it’s a moment, not a place you get to live for very long. It shows up, you enjoy it for a bit, and then it leaves faster than it arrived. The business goes back to being imperfect, and that’s not a sign you’re failing. 

I’ve talked with thousands of founders over the years, and the ones who struggle most aren’t the ones with the messiest companies. They’re the ones who believe the mess is temporary and that everything will finally settle down once they figure it out.

Your startup doesn’t settle down. It changes shape. It moves. Perfection is elusive. It never stays for long.

Finding your first ten customers gives you the problem of serving your first hundred. Raising money gives you the problem of spending it wisely. Hiring a great team gives you the problem of leading one. Every solved problem is really a trade for a more interesting problem, and if you’re waiting for the day the problems run out, you picked the wrong job.

That’s why I tell founders they have to get comfortable with the uncomfortable. 

Not tolerate it, not white-knuckle through it, but actually get comfortable, the way you eventually settle into a middle seat on a long flight. The most uncomfortable part of all is that you will never have enough data to make the next decision a slam dunk. Never. I’ve watched founders wait for one more customer interview, one more survey, one more month of numbers, convinced the right answer is hiding just behind the next data point. 

The founders I admire most make the call with about seventy percent of the picture and a gut that’s been paying attention. They get some of those calls wrong, and then they adjust, which is the whole game. Being wrong early and fixing it beats being right eventually, because eventually is usually too late.

So enjoy the perfect moments when they show up. Take the photo, buy the team lunch, tell somebody about it. Just don’t build your plans around them lasting. The imperfect stretch is coming, and it’s where the real work (and honestly, most of the fun) happens. Make the call, learn something, and go make the next one.