Hey!

Chris here. Welcome to Blueprint—the newsletter to help you build a winning engineering team.

A lot of founders carry a low-level suffering that they can't quite explain.

The business is running well and the work's getting done, but it still feels like something is wrong. It's as if you're always 1 problem away from the whole thing falling apart.

I felt that for years. And I spent a long time thinking the answer was building better systems or hiring a stronger team.

Fix the external stuff, and the internal stuff would follow...or so I thought.

But it never did.

That's because I had misdiagnosed the pain. Let me explain. 👇️ 

📒 DEEP DIVE

Your Business is Supposed to Be This Crazy

Why pain tolerance is the essential founder skill—and how you can build it. 

When I started building my first business, I expected things to be good. I expected things to be normal.

But as I quickly discovered, that's the exception, not the rule. New businesses are chaotic and a complete disaster most of the time.

And what I've realized is that most of the pain founders like myself feel isn't actually coming from the chaos itself. It stems from the belief that the chaos shouldn't exist.

You're treating every fire as proof that something is broken, when really it's just proof that you're running a business.

Your business is supposed to be exactly that crazy. The only thing businesses do is solve problems. So you have problems being thrown at you 90 miles an hour, all the time. That's the normal state of affairs.

When you're fortunate enough to get a day or 2 where things genuinely aren't that bad, enjoy it. But it's not going to last. And if it lasts too long, you've probably stopped solving real problems for people—which creates a much bigger problem down the road.

The moment you stop expecting calm, the chaos stops feeling like failure. The pain doesn't disappear, but it changes. Instead of fighting the job, you just start doing it.

The Real Leadership Skill

This is where the conversation gets uncomfortable for a lot of founders.

Your success in a high-level role is primarily about how much pain you can tolerate.

I've learned this over 20 years of living through the chaos. Early on, every hard stretch felt like a signal that I was doing something wrong. Now I understand those hard stretches are the job.

The founders who last are those who find a way to build a higher capacity for it.

Your capacity to handle ongoing pressure, uncertainty, and recurring difficulty is one of the most important things you can develop as a leader.

How to Function When It Gets Bad

Accepting that pain is built into this job is one thing. Knowing what to do when it hits is another.

Here are some helpful strategies I've developed over the years:

→ Finish something small

When a day goes sideways, and the pain of stagnation starts to set in, don't end the day there. Pick the smallest task you have and finish it.

Around 3:30 or 4 in the afternoon, if I haven't been able to complete what I needed to, I will literally pick the smallest task available just so I can close the laptop and go, "I did a thing."

It's a mind trick, but it works because what's really hurting you is the feeling of not moving forward. So give yourself some progress, even if it's small. It takes the edge off in a way that's hard to explain until you try it.

→ Stop chewing on your problems

Some of the most acute founder pain comes from people problems. An employee who feels burned or a client relationship that's gone sideways. And the instinct is to keep turning it over until you can get to a solution.

The problem is that the more you chew on something painful, the worse it gets. Your mind will circle back to it every 60 seconds, no matter what else you're trying to do.

The move—and it feels counterintuitive—is to put it away. Turn around, pick something productive, and do that instead.

You can move through these things much faster than you'd expect, but only if you stop feeding the loop.

→ Work with your brain

There's a mental state that's the worst possible state for getting anything done: being rushed and anxious. The irony is that you end up rushed and anxious because you're trying to get things done.

The harder you push, the worse it gets.

The solution is to come to terms with the fact that there's no beating your brain. When the pressure is high and the pain is real, trying to force your way through it only makes things worse.

What you have to do is get honest about the mental modes that aren't serving you and find ways to shift into ones that will. That starts with actually understanding what those states look like for you.

→ Get distance before you respond

When something hits hard and really gets under your skin, create space before you react. Acting from inside the pain rarely produces the outcome you want.

My process: I sit down and write a rough draft of whatever I need to say to that person. I get the words out of my head and onto the page. And then I sleep on it. You should never send your first draft when you're emotional.

When I come back to it, I can edit it into what I actually wanted to say—or pick up the phone instead. Either way, getting the words out stops them from bouncing around in your head, which is usually most of the problem.

BEFORE YOU GO…

Building a company is painful. I'm not going to tell you otherwise.

But a lot of that pain is made worse by expecting the job to feel different from what it does. When you carry the belief that things should eventually calm down, every chaotic week becomes evidence that you're failing—and that compounds the pain significantly.

Building a business that stops being hard is an impossible goal. The real mission is to become someone who can still function when it is.

And that's why your capacity to handle pain is one of the most important things you'll ever build.

Talk soon,

Chris.