A few weeks ago, I was on a coaching call with a technical founder. He's a brilliant guy, and possesses deep domain expertise. He also has a product that solves a real problem, and a pipeline of warm leads that most early-stage founders would kill for.

He also hadn't made a single client call in over three weeks.

When we started our call, it was clear something was bothering him. He said he felt stuck and stressed, like he wasn't properly leading his company.

So I asked him what he'd been working on since we last spoke. He gave me an impressive list:

"I've been working on product architecture, and I redesigned our internal workflows too. The engineers have a much better standup cadence, and we're working on a much more elegant demo experience!"

My reply was something along the lines of, "...okay, so you did a lot of BUSY work. You didn't work on the thing you knew you needed to work on: talking to customers!"

Sheepishly, he murmured, "Well, no. I guess I didn't."

The part that gets me is, he knew this! Like many of the founders I work with, I didn't have to be the one to tell him that he was probably bullshitting himself if he thought the work he was doing was actually helpful to the company's progress.

When I pressed him on it, he said something that caught my attention:

Here's the thing: nearly every founder and operator I've worked with over the past year has engaged in this behavior one way or another.

We want to feel in control, especially when building a startup feels so out of control. But this is one of the most dangerous forms of self-sabotage when running a high-performing company.

The controllable hard vs. the uncertain hard

There are two types of difficult work: the "controllable" hard, and the "uncertain" hard.

Controllable, hard problems are challenging, but they have a clear shape to it. You know what the output looks like, you know when you're done, and you can feel that satisfying click of progress when you finish.

Things like architecting a system, building a deck, or reorganizing your team's project board all fall into this category. They require real skill, feel productive, and your brain rewards you with a dopamine hit getting them done.

Uncertain, hard problems are difficult in a completely different way. They are ambiguous. The outcome is uncertain. There is no objective metric on whether you did them correctly or not. The measurement of success is not binary. You might get rejected, or you might sit with a blank page for an hour and still not have clarity. 

Making 20 sales calls when you haven't done founder-led sales, having a hard conversation with a co-founder about direction, or sitting alone with a notebook to figure out what your product actually is all live in this category.

In my coaching practice, I've observed that the more capable and intelligent someone is, the more sophisticated their avoidance becomes.

These people are doing genuinely hard work. It just happens to be the wrong hard work.

What this actually looks like

I'll give you a few more stories of founders picking controllable problems to avoid tackling uncertain ones, since this can show up differently depending on who you are.

One founder I work with was spending two hours every morning onboarding new junior hires and reviewing their output. Meanwhile, the single most important thing his company needed was a cofounder to balance the incredible team he already assembled. He wasn't procrastinating in any traditional sense. He was being a good manager! But the engineer search required cold outreach to people who might say no, and navigating a hiring market where his network wasn't generating results. That felt terrible and uncertain. Reviewing a teammate's work felt productive and clear. Guess which kind of problem he kept choosing to solve.

I was talking with a COO at a scaling company who kept getting pulled into fire after fire. Someone on her team pushed code to production with bugs. A team member created false urgency on a deal that turned out to be nothing. She spent days in reactive mode, fixing things that genuinely needed fixing, but that also conveniently kept her from the strategic product vision work she'd been putting off for weeks. She eventually had to physically leave the country and go sit alone in a Swiss hotel room, just to get herself to think about the big picture. Turns out, a change in scenery can give you the confidence you need to tackle uncertain, hard problems.

That should tell you something about how powerful this pull is.

And then there was the founder who couldn't stop architecting. His team had actually given him direct feedback: "You're prioritizing product too much and not talking to customers enough. You can't build the right product until you know what the customers want." He agreed with them. He knew it intellectually. And still, every morning, he'd reach for the Figma file instead of picking up the phone. When we dug into why, he was painfully honest about it.

"I'm procrastinating on doing things imperfectly. I just don't want to fuck up. At least I have control over a Figma file, and I don't have to talk to anyone."

I think that one sentence captures everything I'm trying to say in this article.

Why this happens, and why it's not a character flaw

If you're recognizing yourself in any of this, I want to be clear: this isn't laziness, and it's not a lack of discipline.

It's actually the opposite. The people who fall into this pattern are usually the hardest workers in the room, and that's exactly what makes it so tricky to catch.

What's happening underneath is a perfectly rational response to uncertainty. Your brain is wired to prefer known outcomes over unknown ones. When you're building something from zero, the amount of ambiguity you're expected to sit with on a daily basis is genuinely unreasonable.

So your nervous system does what it's designed to do: it steers you toward the thing that gives you a sense of control and completion.

The problem is, almost everything that matters at the early and scaling stages of a company lives in the ambiguous zone. The sales calls you haven't made, the strategy you haven't articulated, the conversation you've been avoiding, the hire you need to make but don't have a clear path to. All of that discomfort is where the real leverage lives.

What to do about it

I hear a lot of founders say, "OK, I just need to be more disciplined."

Wrong. I don't necessarily think the fix here is willpower. Willpower is what got you into the pattern in the first place! You're already working incredibly hard. The fix is building a structure that makes avoidance harder than action.

Here are the steps I recommend to my founders.

1. Name the one thing. Every morning, before you open Slack or check email, write down the single thing that would make today actually count. Write ONLY the one thing. Write it on a Post-it, and stick it on your monitor. You are not allowed to leave the office until that one thing is done. If you get to the end of the day and you didn't do that thing, everything else you accomplished was a consolation prize.

2. Audit your energy, not your calendar. When you find yourself deep in work that feels productive and engaging, pause and ask yourself: "Am I doing this because it's the highest-leverage thing I could be doing right now, or because it feels good to be in control?" Be honest with yourself. The answer will usually be obvious once you actually ask the question.

3. Make the ambiguous work smaller. The reason you avoid the uncertain stuff is because the whole thing feels overwhelming. So make it less overwhelming, by making the goal achievable - especially if it's out of your typical comfort zone. Shrink the scope until it feels almost embarrassingly small, and then go do that. But be honest with yourself - if you're setting bullshit goals, you won't get very far and you should have a coach, a co-founder, or Chief of Staff call you out on it.

4. Create external accountability. Remember the founder I mentioned in the beginning? Here's what we ended up doing: we set a specific commitment together. He promised me a real, clear outcome in two weeks, and we decided to make the consequence of not doing it very painful. He decided that if he didn't get to the outcome and do the uncertain, hard work, he would make a donation in his own name to an organization that was against his values. (No surprise there, but he got it done.) The structure made avoidance more uncomfortable than just doing the thing.

The question underneath the question

When someone comes to me and says they're stuck, or overwhelmed, or can't figure out how to prioritize, I've learned to listen for what's actually going on underneath. More often than not, they're not confused about what to do - they know exactly what they should be doing. But they're avoiding it because the outcome is uncertain, and sitting with that uncertainty feels worse than staying busy with the wrong things.

The most honest thing you can do as a leader is admit that to yourself. And then go do the scary thing anyway, even if you do it badly.

So I'll leave you with the question I keep coming back to with my clients:

What is the one thing you've been avoiding that you know would change everything if you actually did it?

You already know the answer.

Until next time,

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