02. GET Comfortable Being Uncomfortable

I don’t have any formal education beyond high school.

I think a lot of people assume that’s something that should have held me back professionally, but honestly, I think it accidentally forced me to develop a much more useful skill.

I became very comfortable not knowing what I was doing.

Or more accurately, I became comfortable figuring things out in real time.

When I look back at the biggest leaps in my career, they almost always came from stepping into situations where I had no real right to feel comfortable yet. New industries, new technologies, new responsibilities, new types of problems. Most of the time, I was learning while already in motion.

Over time, I realised that this is probably one of the defining characteristics of founders and strong operators generally.

Not that they know everything. But that they’re very experienced at being inexperienced.

I think a lot of people pull the parachute too early.

The moment they hit:

“I don’t know how to do that.”

Or:

“I’ve never done that before.”

They stop.

But if you’re building a company, especially now, that mindset becomes incredibly limiting very quickly. Most meaningful work sits beyond the edge of your existing competence. That’s kind of the point.

If you only ever operate inside areas where you already feel qualified, experienced and comfortable, you rarely build anything ambitious.

One of the biggest things I try to encourage culturally inside our team is building the muscle of being comfortable being uncomfortable.

Because the reality is that a huge amount of company building is just sequential problem solving.

You solve one problem.

Then the next.

Very rarely does someone arrive with a complete map of how everything works.

Most of the time you’re standing in partial fog trying to work out:

“What’s the next solvable step?”

And then repeating that process over and over again for years.

Ben Horowitz talked around the concept that:

“There is always a move.”

I’ve always liked that framing because it feels very true when building companies.

Most of the time you don’t have a perfect answer. You just need to find the next move, then the next one after that.

A lot of company building is really just the repeated process of refusing to stop at uncertainty.

I actually have a theory that formal education unintentionally trains the opposite behaviour.

School and university often place you inside a very structured relationship between student and teacher. There’s always an authority figure who ultimately has the answer. There’s always a lecturer, tutor, assignment brief, marking scheme or predefined path.

Over time, I think that can subtly rehearse a way of working where people become conditioned to wait for guidance, approval or instruction before moving.

You see it a lot with people coming straight out of uni.

The moment they encounter ambiguity, there’s often an instinct to immediately put their hand up. Not because they’re incapable. Because that’s the system they’ve spent years optimising for.

High-growth companies, works very differently. Nobody is standing with the answer sheet. Most of the time, nobody fully knows what they’re doing.

You’re expected to work the problem yourself. To navigate ambiguity independently. To make progress without waiting for perfect clarity first.

I think it takes people a while to unlearn that dependency on predefined structure.

I think this is becoming even more important in the age of generative AI.

The number of genuine dead ends is collapsing.

Most of the time now, unless something is physically impossible, there’s usually a path forward if you’re willing to stay with the problem long enough.

You can research faster. Prototype faster. Learn faster. Test ideas faster.

The bottleneck increasingly feels psychological rather than informational.

A lot of people still tap out mentally far earlier than the tools require them to.

That doesn’t mean expertise is unimportant.

There are absolutely moments where you need someone who has done something ten times before. In any reasonably sized company, there should be people with genuine depth in specific areas.

But I actually think those people are rarer than most organisations assume.

If you had a team of 100 people, maybe 10 should be deep specialists.

For the majority, I’d rather heavily overweight towards elite problem solvers. People who can enter unfamiliar territory without panicking. People who know how to stay calm inside uncertainty long enough to work the problem.

People who don’t treat “I don’t know” as the end of the conversation.

At a recent team day, I kept repeating a phrase:

“There are no passengers. No one is coming to save you.”

What I meant by that wasn’t that people are unsupported.

I meant that high-performing teams tend to have a very different relationship with ownership.

Nobody is sitting waiting for the perfect instructions. Nobody assumes someone smarter will eventually arrive and solve the hard part for them.

Everyone is expected to lean into the problem.

That creates a very different culture.

I think a lot of modern work culture unintentionally trains the opposite behaviour too.

People become overly dependent on predefined roles, predefined expertise, predefined responsibilities.

They become uncomfortable stepping outside clearly mapped territory.

But company building doesn’t really work like that.

The most valuable people are often the ones who can absorb ambiguity without freezing.

The people who can think:

“I’ve never done this before… but I can probably work it out.”

Founders get unfairly mythologised sometimes. People talk about them like they possess some unique personality trait or superhuman confidence.

Most of the founders I know are just unusually accustomed to operating outside their comfort zone.

They’ve repeated that process enough times that uncertainty stops feeling exceptional.

It just becomes normal.

And eventually, if you do it long enough, you start to trust your ability to work through unfamiliar problems even when you don’t yet understand the full picture.

That trust compounds.

I think this is one of the most underrated cultural traits a company can build.

Not confidence.

Not bravado.

Not fake certainty.

Just a collective comfort with discomfort.

A team full of people who don’t immediately retreat when things become unfamiliar.

People who know how to stay with the problem.

Because most difficult things are not solved through brilliance.

They’re solved by people who stay engaged long enough to work through them step by step.