The 3:43 a.m. Problem

You didn’t lose confidence. You lost the rules you were playing by.

If you’re a high achiever thinking about entrepreneurship, the thing that usually stops you isn’t fear.

It’s not knowing.

Or more precisely: being acutely aware of everything you don’t yet know.

The thing that usually stops high achievers isn’t fear.
It’s being acutely aware of everything they don’t yet know.

The part corporate trained you for (and the part it didn’t)

Corporate life trains you well for this.

Know the answer before you speak.
Understand the system before you act.
Reduce uncertainty before you commit.

Bonus points if you can do all three in a meeting with no agenda.

So when you start imagining your own business—and you can’t see the whole path—your confidence doesn’t gently wobble.

Usually at 3:43 a.m., when your mind turns on after a trip back from the bathroom.

It tightens.

If you’ve had that moment, you know exactly what I mean.

Not because you’re incapable.
But because the rules you learned no longer apply.

And that’s disorienting—especially when you’ve been good at the game you were playing.

Why the uncertainty rears its head in the middle of the night

What’s easy to miss in this moment is how much corporate rhythms used to chase away that uncertainty for you—as a matter of course.

Mostly by wrapping uncertainty in familiarity—so it didn’t come knocking at 3:43 a.m. when you were half awake and heading back from the bathroom.

Corporate rhythms wrapped uncertainty in familiarity—
so it didn’t come knocking at 3:43 a.m.

I’ve written before about what happens when you step away from a familiar social fabric—the routines, rhythms, and everyday interactions that quietly held things together.

This is often what comes next.

The social fabric you took for granted

Much of that structure wasn’t formal.

It lived in the everyday interactions that kept you oriented without you having to think about it.

When I left my job, I expected to miss the work.

I didn’t expect to miss:

• the impromptu brainstorming in the hallways
• the quick catch-ups while grabbing coffee
• the small talk in the elevator or at the snack bins

I was also surprised by how much I missed the all-hands meetings—the ones I used to spend time figuring out how to skip with plausible deniability.

Not for the content.

But for the simple feeling of being part of something larger than my own to-do list.

It took me a while to see those moments for what they were.

Not background noise—but social fabric.

Steady, low-effort human contact.
Places to think out loud.
Ways to stay oriented.

When that fabric disappears

When that fabric disappeared, there wasn’t an obvious replacement.

What I hadn’t fully appreciated was how much corporate life had been carrying for me.

I didn’t have to build that social fabric.
It was simply there—absorbing the swings of the work.

The moments of peak flow.
The moments of deep disappointment.
Everything in between.

Once I stepped out of that environment, I had to weave my own social fabric to get through what I now think of as the valley of joys and sorrows.

Wins and doubts coexist here.
Expansive days sit right next to heavy ones.

Wins and doubts coexist here.
Expansive days sit right next to heavy ones.

Without social fabric and social scaffolding, that valley can be disorienting.

• Joys have nowhere to land.
• Disappointments linger longer than they should.
• Everything stays inside your own head, carrying more weight than it needs to.

Over time, that adds up.

This is the part people underestimate.

Isolation doesn’t announce itself

Left unattended, many founders default to isolation.

It rarely announces itself as isolation.

It shows up as “just getting a lot done.”
(Which, to be fair, is usually rewarded.)

It looks impressive—right up until you realize no one is actually there to see it.

More heads-down work.
Fewer places to sense-check ideas.
Fewer people to celebrate progress or witness real disappointment.

Social circles shrink.
Social trust thins.

What actually helps here

So the real question becomes:

Where does your thinking go now?

The good news is you don’t have to wait for someone else to solve this for you.

There are ways to begin rebuilding social scaffolding—not by recreating corporate, and not by forcing connection, but by being intentional about a few foundational choices business creators can shape early:

• where you think out loud without performing
• who sits in your circles of trust
• what rhythms bring regular human contact back into your week
• and which circles can hold ambiguity, not just outcomes

Want to go deeper?

I wrote about this phase earlier in my own journey—why it shows up, why our biology actually demands these kinds of supports, and practical ways to start rebuilding them yourself.

You can read it here.

That piece is part of a short series called The 5 Common Mistakes Business Creators Make. If this resonates, you may want to sign up for the full series here.

Rooting for you,

Pierre

Certified Professional Coach

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