Why founders are miserable running their own companies

Dominic Monkhouse21 August 2026

Look at your phone tonight. Count the quick ones.

Nothing that starts with “quick one” has ever been quick. Half of them open with “sorry to bother you.”

They’re not sorry. You’re always bothered.

Every single one is someone checking with you.

Because checking with you is safe and fast, and you’ve never once said no and meant it.

Then there’s the laptop that came on holiday. It’s seen more of Tenerife than you have. 

You’ve read the same page of that novel 4  summers running.

The second shift after the kids are down. 

And Sunday night at the kitchen table with something heavier than stress that you can’t name.

And there’s nobody to tell.

Tell your team and they start quietly updating their CVs. 

Tell your investors and they schedule a call. 

Tell your mates and they say “alright for some” and let you buy the round. 

Tell your partner and you’ll spend the rest of the night reassuring them instead.

So you google it at midnight, find something about gratitude journaling, and close the tab. 

Then you spend twenty minutes on Rightmove looking at houses you have no intention of buying.

It wasn’t always like this.

There was a version of this company you’d have run for nothing. 

Eight people and a bad coffee machine.

You knew every customer by name. You did the deals yourself, badly, and won them anyway. 

You went home most nights having made something exist that didn’t exist that morning.

Then somewhere between there and here, you stopped doing that job. 

It just went, one hire at a time.

I sat in exactly that seat at Rackspace. Twenty jobs. The laptop on holiday. 

The second shift. I didn’t fix it by working harder.

So you assume it’s you. It isn’t you. And it isn’t a wellbeing problem either. 

It’s costing you money right now, this quarter.

I’ve explained the whole thing here.

Why founders are miserable running their own companies

I’ve left a tool in this weeks video. Links above.

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