Why Founders Are Their Own Worst Boss

In ten years of mentoring founders, I've noticed something uncomfortable: most of them are the worst boss they've ever had.

To themselves.

They don't see it. Or if they do, they don't name it.

But I notice it constantly.

The founder who left corporate because her manager expected her to respond to emails at 10pm? She now checks Slack until midnight.

The one who quit because his boss never acknowledged when he was overloaded? He's now running on three hours sleep and calling it "just how it is right now."

The founder who walked away from a toxic productivity culture where taking a sick day felt like failure? She hasn't had a proper day off in eight months.

They escaped the bad boss. Then became one.

Just to themselves, which somehow makes it acceptable.

Here's what it looks like:

They set deadlines that are unreasonable and then beat themselves up for missing them.

They take on too much, refuse to delegate, and then blame themselves for not being able to keep up.

They work through illness, exhaustion, and burnout – the exact behaviour they'd never tolerate from an employee.

They give themselves no boundaries, no time off, no grace for being human.

And when I point this out? The response is usually the same:

"Yeah, but I have to."

Or have you just internalised every bad management practice you ever experienced and decided it's fine when you do it to yourself?

The difference is you can't quit.

When you had a bad boss in corporate, you could leave. Update your CV, start looking, eventually hand in notice.

But when you're your own worst boss? You're stuck.

You can't escape yourself. Can't resign from your own brain. Can't walk away from the person making unreasonable demands.

So you just... keep going.

And that's when the real damage starts.

Because at least in corporate, there were limits. HR policies. Employment law. Someone else setting the hours, the expectations, the boundaries – even if those boundaries were terrible.

When you're self-employed, there's none of that.

Just you, setting impossible standards and then punishing yourself for not meeting them.

I see this play out in specific ways:

The founder who won't close their laptop until every email is answered, every task is done, every loose end is tied up – which of course never happens, so they just work until they can't anymore.

The one who knows exactly what they'd tell a team member who was burning out – rest, delegate, say no – but somehow those rules don't apply to them.

And here's what I notice most:

They know it's unsustainable. They'll say it out loud. "I can't keep doing this."

But then they keep doing it.

Because somewhere along the way, they learned that pushing through is professionalism. That rest is earned, not required. That if you're the founder, you don't get to be tired.

They absorbed every toxic message about work from every bad boss they ever had.

And now they're repeating it. Daily. To themselves.

The hard bit is this:

You left corporate to get away from unreasonable expectations.

But you brought them with you.

And now you're enforcing them more strictly than any manager ever could.

At least your old boss went home at 6pm. You never clock off.

At least your old boss had someone above them setting policy. You've given yourself unlimited authority to demand more.

At least your old boss had to worry about employment tribunals if they pushed too hard. You have no protection from yourself.

So what changes this?

Not self-compassion. Not another article about boundaries.

Recognition.

Actually seeing that the voice in your head telling you to work harder, do more, push through – that's not your ambition talking.

That's your worst boss.

And you wouldn't work for them anymore if they were someone else.

So why are you tolerating it now?

If this landed – if you're reading this and thinking "how does she know?" – that's the work.

I help founders spot the patterns they can't see in themselves. The management practices they're using without realising. The ways they're recreating exactly what they left corporate to escape.

Not through frameworks or productivity systems. Through pattern-spotting and uncomfortable truths.

If you're stuck in a cycle of overwork you know is unsustainable but can't seem to break, book a discovery call and we'll figure out what you're actually managing – and what needs to change.