I Work for Myself, So Why Can’t I Take a Break?

Why is unplugging so hard when I’m the one in charge?

For the past four and (almost) a half years, I’ve been my own boss. No morning alarms dictated by someone else’s schedules (unless I have important client meetings), no PTO requests, no awkward “circle back on this” emails. Just me (and my team), my laptop, and the kind of freedom I always thought I wanted.

What I know now is that freedom doesn’t always feel the way you think it will. No one tells you that when you work for yourself, your boss is you. And sometimes she’s not an ally.

I realized I had a problem with disconnecting while in Paris in 2021 on my birthday. Lebo and I were out, exploring the city, and instead of being fully present, I was ducking into cafés to take client calls, laptop open, responding to emails. Lebo was just sitting there, waiting for me to finish. I hated that moment. I hated that I had to do it. And yet, even now, I still struggle to disconnect.

Paris 2021. It looked cool, but I was fighting for my life to be present.

When you’re an entrepreneur, there is always more to do. There’s no one above you saying, “Okay, you can log off now.” There’s no paid leave, no automatic deposit hitting your account every two weeks whether you work or not (although I do advise paying yourself consistently). In the early days of building a company, if you stop moving, things stop moving. That kind of pressure makes it hard to walk away—even when you really need to.

I tell myself I have business hours, but if we’re being honest I could stay on my laptop for 12 hours straight if I let myself. I love what I do, which makes it even harder to step away. I see people who completely unplug on PTO or delete social media off their phones, and I genuinely don’t know what that life is like. The idea of being unreachable for days is a figment of my imagination.

And then there’s the financial side of things.

Taxes? Confusing.

Health insurance? Expensive.

Buying a house or a car? Hope you love explaining your income in painful detail.

I write off my laptop, my WiFi, my work dinners and fancy coffees, the percentage of rent that covers my office space and more. But when it’s time to prove my income? That means bank statements, invoices, tax returns and explaining to lenders that yes, I really do make money—even if my paycheck doesn’t look like everyone else’s.

Would I trade it?

Not a chance.

Yes, I need a real vacation. I need to go somewhere and not open my laptop “just to catch up.” I need to learn to be okay with stillness.

But at the same time, I love the life I’ve built. I love that I can decide to meet a friend for coffee at 11 a.m. on a Tuesday. I love that I don’t have to ask anyone’s permission to take on a new project, pivot my career, or explore something new.

The hardest part of working for yourself is also the best part: No one is coming to save you. But also, no one is stopping you.

If You Work for Yourself, Read This

If you’re an entrepreneur, freelancer, or creative running your own thing, here’s what I’ll say:

• Rest is necessary, not optional. No one will tell you to take a break, so you have to do it for yourself.

• Define success on your own terms. It’s easy to feel like you’re not doing enough—but who actually gets to decide what “enough” is?

• You don’t have to be available 24/7. The world won’t fall apart if you unplug for a day. (This is a message to myself).

• Give yourself permission to enjoy the freedom. You built this life for a reason—don’t forget to live it.

Now, if you’ll excuse me, I am going to try to unplug.

xx

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