The Loneliness Nobody Warns You About

Nobody tells you how lonely it gets.

They tell you about the long hours. The financial risk. The stress of making payroll. They warn you about cash flow problems and difficult clients and the constant hustle.

Nobody mentions the loneliness.

I’ve been running this agency for 12 years. I have a team I love. Clients who trust me. A business that’s stable. By most measures, things are good.

And still. There are days when the loneliness is heavy.

What it actually feels like

It’s not about being alone physically. I’m surrounded by people most days. Team members. Clients. Family.

It’s about carrying things that nobody else can carry. Decisions that nobody else can make. Worries that don’t have anywhere to go.

It’s lying awake at 3am running numbers in your head, while the person next to you sleeps peacefully because they don’t know what you know.

It’s being in a room full of employees who look to you for confidence, and feeling like you’re performing a version of yourself that doesn’t quite match what’s happening inside.

It’s hearing “must be nice to be your own boss” and swallowing the thing you actually want to say.

It’s the weight of responsibility that sits on your chest and doesn’t lift, even on vacation, even on weekends, even during the good times.

For years, I thought this feeling meant something was wrong with me. That I was doing entrepreneurship wrong. That other business owners had it figured out and I was the only one struggling.

Half of us feel this way

Then I learned the statistics.

Fifty percent of CEOs report feeling lonely in their role. Not sometimes. Regularly. Half of us are carrying this quietly.

Seventy-two percent of entrepreneurs report mental health concerns. That’s significantly higher than the general population.

Nearly half of us struggle with isolation. We work surrounded by people who depend on us, and still feel fundamentally alone.

When I read those numbers, something shifted. I wasn’t broken. I wasn’t doing it wrong. This is just what the job is.

There’s something strangely comforting about that. Not because the loneliness goes away. It doesn’t. But because at least now I know it’s normal. At least now I know half the CEOs in those networking rooms feel the same thing and are just too proud to say it.

Why success doesn’t fix it

Here’s the thing that surprised me most: getting more successful didn’t make it better.

I thought it would. I thought once the business was stable, once we had a solid team, once we’d proven ourselves, the anxiety would quiet down. The loneliness would lift.

It didn’t.

In some ways, it got heavier. More employees meant more people depending on me. More clients meant more relationships to manage. More success meant more to lose.

The decisions got bigger. The stakes got higher. And the number of people I could really talk to about it got smaller.

When you’re struggling and small, at least you can commiserate with other struggling small businesses. When things are going well, who do you talk to?

Complaining about success feels obscene. But the pressure is real.
This is why so many founders spiral right when things start working. The outside looks good. The inside is chaos.

What actually helped

I tried a lot of things that didn’t work.

I tried ignoring it. Pushing through. Telling myself to be grateful and stop complaining. That just made it worse.

I tried working more. If I’m going to be stressed anyway, might as well be productive. That burned me out faster.

I tried numbing it. A glass of wine at night. Scrolling my phone until my brain went quiet. Short-term relief. Long-term damage.

What actually helped was the stuff I resisted.

• Coaching. In 2016, I started working with a leadership coach. Not a business coach. Someone who made me look at myself, not just my strategy. It was uncomfortable. I wanted tactics and she gave me mirrors. But it changed everything.
• Therapy. Somewhere along the way, I stopped seeing therapy as something for “people with problems” and started seeing it as maintenance. Like going to the gym, but for your head. Having a place to put the thoughts that can’t go anywhere else—that matters.
• Honest conversations. I started being more real with other business owners. Not the highlight reel version. The actual version. And I found out they were struggling too. They were just waiting for someone to go first.
• Boundaries. I stopped working weekends. Not every weekend. But most of them. I started protecting time that was actually off. The business didn’t collapse. In fact, I made better decisions when I wasn’t exhausted.

The hardest part

The hardest part wasn’t finding solutions. It was admitting I needed them.

I had built my identity around being strong. Capable. The one who handles things. Admitting that I was struggling felt like admitting I wasn’t cut out for this.

But that’s the trap. The thing that makes entrepreneurs successful—the drive, the self-reliance, the ability to push through—is the same thing that makes us terrible at asking for help.

We think we should be able to figure it out alone. We think needing support means we’re weak. We think everyone else has it together and we’re the only ones faking it.

None of that is true. But it feels true. And the feeling keeps us stuck.

Why I’m writing this

I’m writing this because I wish someone had told me earlier.

I wish someone had said: the loneliness is normal. Half of us feel it. It doesn’t mean you’re failing.

I wish someone had said: success won’t fix it. You have to address it directly.

I wish someone had said: there’s no shame in needing help. The strongest leaders are the ones who know when to ask for it.

So here I am, saying it.

If you’re running a business and you feel alone—you’re not. If you’re lying awake at 3am wondering if you can keep doing this—you’re not the only one. If you’ve convinced yourself that everyone else has it figured out—they don’t.

The hardest work wasn’t building the business. It was building myself.
And I’m still working on it. Every day.

Kimberly Biggs is the CEO of POP INC Digital. She lives in Chelsea, Quebec, where she runs a marketing agency and talks openly about the parts of entrepreneurship that don’t make it into the success stories.