Loneliness of the Entrepreneur
When everyone in the room understands your world, but no one can afford to be honest about their experience of it, you haven’t escaped the loneliness. You’ve just given it better lighting.
I like to say I haven’t had a real job since 1996 - that’s when I resigned from my role running Bendigo Regional Arts Centre and started life as a consultant, a path I’ve been on ever since, that’s 30 years working as a contractor or consultant to companies in Australia and the USA, or founding and running my own businesses.
It’s a curious life being a business owner. There’s a particular kind of loneliness that comes with entrepreneurship, and it isn’t the one most people imagine.
It isn’t the late nights while everyone else is at the pub. It isn’t the financial stress or the long hours. Those things are real, but they are visible, at least in outline. People can nod at them. They can say, “That must be hard.”
The loneliest part happens on a Tuesday morning, in a room full of your own people. In all likelihood, they are all marvellous staff, after all, you’ve hired them. The energy is positive. Everyone is engaged in the meeting topic, contributing ideas, and solving problems. And yet what many people won’t appreciate is that you are completely alone in the room.
It’s nothing to do with the staff, but there is the reality that you are carrying something they are not.
When you co-found a business and take responsibility for keeping it alive, you exist in a fundamentally different relationship to the work than anyone else does. Your staff may care deeply about the mission, but they are also treating their jobs sensibly. They have lives, families, and other priorities. In Australia, we now have right-to-disconnect laws. If you’re deep in work on a Sunday afternoon, that’s your choice. It’s not appropriate for them.
This isn’t a complaint. It’s just the reality of the asymmetry.
History is littered with endless attempts to create community for entrepreneurs. I can remember attending First Tuesday meet-ups in the late 1990s - it was a monthly networking event for internet and tech entrepreneurs, venture capitalists and service providers. First Tuesday started in London and then expanded worldwide. It died after the dot-com crash (at least in Melbourne).
I’m in a bunch of Slack groups for technology and business startups, some with thousands of members, yet the channels are just swamped with endless promotions for networking events, and often thinly veiled attempts to promote products or services. There’s no actual community.
I’ve been a member of a couple of industry leader groups, the types where your company needs to have a certain revenue level (in $million) to join, the threshold is there to keep out the wanna be riff raff, of course. I’ve tootled along to a few monthly dinners and ‘exclusive’ events - after a while, you realise that the attendees are the same people every time with the same conversation threads.
Here’s the thing - I doubt anyone actually is being truly honest at these gatherings. It’s very performative. Everything is always fantastic, sales are always up, and everyone is always kicking goals. You just know it’s not true, and are way too polite to question.
It’s rather the same when you are in a meeting with your staff. You can’t walk into that meeting and say what you’re actually thinking about. You can’t say you’re running scenarios in your head about whether you can make payroll in three months if the next funding round falls through. You can’t say you’re quietly wondering whether pivoting the entire product strategy will alienate your existing customers. You definitely can’t say you sometimes wonder whether you should have chosen a completely different path thirty years ago!
There are days when you just want to punch something.
There are days when you just want a hole in the ground to swallow you up.
You carry your concerns and worries everywhere. They follow you to bed. They’re there when you wake up. You can’t share them in the meeting room; it wouldn’t help anyone, and transferring your anxiety to people who cannot do anything about it has zero return.
The loneliest part of entrepreneurship is that you choose the work, but you didn’t choose the silence.
I’ve spent decades unable to speak to the people I see every day about what I’m actually experiencing. That’s the loneliness no one sees. Not isolation from others, but isolation alongside them.
This isolation shows up whenever someone tries to “solve” entrepreneurial loneliness by adding more community.
In 2012, Tony Hsieh invested $350 million of his personal fortune into an audacious experiment called the Downtown Project in Las Vegas. The idea was elegant. Entrepreneurs are lonely, so put them all in one place. Create density, collisions, connection. Build the most community-focused large city in the world.
By 2014, three of the entrepreneurs involved had died by suicide.
The failure of the Downtown Project wasn’t about money or real estate. It was about misunderstanding the nature of entrepreneurial loneliness. The problem isn’t that entrepreneurs are physically alone. The problem is that they’re carrying something they can’t share, even when surrounded by people who should understand.
As I’ve experienced numerous times, when you put entrepreneurs together and call it a community, something unexpected happens. Instead of creating safety, you create another stage for performance.
You are dedicated to maintaining the façade. Your social life becomes indistinguishable from your professional life. The person you’re having a beer with might be a potential investor, a future collaborator, or just another founder who’s barely holding it together but can’t admit it.
One entrepreneur from the Downtown Project described it as a culture of “keeping face”, where everything is always great. Another spoke about the loneliness of the happiness mandate itself, the pressure to socialise, party, and remain perpetually enthusiastic about the vision.
The very structure that was meant to solve isolation became another place where honesty was impossible.
Even among entrepreneurs, the asymmetry doesn’t disappear. One person’s company is thriving while another’s is hemorrhaging money. One has family wealth as a safety net, while the other has burned through their life savings. One is performing with confidence while quietly drowning in debt.
A community built around entrepreneurial identity is still a performance space. It doesn’t remove the silence. It refines it.
Perhaps the real question isn’t how to create better entrepreneur communities. Perhaps it’s whether entrepreneur-only communities can ever address the specific loneliness they’re designed to solve. Given my decades of experience, I’m just not sure they can.
When everyone in the room understands your world, but no one can afford to be honest about their experience of it, you haven’t escaped the loneliness. You’ve just given it better lighting.