One Is The Loneliest Number Or The Truth Entrepreneurs Don’t Tell

When people ask what it’s like being an entrepreneur, I usually joke how running your own business is like a crash course in handling rejection. There are sales you don’t make, clients you don’t land, proposals that go nowhere, offers that get turned down. If you don’t make the ask, you don’t get the work and if you don’t get the work, you don’t pay your bills. So, you ask and for every yes, there’s a no, or maybe there are ten nos or even a hundred. Eventually, it stops stinging as badly.

What I talk about much less is the loneliness. Even if you’re successful, being self-employed is lonely and if, by nature, being isolated and unmoored brings out the darkest in you, well, buckle up. Once you file those incorporation papers (hint: do it in Delaware), you’re flying solo.

Being a one-person empire encourages a certain kind of nihilism. There is no infrastructure or hierarchy for you to find your place in or define yourself against. You don’t spend eight hours a day rowing in the same direction as dozens or hundreds of other people who all park in the same parking lot, take the same elevators, pass the same mission statement mounted on a wall plaque outside the breakroom. No one is timing your lunch hour. Stretch it until 2 and have a martini and no one will make a peep.

You find yourself weighing freedom against insignificance. Yes, I can go grocery shopping in the middle of the day, but does that have more to do with being my own boss or is it just because I don’t really matter and I’m not needed elsewhere? If you tell me you’ve never wondered that, I’ll tell you you’re a liar. You start to get a sense of how low your stakes are and sometimes that gnaws at your brain while you’re trying to fall asleep. If you screw up, you might lose a client or owe the IRS some money, but your carelessness won’t cripple a Fortune 500 company and be splashed all over The New York Times. The power you gain over your own self-determination is directly offset by the realization that your failure hurts only you and therefore only matters to you. Whether you have a six-figure year or close shop after six months and quietly slink back to being some else’s employee is irrelevant to the rest of the world. It will go on either way.

Sometimes, being your own boss feels amazing and empowering and sometimes, it feels pointless and lonely. You are whatever you say you are, you do whatever you say you do. And that’s both the best and the worst feeling.