The Loneliness of Entrepreneurship

I am going to preface this post by saying it is not me complaining about anything. I am blessed beyond words. A significant chunk of those blessings are the result of working my ass off, but nonetheless, this has nothing to do with complaining. This is about letting others chasing the entrepreneurial dream know that I get it. I see you. I have been there. I am still there. I will be there forever.

A couple of years ago, in one of my MBA classes, we had to write about how lonely it is to be a business owner. I hadn’t really thought about it that way. I had just said that it was a different kind of stress than employee stress. I didn’t want to trade it for a desk job, by any means, but it is really hard to describe to someone with a “regular” job.

There’s no real way to say it in kinder words: being an entrepreneur is lonely. I have a loving and supportive wife. I have an amazing team around me. I have agents that are awesome. I am, at times, completely alone. I might argue that I am alone more often than I am not.

A couple of things to point out. First of all, being alone shouldn’t be taken in a negative connotation. I am comfortable alone sometimes. I prefer the alone sometimes. In that stillness, a lot of good happens. For example, writing about my feelings of loneliness in a blog that 74 people will read.

I think a lot of people struggle with being alone. It’s not our nature to be solitary figures. We are tribal folk. It’s what we do. It took me some time to get used to the quiet, to my thoughts, to nobody needing me or wanting to sell me something, to just this. It’s 11:30 on a Tuesday. Everyone in my house is asleep. This is my time to really do my focused work. I actually love it.

The second part is the fact that alone when things are good is very different than alone when things are bad. The hard truth is that it just doesn’t fucking matter. You’re still alone. There have been nights that I have stayed up planning with hope. There have been nights that I stayed up filled with anxiety and despair. Sometimes those nights have been in a pretty short distance from one another, like the same month. It is hard to relate that to someone who doesn’t have the same skin in the game as you do.

As a funny side note to that last paragraph. It’s funny just how alone you are when you start. Once you start seeing some success, everybody wants to be your friend. Where the fuck were they before? Whatever, though, it’s all part of the journey.

With time, and experience, you learn to look at the longer horizon and the immediacy of the stress lessens (sometimes). When you aren’t prepared for “worst case” you run a million scenarios in your head. When you are, you still run the scenarios, there’s just more bargaining. 15 years ago that looked like applying to stock shelves at HEB at night while I was trying to start a family and a business. Mind you, my dumb ass left a six-figure salary to do that, in the worst housing economy of our lifetime, with a wife who worked part-time, a new baby, a mortgage, and everything life gives you. You remember the dumbass part at the beginning of that last sentence right? Today, that internal conversation looks (a little) different, but know these two things: I would gladly still go stock groceries if need be to work through things, and we learned from last time to do our best to avoid a next time. It doesn’t change what plays in your head, though. That’s for sure.

At the end of the day, no matter how many good people surround you, it’s your dream. It’s your company. It’s your ass on the line (ass is code for money, future, reputation, obligations, and everything else you can possibly imagine). There is a saying that entrepreneurs work 80 hours a week for themselves so they don’t have to work 40 hours for someone else. It’s true. What’s missing in that statement is the loneliness of that endeavor. There’s not one person who hasn’t been through it that can relate.

You are the one. One is the loneliest number.