The Loneliness of the Long Distance Entrepreneur

Here I am. Another country I have never been to, another city. Hoping I have the right clothes for whatever climate I am in. I guess I will find out tomorrow when I step outside for the first time since I got here.

Today I got up at 4am to get to the airport in time. I got coffee at the hotel in London, I had a sort of faux-camaraderie with the staff. They knew what kind of coffee to make me before I asked. I had been there for a week so I was kinda a local to them. They didn’t check my room number at breakfast anymore, they pretended to relax as if we knew each other. I played along with it as much as they did. It makes the days easier.

Not that the days are hard. I enjoy this way of working. Constantly moving, meeting new folks, jamming new collaborations, disarming people with my kookiness. I feel in my stride in this mode. It works, and I know how to work it.

Not that this life is without its challenges. I have plenty of friends but most of them don’t know each other. My closest friends are almost all on different continents. I check in on them when I am close by, but sometimes my schedule means I don’t know where I will be and when, and then they get mad when we couldn’t connect. And I don’t care, it means nothing to me because that’s just how it is. My stability is in passing through at unknown times. It becomes hard to empathise with those that need to know when to be home in case I turn up.

Sleep comes also like this. At odd times. I wonder if I should just jump out of bed at 3am and use my energy to do something, or if I should just lie there and try and make myself tired. Sometimes I simulate timezones, sometimes I fight them. I don’t know which strategy is best. The only thing I have worked out is that it doesn’t pay to stress about it. I listen to podcasts to keep me company.

And then there is the serial entrepreneur bit. The deliberately chosen hard road. I don’t just make things to sell, I make things that don’t make sense and then try to sell them. And then there is the ethical bit, the deliberate choice to make the hard road harder. So not only should you buy this thing that you aren’t really sure makes sense or even exists(!), but it comes with a whole load of caveats. 🙂 I find that kind of funny. …And then there is the normal entrepreneurial anxiety of mouths to feed and deals to make. Of wondering how to make it all work as one giant inter-connected system of ideas, people, money, value. How to make and sell crazy ideas with uncompromising attitudes. It’s harder than you think.

How to keep it all up in the air while also being, most of the time, up in the air. Learning to sleep sitting up. Finding solitude in headphones.

It’s sometimes all a little too much. But I can’t give up. I just don’t know any other way. And no matter how much I succeed it never feels like success. Except when I see what other people do with it. People I love and trust. Strangely, I find that very satisfying.

But generally I just keep wanting to make the road harder. I choose even harder routes, with bigger ideas, and even more uncompromising attitudes.

It’s just how I like it.

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