Reflections on three years of self-employment

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I just realized that this month I passed my three-year anniversary of self-employment.

It’s really strange to think it’s been that long since I had a traditional job where I went into an office. People often ask me what it’s like to work for yourself, and I can tell they’ve daydreamed about the prospect of setting their own schedules, being their own bosses, and following their passions.

But I don’t really evangelize on behalf of this lifestyle. I tell them it has its ups and its downs. Yes, the flexibility can be nice, but it also gets really lonely sometimes. I’ve made the vast majority of my friends through previous jobs, so I have a harder time making new friends when older ones move away.

I also feel a lot more pressure to be productive, to an extent that’s sometimes unhealthy. Back when I had traditional jobs I felt OK when I occasionally had a day that consisted of doing very little. Now I’m hyper aware of how every hour that gets away from me is potentially costing me money or success. I often work late into the night and feel guilty when I take a weeknight off to have dinner with friends or family. I worry constantly about whether I’m hitting the benchmarks I set for myself or if my new venture is working out. I view vacations and traveling as obstacles that keep me away from my content production. I think about work virtually all the time.

That being said, I’ve been self-employed for longer than I’ve held any one job. Something prevents me from monitoring job listings or paying much interest when a recruiter contacts me. Sometimes I try to imagine myself in a normal job again and I have no idea what that position would be or what would induce me into taking it. For all the stress I’ve endured, I must derive some pleasure from building something on my own and setting my own course.

My only hope is that whatever destination I’m aiming for, I eventually get there. One day.

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Tech and media journalist. Email me: simonowens@gmail.com

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