Lessons from running my business

Millions of people are self-employed or run small businesses, and millions do one of those for a while and then move to something else. It’s hard for me to imagine that any of us has learned something unique to us individually.

It’s also incredibly easy to find other writers talking about it, sharing the things they learned, and the lists have a lot of overlap. A lot of the lessons also come across as pedestrian.

Still, I wanted to do a retrospective of my own experience. I wanted to approach it from a somewhat narrower perspective. To compile my list, I asked: What made an impact? What lessons did I learn from starting, running, and closing a one-person business that will cause me to act differently than I acted before I ran the business? Here are some of my answers, which of course I reserve the right to revisit.

People will give way more power to you than they should, and you have to be ethical about that.

I always asked permission before going into people’s files. And yet I was consistently told, “Oh, there’s nothing in there that’s secretive or anything, do anything you need to.” This was stunning to me.

I also saw the downside of this trust, repeatedly: computers bricked entirely by the IT support scam industry exploiting predominantly elderly people with little computer savvy and trusting hearts. On a few occasions I saved the computer only because of the sheer laziness of the scammers: one locked up a Windows computer with a particular encryption tool and set the password to “123456”.

Work honestly, and beware people who are willing to do otherwise.

Sometimes you fail. That hurts but it’s (probably) okay in the end.

This was especially true late in the business, as I was winding down and could see I had too little time to finish everything. I had a few uncomfortable phone calls and text exchanges trying to establish a compromise that met as many of my (understandably) annoyed client’s needs as possible within some tight time constraints. The end results were good for none of us but acceptable for all of us.

You will make mistakes and fall short. And that’s (usually) fine, if you patch it up as best you can, make amends, and learn from the experience.

Location is important.

I did not quit because I didn’t like the work. The job itself was fine. A few projects were great, a few were terrible, and most were in between.

I quit because the place I was living didn’t have what I needed for personal and social fulfillment (I’ll likely return to this topic in the future). I’ve never wanted to define my life around economic considerations alone, and I have the luxury of making that choice. When I got the chance at a job that paid about the same, in a place that in other respects was much better for personal development, I took the opportunity and left.


I closed down but mostly consider the business a success. I started because I needed to generate money for student loan and car payments. I made some money, got a few nice things, built my confidence, and proved my self-sufficiency. I figured out a few things I don’t want to spend my life doing. I could hardly have asked for a better first job after college.

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