Entrepreneurship, or lack thereof

Many years have passed since I delivered software or published blog posts. I can hardly even identify with the person I was in those times. People who used to know me probably think I’m “retired”. I guess maybe I am, though I still work as hard as ever. I just don’t ship, and not everything I work on is software.

From 1995–2010 I worked myself to the bone. It was a happy time, for the most part, but spotted with uncomfortable memories. I loved programming and designing — I have nothing but good memories about that. What haunts me are all the clumsy social interactions and awkward relationships that followed from the attention my work brought me.

I used to think I was going to start a software company. Even after I realized it was the wrong thing for me, I continued to let “software entrepreneur” be my identity, and many people saw that as my career path. Running a company means stepping away from the code editor and putting all of your energy into organizing teams of people. That’s not something I’m remotely interested in, even if it means I can bring big ideas to life and make boatloads of money.

During my career I managed to avoid being part of a team for 95% of the projects I worked on. I ignored what my employers asked for and worked independently on whatever caught my fancy, often starting new projects that they never asked for. I got away with it because at the time my skillset was rare. I was willing to get fired because I knew there would always be another opportunity. Because I worked my tail off, my bosses grudgingly came to see me as a team of one, and many of my projects became valued assets that were staffed by large teams after I moved on.

So I was never forced to develop the social skills needed to be a collaborator. I don’t regret this at all. What I do regret is that I took way too long to lose my ambition to found a company. I said “yes” to the wrong things over and over and over again. I disappointed so many people. It’s embarrassing how many times I cancelled talks I had agreed to give at conferences. I was an EIR but never bothered to show up at the office. I had countless lunches and coffees and interviews with people wanting me to work with me. I should have immediately said “no” to all of these, but I was fooling myself.

After I left Facebook I bought a house with a big backyard. This open space lured me into a gardening practice that has been so cleansing for my mind and body. I now spend about half the year working obsessively on software projects. I work just as hard as I did in my twenties and I burn myself out just like I always did. I gain weight. I become unreachable by friends and family. Then spring comes and my garden beckons. I mothball my laptop and spend the next six months planting and pruning and weeding. I regain my health and repair my relationships. Then my starved brain demands stimulation and I must return to software for the next six months. This cycle has been unbroken since 2011.

I’m growing comfortable with the cycle. It would be nice if I could splice the gardening phase and the coding phase into one balanced lifestyle, but I am only good at focusing on one thing at a time. Though I still dream of shipping software, I am reluctant to have actual users depending on me. Nobody wants to have their bug marked as “WILL FIX AFTER GARDENING SEASON”.

So my projects will never be used by anyone. I’m sure there is some eastern philosophy to explain why there is so much joy in building elaborate sandcastles that are destined to vanish with the tide. I’m not looking to change that.

What I am looking to change is the fact that I stopped writing. I miss the closure that comes from sharing my thoughts and the comprehension that comes from articulating fractured ideas. I don’t need anyone to read this. It’s about the exercise. So this one’s in the books! Let’s hope I come back for another one soon.