I started a new job today. Again.
I’ve changed jobs a lot in my career: 13 times in almost 32 years — including five times in the last six years. It’s true that the software industry, in which I work, is volatile. Everybody in this industry knows we’ll work for several companies before we retire. But I think my career is a little extreme.

I’ve been laid off a couple times when a company’s fortunes fell. I was also fired twice. The first time I was also un-fired, which is quite a story. The second time was just a couple years ago and was the most painful experience of my career. But most of the time I’ve left of my own volition. A couple times I quit a bad situation and the rest of the times I was recruited away for a better opportunity.
My career has been anything but a straight line. I went to school to be a software engineer, but I graduated during a recession and jobs were scarce. The best job I could land was one writing software user manuals. I liked it a lot and did it for eight years, at which point I saw I’d gone as far as I could go in technical writing. My programming skills had gone stale so I took a job in Quality Assurance as a tester. There I was shortly promoted to manager, and over the next 17 years I built and led testing, test automation, and performance testing teams at various companies.
In 2015 I had been Director of QA at a startup (Company Zero) for 2½ years. After some terrible financial results they laid off a lot of people, including me. I did some consulting that summer before being picked up as Director of QA at another company (Company One). While there, I came to realize I’d gone as far as I could go in QA. I set my sights on moving into Engineering, but didn’t know how to get there. Then the company needed someone to lead its Product Management group, so I took that on too.
After I’d been there about 18 months, a startup founder with whom I was acquainted asked if I’d join his company as Director of Engineering. That was a huge stroke of luck! So I joined his company (Company Two). After about nine months that founder was forced out in a management shakeup. The the person who replaced him ran off or forced out the entire management team she inherited. She finally fired me late in 2018.
The best job I could get before money ran out was a step back, as Engineering Manager at a large, established company (Company Three). It was an okay place to work, but I had concerns about the company’s future. I’d been there only a few months when another large, established company (Company Four) recruited me to be a Senior Engineering Manager, leading four teams and their managers. It was easy to say yes. That company had a wonderful culture, an excellent software delivery process, and an outstanding product architecture. It was a genuine pleasure to work there. I felt like I’d hit the workplace jackpot, and decided to settle in for a long stay. I still wanted to be Director of Engineering again, but this company was such a good fit for me that I decided to enjoy the ride. But then last autumn the company made some changes that affected me and my teams in some ways I didn’t enjoy. A couple key reasons I had been happy evaporated, and I couldn’t see my own future there anymore. I was underutilized and bored. I remain shocked by how quickly things changed for me.
Today I start as Director of Engineering at a young company (Company Five) that I would say is coming out of its startup stage. Going on two years ago a colleague introduced me to their Chief Technology Officer and their (now previous) Director of Engineering. They were looking for some perspective on building out their testing team. I was happy to share my experience with them, and they were able to adapt it well to their situation. When their Director of Engineering decided to start his own venture late last year, they called me about taking on the role. This company makes a useful product, has solid financials and a great growth strategy, and has a reputation as being a wonderful place to work. It was easy to say yes.
And so today I begin. Again. I’m eager to stop this merry-go-round of job changes and do good work here for a long time. Everything I’ve been able to learn and discern about this company gives me great hope that I can.
Because I’ve changed jobs so often, I’ve learned how to recognize when it’s time to go. I wrote a couple posts about it on my software blog: here and here.
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