Like a Boss


I’m not so much like a boss, because I am a boss. And honestly I rather like it that way.

My first manager job was at 18 as an assistant manager at a movie theater. Its not exactly prestigious and the qualifications are pretty much that you are work harder than the average minimum wage person and show some tendency to being responsible. In many ways its not a lot different than what I do these days, leading a small team with a specific mission; running auditoriums, concessions, box office or sometimes all 3.

At 19 through some twists of fate I actually go my own theater and was a general manager. It was a run down theater on the verge of closing, it was pretty much just for a few months, and the place was small as multiplexes go (a 3 screener with one big auditorium) bit it was mine! I actually got it pretty cleaned up in that time. I also made some real rookie errors as a manager and learned a lot in a short time. I’ve always been proud of it and I have some great silly stories from those days.

My next stint as a manager was many years later was when after about 10 years as a developer at Mammography Reporting Systems my boss left the company and I wrangled myself a job as Program Manager. At first it was a glorious ascent, I was told I shipped more products in six months that we had in 4 years and was lauded as a guy who could wear a lot of hats at once and wear them well. Unfortunately things started to go sour on that. I clashed with my bosses (the CEO mostly) about how software should get made and lost the argument. I inited in rivals and one of them really did me in turning my disagreements into demotion until he had about shoved me into the lowest run of the department at which point I left.

Finally my current job at Trupanion where I currently manage a small team of developers in a slightly larger cross functional team. I started as a somewhat senior developer. For a very brief time I managed all the developers there, but it was due to some chaos where there just wasn’t anyone else to handle it. As we grew I scaled back a bit to managing the cross functional teams but try to keep a hand in larger strategy when I can.

There is a lot to say about being a boss, lots I’ve learned from mistakes and successes but I’ll save that for the next post. So stay tuned for words of limited wisdom on the topic of leadership. 🙂


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