Looking Back on a Career in Tech
If I map the path from a TRS-80 in high school to a classroom in Florida, it does not look like a straight line. It looks like passion, hard work, a few dream jobs—and more than once, watching someone else get the chair.
It was passionate early. Sophomore year at Fort Osage High School I got a TRS-80 Model I, and that little machine ate my free time in the best way. Limited memory forced you to be clever. BASIC was a puzzle you could hold in your hands. From there it felt inevitable that I would end up in computer science at CMSU—what is now the University of Central Missouri. The truth is I was ahead of a lot of the early coursework and a bit bored by the general studies. It took a while to get to classes that really challenged me. I never had a science class after ninth-grade physical science. In that era, computer courses counted as science because they included “lab” time—ostensibly. So it goes. The industry did not seem to mind. I was snapped up by the first and only company to offer me a job: TWA.
At TWA my colleagues and I excelled. We did great work on airline systems, the kind of work that has to be right because people are depending on it. I was proud of that. I was also frustrated. Leadership kept arriving from outside instead of being grown from people who already knew the systems and the culture. So I left for American Airlines in Dallas to work on Confirm. When Confirm failed, I moved to SabreVision. After that I consulted for a year—useful, unsettled, the kind of year that teaches you what you miss about belonging somewhere.
Then Microsoft hired me. Dream job. I worked my butt off and had a blast for five years. That stretch included launching Expedia in its early life, building what we believed was the world’s first Internet test suite, and shipping a 3D space combat game—Allegiance—that we took to two E3 conferences. It was exhilarating. It was also exhausting. After a grueling product cycle I needed time away. We moved to Missouri and bought cattle. I started teaching to support my farming habit, which still makes me smile when I say it out loud.
I left the college when they failed to promote my division chair to dean. Instead the outgoing president planted his buddy in the post—someone out of his depth. That pattern would become familiar. Duck Creek hired me next, and over time I led the whole development team through .NET and Agile. Good work. Real responsibility. Then I learned my boss was undermining me behind my back. I quit and went back to Washington—to Expedia.
That return paired me with Dan Reed and an aggressive team that did some genuinely great things. I estimate we brought in easily a couple hundred million in new revenue over about five years. Then Dan moved to London, and they brought someone in from outside and installed him as senior director—again, out of his depth. That lasted a few months. They managed me out. It is a particular kind of melancholy, watching revenue you helped create continue while your badge stops working.
I spent a year at a smaller company building them a development team. One day at lunch with my boss I made the mistake of suggesting that my three development leads had real potential, and that it would be cool to see what they could do without me sitting above them on the org chart. So they took me up on it. It was an amicable departure, and it worked out fine—because it brought me to Level 11. That was a great company, perched on the top floor of a cool building in downtown Seattle. We built some neat internal positioning software: routes for people through the ship, directions you could text, a local global mapping system that ran on a couple of NUCs in Docker containers. Cool stuff. The kind of work that reminds you why you got into this in the first place.
Then I went back to Microsoft. Windows IoT, then Windows proper—fixing security bugs, learning the internals of a system I had admired from a distance for years. I was happy in that work. Then I made a bad choice. I moved to Azure, onto a team that had been absorbed from AT&T and was already in trouble. It was hugely bloated. When they asked my advice, I answered honestly: at Microsoft, that team would have been about a quarter the size for that amount of scope. So…they took me up on the offer. They laid off most of the team, keeping a small core in hope of focusing the effort and making real progress. They could have at least let me go back to Windows. Oh well.
That chapter brought me to Florida. By the time the severance ran out I already had a contract to teach at Florida SouthWestern State College. Looking back, the thread is not that I failed to work hard or care enough. I cared a lot. The thread is that honesty and usefulness do not always protect you when the org chart rearranges itself around someone else’s friend, someone else’s hire, or a suggestion you meant as generosity. I still believe in the work. I still like building things and teaching people how to think. We’ll see where the adventure leads next.