Start of a new Chapter

For the first time in over a decade, I’m free of all professional obligations and must answer the question “what next?”.

I’ve completed my last day at my previous employer. It’s the end of a journey that started 12 years ago, when I joined AppAssure Software as their first (and, up until now, only) engineering lead. I built that team up through the years until the acquisition by Dell in 2012, and continued to grow it under Dell until the software group was divested in 2015 into Quest Software. Along the way I picked up some more titles (Executive Director), some awards (Distinguished Engineer), and lots of great experience managing a software engineering team in a large, legacy software company.

Though I wouldn’t trade that experience for anything, it was not without its downsides. As the years went by the scrappy, deeply technical, product-oriented execution of the startup days became more bureaucratic, more political, and must less accountable. While I’m sad to see the team go, I know what a strong team we had and I know they’ll all have no trouble at all finding other opportunities. As for me, it’s an excellent time to take stock of where I am and figure out what I want to do with the back half of my career.

I know what I don’t want to do: work at another large company. I crave deeply technical problems to solve, limited resources with which to solve them, and the focus and shared purpose that thrive in early-stage startup environments. While I take great pride in the team I built, which at its peak was over 150 engineers spanning half the globe, I must admit that I was disconnected from much of the engineering org by the end, with layers of management between me and the rank and file. That was a necessary adaptation at the time, but not one I enjoy. I prefer to be on the front lines, so to speak, getting a little dirty, sharing struggle and triumph with the rest of the team.

I also know that whatever I do next, I want to do it overseas. While I love the apartment and city and state and country I live in now, I’m restless and want to experience a different kind of life. America is a land of plenty, of boundless consumerist ecstasy, of wealth and privilege and – among the upper classes at least – a life of ease. America also has its share of problems, about which nothing more need be said. In any case, I know from past adventures overseas that I enjoy the experience of a different place, even (especially?) the hardships and endless possibilities in developing countries.

I’ve spent the most time in Ukraine, where I managed a large team of engineers for the last 9 years. Kiev is a great city to be a foreigner in, and in the years since I first came it’s transformed dramatically for the better. It’s also a very cheap place to live by American standards, which means my available investment capital will go much further. Finally it’s home to a highly educated population with a culture that I very much appreciate, which I’m glad to say includes a number of colleagues I count now as friends.

Have I just reasoned my way into launching another startup? In Ukraine? Where there’s a war? It sounds absurd, how would one even undertake such a thing? How do I get a work visa? I barely speak any Russian and absolutely no Ukrainian. What about corruption, and crime, and bitter cold winters?

It sounds crazy. But I can’t get the idea out of my head…