How I came to my farewell

Last week I posted my farewell message to Microsoft. This post will talk a bit about how I got to that. The next will talk about where I think I’m going from here.

If you know me, you know that I’ve always been incredibly passionate about my work at Microsoft. More than that, I always loved the company (and still do!). A rare confession: I actually teared up at last fall’s Company Meeting. A few things built it up, but what pushed me over the edge was seeing first Surface ad previewed on the giant Key Arena screen. It was a magnificent moment, and in it I felt an overwhelming sense of pride. I know I’m not the only one who felt it. Thousands of us were witnessing the culmination of years of incredibly hard work, seeing all the pieces come together in a way we previously had to imagine (which sometimes took some effort!). After years of working on individual pieces and prototypes, we were finally seeing it the way it was about to be delivered to the entire real world.

At the completion of Windows 8, much of the team understandably took a moment to step back and catch our breathes. I dabbled a bit in hobby app development, and for the first time in a while found myself with enough free time to actually invest myself in a romantic relationship (maybe too invested, in retrospect, but that’s another story). On the work front, I took an opportunity to follow a couple of awesome managers to work on a new team in a different area of the product, and was pretty excited about the work we were signing up for. I had worked primarily on Search in different capacities for my entire tenure at Microsoft, so felt that I was ready to dive into something new.

Something else commonly happens as you transition from one product cycle to the next: You consider all your options. I felt it was prudent to give some thought to what they were and whether any of them seemed more interesting than the last time I’d done this exercise. I fear this will sound like gloating, but one of the great things about being an experienced software developer these days is that options are plentiful. I sorted the ones I found reasonable into four rough “buckets.”

1. Stay where I was and continue driving forward along the path I was on. This was my default, and almost assumed, really.
2. Try out another “big” company (Amazon, Facebook, etc) either in Seattle or someplace I wanted to move.
3. Find a small startup to join or co-found.
4. Start my own.

On a Monday evening in the middle of November I left work a little earlier than usual. I went to one of my favorite cafes in the Lower Queen Anne neighborhood of Seattle, and started reading several blogs and articles about experiences others have had with similar decisions. I found some interesting reads (a couple of which I wish I could remember how to find!), but actually found myself being more interested in adding a couple of user-requested features to 4th at Square. However, that process was soon interrupted when I saw what appeared to be an odd sort of joke appear in my twitter feed. “Steven Sinofsky to leave Microsoft.” Right, and a pig learned to levitate. But then more came, and soon I received an e-mail confirming that this was, in fact, happening.

I still know nothing about how or why that came to be. I think I’m within my liberties to say that from my perspective, absolutely nothing about the Windows team’s plans or directives seemed to change from the course he’d had us on. But in retrospect I think in some strange way it had an effect on me. In particular, it led me to revisit certain things I’d thought of as fairly set in stone. Or if not set in stone, at least highly predictable given my own insight and that of others made available to me.

And yet, my main focus was on work, and continuing to ramp up on my new areas of ownership and help my team figure out what needed to be done. Between that, the rather difficult end to aforementioned relationship, some family issues, and a minor surgery I undertook that month, I had enough on my mind that making a major life change wasn’t really something I had the bandwidth to even ponder. Certainly not with due clarity. What I did find was that I was looking forward to Christmas vacation a lot more than usual. Most years I’d have to essentially be pried away from my work. Looking back, I think I expected that the holidays would finally give me the chance to reflect and give some actual thought to those options.

And yet, that’s not what I did. What actually happened was that I spent my holiday break relaxing in St. Maarten and then North Carolina with family. I did zero work of any kind, and I gave pretty much no thought at all to big life changes. It really was a vacation, and one I hadn’t realized I was long overdue for.

Upon my return home and to work, though, all those stresses immediately came flooding back. It was as if something had momentarily blocked a fire hose pointed at me, and grateful as I was for that respite, it just made me all the more uncomfortable when it began dousing me again. There were a lot of things in my life I felt I couldn’t control at that time, but one of the few things I could control was my career. I thought it over for a few days, and then one morning before going into my office at work, I called my father. I walked around the periphery of my building’s parking area talking to him, freezing just a bit. I told him I’d decided to leave Microsoft, but that I didn’t know what I’d do next. My only plan was to take some more time to decompress, try to get some non-work things in order, catch up on some traveling I’d been putting off, and figure out where I wanted to be and what I wanted to be doing. I wanted to spend some time on the east coast and seriously think about moving back there. One reason among many to consider was to be nearer to family. I think he was surprised, but didn’t really try to talk me out of it, and I’m grateful for that support.

I’ll avoid going into much detail about what followed. I will say I am immensely grateful for the understanding my management chain showed, and for the options availed to me. In particular, time to work things out so that I could make a decision with clarity instead of to release pressure from the flood. As you now know, in the end I decided to leave after all, but with clarity of purpose: To build something of my own.

For now I remain in Seattle. One advantage of a solo project is that I have unparalleled flexibility to relocate. Seeing as I paid my dues through the dreadful Seattle winter, I am keen to make the most of the glorious summer days (which we’re already getting a taste of). Following that, I’m undecided. I’ve reeled in my anchors, whether the wind takes me away remains to be seen.