There's a well-known guy from Microsoft who, for a short time between re-orgs, worked in the same org as me about 8 years ago. He was here this week for a conference, and was nice enough to speak to our local user group. We talked ever briefly about the old MSDN days and some of the people we both knew at the time. Then, Facebook reminded me that this is the seventh anniversary of the day we packed all of our crap onto a truck headed from Snoqualmie, Washington, to Brunswick, Ohio. This brings back a lot of crappy feelings, and I think I'm long overdue to unpack all of that and understand the feelings.
Let me say that I love where we are now. Orlando feels so right and I love it here. That's the part that makes the least sense, because had we not left, we wouldn't be where we are. Moving here was a correction, so maybe it's just that I don't like being wrong.
In 2009, about six months after Diana and I got married (and with her being about five months pregnant), we moved to Seattle from Cleveland on Microsoft's dime. We left Ohio with two unsold houses, hers and my own. It was enormously stressful, given all of that transition. New marriage, baby on the way, new job, new city, almost two weeks being transient, and unresolved real estate situation 2,600 miles away... it was a lot to process at once. But we found an apartment pretty quickly, even if it did end up to be suboptimal, and joining The Empire and being on campus was a fairly exciting thing. My brother-in-law and his family were pretty close to us, too, so my baby had cousins. We had an instant social scene because of the parent group.
About two years later, Diana's house had been sold in a short sale and mine still wasn't going anywhere. We had not really banked any significant cash, and I was endlessly frustrated with paying for two places to live. On a trip back to Ohio, there was a little nostalgia, and the idea popped into our heads that we could solve much of our financial non-action by moving back and living in that house, assuming that the job market there had improved. I quickly got a job, and we just decided to do it. From that moment on, I didn't feel good about it, and there were a ton of reasons for it.
First, I hated the idea of leaving Simon's cousins. I think I struggle with it even more now because of his social challenges, and I assume that cousins don't get to say things like, "I'm not your friend," to him. I'm so happy they have a Florida house now, and even Disney passes, but it's still going to be limited to two or three visits per year.
Leaving Seattle itself kind of hurt. I can't really put into words how beautiful the Pacific Northwest is. Seeing those mountains every single day inspired a sense of peace. There was a sense of belonging I felt there that was unusual for me. There were so many great people I would encounter every day.
Then there was leaving Microsoft. I think I could have stayed, but I definitely was going to struggle a bit where I was, after I changed positions. My peers had quit by then, and my boss, through no fault of his own, was relatively inexperienced and schooled in the old way of making software at Microsoft, which was fundamentally incompatible with everything I had seen and done for the previous decade or so. That may have made it harder to move to a better scene. The company was still a few months away from ditching the stack ranking and toxic obsession with promotion, so it's hard to say. I truly loved that company, and leaving it felt like some kind of failure. I don't know if I'll ever be at peace with that.
I didn't have a high level of confidence in the job I found, but also appreciated that there was a lot out there. It wasn't going to be Redmond, for sure. I landed at this marketing agency in downtown Cleveland, and they had nothing for me to do. What's worse, they wanted me to be in the building 8:30 to 5:30, which was wholly absurd, and particularly horrible given the general desire to not drive during rush hour. When I questioned this, of course, I was no longer a good fit. That day I got an offer from someone else, and within a few weeks, I got the Humana offer to work remote (that job was insanely frustrating, too). This wasn't great career focus.
The 21 months that followed in the Cleveland burbs came with weird feelings too, and they probably had more to do with the feelings of regret than anything. At first, it was cool because we squeezed in a few Cedar Point visits in the fall, which is one of my favorite things ever. But then it got colder, and winter eventually brought snow, and I just loathed it. Everything was gray. As I was working remotely, I would stare out my window and it was just bleak. I felt stuck, but more than anything I just felt as though I made a lot of mistakes. I'm OK with being wrong, but it felt like I made too many mistakes around that move.
All this said, a year into that move, it was pretty clear that the financial turnaround was working. Early in 2013, after I bailed on Humana, I took a lucrative (if impossibly boring) contract gig with the specific intention of moving again, either back to Seattle or to Orlando. We all know how that turned out.
If I were silly wealthy, I think I would spend summers in Seattle and the rest of the year in Orlando. I say silly wealthy, because Seattle is too expensive to own a place you only spend three months a year in. Real estate there is at least twice the cost per square foot as it is here. I miss the people, the technology vibe and the beautiful landscape. But I love Orlando, too. It has been really good to me.