Five years after Microsoft

posted by Jeff | Friday, September 9, 2016, 10:00 AM | comments: 0

On this day in 2011, I turned in my blue badge, Prime card, AmEx and ORCA card at Microsoft, in a somewhat unceremonious visit to some random office on the Redmond campus. The range of feelings was pretty broad, and the decision to leave the company and Seattle is something that I've struggled with, and often regretted, ever since. I'm not sure why I've never been able to let it go. On this day in 2009, I began the process of making arrangements to fly out and interview there.

My mindset at the time was this: I was indifferent about the group I was working in at Microsoft. I felt that I had been underhired, not in the leadership role that was becoming routine success for me at my previous jobs. (Looking back, apparently they were interested in me in a leadership capacity, but for whatever reason it didn't work out that way, and the second group I worked in didn't lead much of anything, or ship anything.) The psychic weight of my unsold house in Cleveland was getting to me, not because it made money tight, but because we weren't accumulating anything. I thought I missed the social impact of living in Cleveland. All of these things combined made it seem like moving back into the house in Brunswick, Ohio, was a good idea.

I've written countless times about the outcome of the decision. Financially, it was huge, reversing some relatively minor credit card debt to massive savings. That was pretty much the end of the upside. Career wise, there was nothing excellent in CLE, and in fact I spent a year working remote for Humana, an opportunity that sharpened my soft skills considerably, but wore on my soul (because health insurance and healthcare is broken). I landed some consulting work at ridiculous rates that further padded my bank account, but there was nothing for us in Cleveland. Even our social circles weren't what they once were.

We missed Seattle, and it was on the table, but Orlando won when I scored the contract gig at SeaWorld Parks. The house sold in 48 hours. We've been in Orange County now for three years. I'm not saying it's permanent, but we do like it here. No winter, lots of sun and theme parks aren't a bad way to go.

The funny thing about working at Microsoft is that no one in Seattle cares. It doesn't make you special. Tens of thousands of people in the Puget Sound region work for the company. But move to the east, and it's surprisingly a big deal. Finding work was not hard. The crappy agency I worked at for a few weeks ("work," because they had nothing for me to do) involved no technical interview. My Humana interview was 20 minutes, and I'm still not sure how they found me. Fortunately, my two Florida jobs involved real interview processes, but the experience I had in Redmond played heavily into the conversations. The scale of what I got to work on was a bid deal. The program manager position may have not been ideal, but my takeaways from it still play well into my skills and experience. The bottom line is that my Microsoft experience made me better in every way, and it has opened countless doors for me since.

I still look fondly at the company. In my years there, it was a company very much in transition. At a high level, they were starting to understand the toxic side effects of stack ranking (a disincentive to collaborate) and golden handcuff incentives (hanging out just for the money). At the smaller levels, one group at a time was learning to be agile and faster. From what I hear, that transition is still in progress, but it's getting better because of the culture change that is largely advocated from the top. I'm impressed with what has been going on with the developer tools and Azure in particular. Lots of growing pains, but they've come a long way in five years.

Would I ever go back? Yes, but the only way I would ever leave my current gig and Central Florida is if the job was really the kind of clear, forward motion opportunity that makes the move logical. Going there the first time would have been a lateral move if not for the fact that there was no work in Cleveland, but the market isn't like that now. Relocating life has to come with clear advantages. But yes, I still admire the company, and I'm amazed at where it has gone in the last five years.


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