I can't say I've ever had any true regrets once time has passed, but I do have one that has been nagging me for a couple of years. Today I had another of a series of events that have helped me correct it.
I've made no secret that I think moving back to Cleveland after two years in Seattle was a horrible decision. I think this despite the fact that financially it exceeded my expectations in every way, and to be sure, we had some really good times and made some great memories there. More than anything, it was the professional regret. While I wasn't crazy about the team I switched to in those last six months at Microsoft (because it never shipped anything), I think in the bigger context there was a place for me there. At the very least, there was no shortage of great opportunities around town. The weird thing is that I remember standing at a window in Building 34, looking out at the mountains, accepting a job that I knew deep down was probably a mistake. But I put that instinct aside with the thought of finally getting ahead and not paying for two houses. That, and summers at Cedar Point.
About six weeks later, I started that job in downtown Cleveland, working for a marketing agency. I remember something about an email exchange I had with my would-be boss during the drive cross-country that set off red flags, though I don't remember specifically what it was. As fall was setting in, and Cleveland went from green to gray, I was already getting a sinking feeling, like I made a horrible mistake. I felt like I had failed and I couldn't even tell you why.
After a week and a half at that job, they still had no work to give me. Not content to sit around, I spent a couple of days prototyping something that I thought they needed, and that would differentiate them from other agencies around town. I brought it to a partner, and we did some napkin math around what it would take to build it. It felt like something interesting was happening, finally.
By the end of the third week, the only billable work I had to do was to FTP some files for someone. That wasn't exactly something that was using my skills. That day, they called me into the office and let me go, not because they didn't have any work for me, but because I didn't adhere to their strict policy about office hours. So they wanted me to physically be there until 5:30 and navigate awful downtown traffic at that time after doing only whatever I could find to keep busy.
What had I done? I moved my new little family for that? Was I, in some way, just being unrealistic? I was so used to working with amazing people. I felt awful for the stress I was putting on Diana over the situation. Fortunately, it was bonus and vesting time just before I left Seattle, so there was no real financial danger. I also never really stopped looking, and had an interview that very afternoon. It wasn't long before I had an offer from Humana, and began working remotely. Still... I remember being in that dark, downtown office in a trendy repurposed century building, and thinking I made an awful decision.
Now, to keep some amount of perspective, even then I knew that the feelings of regret were over something that was likely short lived. I had been there before. The layoffs in the early part of the decade and in 2008 most obviously led to new things. Life isn't permanent, and as it turns out, not much that happens in life is either.
Since that time, there have been several events that have helped heal that regret. I haven't been able to totally let go, but I'm getting there.
It started with my year at Humana. While the work and the position wasn't always as challenging as I would have liked, what was completely validating about it was the fact that I was working remotely. For me, it not only proved that I had the discipline to do it, but it proved in the general sense that distributed teams can work. It meant that geography wasn't nearly as important as I thought.
I did leave Humana to be proactive (I wasn't convinced my position would be there much longer), but after some less than stellar contract work (that did pay insanely well) and the whole desire to change climates, we landed in Orlando and I got a year to work at SeaWorld Parks & Entertainment. The work wasn't unfamiliar, but the scope was insanely huge. I was making design decisions that would impact the company for some time to come. I was having opportunities to mentor developers, learn new things about security and compliance, work with some great vendors, and, oh yeah, it was a theme park company. I don't know that I would've had an opportunity with that kind of scope and responsibility when I was in the PNW.
Then there was something that happened today. Keep in mind that I've had a number of false starts with companies that make software on a sort of agency model. I joined one early last summer, sort of. While it is a company that makes software as a third-party, its methodology is a lot closer to what a pure software player would do, and does it exceptionally well. In fact, it's not really an agency model at all. The short version of my position is to run a development team in a technical capacity, which can include everything from design and code review to in the weeds coding. I have a lot of autonomy (and work mostly remote again). Today one of the senior managers from the client I'm working with cornered me after a meeting, and was just gushing about how awesome our team has been on this project. I deflect most of the credit to the team, but secretly it feels awfully good to get that kind of validation that you're doing it right.
I miss Seattle every day, including everything from the people to the mountains. But there's no question that the future I've tried to make since then has been remarkable. There's an important lesson there, that I've learned before, but don't always retain. There are few things that end in your life that don't make way for something new, and you're likely going to be better for the experience. Being in that shitty office in downtown Cleveland on a dreary day in October felt gross, but it gave me focus, and I'm in a better place because of that seemingly poor decision. That regret is finally starting to fade.