I thought I'd describe a bit about the (many years of) thinking I did that led me to retire now.
My planning for retirement started about 12 years ago, though I would describe it more as "thinking about retirement". I would run into peers at conferences and elsewhere who would tell me they were thinking about retiring, and I always asked them "what are you going to do in retirement?". At the time, this was truly a puzzlement to me. I really couldn't imagine what I would do if I didn't have my career. Sure, I could imagine sleeping in, doing more gardening, travelling more, even doing the NYTimes crossword, but that clearly wasn't going to satisfy me for 25+ years. People seemed to fall into two categories: 1) either health or the availability of grandchildren drove them to retire; they wanted to do less of what they were currently doing, but other than the grandchildren, really didn't mention things they would do more of, and 2) people who had some sort of passion (from rails-to-trails advocacy to model train layouts) that they wanted to spend more time on. I didn't want to retire for the first reason (no one hopes to retire for health reasons, and even now, 12 years later, grandchildren are pretty far in the future for me), and I didn't have that grand, ongoing passion that would drive the second reason. Notice that no one said "my job is boring/stressful and I want to do something different". I'm sure that lots of people retire for that reason, but not in my social circle, apparently.
The strongest advice I got from people (none of whom had retired yet, but they had been talking to people who had) was not to retire "from" something but to retire "to" something. I spent many years trying to figure out what to retire "to". I don't yet have an answer for that for me. I think that if you have a hobby/passion that could be a part time job (in terms of how it would fill your days), that's fantastic. I tried to see if I could turn some things I have always wanted to do into that passion, but my life was busy enough that I could never find the time to get started with more than "dipping my toe in". I finally made a list of all the things I would like to explore as possible post-retirement activities, and that list is so long that if even half of them pan out, I'll be happily busy for many years. At that point, I stopped worrying about what I would retire to.
The second part of my thinking was to recognize how much my profession was a part of my identity. When I was at my penultimate job, about nine years ago, there were things going on (as in, the company was on a path to self destruction) that I couldn't buy into, so I ended up taking a six month leave of absence to de-stress and decide what I wanted to do. (My boss's last ditch attempt to keep me was to offer me the LOA, rather than accept my resignation). During that time, I considered retiring. The money was there, although it would have been a more frugal retirement than I can enjoy now. That was when I recognized that a lot of my personal identity was tied up in my profession. When I thought about not having regular discussions about UI design or User Experience research and methods (or interesting papers I had read or how to attack hard problems) or about how I would introduce myself to people I'd meet, I just couldn't imagine myself as retired. I did consider consulting, but I think that building up a consulting practice is a full time job plus, not a way to make time for other activities, so that didn't seem like an option. I ended up leaving that company and moving to Google, where I've had many opportunities to approach new problems, discuss research issues with others, analyze complex data, and all the other things I love about my work. I believe I've done some of the best work of my career during this time. But as the years went by, the concept of being a User Experience person became less important to me (I started to feel that I had pretty much done all the things I could imagine doing in my career -- doing them another time, with new bright young faces, was fun, but not novel enough to be worth the cost of working full time.) The notion of introducing myself as 'retired' became less of a feeling of "OK, I admit it, my working life is over" and more of "Look at me, I have so many opportunities. My life is a lot more varied than yours (if you are still working)".
This happened to me very gradually. I slowly started noticing how my priorities were changing -- I wasn't as excited about new work opportunities as I had been in the past, much less concerned about 'getting ahead', and more interested in having my evenings and weekends for things other than work. I also had some health problems that led to me being on short term disability and part time work for short periods, and I enjoyed those times more than I had for similar situations in the past. For a long time I wasn't ready to admit this shift, even to myself. Next time I'll talk about what happened when I did admit to this change in attitude.
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