Deciding when to retire is a tough decision. For those of you who have retired, what was the tipping point? Do you wish you had kept working longer or that you had retired earlier?
My wife and I were both career Colorado state employees. Our jobs were both nonpartisan but involved working in a political environment, and my job, in particular, involved quite a lot of night and weekend work and sleep interrupting, weight gain promoting, short temper inducing stress.
We don't have kids, have been pretty conservative with money and savings excluding travel, and had started our careers long enough ago that we were lucky enough to be locked into a generous (not NY, California, or Illinois crazy generous and overly gameable, but generous) defined benefit pension plan (which has since been modified several times to become progressively less generous for more recently hired state employees so that virtually all new hires choose a defined contribution plan instead) that let us retire without early retirement penalties at 55 with any number of years or service or after 50 with thirty or more years or service.
A big factor for us was our mortgage, which we'd been rapidly paying down with significant extra principal payments and paid off in full in September of 2024. My wife retired just before that on July 1, 2024, at 57, and I called it November 1, 2025, at 56. I'm an attorney, and post-COVID, public sector attorney compensation generally rose a lot faster than it had previously, and I got promoted in 2021, so, to capture much of what easily were the best raises of my career in my pension benefit (which is based on the average of the three highest years of salary with some guardrails to avoid "bumping" abuses so I got super-lucky with the post-COVID public attorney market reset), I worked one more year than I'd initially planned to. Even with that, I actually left quite a bit of pension money on the table by not working another additional year, but the extra money wouldn't have changed how we live and I'd simply hit the wall. Ultimately, I felt as though the combination of being surrounded by the toxicity of politics and the workload over the last few years was starting to age me 3-4 years for every 1 that I worked.
I think I retired at the right time in that I both improved my pension considerably by working one more year and also allowed my wife to adjust to retirement for over a year before I joined her. We also had a lot of turnover in my former office, and especially on my team, in the last few years, and working the extra year allowed me to keep training up and supporting younger attorneys and plan the transition for the woman (who I worked with for 26 years) who took over my position. While one more year would have both allowed me to do more of that and improved my pension quite a bit more, as I said, I'd hit the wall, especially when being made aware on a daily basis of the difference in my retired wife's stress level and mine. I just couldn't stand it anymore, maybe most of all the daily effort of maintaining a positive face and doing my best not to be the burnt out old guy that makes the younger employees question what they're doing with their careers. I never wanted to be that guy.
While I haven't yet figured out what retirement is going to look like for the medium and long term, without the stress I have slowly lost 10 or so pounds total while adding muscle and getting measurably stronger through better sleep, more exercise, and more intentional eating habits while reading more books, trying to learn a foreign language, and slowly feeling my brain, which I truly think was being impaired by my work, get a bit sharper. I likely will do some sort of work again down the road, as I am struggling a bit with feeling "unproductive", but I think it's going to be a reinvent myself kind of self-employment or side gig thing rather than anything to do with law or government. Year one of retirement is mainly about getting my body, mind, and house (literally in terms of decluttering and some repairs ) in order, and reconnecting with people who I like and have frankly neglected for quite some time. We've also got some pretty great travel plans. Sometime late this year or early next year, I think I'll be ready to get more intentional about what the long term looks like in terms of "productive" living.
As for your own decision, leaving the more personal questions, like "how much of my identity, if any, is related to my work/how much might I miss it?" "will I be bored without it?" etc ... aside, make sure you, and your wife/partner if you have one, know and are on the same page about what your retirement wants/needs/expectations are and how much they'll cost and know how much income you'll have to pay for them. Insurance generally, and especially health insurance, is a bitch, at least pre-Medicare, unless you have some sort of subsidy for it.
If a defined contribution retirement account is a big part of your plan, make sure you KNOW how much you can take on a monthly basis without putting it at risk of running out. My in-laws actually saved enough to retire on, but my MIL, who we didn't know didn't know about things like the 4% rule, grossly overspent their retirement accounts until they ran out (spent on what I don't really know), and they are now in a position they don't like to be in and didn't need to be in even after my wife and I bailed them out of the credit card debt that she'd been too embarrassed to tell us she'd taken on once she drained the retirement accounts (we had to do it as by the time she got desperate enough to tell us about it the balances were snowballing at a horrifying rate). If you don't have a fixed fee-only financial planner or a tight financial plan, I strongly suggest using one and making one before making the retirement leap.
