It took me years, but I eventually got over the poor decision to move back to the Cleveland from Seattle. Oddly enough, letting go of that regret in part became easier by taking on a different regret, which was spending money I didn't have on pointless shit in my 20's. The pandemic and middle age only make this worse.
While we certainly could have made Seattle work in terms of home ownership eventually, there's no question it would have taken many years more to get there. And with many more years having actually occurred since then, boy am I glad we're living in Central Florida, where the McMansions are cheap and appreciating quickly. A fair amount of our net worth, on paper, is tied up in our house now, which is an extraordinary change from being underwater eight years ago.
But the last few years I've been in a state of background anxiety over the fact that retirement is now closer than college graduation, and that's horrifying. Not only did I piss away money on things in my 20's for which I have nothing to show for, but I didn't even start a retirement account until I was 33, and didn't really even put anything in it until the next year. By conventional wisdom, I should have accumulated around $140,000 when I was 35. I had exactly $1,000. Getting divorced in that period of time had some positive long-term outcomes, among them being that taking care of yourself wasn't just about being healthy, it was thinking about your future.
When I got to Microsoft in 2009, they were known for great compensation, and at coastal wages. Being a newlywed with a child on the way, I got my shit together and participated in the 401k. Over that two years, I contributed about 5% of my salary, and the company would match half of that. In other words, I made an extra 2.5% just for getting my part in. It was tight, for sure, because we were still paying for both Cleveland houses and the Seattle rental. But note to 25-year-old me: That contribution multiplied by 6 in less than 10 years. And I can't touch it until I'm 59.5 without the feds taxing the shit out of me.
Could I afford to save like that in my 20's? Well, I balanced my checking account with Microsoft Money '97, which I still use, so I know what I spent money on. The answer is, yes, I could have saved probably 5% of the $25,000 I made in 1997. That would have been $104 per month, which apparently was what I spent going out to eat (and drinking beer) every two weeks. (By the way... the bills I had then included long distance phone service, a pager and rent of $615.) If I would have invested just that much every month for all 23 years, I would have $71,000 today. Time does extraordinary things to the money you save.
I'm not sure I would call my lack of discipline a regret, but it doesn't feel good in my 40's. If social security survives the next 20 years, we'll be comfortable. If it doesn't, we'll have to be disciplined until that time, which will be less fun given our desire to do stuff. Invest, my friends, especially if you're young. Put something into an IRA. It'll be worth more than the used beer you evacuate every weekend.