As I head towards 50 (in 19 months), I already confront the big-R: retirement. When could/should I retire? How much money do I need to save? Where could I live? What do I want to accomplish before I retire? What do I want to do after I retire?

Jay tells me of an accounting approximation that suggests you should save in total 25 times your anticipated annual consumption rate while retired. I estimate I only spend about $50k per year with half of that amount dedicated just to rent. I don’t have a lot of other monthly bills. I don’t have a car; I cook almost all of my own meals. So if I plan to spend just $60k per year when retired, I need to save 25 x $60k = $1.5M which is a lot of money, or is it?

I have few people I want to tell that I recently passed one million dollars in savings, 30% of which is in a retirement account. I’ve been very lucky and privileged. I’m also a cheap bastard that lives small. Recently, I’m making big (unwise) plays in the stock market, putting up $10k for a small buy and over $50k for more confident investments. I buy when a stock drops 20%, sell again when it rises 20%. I made twelve-thousands dollars off a trade in just one week of January. I feel crass even writing all this. Money isn’t something our culture and especially our family discusses.

Dollars come and dollars goes. On the one hand, I might write mid-year that I lost my shirt in the stock market. On the other hand, I may have that $1.5M saved by 50. I grumble much about my current job, but sticking with this employer for the next two years may mean I don’t need to work again, especially if the company goes public. Then what? I’m not planning to stay in San Francisco past 50, which will come sooner than felt in September 2022. I can’t afford to retire and stay in this city. I’m also done with San Francisco; it taught me what I needed to learn. I’m ready for another community to teach me more how to grow. Retire at 50? That’s a lot of free time ahead, but no one can plan how long is life.