Looking at my Social Security earnings history, my total lifetime earnings will be almost $4 million by the end of 2025. But I’m broke and have very little to show for it. No big paid off house or fat 401(k) account. By one measure, I should have able $2 million in investments with a modest savings rate. And this isn’t even counting the Amazon RSUs I got 20 years ago, which easily would add another $500k. Yet here I am, approaching half a century and figuratively broke.
I would like to think that it wasn’t all for naught. Experience is what really matters, they say. I have traveled around the world. I have played golf at the fanciest courses and driven some very nice cars. It wasn’t like I got scammed out of my money or poured all my money into a failed business. But as I start focusing on retirement, it does make wonder if that $1,000 Pebble Beach round was worth. Maybe the first time but the second and third time maybe I should have just bought some $VOO. Was the 911 worth it, or maybe I should have just gotten a Lexus and invest the difference.
In the multiverse, there is a 50 year old version of me who has $3 million in investments but none of the experiences. But in that universe what would that version of me do with $3 million? Responsible me wouldn’t suddenly go buy a $200k car, would I? And even if I did splurge, would a 911 at 50 years old be the same as one at 35? Or would it be the classic midlife crisis trope of the old guy buying a convertible sports car to recapture his youth? It feels impossible to truly know what version is better, because in each version your entire personality and perspective changes. You just can’t really grasp what you never experienced.
My Anonymous Life 
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