Gaming out the end of your life

posted by Jeff | Friday, August 18, 2023, 10:02 PM | comments: 0

Ah, the things you think about when you reach an arbitrary number of decades in your life. I was reading an article today about the potential lack of preparedness on the part of my generation for retirement. The short story is that Gen-X'ers on the whole have been only marginally good at preparing for their retirement years. A great many (though not as many as Millennials) are in the student loan debt situation because they borrowed to go back to grad school. But more common is that we just weren't thinking ahead much, and spent our money on stupid shit in our 20's. I can closely identify with that. If it weren't for the industry that I work in, and trying to put away the maximum allowable amount into retirement accounts, I'd be in the same boat. (And I would be in the clear of even having to do that if I would have sold all of my equity post-IPO on my last job, when it was worth five times as much. All I can do is cross fingers and hope it's in a better place ten years from now. I was waiting for "fuck you money" instead of "reduce lifetime risk money.")

Conceptually though, considering my overall generation or not, it's pretty weird to be literally gaming out the rest of your life, until you die. I personally don't look at this as a morbid fascination, because I'm at peace with the transient nature of our existence. It doesn't mean that I don't want to make the most of my time, I'm just not troubled by the fact that there is an end that I can't avoid.

You know the dumb cliches, that youth is wasted on the young. The problem in our 20's is not that we don't appreciate the benefit of early saving and investing, however small it might be, it's that we don't appreciate that time is finite. I just couldn't be convinced of it at the time. I know my dad tried to on a number of occasions, but I ignored him (sorry, Dad). And it really hits home because I do a bunch of interviews almost every week, often three or more, and often (but not always) with people younger than me. When I hear them talk about their career intentions, it makes me hyperaware of the opportunity to do at least some basic planning.

It also reminds me how much we don't know. There are not shortcuts for wisdom and experience. My dad wasn't wrong, I just didn't care because I lacked the wisdom and experience. It's the fascinating anthropological process that I keep coming back to, that we as humans continually take in more information, but we either continue to evolve our world view, or we double down on the one we had. Either way, we don't have a lot to go on early in the process.

I spend a fair amount of time thinking about all the things. How will it go when my son reaches adulthood? How can I or will I support him in that transition? When can I realistically stop working? Do I stop working, or just decide to do something that's purely fun and inconsequential? (Guardians of the Galaxy ride op at Epcot? Bartender at Epcot? LD at the American Gardens Theater at Epcot?) Should I start a business doing something outside of my current expertise? Do any of those things make it more or less possible to travel to the places that I haven't been? Do I need to get life insurance outside of work for the long term? (Another thing I should have listened to my father for.) What should the remaining vehicles in my life be? At what point do we down-size to a smaller house? Is there even the most remote chance of owning property near the ocean? Do we keep up donations to the non-profits we care about? How do you consider all of this while still enjoying life?

I am quite literally thinking about a "retirement career." I've been thinking about that quite a bit. I was already thinking about it by making my documentary, but I'm not sure if that's a career or a one-off thing that I will be able to say that I did, like writing a book. I always wanted to be a rock star, but I don't play anything or write songs. International Man of Mystery is also not actually a thing.


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