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Wed, 31 Jan 2024 06:51:38 -0800

Wily from private IP /all On having a lost decade Hitting the end of my 30s this year. As old JDU knows well, I basically had an entire lost decade from age 20 to 30 full of online poker, delayed college graduation, and shitty times living in a dumpster-apartment and pissing out of law school before I quit it all, moved to Asia, and started a new life basically. Nine years later, I'm at an OK spot for 39, equity owner in a education company that just got a low 8 figure valuation for possible VC funding. I'm CEO on the US side and poised for visiting possible sites for expansion in East Coast and West Coast in the spring, and can take my family and parents along and never fly economy. But I'd be at an EXCELLENT position if I were like, 31 today. I could've done literally everything I've done here right out of college. I'd be able to take a lot more risks today. I'd for sure take the VC pill of steroid growth or fail-fast, which, to be honest, I'm probably going to turn down now near 40 and not liking the fail-fast part. I'd be young enough to probably pick up a normal MBA along the way instead of looking at toolish / super-expensive eMBA programs. I wouldn't be super delayed on normal milestones like having a kid or buying property or having a retirement account. Hauling around a toddler with a 39-year old back sucks much more than it would've at 29. Also, I'd actually enjoy a lot of expensive stuff I didn't get to do because I was too busy playing Magic cards and chewing anti-depressants in my youth, haha. Like really travel in Europe, learn how to scuba/fly a plane/climb in the Himalayas, spend a few weeks on a beach in Bali, all the stuff that make sense when you're 27 and fit but are ugly and gauche when you're 45 and flabby. Humblebrags aside, I'm grateful for what I have even at 39, but this is an earnest post. Curious what fellow old Millenials / Gen X feel about a sudden turn of fortunes - like whether it makes them regret not doing more earlier as it does for me. _reply Wed, 31 Jan 2024 07:36:34 -0800
Andy from private IP /all I for sure feel like there were many missed opportunities in my life and a lost decade from 21-31, principally due to sticking with stupid decisions rather than cutting my losses and moving on. I posted at length this last November (need to add a post linking feature here) about the biggest forks in the road of my life, and I concluded that I had made reasonable decisions at each decision point-- even though (looking back) there were mistakes. If I could do it all over again, I never would have gone to law school because there are so many opportunities for intelligent, hardworking people that don't involve the toxicity of law. Had I quit in 2009 like I should have, I wouldn't be stuck with this career like I am now, even though this is basically optimal and also a very reasonable outcome. But what about what I want to do, as opposed to what other people want for me? I feel like Pinocchio, because I just want to be a real boy 😢 _reply Wed, 31 Jan 2024 13:39:00 -0800
zerosugar from private IP /all Wily, You are too hard on yourself. You are also not really an old millennial, but mid. An old millennial born in 1980 would be 44. 1980-1983: old millennial shares kinship with Gen X 1984-1989:core millennial 1990-1994:young millennial 1995-1996:really get z _reply Wed, 31 Jan 2024 13:39:50 -0800
zerosugar from private IP /all *gen anyway, maybe you came from a family with really high standards, but stop the regrets. _reply Thu, 01 Feb 2024 07:08:55 -0800
Wily from private IP /all Yea Andy I read your long bio, and your decisions at least made sense with the info presented. Mine did not, haha. Like, let's throw away your Ivy League college experience to try to go semi-pro as a poker player? Let's just pay for law school but play Magic cards all day? Yea they were all based on dopamine needs, impulse, and procrastination, not logic. Hence the regrets. But yea to answer zerosugar (what was your old handle by the way?), it's not even my family, it's mostly just self driven dissatisfaction and impossibly high goals. Like it was so bad in my lost years to not achieve greatness that I chose total failure and quitting normal life. Now I'm doing fairly well and trying hard but just regret not doing it earlier. I actually have a very high work ethic for my generation and compared to most people I encounter today, but it's much harder to hit milestones when I was just sitting on my ass moving backwards for a long time. _reply Thu, 01 Feb 2024 07:25:21 -0800
Andy from private IP /all @WilyTest would you consider yourself a perfectionist? All or nothing? If so, I used to have the same issue. It can be a blessing and a curse. I decided that I'm okay with settling for imperfect in every area except dating (lol), and that's worked out reasonably well. _reply Thu, 01 Feb 2024 08:00:04 -0800
Wily from private IP /all It's only a few areas in my life, but they're all academic or career oriented. When I make a slidedeck, for example, I'm like Michaelangelo painting the Sistine Chapel or Beethoven composing the Ninth, got to get every color scheme and animation and font right (I'm big on Avenir Bold these days), even if it's just for like 20 Asian moms who can't speak English and just want to figure out where to stick their kid on weekends. Most things I really don't care. Wasn't too picky with dating, food I can eat at any level, and personal appearance IDGAF. I just don't want to be too perfectionist in raising my kid, because I see that happening since I know the ins and outs of education and the ultra competitive path well now but fear damaging them if I try to push too hard.
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