Wed, 31 Jan 2024 06:51:38 -0800
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
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
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.
Wed, 31 Jan 2024 07:36:34 -0800
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 😢
Wed, 31 Jan 2024 13:39:00 -0800
from private IP
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
1995-1996:really get z
Wed, 31 Jan 2024 13:39:50 -0800
from private IP
anyway, maybe you came from a family with really high standards, but stop the
Thu, 01 Feb 2024 07:08:55 -0800
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.
Thu, 01 Feb 2024 07:25:21 -0800
@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.
Thu, 01 Feb 2024 08:00:04 -0800
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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