why i (intentionally) made the worst financial decision of my life

there's this mentality that i have had for quite some time. not sure where it came from. i see it a lot among people who grew up in wealthy families, but that wasn't really the case with me.

i did have some baseline of financial privilege that likely contributed. while we weren't rich nor did i spend much money as a kid, i did face the attitude from my parents that if i did want to buy something, i generally could. moreover, when i was building my nonprofit at 15, i did get unconditional financial support from my parents during the first period before we began generating revenue. this was likely the biggest factor: i directly engaged in career & growth-oriented work by abstracting away from the worries of money.

being in a relationship with money

from what i see, i think most people have some sort of relationship with money, one that feels slightly more intrusive than sought, like viewers' frequent parasocial relationships with streamers. for some it's a mirror: if you have a lot, you feel good about yourself, if you don't, you're insecure. for others it's a romantic partner: they're in love with it, there's passion, and if it's taken away they crave it. for others it's a toxic ex: they know it hurts them, but they keep going back and can't figure out why.

the issue is that this approach fundamentally inhibits growth. it's like being attached to your subway line that you use for commute. if it goes into maintenance one day, you're devastated and give up on the commute. when it's crowded, you're jealous that you can't have it to yourself. i.e., instead of focusing on simply getting to work and engaging in the thing that creates returns, you're emotionally invested in a distraction.

i think society's the one that's taught us to treat money like we're in a relationship with it. but I can't really blame society b/c money is fundamental to how we live. think about your closest friends from high school. how'd you end up at that high school? probably your neighborhood. what decided your neighborhood? the size of your house. and that came from how much money your parents had. divorces happen over money. people can't afford food. a startup with 50k in the bank has three months to exist before it has to raise. money is fundamental. I couldn't go a week without my phone, and money is the same. that's okay. but we can shift the relationship we have with it.

the worst financial decision i've made

so then what's the alternative? treating money as a tool. a resource. with zero attachment.

the best illustration of that is my current situation: i'm in sf right now and without this mindset shift this wouldn't exist. up until may, i was in toronto for an internship. and i had nothing lined up for the summer. i hated college and did not want to waste my summer away in saskatoon, my college town. i applied to a few hundred internships and networked with as many people i could meet, but it bore no fruit.

i asked myself where i needed to be. the answer was sf. but i only had money i made from my internship, which was 60k cad/year (i interned for 12 months). post-tax and living expenses, i probably had ~20-30k cad (14-21k usd), which would be all that i would have to get me through the summer + my senior year (tuition + living expenses). not a lot. especially if i wanted to live in a top 5 most expensive city in the world with no income.

it's the worst financial mistake I've ever made. it's the best life decision I've ever made.

if i chose the path of financial responsibility, and more accurately the path where i have an attachment to my money, that this decision would have never surfaced. but b/c it did, it enabled me to capture a major inflection point in my life that happened earlier this month, which will definitively set the stage for the next few years.

the 65 paradox

abstracting one level further, the conventional wisdom on money is to seek financial responsibility. it's the asian immigrant mentality. get your first paycheck, max out your 401k, then buy a house. then buy a second house. then buy a third house.

why? so u can finally live life at 65? in the pursuit of wanting to live life, you paradoxically forfeit life.

maybe your reason is that you want to, generously, enable your kids to live life. but that won't happen either b/c humans are monkey see monkey do. the kids are going to learn from your actions and end up perpetuating the cycle.

additionally, let's assume you do make it to 65 and are now reaping the benefits of your savings. what are you going to do? visit places you always wanted to see, spend time with friends and family, work on your hobbies. you're in fact using the money as a tool anyway. then why not practice the same behaviour at 18 instead of 65??

perhaps a counterexample is the time value of money; a thousand dollars now is worth more than a thousand dollars in ten years. I agree with that completely. i'm arguing for the same principle, actually, but simply replacing the reinvestment from money with myself. i'd rather obtain compounded returns on my goals than the s&p500.