💰The Root Of All College Money Challenges
Our relationship to money in college is not a financial problem. It's a self problem.
We treat money like it lives in a spreadsheet. Budget better, compound earlier, cut the lattes. And sure, that stuff helps. But it skips the part nobody wants to look at: the reason we spend, save, hoard, or avoid money the way we do has almost nothing to do with money. It has to do with the self carrying the wallet.
A kid who grew up watching their parents fight over rent builds a different financial nervous system than one who never heard the word "mortgage" until college. A student chasing FIRE isn't just chasing a number. They're chasing a feeling of safety, of control, of an identity that finally makes sense. The financial decisions are symptoms. The self is the diagnosis.
That's why most money advice feels like putting a bandaid on a broken bone. It addresses the behavior without touching the thing generating the behavior. Our developmental stage, our attachment patterns, our childhood context, the identities we've built to survive college: all of it shapes what money means to us before we ever open a brokerage account.
Creating a healthy relationship with finances isn't a math problem. It's a self-understanding problem. And until we look there, we'll keep optimizing the spreadsheet while the thing underneath it stays exactly the same.
The Carrots And The Non-Professor Kids
Growing up, I didn't really care much about money.
My father is an environmental studies professor and my mother a high school biology teacher, both making over six figures a year. We weren't jumping into a pool of gold coins every evening. But I didn't have to worry about buying fresh local carrots, restringing my tennis rackets, or even a $2,500 Alienware gaming PC that I used almost exclusively to play The Witcher 3 at settings no human eye could distinguish from the next tier down.
The best thing my parents did for my financial future was financing growth-oriented things like sports and education, but not entertainment or relaxation. I had to earn my movie tickets working odd summer jobs: coaching kids tennis, caddying at a golf course. Some of the least hardworking, least skilled people I've met in life are the children of parents who handed them everything. Their biggest survival challenge is deciding between the Audi and the BMW for their sixteenth birthday. My parents made sure I wasn't one of them.
Meanwhile, I watched the non-professor kids in my town with complete estrangement. Dirty jeans and discounted school lunches. Even our classes were separated. Pretty early on the professors' kids got funneled into the advanced track and many of the non-professors kids were left behind.
It really hit me the year I didn't make advanced math and landed in Algebra 2 with them. First day of class, the teacher put an equation on the board. Something like 2x + 6 = 12. She asked if someone could solve it. I watched as nobody moved. Not confusion, not hesitation. Just blankness.
My self now feels only compassion for those students. It's not their fault they were born in their situation and me in mine. But I'm ashamed to say that in the moment I felt only horror, and a single-minded ambition to never let myself get put in such a sorry state again. I studied my way back to advanced math by the next year.
I was beginning to realize personal finance is a lot more personal than it is finance.
The environment you grow up in has more influence on your outlook toward money than any book, course, or guru. That's why universal money advice is so absurd. If you're super frugal, it might be because you grew up in poverty and never want to risk returning there. Look at the World Values Survey, or any serious human development theory, and you'll see that growth needs like love, expression, and purpose are all associated with higher income security.
You can't judge someone from rural India for having different financial priorities than you. Their environment required it. Financial relationship, like everything else in life, sits on a developmental arc. As you develop, your relationship will change. (Check out my article on College Freshman Ego Development to learn more.)
But knowing that intellectually and feeling it in your bones are two very different things. That gap would take me years to close.
The Tractor King
There was one purchase in particular I remember having a large effect on my relationship with finances. My dad bought a tractor that cost as much as a year of tuition at an average U.S. university. I was bewildered.
Then I saw him ride it out to our land for the first time. Smiling like a kid king atop his throne. No gold, no expensive clothes, no audience. He just loves shaping our land with the tractor. It wasn't about the money. It was about the relationship the money purchased.
I watched him buy other things too. Cameras to watch animals. Bags of bird seed that he refilled with the quiet devotion of a monk tending an altar. Not every purchase was a score. We don't really use our tennis ball machine much. But that personal aspect of finance stuck with me. My dad wasn't optimizing. He was listening to what actually brought him alive, and spending there.
The idea that money doesn't buy happiness is rubbish.
Money absolutely does buy happiness, but indirectly.
It affords things or experiences which make you happy. More importantly, it affords a relationship to life. One in which you don't have to worry about being forced into decisions out of survival. In which you have the independence to focus on your growth needs: purpose, love, creative expression, becoming the kind of person you actually want to be.
Most advice stops at "spend less, save more, compound early." And that's fine as far as it goes. But it doesn't go far enough. Because it doesn't ask: what are you actually trying to buy? My dad knew. He was buying mornings on a tractor with nobody watching.
I wouldn't discover my answer for years, and the search would cost me more than any tractor.
The Book That Lit The Fuse
Junior year of high school. Tennis sectionals tournament. The day was perfectly sunny, the kind of day that usually pulled me into the match completely. But today my attention kept drifting back to the book in my bag.
The Four Hour Work Week by Tim Ferriss.
I don't know if you've ever read a book that rearranges the furniture in your brain while you're still sitting in it. This one did that. The idea was simple: automate passive income, eliminate waste, design your life around experiences instead of obligations. I lost my tennis match that day. I blame Tim Ferriss and I don't forgive him.
By the time I got to Cornell, I was fully immersed in the FIRE movement. Financial Independence, Retire Early. For me it represented so much more than money. It represented a life of focusing on growth needs without worry, of not becoming beholden to some office cubicle checking the clock every five minutes for when Friday would come.
The book awakened something I still believe to this day: being rich does not mean being wealthy.
Wealth is control over what you do, how you do it, where you do it, when you do it, and why you do it. Take an investment banker making $200,000 a year. Rich yes. But not wealthy. They have to work inhumane hours to make that pay check. Factor in all the things they are probably buying to stay high status in their friend group and they're not even as rich as they seem.
I didn't want to be rich. I wanted to be wealthy.
I wasn't trying to buy a thing. I was trying to buy a relationship to life.
This drove me every second of every day. If I stopped for even one moment, I wouldn't just be forced into a cubicle. I'd lose the ambition that was keeping me from feeling how lonely I actually was.
What I didn't understand yet was I pursued FIRE partially for freedom, but the deeper reason was survival. Identity survival. From the moment I arrived at Cornell, I felt disconnected from my fellow students. I left my first freshman friend group after a couple of months. The breaking point was a dinner where they all sat watching TikTok. The whole meal. We barely exchanged three sentences. I left my steamed beans and tofu inside the trash uneaten and walked out.
The less connection I felt, the more I used FIRE as an identity escape. The FIRE spreadsheet became what prayer is for the anxious believer: something to return to when the world stops making sense. While students spent their money on boba tea, vacations, and 3:00 a.m. visits to Target, I bought the Part Time YouTuber Academy for $1,500. Later, Building a Second Brain and Linking Your Thinking for $750 each. I genuinely saw them all as investments into my FIRE future.
What I didn't appreciate was the systemic reality shaping my fellow students' different financial relationships. Many were taking out massive loans to pay America's cartoonishly inflated university costs. They couldn't afford the risk of pursuing FIRE. I could, because my parents were funding my education.
That context shaped everything, and I was too deep inside my own identity to see it.
The Golden Cage
I wasn't unhappy during FIRE. Not depressed. But discontented in a way I couldn't name.
My friend John Mavrick and I built Obsidian University, an info product teaching people how to use Obsidian for personal knowledge management. It made $20,000. For a college student, that should have felt like triumph. Instead, I felt annoyed.
I was sitting at the coffee shop in Olin Library thinking about creating another video on how to take linked notes in Obsidian and felt like vomiting. Really? There was better Obsidian content out there already. Was I providing something new the world actually needed, or was I just feeding the identity machine? I talked with John about moving on and he was in full support. Incredibly conscious friend. I'm grateful for that conversation more than almost any other in college.
But the cage wasn't just professional. It was personal. Many of my closest relationships were people in the FIRE movement: my brother, John, online friends. While my identity stayed fused with financial independence, everything became about getting there. I almost lost my first girlfriend halfway through our relationship because she felt I wasn't paying enough attention to her. She was right. Every purchase, even a $3.00 black coffee, became something standing between me and those two magic words: financial independence.
My parents expressed doubts about my path, which I now recognize as perfectly wise and well-meaning advice. They were baby boomers who grew up in a different financial era, one where going to work and getting a paycheck was expected and valued. So I brushed off their concern as ignorance.
The irony is rich: I was so attached to my identity as a free thinker that I couldn't take feedback from the people who knew me best.
My pursuit of FIRE was never just about money. It was about surviving the identity helping me get through college. Pursuing FIRE was a rebellion against the loneliness I felt in my first two years, a way of proving I could make something of myself even if I couldn't make friends who understood me. The loneliness fueled the hustle, and the hustle distracted from the loneliness. A tidy loop with no exit. (Check out my article on how the self is the root of all college freshman challenges to learn more.)
Most people think about getting the money. Almost nobody thinks about the path to getting it. What do you have to sacrifice to arrive? Sure, I might reach FIRE in five to ten years. But what would I lose along the way?
Pine Needles And Silence
I switched out of Obsidian content and had a couple years where I just created anything I wanted. Spirituality videos. Gamification essays. Whatever pulled me. It was wonderful for my soul.
And terrifying for my bank account. My income from YouTube AdSense and Obsidian University got cut in half. I was in the privileged position of having my parents fund my undergrad education, so most expenses were just subscriptions and my YouTube editor. But watching that number shrink still triggered something primal. Not shame in front of friends. Shame at seeing myself being slowly chained to an office job. Chained to a life where I didn't control my time. The exact thing FIRE was supposed to prevent.
During this period I found myself happier than I'd been in years. I had more time to focus on what I'll call internal character: the texture of who you actually are when you aren't performing productivity. I learned Spanish. Started attending a spiritual college club called Bhakti. TA'd a backcountry cooking course in the woods.
One day on that backcountry cooking course, we had a full afternoon of activities planned. After lunch, a student asked if we could just, well, do absolutely nothing. So we did. We spent an hour in silence. Some students did arts and crafts. Others sat watching the afternoon sun warm the pine needles. I went on a short hike where the loudest sound was gravel crunching underfoot.
It was magic. Disconnection with a group, something some of those students may never have experienced before. And I didn't feel bad at all for not creating.
The character you build is more powerful than anything money can buy.
A good life is everything you need, and a little of what you want. Nobody on their deathbed names their material possessions. They reflect on character. On the moments that made them feel like the sun on those pine needles actually landed somewhere inside them. What we should be thinking about when earning money is giving ourselves the foundation to focus on character as freely as possible.
Happiness is in many ways reality minus your expectations. Not that we shouldn't have expectations. Without them we'd have no ambition. But expectations that say if I don't have this, I can't be happy are a different animal than expectations that say I'm content as things are, and I value growing toward something more. If you aren't fulfilled in basic survival needs, you might genuinely need certain things before happiness is even on the table. But once you're there, the game changes entirely. (Check out my happiness video to learn more.)
The question nobody was asking me during FIRE, the one I wish someone had, was simple: what kind of character are you building on the way to the money?
Slay The Spire On A Tuesday Morning
I'm back to creating niched content now. Conscious College. I've been working a full-time remote job for the past year. It's everything my past self would have dreaded: trading time for a paycheck.
It's not perfect. Sometimes I work more than I'd like, and balancing relationships with work remains an open question. I moved to the Netherlands to experience a culture less obsessed with defining itself by what it does. The Dutch, for all their directness, have a relationship with leisure that most Americans would find suspicious. They leave work at 5:00 p.m. and mean it.
Last Tuesday, I played Slay the Spire 2 in the morning. I started writing and just didn't have the FIRE (pun intended) to keep going. So I closed my laptop and loaded up the game. In the afternoon I called my dad spontaneously, without guilt, and we talked for an hour about nothing in particular. Our apartment rentals. The end of his semester.
Three years ago that Tuesday would have sent me spiraling. A wasted morning. Lost income. One more day further from financial independence. Now it felt like exactly what a good Tuesday should be.
I'm still hopeful of becoming financially independent. But I'm much more patient than I used to be. Perhaps it will take five years, ten, twenty. I don't know. I'm enjoying the days I'm in too much to let the timeline run my life. Memories and experiences compound over time in ways no interest rate can match. What do I spend money on now? Lectures. Board game club admin fees. Roleplay social events. Books and courses. Things I know will genuinely bring me joy because I've done the work of figuring out what joy actually means to me.
I'm experiencing a slow change from valuing freedom above all else to valuing stability and care. College gives you a structure off which you can have less structure. I was privileged to have that. Now that I'm building something for myself rather than relying on my parents, I don't have the freedom to be so free.
The Real Currency
Our relationship to money is not a financial problem. It's a self problem.
We carry our upbringing, our fears, our identities, and our developmental stage into every purchase, every savings goal, every late-night Amazon scroll. A kid who grew up watching non-professor kids get left behind in Algebra 2 builds a different financial self than one who never had to notice the gap. A student drowning in loans has a different relationship to risk than one whose parents funded their education. Neither is wrong. Both are shaped by context neither of them chose.
If we don't pay attention to what actually makes us happy, we'll keep thinking money buys happiness directly. It doesn't. It buys the conditions. The tractor your dad rides with nobody watching. The silence on a backcountry afternoon. The phone call with no agenda. But only if we know ourselves well enough to spend there.
In many ways, creating a healthy relationship with finances is creating a healthy relationship with your self. Understanding your developmental context. Questioning the identity money is propping up. Noticing what you're really purchasing when you click "add to cart" at 2:00 a.m.
I spent years trying to buy freedom and accidentally built a cage. Then I spent years buying nothing and found more freedom than any spreadsheet ever promised. Now I'm somewhere in the middle, which turns out to be exactly where a Tuesday morning of Slay the Spire and an afternoon call with your dad belongs.
Finances are personal. And the most personal thing about them is that they're really about who you're becoming.
That, and bird seed. Always invest in bird seed.

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