May 24, 2023

What Making $86,000 in One Day Taught me about Money.


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A few years back, I was lucky enough to have $86,000 dropped into my bank account one day.

No, I wasn’t some day trader for whom this was a regular occurrence.

I was just another guy who’d never made a ton of money (and had a fair bit of debt) but happened to time the real estate market well in Seattle and found myself the recipient of a big payday.

In a short amount of time, the condo I bought for only $280k appreciated to $400k. I sensed the market was about to turn, so I listed it and got out just in the nick of time before values started to plummet.

Yes, I was one of the lucky ones who got out before a bad downturn.

As a result, in one day, a $120,000 windfall came my way.

(And if you’re thinking: wait, dude, that profit was the result of steady gains over two years, the point is I only got paid at the end of it. Wall Street bonuses happen the same way.)

Anyway: this meant, after realtor fees, closing costs, taxes, and so on, I cleared $86,582.

And it was all wired to my account at once.


My savings account went from something like a just-gettin-by $7,000 to $94,000.

I was suddenly “rich,” according to my previous self.

I was in my early 30s and had spent my entire 20s being exceedingly broke. I started my career as an English teacher making only $30k per year, then quit to study film and acting (read: I was a bartender), and then was in grad school, broke and tutoring SATS on weekends. By the end of my 20s, I was barely making $35k again as a professional writer but also owed that same amount in debt to grad school loans and credit cards.

Meanwhile, friends of mine from college—friends whom I frankly had much better grades than—had gone off to law school and business school and were now working in corporate America making $100k plus salaries. While I drove a 14-year-old car with rusted fenders, they drove new Audis and BMWs. And while I could have been one of them, I wasn’t, and boy was I jealous of their pockets.

I truly believed, one day, I’d have it—or at least a taste of it—and then, all would be well.

And then finally, there it was: dumped in my bank account.

All of my debts could be paid off in an instant.

I realized I could go out and buy a car with cash. Or buy a house! I was “free.”

Or so I thought.

But even as I called up a few close friends (who knew my money struggles well) and told them the good news, I waited for that feeling of salvation to truly take hold and change my life.

But it wasn’t quite there yet.

That belief I had that getting rid of my debts and achieving a new threshold of wealth would finally give me some sense of completeness and fulfillment? It was annoyingly absent.

I even went out with my girlfriend for dinner to celebrate my newfound lack of debt and quasi “wealth.”

But as I went for a run the next morning, I had to admit, I didn’t really feel so “changed.”

I thought maybe it hadn’t sunk in yet. The next day, I paid off $25k of remaining grad school debts, and while on paper I knew I was “free,” it strangely felt no different than paying off a parking ticket.

For years, I resented that burden of debt on my shoulders, and felt certain that when it was gone, I would feel like I’d “arrived.”

But I was still me. Still had the same body, same mind, same existential reality, just no annoying bills in the mail to haunt me.

But then finally, that night, the feeling of transcendence I’d been longing for finally arrived.

But: it wasn’t from the new money in my bank account.

It came from playing music.

I’m a singer and songwriter outside of my writing career, and that night I finally got to headline a show at my favorite venue in Boston, Club Passim. I had nearly 100 good friends in the audience, many singing along to nearly every word of my songs. I was joined onstage by some of my fave Boston musician friends, and after the show, we all hung out for hours and hugged and traded laughs.

It was all the meaning and connection and inspiration I could have ever asked for.

And suddenly I knew in an instant how truly limited money’s power was. I only made about $250 from that show I played that night. But the sense of connection and interpersonal bonding I got was immeasurable. One night of music magic gave me more of a sense of meaning and completeness than getting $86,000 in my bank account.

Sure, one got me out of debt in a matter of seconds, and the other can’t really be measured on paper.

But that night of music was immeasurable in my heart. When I’m lying on my deathbed, I won’t remember staring at my bank account online seeing $94k in the bank. But I’ll probably remember playing music that night onstage, friends howling out my songs with me, cheering, sticking around after to connect and bond. One fan even asked me to sing at their wedding that night.

And that’s the ultimate thing I learned about money; it can only do so much.

Yes, it’s necessary. No, you can’t go through life with a pile of unpaid bills.

Because the real measure of our lives is this: life comes down to the impact you have upon others. How you make a difference in their lives.

That night at Club Passim, I felt that impact. I didn’t feel it when $86k dropped in my bank account.

If you manage to earn yourself a huge pile of money that improves your station in life, gets you the house or car of your dreams, but you don’t really change anyone else’s reality in the process? I don’t think it’ll mean as much to you as you hope.

Sorry to say, but the more truly wealthy people I meet, the more they agree. The wealthiest friend I have is a guy who has a net worth of over $300 million dollars. And he says the best part of his day is when he reads to his four-year-old daughter.

So let’s all know this about money:

Sure, it can remove anxiety, it can give you a sense of safety, and it can buy you a new X, Y, or Z. But it won’t really make your spine tingle. Not the way deep interpersonal connections will.

So if it’s true happiness and transcendence you’re after, I’ve got good news and bad news.

The bad news is: it probably won’t come from an annual bonus, or a stock dividend, or some windfall from playing the market right, or from a winning lottery ticket.

The good news is, it can come fairly easily from the difference you make in the lives of others.

So if you’re spending your life waiting to collect a big payday, stop.

Go make a difference in the lives of your kids, family, or close friends instead.

That’s the kind of “windfall” we should all really be chasing.


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