What It Feels Like to No Longer Worry About Money

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Growing up in a poor neighborhood with a single mom was not, as they say, child’s play. Drinking and drugs and familial anarchy permeated the walls of our cockroach-infested apartment. Not to mention all the baggage that comes with that lifestyle: discontent, anxiety, uncertainty, depression.

To add insult to injury, we were broke. Like flat broke. Dead broke. Poor as church mice. I’d have to remove my shoes to count how many times our electricity got shut off on Warren Street. I shit you not.

By the time adulthood was at my doorstep, I thought if I made enough money, I could circumvent Mom’s path; I could somehow achieve happiness (or at least finance it). So I spent my twenties traversing the corporate ladder.

Fresh out of high school, I skipped the whole college route and instead found an entry-level sales job with a corporation that “let” me work six, sometimes seven, days a week, ten to twelve hours a day. I wasn’t great at it, but I learned how to get by—and then how to get better.

I bought a big-screen TV, a surround-sound system, and a stack of DVDs with my first big commission check. By 19 I was making over $50,000 a year, twice as much as I’d ever seen Mom bring home, but I was spending even more, racking up the credit-card debt. I obviously needed the three M’s in my life: Make. More. Money.

So I worked harder, much harder, and after a series of promotions—store manager at 22, regional manager at 24—I was, at age 27, the youngest director in the company’s 140-year history. I’d become a fast-track career man, a personage of sorts. Which meant that if I worked really hard, and if everything happened exactly like it was supposed to, then I could be a vice president by 32, a senior vice president by 35 or 40, and a C-level executive—CFO, COO, CEO—by 45 or 50, followed of course by the golden parachute. I’d have it made then! I’d just have to be miserable for a few more years, to drudge through the corporate politics and bureaucracy that I knew so well. Just keep climbing and don’t look down.

And so I didn’t look down; I looked up. And what I saw was terrifying…

“You shouldn’t ask a man who earns $20,000 a year how to make a hundred grand,”…[Read more on The Minimalists]

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