How I Learned To Stop Chasing (More) Money

Money should never dictate your identity as a man. James Woodruff discusses how a weekend vacation changed his views on finances.

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On Halloween, I was sitting on a flight to San Juan, Puerto Rico. The one-way flight only cost me $31, thanks to a flight deal on JetBlue. Apparently, a lot of people had the same thought; get out of the dreary blanket of Fall weather for a few days. I was sitting across the aisle from this older couple in their 60s. Normally I’m not conversational when I fly. But, it was noon and I had gotten a full night’s sleep.

So talk we did.

The husband shared how this was the first real vacation with his wife since they’d both retired a few years ago. When I asked if he and his wife had any grandchildren and if they were missing out on the cute Halloween costumes, the wife said “oh honey, we see enough of the kids. I keep telling him it’s time we enjoy our lives like we used to.” After some sports talk about the Knicks and Mets, I politely backed out of the conversation to retreat into my own mind.

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I thought about what his wife had said. It’s interesting how much time we spend taking care of others. We work to provide stability for ourselves and those who depend on us. We make money only to have a great portion of it spent before direct deposit clears. It’s hard for the average American to have any disposable income stashed away. For the majority of us, whatever socioeconomic status we’re born into is often the class we die in. In other words, being financially comfortable is elusive.

For my entire adult life, I obsessed over making money because it’s the currency for everything. When people see (read: think) that you have money, they respect you. They admire you. They envy you. They want to copy you. I defined myself by the ability to spend and provide with no worries. I learned quickly that money equals opportunity. I took advantage of that. However, my account in terms of my character was operating in a constant deficit. Being morally or spiritually bankrupt is no replacement for money.

When your decisions are motivated by money, you tend to lose sight of the end goal. You lose sight of the very passion that’s driving you. Men measure their manhood by the ability to take care of a wife and family. It’s often a bone of contention in marriages. Either the man doesn’t make enough so he over-compensates in other areas that aren’t healthy for himself or the family. Or, on the other extreme, the man makes a lot of money and because of that, being an available family man might not always be a high priority.

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My very first job in my field was overseas. What people don’t know is that the living conditions were far from ideal. Even though my position was in the front office, I made about $1400 per month; much of which I sent back home. When I talk about that job, though, I focus on the positives. The money was tax-free. I lived in another country. I learned so much about a franchise that is now hugely successful. People assumed that I made great money and I let them.

However, I don’t forget the nights where I tried to make bland, burnt chicken taste edible. I always look out for the few friends that let me stay on their couch or bottom bunk when I was going through family shit. A few times during the year, I take the train to my my old neighborhood alone so I never forget what not having money really feels like. I never want to feel that. I also didn’t like the person I became when money was everything.

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