Courtesy of Paul Ollinger
This as-told-to essay is based on a conversation with Paul Ollinger, author of "Reasonably Happy: The Skeptics Guide to Achievable Contentment." It has been edited for length and clarity.
I grew up one of six kids in Atlanta. When I was around 11, my dad was taking me to get my first cavity filled. I was super nervous, but my dad, it turns out, was thinking about money. As we walked in, he said, "Don't get the novocaine. It's $20."
That anecdote sums up everything about finances in my childhood home. My father worked for the power company, so he always had a job, but he was never rich. I had everything I needed, but scarcity was the subtext of our economic reality.
That's very different from how my own kids, who are 13 and 15, are being raised. I was one of the first 250 employees at Facebook. I left the company about 13 years ago, but due to good pay and stock options, I'll likely never need to work again as long as I make smart choices.
That means my kids are growing up in a very different financial reality. When my son was 7, he came home from one of his even richer friend's house. He said, "When are we going to hire a chef?"
The reaction in my head is one I can't repeat here. I wanted to yell, "A chef? The only chef I grew up with was Chef Boyardee!" But I realized my son only knew what he sees.
I joked about sending my kids to middle-class camp at Grandpa's, where they had to face horrors like having a fan instead of air conditioning. I approach the difference between my upbringing and theirs with humor, but the truth is no one imagines raising kids in an economic situation that's so vastly different from how they were raised.
One book that's helped me greatly is "The Opposite of Spoiled" by Ron Lieber. He talks about the importance of giving kids allowance, because that allows them to make mistakes with small amounts of money.
My wife and I give the kids a modest monthly allowance. That means we don't have to talk with them about money every day, and they weigh up whether they really want something, like a new soccer ball.
It's important to me that the kids know that money isn't in endless supply. If they buy X, they might not have enough money to buy Y. Although I have substantial wealth, I still prioritize my financial decisions.
For example, I could fly private, but that would require me to work in a traditional job to have more income coming in. Yet, it's more important to me to be able to do the type of work I enjoy, comedy, which happens to pay less. I value professional flexibility more than the status of flying private or the joys of getting to skip TSA, so I prioritize that.
I've loved comedy since I first got onstage at Dartmouth College during grad school. My parents paid for college, but I had $80,000 in student loans for graduate school back in 1997. That financial reality meant that I had to take a traditional job in the tech world rather than chase my dream of being a comedian.
After working in tech for a few years and paying off my student loans, I quit to pursue comedy full time for two years. My standard of living was still good because I had a lot saved. But when I met my wife and knew we wanted kids, I returned to the tech world because I wanted more financial security than life as a standup comedian could give me.
Working at Facebook ended up being a bigger home run than I could have ever imagined. I remember saying to my wife, "This might be as big as MySpace one day." I couldn't even imagine how big Facebook would become or the changes it would bring to my life.
Now that I spend time writing jokes about my financial situation and talking about money on my podcast, I've realized that happiness comes from making a choice to be grateful, not from a number in your accounts.
