Wealthsimple is a whole new kind of investing service. This is the latest installment of our recurring series “Money Diaries,” where we ask interesting people to open up about the role money has played in their lives.

I grew up in St. Louis, Missouri. We lived in a big house with a giant yard, and as a kid I raked leaves, pulled weeds, cut down dead branches. In the winter, I shoveled snow off the driveway and the front walk. These were chores, not a real, paying job, but from time to time my grandmother would slip me a few bucks. The money didn’t change my attitude. All these decades later, I still hate yard work.

No one should be able to work in Hollywood if they haven’t worked in a restaurant—you quickly learn what a difference a little bit of kindness can make.

But a few years later, when I was a teenager, my attitude about work changed. I got a job at a Greek restaurant in North St. Louis called Sweet Rose. At first, I was a busboy and a dishwasher, and eventually I worked my way up the ladder and became a waiter. Sweet Rose was a sweet place. I learned how to cook and how to keep a clean kitchen. I learned how to be nice to people and to ask for help when I need it. I learned to love work and find meaning in it. To this day, I like going to work, clocking in and clocking out, the satisfaction of a job well done.

Working in a restaurant is a good life lesson for anybody. My friend used to say that no one should be able to work in Hollywood if they haven’t worked in a restaurant. The appreciation you have for anyone working in a service capacity goes up radically the longer you work a service job yourself—you quickly learn what a difference a little bit of kindness and common courtesy can make for people. It’s important to know how to treat people, and to learn how to respond when someone you’re working with is having a bad day. Understanding other people’s problems—that’s the cornerstone of the service industry, and it’s essential as an actor, or whatever field you’re in. That’s especially true when you’re bartending, which is something I also did. People get a little loose and start spilling their guts to you. And you realize this person just needs someone to talk to; they need someone to show them a little bit of kindness and give them a break.

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I worked in restaurants for a long, long time. Recently, I realized that I’d crossed an interesting threshold. I’ve now—just recently—been working as an actor for longer than I worked as a waiter and bartender.

The main reason to have money is to remove the hindrances that accompany being broke. Otherwise, it doesn’t matter if you have a ton of money or just a comfortable amount.

The other job I gained a lot from was being a teacher. When I was still in my twenties, I went back to my old high school, John Burroughs in St. Louis, and taught acting, improv, and public speaking. It was a really progressive school—I felt that they had done so much to set me on a creative course, it was only fair to find a way to pay them back a little. I didn’t have a multimillion-dollar foundation or anything, so I decided I wanted to just give my time in a direct and personal way. And I enjoyed it even more than I thought I would. The students were great, and I found myself learning something from them every day.

The downside is that teachers in general are pretty under-respected and underpaid. That’s a real drag. Investing in higher teacher salaries is one of the most obvious things we could do to improve life in our society. I spent two years teaching drama, and then came back to L.A. Since then, I’ve found a little success, and now I’ve been able to endow a scholarship for John Burroughs students in my mother’s name: the Deborah Garner Hamm Memorial Scholarship. We just helped one kid to graduate college, and another one is working his way through right now. That’s been a gratifying way for me to spend some money.

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Money, for me, is a means to an end: to pay your bills and eat. Growing up, we were never rich, but I was around money a lot—I had friends who had money. And I didn’t see that people with money seemed any happier than those who got by on less. I’ve never been driven by money—there are more important things to life. But not having money can be a hindrance—it can make life hard, and you spend time worrying about not having it. To me, the main reason to have money is to remove the hindrances that accompany being broke. Once those hindrances are out of the way, it doesn’t matter if you have a ton of money or just a comfortable amount.

If you take a wrong step, you’ll find the right one. If you lose half your money, you’ll find a way to make more.

Money can buy a lot of things, but not everything. Like a time machine. If anyone invented a time machine, that’s something I’d line up to buy. Personally, I’d love to visit Italy during the Renaissance, in the fourteenth to the sixteenth century. First of all, I love Italy. And second, I love the idea of being in a place where everybody is obsessed with learning, an explosion of knowledge and creativity. Every field of study was having massive breakthroughs—people were learning how to paint with perspective, exploring astronomy and physics, and even discovering how to cook better. There was so much cross-pollination between artists and scientists, all of which led to new discoveries. Now, there are things I’d miss, too—painless dentistry seems important, or electricity. But if I could visit temporarily and pop right back, that would really be thrilling.

Some people say that the older you get, the wiser you become and the easier life gets, but I don’t find that to really hold true. As you get older, making decisions can become even harder, since it feels like there’s so much more at stake. There’s more at stake with relationship stuff, with career stuff, and with money stuff. I think the best advice I have for anyone facing tough decisions is not to let the stakes loom so large in their mind that making a decision becomes impossible. You have to keep a healthy sense of perspective—don’t sweat every choice too much or overthink things. If you take a wrong step, you’ll find the right one. If you lose half your money, you’ll find a way to make more. The older you get, the more crucial that is to remember.

As told to Davy Rothbart exclusively for Wealthsimple. Illustration by Jenny Mörtsell. We make smart investing simple and affordable.

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