Photo by JC Rodriguez/For The Washington Post
This article is from “Let’s Talk Numbers” by JC Rodriguez, a personal finance coach and one of our Featured Voices, The Washington Post’s platform highlighting content from independent creators.
From expensive cars to missed investment opportunities, Americans across generations are sharing the financial decisions they wish they could take back.
For some Americans, it's an expensive purchase they wish they'd never made. For others, it's waiting too long to invest, taking on credit card debt or simply not understanding how money works.
In the season two premiere of Let's Talk Numbers, a series produced in partnership with The Washington Post, personal finance creator JC Rodriguez took to the streets to ask Americans across generations about their biggest financial regrets - and what they've learned along the way.
The answers revealed some surprisingly universal lessons.
The cost of keeping up appearances
At 19, Anthony bought a Porsche that cost nearly $100,000. With insurance, he was paying approximately $1,100 a month. Decades later, the now-54-year-old remembers it as one of his biggest financial mistakes.
"Buying a car that you can't afford when you're young," he said.
He's not alone. Tyler, 31, admitted that his history of buying cars was largely driven by appearances.
"Every car that I've ever purchased, it's just upgrading to upgrade," he said. "It's all for show."
Blackmer currently pays $589 a month for a 2017 Ford F-150 he purchased in 2024.
Even Phil, who was approaching his 94th birthday, had advice about car expenses. After leasing a vehicle for his business, he came away with a simple recommendation: "Don't lease."
The money mistakes that compound over time
For Jess, a millennial who earned money acting in her early 20s, the regret wasn't a single purchase. It was spending income she could have saved and misunderstanding the cost of credit. After a 12-month interest-free credit card promotion expired, she found herself facing unexpected charges.
"All of a sudden, I was like: 'What is this interest that I have to pay?'" she recalled. "That was a really bad mistake that I made."
Others regretted what they didn't do with their money.
Bill, who began investing in his mid-30s and eventually became a millionaire with his partner, wished he'd started earlier.
"Time is on your side for the young ones," he said, referencing the Rule of 72, a formula estimating how long an investment takes to double at a given rate of return.
What younger investors can learn from older generations
At 23, Hunter is already investing through Robinhood, although he acknowledged that picking individual stocks can be risky. He's now considering exchange-traded funds and retirement accounts as part of a longer-term strategy.
Meanwhile, Laura , 71, offered a different perspective shaped by decades of economic ups and downs.
Wyant, who paid for her PhD while working, said she doesn't regret investing in her education. And when it comes to the stock market, she avoids obsessing over daily fluctuations.
"I don't look at the stock market every day like a lot of people do," she said. "It'll get your nerves if you're not careful."
Across generations, the interviews revealed a common theme: Financial wisdom often comes from experience, but learning from someone else's mistakes might be the better investment.
This story is part of Verified, a newsletter that is published by Washington Post Creator, a team outside The Washington Post’s newsroom that is focused on the creator economy and content partnerships with independent creators. Learn more about Washington Post Creator.
