Financial experts share their biggest money regrets of the decade



Myles Ma

Myles Ma

Senior Reporter

Myles Ma is a senior reporter at Policygenius, where he covers personal finance and insurance and writes the Easy Money newsletter. His expertise has been featured in The Washington Post, PBS, CNBC, CBS News, USA Today, HuffPost, Salon, Inc. Magazine, MarketWatch, and elsewhere.

Published December 31, 2019 | 4 min read

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Featured Image Financial experts share their biggest money regrets of the decade

We're entering a new decade. It's a good time to look forward, but it can be hard to avoid dwelling on mistakes.

Jay-Z describes regret as "that last feeling you have before you go to sleep, or feel when you wake up and look at yourself in the bathroom mirror." But on the final song of his debut album, "Regrets," he offers this truth:

This is the number one rule for your set In order to survive, gotta learn to live with regrets

In the interest of confronting our regrets and (hopefully) dispelling them, we asked a few of our favorite money experts about their biggest money regrets of the decade.

We also asked hundreds of people about their financial regrets in a survey. Here's what they said.

Kristin Wong

My biggest money regret is not taking full advantage of a 401(k) match early in my career. It was my first job and I didn't realize how good of a deal this was. I saved a little bit, but not enough to get the full employer match. And in a way, it was like I left free money on the table – money that would have added up to quite a bit. If I could go back in time, I would have maxed this out.

Kristin Wong is freelance writer and journalist who frequently covers human behavior, gender, identity and relationships. She published her first book, "Get Money," in March 2018.

Trae Bodge

I don't have too many financial regrets from the past decade because at 51, I finally feel like I have a solid grasp on my finances! But, one regret I have is that I didn't take the time to learn about life insurance when I was with my former employer. The company that employed me from 2012 to 2015 contributed to a term policy, but I didn't know to ask about more permanent options.

When I was laid off, I was surprised to find that my policy had vanished and had no value. I wish that I had at least investigated whole life policies, which would have allowed me to build up some cash value during those three years. (Read the Policygenius guide to the differences between whole and term life insurance.)

Trae Bodge is a shopping expert who has appeared on Rachael Ray, Inside Edition and CNBC.

Jeff Rose

My biggest regret of the past decade was not identifying what my Unique Ability was sooner. While I always gravitated towards things I love to do — creating content and educating others on wealth building — I often bogged myself with tasks that drained the creativity out of me. When I learned to spend more time doing the things I absolutely loved to do (that also paid me exceptionally well) my business took off as well as my creative juices. 

Jeff Rose is a certified financial planner and founder of

Jill Schlesinger

Over the past decade, I have ZERO money regrets! Oh sure, I could say that I wish that I had backed up the truck and purchased as much of the US stock market as possible after it bottomed out in March 2009, but that is just hindsight – and wishful thinking that I could have somehow been able to time the market, which of course none of us can do over the long term. Here’s what I did right — and hope you did too: I didn’t get freaked out at the bottom or greedy at what seemed like market tops. Instead, I stuck to my game plan over the course of the past 10 years. Whenever there was the urge to do something different, I went back to the plan and it guided me through the ups and downs of the decade.

Jill Schlesinger is a certified financial planner, CBS business analyst and host of the "Jill on Money" podcast. She published her first book, "The Dumb Things Smart People Do With Their Money," in February 2019.

Ashley Feinstein Gerstley

I’ve made many (many) money mistakes over the last decade but the one I most regret was one that negatively impacted someone I care about. When I was around 25 I was so proud that I got renters insurance for me and my roommate. It’s still one of the smartest purchases I ever made. After about three years of making our payments, my roommate experienced a significant theft in another country and needed to make a claim. She wasn’t able to because her name wasn’t on the policy. I didn’t know I had to add her name to the policy for her to be covered. It wouldn’t even have cost anything extra to add her! I felt horrible! 

Ashley Feinstein Gerstley is the founder and CEO of the Fiscal Femme. She published her book, "The 30-Day Money Cleanse," in December 2018.

Image: H. Armstrong Roberts (Getty)