Dollars & Sense with Michelle Singletary

A Gold Medalist's Olympic-Sized Money Mistakes

Tue, 27 Oct 2026 04:01:00 GMT

When Lauryn Williams became a professional athlete at just 20 years old, she started earning big money. She went on to win four Olympic medals but found herself in several bad financial situations. Without a strong foundation in personal finance, she relied on financial advisors who didn’t have her best interests at heart. After experiencing the fallout of poor guidance, Lauryn realized she had to take control of her own financial future. Now, she’s helping others do the same.

This week, Lauryn tells Michelle about her journey from becoming the first American woman to medal in both the Summer and Winter Olympics, to building a second career as a Certified Financial Planner. Together, they discussed the costly mistakes athletes and young professionals often make and how to avoid a “dud” when looking for a financial advisor.

Want Michelle to answer your money question? Email dollarsandsense@washpost.com for a chance to be on the show.

00:00 Welcome to Dollars & Sense with Michelle Singletary

01:29 Meet Lauryn Williams: From College Athlete to Olympian

03:09 The Financial Reality of Becoming a Pro Athlete

04:56 Early Money Mistakes and Hiring the Wrong Advisor

06:08 The Two-Mortgage Mistake and the Real Estate Crash

09:37 Navigating Sponsorship Contracts and Financial Anxiety

12:27 The Lack of Financial Coaching in Professional Sports

16:46 What Is a Fiduciary and Why Do You Need One?

19:12 Pivoting From Athletics to Financial Planning

23:54 Relocating to Colombia for a Better Cost of Living

26:45 Overcoming Financial Shame and a $150,000 Mistake

29:39 Navigating the Finance Industry as a Black Woman

31:10 Budgeting and the Pressure of Keeping Up With the Joneses

34:50 The Ultimate Freedom of Paying Cash for a House

38:28 Tackling Student Loans and Defining Financial Security

39:59 Feeling Green: Balancing Cash Flow and Retirement Contributions

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The surprising mistake many retired people make

Tue, 20 Oct 2026 04:01:00 GMT

Marian is retired and enjoying the life she worked so hard to build. But as she watches her friends age and lose their independence, she can't stop wondering what her own version of that might look like — or how to pay for it.

Michelle and Marian talk through her retirement "buckets," explore the possibilities of long term care, and whether she’s really prepared for what lies ahead.

Want Michelle to answer your money question? Email dollarsandsense@washpost.com for a chance to be on the show.

00:00 Welcome to Dollars & Sense with Michelle Singletary

02:08 Meet Marian

03:31 Losing Her Husband and Estate Planning

04:56 Selling the Business During the Pandemic

06:20 Inheriting an IRA and Explaining RMDs

07:52 Social Security and Consolidating Investments

12:25 Breaking Down Marian's Current Financial Plan

15:35 The Bucket Approach

17:48 Long-Term Growth and Coverage

19:09 Grieving the Business You Built

21:13 Aging Without Kids: Who Will Look After You?

27:08 The Chapter In Between

28:12 Staying Put vs. Pivoting: Six Steps to Smart Decisions

35:15 Giving Yourself Permission to Spend

38:28 Final Thoughts: Why an Objective Third Party Matters

Hosted on Acast. See acast.com/privacy for more information.

How Much Should Parents Sacrifice to Pay for College?

Tue, 13 Oct 2026 04:01:00 GMT

When Lauren’s daughter wanted to go to college, there was no question–she was going to be allowed to go wherever she wanted. For Lauren—who is a teacher—a good education was worth the price. But after helping their daughter through college and graduate school, Lauren and her husband are staring down nearly $92,000 in Parent Plus Loans and wondering what that debt means for their future.

Michelle sits down with Lauren to figure out how the couple should tackle their loans, where they can cut back, and whether they can help their daughter with some of her own student loans.

Want Michelle to answer your money question? Email dollarsandsense@washpost.com for a chance to be on the show.

00:00 Welcome to Dollars & Sense with Michelle Singletary

01:00 Meet Lauren: A Mom Facing $92K in Debt

04:33 Paying for College While Managing Life's Expenses

06:26 Was Out-of-State College Worth the Debt?

10:33 Why Her Daughter's Education Was Worth the Sacrifice

14:05 The Money Conversations Parents Avoid

15:21 Debt Dash: Breaking Down the Numbers

20:00 Credit Cards, Eating Out, and Hidden Expenses

23:47 Michelle's Debt Payoff Plan: Start Small

27:07 Understanding Parent PLUS Loan Repayment Options

31:27 Teaching Your Kids to Talk About Money

37:13 Helping Your Adult Child Become Debt-Free

40:39 Lauren's Financial Action Plan

Hosted on Acast. See acast.com/privacy for more information.

Introducing: Dollars & Sense With Michelle Singletary

Tue, 06 Oct 2026 04:01:00 GMT

How do I make sense of my money? This isn’t an easy question to answer, and it’s not one you have to answer alone. On Dollars & Sense with Michelle Singletary, the Washington Post personal finance columnist Michelle Singletary gets candid about the financial decisions that shape our lives. Michelle talks with everyday people, experts, and public figures to help make sense of your dollars.

Tune in every Tuesday for Michelle’s advice on questions directly from listeners. Want Michelle to answer your money question? Email dollarsandsense@washpost.com for a chance to be on the show.

Hosted on Acast. See acast.com/privacy for more information.