Dollars & Sense with Michelle Singletary

For decades, financial journalist and HerMoney CEO Jean Chatzky has told people to save, save, save for retirement. But what happens when it’s finally time to spend that hard-earned money? This week, Michelle talks to Jean, her longtime friend, about her new book, “The Forever Paycheck,” and the challenges of turning a lifetime of savings into retirement income. Together they explore why so many struggle to spend in retirement and how to start building a forever paycheck.

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

01:41 Meet Jean Chatzky: HerMoney Founder

02:58 How Has the Conversation Around Money Changed?

05:55 What is a Forever Paycheck?

09:30 Why Jean's Mother Couldn't Spend Her Retirement Savings

12:57 Why We're So Afraid of Running Out of Money

15:25 Michelle Can’t Spend $30 on a Phone Case

18:36 When Couples Disagree About Retirement Spending

20:09 Planning for the Retirement You Want

22:01 How Much Money Do You Really Need to Retire?

25:21 How to Start When Money is Tight

28:49 Investments vs. Annuities: Which is Right for You?

36:11 Give Yourself Permission to Enjoy Your Retirement

38:58 Is the 4% Retirement Rule Still Reliable?

41:17 Jean's Advice to Michelle

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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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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

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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

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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.

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