November 3, 2026

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How to get a paycheck, forever (with Jean Chatzky)


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.

Chapters:
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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