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Nov 3, 2026 44 min

How to get a paycheck, forever

from 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 [email protected] 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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This episode was published on November 3, 2026.

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