HerMoney with Jean Chatzky – Ep 489
Title: Your Retirement, The Truth About Social Security, And How to Prepare NOW
Date: August 20, 2025
Host: Jean Chatzky
Guest: Michelle Singletary, Columnist, The Washington Post
Episode Overview
In this frank, compassionate conversation, Jean Chatzky and Michelle Singletary dig deep into what the looming Social Security shortfall truly means, how it may impact women and their families, what Congress is (and isn't) doing to shore up the system, and the practical steps everyone—especially women—should take to prepare for retirement. The discussion spans how Social Security really works, why so many are claiming early (and the stakes), advice for millennials and Gen Z, and strategies for weathering economic downturns.
Key Discussion Points & Insights
1. Social Security Shortfall: Separating Fact from Fear
[04:02–06:30]
- The trust fund that has supplemented Social Security checks is projected to run out by 2033, possibly triggering a 20–25% cut in benefits if no changes are made.
- Benefits won't disappear, but could be reduced; historically, changes are not retroactive for current recipients.
- Potential fixes being discussed include raising the full retirement age (currently 66–67), increasing the maximum benefit age, and removing the income cap for Social Security taxes.
Quote:
“Your Social Security check won't go away, the benefits won't go away, but it could be cut. I don't believe that they will allow that to happen. Can you imagine the chaos it would create across the country?”
— Michelle Singletary [04:36]
2. Why The Crisis Exists—And The Role of Demographics
[07:24–08:48]
- Fewer workers are paying in, while baby boomers are retiring in record numbers.
- Declining birthrates mean fewer future contributors.
- Michelle debunks “conspiracy theories” about government misuse of funds, explaining the mechanics of the trust fund.
Quote:
“There's nothing nefarious going on. … There will not be enough money coming in from current workers to pay people who are collecting benefits.”
— Michelle Singletary [07:57]
3. Congress’s Reluctance and The Political Challenges
[08:48–12:22]
- Social Security is the “third rail” of American politics; politicians fear voter backlash from reform.
- The system is not an individual account—it's a social contract akin to insurance, ensuring a baseline standard of living.
- The longer fixes are delayed, the harder and more abrupt changes will be.
Quote:
“There's no Social Security account that says, here's all the money Michelle put in and this is all her money to be used for her and be damned the rest of you. … It's a contract between the American public.”
— Michelle Singletary [10:05]
4. The Surge in Early Claiming – Motivations and Trade-Offs
[12:22–15:09]
- Applications for Social Security spiked 13% in the first half of the year, driven by fear of missing out before potential cuts.
- Some people claim early as a hedge against possible changes, even if they don’t yet need the money.
Quote:
“I think people are just scared. … I won't ever tell you not to be afraid and scared because you have to feel what you need to feel, but don't act on that. Really look at your financial situation and does this make sense for you right now?”
— Michelle Singletary [14:26]
5. When Is Early Claiming a Smart Choice?
[15:09–17:15]
- If you need the money for essentials, claim.
- Consider health: If your family’s longevity is low, taking benefits early may make sense.
- Some claim early to fund travel or fulfill dreams while they’re able.
Quote:
“There are all kinds of reasons like that that are completely legitimate. … Again, it goes back to looking at your individual situation.”
— Michelle Singletary [16:32]
6. Social Security for Couples, Divorcees, and Survivors
[17:15–20:05]
- For couples, maximizing one partner’s benefit may help the surviving spouse later.
- If divorced after 10+ years, you may claim on an ex-spouse’s record (without impacting them).
- Survivors may “step into” a spouse’s benefit, but can’t collect both their own and survivor benefits.
Quote:
“The longer I wait or he wait, then the more that survivor benefit will be for the surviving spouse … you can collect on your former spouse's record. … It doesn't affect his benefits.”
— Michelle Singletary [17:47]
7. Millennials & Gen Z: Should They Count on Social Security?
[20:05–22:42]
- Many young adults have written off Social Security as “not for them” due to persistent rumors.
- Michelle says the program will exist, but benefits may be lower or ages higher—so incorporate that in planning.
- The importance of early saving and investing (not being too conservative).
Quote:
“It’ll be there. It may not be as much as I’m getting, but it can be a part and should and will be a part of your retirement plan.”
— Michelle Singletary [22:21]
8. Evaluating Political Proposals: Privatization and Investment Funds
[22:42–25:30]
- Senators Cassidy and Kaine’s proposal: Invest $1.5 trillion in markets to grow over 70 years.
- Michelle opposes privatization, advocating to keep Social Security as an insurance system, protected from market volatility.
- She calls for more straightforward fixes (age increases, tax cap removal) over market-dependent solutions.
Quote:
“We need a plan that is not subject to the craziness that can happen in market at any period. … Social Security is one of those [safety nets]. It was a brilliant concept. That doesn't need to change.”
— Michelle Singletary [23:55]
9. Recession Preparation—What to Do Now
[28:33–31:57]
- Michelle recommends increasing savings and emergency funds now, before recession strikes.
- Start by cutting expenses—review everything from insurance to subscriptions (“I revisit our insurance bill. I talked to our cable company…”).
- For most, aim for at least a one-month cushion if you’re living paycheck-to-paycheck; 3–6 months if you can manage; higher-income earners should have up to a year’s expenses stashed.
Quote:
“If you are a highly compensated individual, meaning you make six figures or more, you need to about have about a year's worth, because … it took people making six figures anywhere from 15 to 18 months to find a job at that same salary level.”
— Michelle Singletary [30:48]
10. The Two-Fund System: Emergency + “Life Happens”
[31:57–33:24]
- Emergency fund = unemployment/disability buffer (not for everyday mishaps).
- Life happens fund = separate savings for unpredictable, but routine, expenses (car repairs, pet care, etc.), so you don’t dip into your core emergency money.
Quote:
“If you got a cushion for the cushion … if you spend the 25 and then as you get past that financial emergency, you want to put the money back into the life happens fund.”
— Michelle Singletary [32:49]
11. Retirement Planning Priorities for Near-Retirees
[33:24–37:42]
- Top tip: Pay off your mortgage before retiring if possible, to free up monthly cash and reduce stress.
- Do a realistic, line-by-line retirement budget—don’t rely on generic calculators.
- Know your numbers: retirement accounts, Social Security statements, pension options, fees, etc.
- Avoid fear-based decisions, mitigate misinformation, and always verify advice.
Quote:
“As you head into retirement, get rid of your largest debt on your books—and that's your mortgage. … I sleep better because of that, not having that debt on my book.”
— Michelle Singletary [33:45]
12. Women & Retirement: Empowerment and Advocacy
[37:42–38:36]
-
Women often live longer and may be single in their later years, so it’s crucial to take charge.
-
Michelle encourages women to “own their financial power” (“I love empowering women… statistically, we’re going to live longer and we’re more likely to not have a partner in our older age. And that means that you have to take care of your money. And you can do it, ladies. I know you can.” [37:49])
-
Fun story: Michelle relishes negotiating major purchases, reminding listeners, “when it comes time to talk to money, they gotta talk to me.”
Memorable Moments & Quotes
-
On early Social Security claiming:
“Don't act on that. Really look at your financial situation and does this make sense for you right now?”
— Michelle Singletary [14:26] -
On the nature of Social Security:
“This isn't your money per se, that we all have to say, okay, and we have different things going on right now, less children, less workers. But we want to fund this very important benefit for folks.”
— Michelle Singletary [11:08] -
On preparing for economic shocks:
“Set it and forget it. … You're not going to invest it, you're not going to put it at risk. It's just going to sit. Find the highest yields account that you can park it there and don't worry about it.”
— Michelle Singletary [31:30] -
On the fundamental freedom of knowing your numbers:
“The more that you can do that and feel comfortable with it, even if inside your head you’re screaming, the better off you will be.”
— Michelle Singletary [37:10]
Timestamps for Key Segments
- 04:02 – The real Social Security shortfall: what’s at stake
- 07:24 – Why the crisis exists, and the myth-busting around the trust fund
- 12:22 – Surge in early Social Security claims and why people are doing it
- 15:09 – When it makes sense to claim early
- 17:15 – Couples and survivor benefits explained
- 20:05 – Advice for Millennials and Gen Z
- 22:42 – Political proposals and the privatization debate
- 28:33 – Are we headed for a recession? Preparing yourself now
- 29:49 – Building your emergency and “life happens” funds
- 33:44 – The top three retirement priorities for those near retirement
- 37:49 – Empowering women to take financial leadership
Final Thoughts
This episode provided a comprehensive, grounded, and actionable look at the realities of Social Security and preparing for retirement. Michelle Singletary’s advice balances tough-love practicality (“pay off your mortgage!”), encouragement for self-education, and a strong call for women to own their future. Listeners—especially those feeling anxiety about the headlines—will come away with clarity, reassurance, and steps they can take right now.
For more from Michelle Singletary, read her column in The Washington Post. To continue empowering yourself financially, check out Jean Chatzky’s newsletter at HerMoney.com.