The 5 Money Fears Keeping Retirees Up at Night

Social Security is back in the headlines, with warnings that the trust fund could become insolvent as early as 2032. Does that mean your benefits are at risk? Should you claim early? Economist Larry Kotlikoff joins us to separate fact from fear. We explain what "insolvency" really means, why the long-term funding gap may be much larger than most people realize, what Congress could do to fix it, and—most importantly—what today's headlines should (and shouldn't) mean for your own retirement decisions. Links: MaximizeMySocialSecurity.com Maxifi.com Economics Matters by Laurence Kotlikoff (Substack) Get What's Yours: The Secrets to Maxing Out Your Social Security (Larry Kotlikoff) Social Security Horror Stories: Protect Yourself from the System — and Avoid Clawbacks (Larry Kotlikoff and Terry Savage) Social Security Insolvency (Terry Savage) How to work in retirement without seeing your Social Security checks slashed (Richard Eisenberg) Social Security: Make smarter decisions to maximize your lifetime benefits (Wealthramp) A Summary of the 2026 Annual Reports  

Retirement confidence has hit its lowest point since post-COVID — and for good reason. From skyrocketing Medicare premiums to housing costs, Social Security uncertainty, growing debt, and the crushing weight of caregiving, retirees are facing a financial storm no one fully planned for. In this episode, Terry, Richard, and Pam break down the top 5 worries from the brand-new 2026 Retirement Confidence Survey (Employee Benefit Research Institute) and, more importantly, what you can actually do about them. What we cover: Why 40% of retirees say expenses are higher than expected The shocking truth about Medicare costs in 2026 (Plan G premiums up 40%!) How housing — even if you downsize — can blow up your retirement budget Social Security: what the 2033 trust fund depletion really means for YOU The debt crisis is quietly growing among retirees (39% are affected) Why 74% of workers plan to work in retirement — but only 31% actually do Caregiving: the retirement wildcard nobody budgets for Links: EBRI 2026 Retirement Confidence Survey These are the top 5 things retirees are worried about right now (Richard Eisenberg) IRMAA Increases Medicare Premiums (Terry Savage) Inflation Isn't the Real Problem: Having No Plan to Account for It Is (Pam Krueger) National Foundation for Credit Counseling

Nearly 3 in 4 couples say money is a source of tension in their relationship. But most never figure out why, or what to do about it. In this episode of Friends Talk Money, Richard, Pam, and Terry talk with Heather and Doug Bonaparte, a married couple and co-authors of the book Money Together. Heather is a business and legal affairs attorney. Doug is a certified financial planner and founder of Bonafide Wealth. And together, they have had every hard money conversation you have been putting off. If you are married, partnered, or thinking about combining finances with someone, this conversation will change the way you think about money together. They cover: Why debt and shame are silently running your relationship How financial power really works between partners Joint accounts vs. separate accounts, what actually works Navigating money in second marriages What to do when you and your spouse have different risk tolerances Why every couple needs a "Sorry I'm Dead" letter

Tax season just got a major overhaul. The One Big Beautiful Bill changed more tax rules than anything since 2017, and if you're over 65, retired, or earning tip or overtime income, you could be leaving serious money on the table. In this episode of Friends Talk Money, we sit down with Lisa Green-Lewis, TurboTax spokesperson and trusted tax expert, to break down every major change you need to know before you file. The NEW $6,000 deduction for seniors and who qualifies Tips & overtime income deductions - brand new for 2025 Auto loan interest deduction - what cars qualify Social Security & taxes - the surprise that shocks retirees RMDs, Roth conversions & how to avoid a massive tax bill IRS audits - should you be worried? Free filing options and how to get help Whether you use TurboTax, work with an accountant, or file on your own - this episode could save you thousands. Don't miss it.  TurboTax Free Filing: https://www.turbotax.com AARP Free Tax Help: https://www.aarpfoundation.org/taxhelp

Description: Becoming a financial caregiver for an aging parent can happen overnight. And even financially savvy families can find themselves unprepared. In this episode of Friends Talk Money, we talk with Beth Pinsker, author of My Mother's Money and personal finance writer at MarketWatch. Beth shares what she learned while managing her mother's finances during a long medical crisis, including: • Why a durable power of attorney is critical • The mistakes people make with Medicare • How long-term care insurance really works • IRS issues after a parent dies • Estate planning gaps that cause family conflict • What every adult child should do now This is a practical and emotional conversation about money, aging, and protecting the people you love. If you have aging parents or want to make things easier for your own children one day, this episode is essential. Links: My Mother's Money By Beth Pinsker (Amazon) Terry Savage Personal Financial Organizer (Terry Savage) Estate Planning Search (Search Attorneys)

The Dow is hovering near 50,000. AI stocks are dominating the market. And investors are feeling both confident and anxious at the same time. It's the first Friends Talk Money episode of 2026, and we're joined by expert market strategist Jim Stack, founder of InvestTech Research, to unpack what's really happening beneath the surface of today's stock market and what it means for investors nearing or in retirement. Jim explains why extreme market valuations don't cause bear markets, but dramatically increase the risk. He also breaks down why indexing may no longer feel as diversified as investors think, how the "K-shaped economy" is being driven by paper wealth, and why capital preservation matters more than chasing upside late in a bull market. In this episode, we cover: Why today's market feels eerily similar to past bubbles The real danger of AI stock mania (and what history tells us) How a 50% loss can delay retirement by years Jim Stack's "Ulcer Index" and the true cost of bear markets Why Warren Buffett is sitting on hundreds of billions in cash Defensive portfolio strategies for investors 50+ Index fund concentration risk most investors overlook Housing, interest rates, and what retirees should consider next Jim has successfully helped investors navigate market downturns for over 40 years, including the 1987 crash, the dot-com bust, and the 2008 financial crisis. His message is clear: this isn't about market timing, it's about risk management.

AI is now answering millions of financial questions every day, but how much of it can you actually trust? In this episode of Friends Talk Money, Pam Krueger, Terry Savage, and Richard Eisenberg dive deep into the surge of AI-generated financial advice and unpack the risks, myths, and surprising mistakes that tools like ChatGPT, Claude, Gemini, and DeepSeek are making. A major study shows AI gives incorrect financial answers up to 35% of the time, and the consequences can be huge when it comes to Social Security, Medicare, retirement timelines, investing, or even basic budgeting. To separate hype from reality, we're joined by special guest Jason Lilly, a highly respected Wealthramp-network fee-only advisor, CFA, CFP®, and founder of Tenere Wealth Advisors. Jason shares exactly how he integrates AI responsibly in his practice: what it's great for, where it falls apart, and why human judgment still matters more than ever.   You'll learn: Why AI sounds confident even when it's wrong What AI can actually do well in financial planning (and what it can't) Why budgeting, Medicare decisions, and Social Security claiming can be dangerous when left to AI Hidden errors of omission most chatbots make How advisors like Jason use AI to communicate better, analyze data faster, and stay human-centered Why AI will never replace real fiduciary advisors (and how to spot one who's overly reliant on it) Whether you're already using AI for your finances or just curious, this episode will change how you think about these tools.   Links: 'Well-Recognized Issues': ChatGPT Gave Wrong or Misleading Answers to 35% of Financial Questions Asked in a New Test (MSN) Should you trust AI for Medicare, Social Security for long-term-care advice? (MarketWatch) How AI Is Revolutionizing Long-Term Care Planning (Friends Talk Money) What will happen to Social Security once AI kicks in? (Terry Savage) Tenere Wealth Advisors

Gen X is officially in the retirement danger zone — and many are worried about outliving their savings. In this episode of Friends Talk Money, Richard Eisenberg, Terry Savage, and I sit down with author and workplace/retirement expert Kerry Hannon to dig into the findings from her new book, Retirement Bites: A Gen X Guide to Securing Your Financial Future. We explore: Why more than half of Gen X fears they won't be financially ready How DIY retirement planning, disappearing pensions & late savings habits created a perfect storm The crushing impact of student loans, credit card debt & supporting both kids and aging parents Why so few Gen Xers work with a financial advisor — and how to find the right kind of help The truth about Social Security's future for Gen X Health costs, layoffs, age discrimination — and how to stay employable into your 50s and 60s The new definition of "retirement" and why working longer can be a superpower  Plus: What Gen Xers can control right now to course-correct Kerry also breaks down the huge differences between older Gen Xers nearing 60 and younger Gen Xers in their late 40s, including who may benefit from the next major wealth transfer.Whether you're a lifelong DIY investor or navigating retirement planning for the first time, this episode is a must-listen for the most overlooked generation in personal finance. Links: Retirement Bites: A Gen X Guide to Securing Your Financial Future (Amazon) Reality Bites: Gen X is Nearing Retirement and More than Half Don't Believe They'll be Financially Ready When the Time Comes (Northwestern Mutual) Portfolio Perspectives: Gen X Isn't Ready for Retirement – How Financial Advisors Can Help and Harness SECURE 2.0 (Dynamic Advisor Solutions) Gen X Nearing Retirement With Worries About Limited Savings, Allianz Life Study Finds (Allianz) Gen X's Retirement Shock: The Truth About Healthcare Costs (Friends Talk Money)   

Three-quarters of Medicare beneficiaries say choosing a Medicare plan is confusing, and nearly 7 in 10 (69%) Medicare beneficiaries have not compared their own source of Medicare coverage with other Medicare options offered in their area during past open enrollment periods, according to surveys. These actions can cost you money and limit your medication coverage and pharmacy access. In this episode of Friends Talk Money, we unpack what you need to know about Open Enrollment and your plan options, diving into the pros and cons of Original Medicare plus a supplement and Part D plan versus Medicare Advantage. We explain what's different this year, including the inconsistency around premiums and the discontinuation of Anthem standalone Part D plans. Our special guest is Diane Omdahl, a nationally recognized expert in Medicare. She's the creator of 65incorporated.com, which guides seniors in their Medicare choices, and author of the bestselling book, Medicare For You. She joins us to explain what steps you can take now to ensure your coverage is fully meeting your medical needs and isn't costing you more than you need to spend in 2026. Medicare Beware! A Special Report (Terry Savage) Survey: 75% of Medicare Beneficiaries Say Selecting a Plan Is Confusing Nearly 7 in 10 Medicare Beneficiaries Did Not Compare Plans During Medicare's Open Enrollment Period

Nearly 1 in 4 Americans over 50 are planning a job change this year, according to a new AARP survey—but here's the surprising part: 65% haven't taken any steps to prepare.In this episode of Friends Talk Money, hosts Terry, Richard, and Pam dig into what's really driving career changes for people over 50, 55, and 60—and what older job seekers need to know to stay competitive in today's market. We cover: Why boomers and Gen Xers are rethinking retirement and launching second-act careers How to avoid the black hole of job applications and get results through networking and research Smart strategies for updating your resume and LinkedIn profile after decades in the workforce Using AI tools like ChatGPT (carefully) to improve your job search How to prepare for Zoom interviews and make a strong impression The realities of ageism in hiring—and how to position your experience as a strength Negotiating job offers: when to push, when to say yes, and how to show employers you solve their problems Whether you're worried about layoffs, craving more flexibility, or simply ready for a new challenge, this episode is packed with practical job search tips for older workers who want to thrive in today's shifting economy. Links: Certified Age Friendly Employer Program (Age-Friendly Institute) Employer Pledge Program (AARP) Retirementjobs.com Layoffs This Year Reach Highest Levels Since Pandemic, According to One Measure (Yahoo Finance) Survey Shows a Sharp Increase in the Number of Older Americans Seeking a Job Change (AARP) Best Ways to Prepare for a Job Search After 50 (Next Avenue)