This week on HerMoney’s special series A Week In Her Wallet, we meet Kaitlyn from Madison, Wisconsin. She’s a full-time state program manager with a side hustle, a toddler, three cats, and a dog — so life is full, to say the least. Kaitlyn and her husband bring in just under $200K per year and manage their money through shared accounts and regular “budget nights.”

As Kaitlyn tracks her spending for a week, she shares her candid voice notes about side gig deposits, why she swears by a monthly cleaning service, and how her love for thrift stores led to a once-in-a-lifetime vinyl record player find. Her week is about much more than transactions; it’s a journey of intentional joy, family memories, and budgeting for what really matters.

💡 Listen in to hear:

Why she happily spends $150 a month on house cleaning

How she and her husband use “funding pots” to budget for travel, gifts, and daycare

The thrift store jackpot that brought her to happy tears

Why they’re winding down their bartending side hustles

A powerful mindset shift around spending money on experiences over things

How they navigate toddler expenses on a budget — and with intention

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This week, Jean sits down with Andrew Ross Sorkin, bestselling author of Too Big to Fail and the brand-new 1929: Inside the Greatest Crash in Wall Street History—And How It Shattered a Nation. Andrew shares why the patterns of 1929 are repeating themselves, from the rise of new technology and market euphoria to record consumer debt and risky new financial products entering retirement accounts. Jean and Andrew break down what’s happening in the markets, what’s fueling the AI-driven investing mania, and what you should be doing now to protect your financial future.

Plus, don’t miss our Insurance Mailbag! Jean and Kathryn tackle your real-life insurance questions, whether you’re downsizing your home, passing down family valuables, or just making sure your coverage fits your next chapter.

You’ll learn:

Empty nest resources from our partners at Nationwide.

👉 Join the HerMoney Investing Club

📰 Subscribe to the free HerMoney Newsletter: https://hermoney.com/subscribe 

💬 Got feedback? We love hearing from you. Leave us a review and tell us what you want more of.

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With healthcare premiums expected to spike and enhanced ACA subsidies set to expire, millions of Americans may be facing a serious coverage crunch. In this timely episode of Your Money Map, Jean Chatzky is joined by retirement experts Marcia Mantell and Jae Oh to break down what’s really happening with the ACA, Medicare, and employer-sponsored insurance, and how you can protect your wallet.

We dig into:

🔗 For more resources and tools from the Alliance for Lifetime Income, visit ProtectedIncome.org

📬 Sign up for their newsletter: protectedincome.org/subscribe

💬 Like what you hear? Leave us a 5-star review and share the episode with a friend!

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Today we’re giving you a first look inside our brand-new Patreon-exclusive Mailbag series — and this one’s powerful.

A listener, a single mom of a toddler, just received a cancer diagnosis. She reached out with urgent questions about how to manage her finances during treatment:

Jean and Kathryn dig into it all,  from the tax treatment of cancer insurance to how to protect your money when life takes an unexpected turn.

This episode is a preview of what’s waiting for you when you subscribe to our new HerMoney Patreon, where you’ll find:

✨ Deep-dive mailbags with Jean and Kathryn

📞 Call-in AMA mailbags with real listeners

🎧 Ad-free listening

🌙 “After Hours with HerMoney” — more daring, personal money conversations

👉 Join us at patreon.com/hermoney to unlock the full episodes and help shape the future of the show.

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What happens to everything you've worked so hard for — your home, your savings, your family memories — after you're gone? If your answer is “I’m not sure,” the time to start planning is now.

In this empowering episode, Jean sits down with Heather Winston, Certified Financial PlannerTM professional of Principal Advised Services, LLC and Assistant Vice President at Principal Financial Group®, to talk all things estate planning; what it can really mean, why it matters, and how to get started, no matter your income level or family structure.

Together, they unpack:

Want help organizing your financial life or finding an estate planning attorney? Subscribe to the HerMoney newsletter at Hermoney.com/subscribe for resources, checklists, and more.

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If you’ve ever felt intimidated walking into a meeting with a financial advisor or unsure if you’re even asking the right questions, this episode is for you. Jean sits down with Pam Krueger, investor advocate and founder of Wealthramp, to walk through actual word-for-word scripts that you can use when meeting with an advisor for the first time, reassessing a current relationship, or navigating retirement planning.

Together, Jean and Pam role-play a variety of real-life money conversations: from figuring out if an advisor is a good fit, to asking about fees, to deciding whether you’re better off managing your own money. You’ll learn how to confidently evaluate the value your advisor brings, how to compare professionals during the interview process, and how to stress-test your financial plan for retirement.

You’ll Learn:

👉 Visit HerMoney.com/FindAnAdvisor to connect with a vetted, fee-only fiduciary advisor through Wealthramp.

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We’re more financially informed than ever, thanks to FinTok, money podcasts, and yes, even chatbots. But when it comes to having real conversations about money with the people closest to us? We still freeze.

This week, Jean sits down with Carl Richards — New York Times “Sketch Guy” columnist, CFP®, and author of the new book Your Money: Reimagining Wealth Through 101 Simple Sketches — to talk about why personal finance is more emotional than we think, and how to start the conversations we’ve been avoiding.

In this episode, we cover:

Resources:

✏️ Follow Carl on Instagram: @behaviorgap

🎨 Explore Carl’s sketches: behaviorgap.com

🧠 Join the HerMoney Patreon for exclusive bonus content: HerMoney Patreon

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Jennifer, 47, lives in Maryland, with her partner of 12 years. She’s the Vice President of Communications for a consulting firm. Her partner is a teacher and voice actor, and together they make about $300,000 a year.

In this week’s A Week In Her Wallet, Jennifer tracks seven days of spending that include thoughtful gift-giving, a haircut she happily budgets for, a hefty mortgage payment on her beach home, and a few well-earned indulgences.

💬 In this episode:

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Have you been laid off, or are you worried you might be? This week, Jean is joined by Laura Brown (former Editor-in-Chief of InStyle) and Kristina O’Neill (former Editor-in-Chief of WSJ. Magazine), authors of the bold and unfiltered new book, All the Cool Girls Get Fired: How to Let Go of Being Let Go and Come Back on Top.

Both women hit the top of their industries… and then got let go. Now, they’re helping other women, especially Gen Xers and those over 40, navigate layoffs, ageism, financial uncertainty, and the terrifying-but-liberating process of starting over.

In this episode, we talk about:

Resources:

💼 All the Cool Girls Get Fired — Buy the book

📲 Follow @allthecoolgirlsgetfired on Instagram and TikTok

🧠 Join our private HerMoney Facebook group: HerMoney Private Community

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On this special HerMoney Mailbag episode, Jean Chatzky is joined by Morgan Housel, bestselling author of The Psychology of Money and The Art of Spending Money, to answer real questions from the HerMoney community. 

From investing a lump sum at midlife to managing fear around paying off debt, Jean and Morgan dive into the emotions and strategy behind smart money moves.

What You’ll Hear In This Episode:

🔗 Resources mentioned:

📚 Order The Art of Spending Money

📘 Read The Psychology of Money — a HerMoney community favorite

🗣️ Join the HerMoney Facebook group for more listener Q&As

Have a question for us? Write to us (or send us a voice note!) at [email protected].  While you’re at it, join the HerMoney community! For the latest episode drops and financial news-you-can-use, subscribe to our newsletter at Hermoney.com/subscribe!

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