In this powerful and inspiring episode of Your Money Map, Jean Chatzky sits down with entrepreneur and author Julie Wainwright, founder of The RealReal, to talk about failure, reinvention, and why it’s never too late to bet on yourself.

She shares candid stories from her new book, Time to Get Real: How I Built a Billion Dollar Business that Rocked the Fashion Industry, and the hard-won lessons she learned about leadership, raising capital as a woman over 50, and taking calculated risks — including the moment she emptied her 401(k) to fund her vision.

Topics We Cover:

👉 Resources & Links:

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Thinking about ditching the 9-to-5? Already navigating the ups and downs of freelance work? This episode is your financial playbook for thriving as your own boss. Jean Chatzky sits down with money coach and longtime freelancer Emily Guy Birken to unpack everything from budgeting on irregular income to choosing the right retirement accounts.

Emily shares her personal percentage-based money system, explains why separate bank accounts are non-negotiable, and reveals the must-have clauses for every freelance contract. Whether you're freelancing full-time or hustling on the side, these tips will help you get paid, save smart, and sleep better.

In This Episode:

Resources & Links:

📚 Emily’s book: Stacked: Your Super Serious Guide to Modern Money Management

🔗 More financial tips for freelancers at HerMoney.com

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In this Mailbag, Jean is joined by financial planner and author of My Mother's Money, Beth Pinsker, to answer your real-life questions about caregiving, estate planning, and financial decision-making for aging parents. Whether you’re currently managing someone else’s money or prepping your own, this episode is packed with compassionate, practical advice to help you protect your finances and your peace of mind.

Mailbag Questions:

1:05: “Should we loan money to a parent for home repairs?” 

7:15 “Who pays the medical bills after someone dies?” 

13:05: “How do I put my RMDs to work in the market?” 

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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When you're suddenly put in charge of an aging parent’s finances, the emotional toll is heavy, and the financial fallout can be even heavier. In this episode, Jean Chatzky is joined by certified financial planner and MarketWatch columnist Beth Pinsker, author of My Mother’s Money: A Guide to Financial Caregiving.

Together, they unpack Beth’s personal journey of managing her mother’s finances through illness, surgery, and estate settlement. Even with decades of experience writing about money, Beth found herself caught off-guard by just how complicated — and expensive — caregiving can be without the right documents and conversations in place.

What You’ll Learn:

💡 P.S. Need help getting your own financial life in order before you take on someone else’s? Check out our FinanceFixx program, our signature coaching experience that helps you get organized, take control of your spending, and build a plan that actually works. 

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This week on A Week In Her Wallet, we head to Atlanta to follow Kristen, a 40-something clinical researcher who earns about $150K a year and travels nearly full-time for work.

She walks us through a week of thoughtful spending, including a $1,300 mortgage payment, $500 toward her HELOC, a $150 yard sale win (promptly spent on music festival tickets), and the small joys that keep her grounded when she’s on the road so much.

💬 In this episode:

Want to better understand your financial mindset? Take our MoneyType quiz to learn how your personality influences your spending.

And if you’re ready to get serious about your budget, check out our FinanceFixx program — real coaching, real results.

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The world of work is changing fast. AI is reshaping how we do our jobs, learn new skills, and even how we write our resumes and cover letters. But the most trusted source of career advice isn’t AI. It’s people.

In this week’s episode, Jean sits down with LinkedIn Career Expert Catherine Fisher to talk about why networking is still the ultimate career superpower. Catherine shares why it’s less about jobs disappearing and more about tasks evolving, what skills are becoming even more valuable now, and how women can use their networks to stay confident, connected, and ahead of the curve.

We’ll cover:

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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.

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📰 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:

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💬 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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