HerMoney with Jean Chatzky: Ep 481 - Top Strategies For Making Your Money Last (And Grow) In Retirement

Release Date: June 25, 2025

In Episode 481 of HerMoney with Jean Chatzky, host Jean Chatzky sits down with Hilary Hendershot, founder of Hendershot Wealth Management and host of the "Love Your Money" podcast, to delve into essential strategies for ensuring financial security and growth throughout retirement. This comprehensive discussion addresses the unique financial challenges women face and offers actionable insights to navigate retirement successfully.

1. Hilary Hendershot’s Personal Financial Journey

Hilary begins by sharing her transformative personal experience with money management. Reflecting on her past struggles, she reveals how overspending and a scarcity mindset led her into severe debt, ultimately resulting in the loss of her home and a plummeting credit score.

"[00:30] Jean Chatzky: [...] women retire with less, we retire with a lot less. According to a 2024 study from Prudential, women have less than a third of the median retirement savings that men have."

"[04:57] Hilary Hendershot: [...] I was a massive overspender. I really had this scarcity mindset. If I made $100 I would spend $120 every single time."

Her turning point came when she realized the unsustainable trajectory of her financial habits. Determined to change, Hilary immersed herself in the study of money psychology and behavioral finance, ultimately pivoting her career towards financial planning to help other women avoid similar pitfalls.

2. Common Retirement Planning Mistakes Women Make

Hilary identifies several key mistakes women often make when planning for retirement:

a. Lack of Empowered Mindset

A foundational error is not prioritizing one's own financial well-being. Hilary emphasizes the importance of recognizing that no one else is as invested in your financial future as you are.

"[09:50] Hilary Hendershot: [...] nobody cares more about my money than me."

b. Distrust in the Stock Market

Many women harbor fears about the stock market, viewing it as unreliable or overly risky. Hilary advocates for building a well-informed and trusting relationship with the stock market, highlighting its role as a primary vehicle for wealth generation.

"[09:50] Hilary Hendershot: [...] you really build that relationship and that deep trust because time in the stock market really matters, makes a huge difference."

c. DIY Retirement Planning Without Professional Guidance

Attempting to manage retirement finances without expert advice can lead to costly mistakes. Hilary underscores the value of consulting with fiduciary financial advisors to navigate the complexities of retirement planning and tax landscapes.

"[13:37] Hilary Hendershot: [...] education, well-meaning women who've been trying to DIY their retirements [...] can be a big mistake."

3. Strategies to Supercharge Retirement Savings

For women feeling behind in their retirement savings, Hilary offers a strategic roadmap:

a. Assess Current Financial Standing

Begin with a comprehensive evaluation of net worth, including assets and liabilities, and determine the essential spending needs for retirement.

"[15:05] Hilary Hendershot: [...] what you spend on needs and wants to live a life that you love living."

b. Eliminate Consumer Debt

Prioritize paying off high-interest consumer debts to free up more resources for saving and investing.

c. Maximize High-Impact Savings Vehicles

Fully utilize retirement accounts such as 401(k)s, taking advantage of employer matches and contribution limits. For those over 50, catch-up contributions can significantly boost savings.

"[16:44] Hilary Hendershot: [...] maximize your company 401k plan. [...] $23,500 per year this year in 2025. And then [...] a $7,500 catch-up contribution."

d. Invest with Intention

Encourage disciplined investing to leverage compound interest, ensuring that savings grow exponentially over time.

"[16:52] Hilary Hendershot: [...] invest intentionally. [...] the word compound interest is synonymous with exponential growth."

4. Wealth Transfer and Inheritance Strategies

As nearly half of American women expect to inherit significant wealth within the next decade, Hilary discusses how to manage sudden wealth effectively:

a. Maintain Good Financial Habits

The way you handle money prior to inheritance strongly influences post-inheritance financial behavior. Maintaining disciplined saving and investing habits ensures that inherited wealth is preserved and grown.

"[18:22] Hilary Hendershot: [...] whatever you've done with money up until the day you inherit is what you will continue doing with money."

b. Understand Tax Implications

Inheritance can come with complex tax obligations, especially regarding IRAs. Consulting with financial advisors can help manage distributions strategically to minimize tax burdens.

5. Making Retirement Funds Last

Transitioning into retirement requires a shift from accumulating wealth to strategic spending and preservation:

a. Emphasize Safe Withdrawal Rates

Adhering to a safe withdrawal rate (typically 2-5%) ensures that retirement funds last throughout the anticipated lifespan.

"[22:59] Hilary Hendershot: [...] the technical term for that is the safe withdrawal rate. [...] somewhere between, depending on who you talk to, 2 and 5%."

b. Avoid Overspending During Market Downturns

Maintaining discipline during volatile market conditions prevents the depletion of retirement savings. Hilary advises keeping sufficient cash reserves and sticking to planned withdrawal rates.

"[24:03] Jean Chatzky: I think such a big range."

c. Implement Tax-Efficient Withdrawal Strategies

Roth IRA conversions can provide tax flexibility, allowing retirees to manage their tax liabilities more effectively over time.

"[26:14] Hilary Hendershot: [...] Roth conversions are beneficial if the tax rate you pay when you distribute is higher than when you convert."

6. Navigating Stock Market Volatility

Hilary addresses recent market fluctuations and offers guidance on maintaining a steady investment approach:

"[28:55] Hilary Hendershot: [...] the stock market lost 30% in the first quarter of 2020 due to the COVID pandemic. But that's all in the rearview mirror."

a. Understand Intrinsic Value vs. Investor Sentiment

Recognizing that stock prices are influenced by both company fundamentals and temporary market emotions helps in making informed investment decisions.

b. Focus on Long-Term Growth

Staying invested and avoiding panic selling during downturns ensures that investments have the opportunity to recover and grow over time.

7. Building Confidence in Investing

Hilary empowers women by highlighting inherent strengths in female investors:

"[30:57] Hilary Hendershot: [...] the data tells us that women naturally invest better than men."

She encourages women to trust their investment instincts and leverage resources and support systems to enhance financial confidence and decision-making.

Conclusion

Episode 481 of HerMoney with Jean Chatzky provides a thorough exploration of retirement strategies tailored to women's unique financial landscapes. From overcoming personal financial challenges to mastering investment strategies and navigating wealth transfers, Hilary Hendershot offers invaluable advice for ensuring a secure and prosperous retirement. By fostering an empowered mindset, building trust in the stock market, and seeking professional guidance, women can overcome the disparities in retirement savings and achieve financial independence.

Notable Quotes:

• "Nobody cares more about my money than me." — Hilary Hendershot [09:50]

• "I'm in it for the long term." — Hilary Hendershot [12:08]

• "Time in the stock market really matters." — Hilary Hendershot [09:50]

• "Wealth transfer is massive, but it's not enough to just have this money. We have to get strategic about how we invest it." — Jean Chatzky [00:30]

This episode serves as a crucial guide for women aiming to enhance their retirement planning, offering both empathy and expertise to navigate the financial challenges ahead.