Welcome back to Ask Hilary, where we tackle real-life money questions from women navigating change. Because if there’s one constant in our financial lives, it’s change.

We grow. We move. We change careers, enter new relationships, end others, care for family, and—somewhere in the middle of all that—we try to build a financial life that actually supports the life we want.

But those transitions don’t come with a playbook. And they often raise hard, vulnerable questions like:

• What if I’m just getting started with saving and feel hopelessly behind?
• What happens when the money dynamics in my relationship start to feel… off?
• How do I care for someone I love without compromising my own security

Today, we’re exploring what happens when life shifts—and your financial plan needs to catch up. Whether you're entering your 30s, becoming the breadwinner, or wrestling with family responsibilities, this episode will help you make empowered, values-aligned decisions with your money.

Remember: It’s never too late to make things better.

Here’s what you’ll learn in this week’s episode of Love, your Money:

• 02:21 Is it too late to start saving and building wealth at 35?
• 09:37 What do I do when I’m the breadwinner but feel less in control of my money?
• 15:39 How can I support my mom financially without compromising my own future?

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-establishing-financial-space

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Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

It’s time to take off your judgy pants, Money Lover, because today we’re sitting down with Jean Chatzky, CEO and co-founder of HerMoney, to talk about the real-world challenges women face when it comes to building wealth—and we’re doing it without shame, guilt, or financial jargon.

Jean’s decades of experience as a financial journalist taught her two critical truths: A) The jargon-filled speak of the financial industry was created largely by men to sell you stuff you don’t need, and B) When you strip that confusion away, money isn’t rocket science.

What a breath of fresh air.

With candor, warmth, and wisdom, Jean shares how she’s navigated everything from raising a medically fragile child to leading a 20,000+ member financial community for women.

Together, we talk about what’s really holding women back from financial freedom, and how to break through it–whether you’re rebuilding after divorce, raising kids while building a business or career, or planning for solo aging.

This episode is packed with real talk, practical advice, and deep validation for women trying to do it all in a system that wasn’t built for us.
(We’re so glad you’re here.)

Let’s jump into this conversation about prioritizing what’s important, letting go of regret, and accepting other people’s judgment without taking it on for yourself. 👇

Here’s what you’ll learn in this week’s episode of Love, your Money®:

• 01:10 Meet Jean Chatzky: HerMoney CEO, bestselling author, and longtime advocate for financial literacy without shame or jargon
• 02:01 Jean’s take on turning the conversation about uniquely female money challenges from pessimistic to optimistic, and how to stop obsessing over the economy and start focusing on money moves that are actually in your control
• 04:41 The painfully slow progress of pay equity, why it’s still hard for women to ask for more, and how practice makes it easier
• 07:18 Encouraging signs in education and career progress and the positive trends Jean sees for women in the years ahead
• 08:06 The high cost of balancing ambition and motherhood—and what Jean and Hilary both learned the hard way
• 12:45 Turning setbacks into comebacks: How women in Jean’s community reclaimed power after divorce, debt, and life upheaval
• 14:05 What women need to know about planning for solo aging, hiring professionals, and building care communities
• 16:39 What to know about living wills, healthcare proxies, and the Five Wishes document
• 17:47 If Jean’s money could write her a love note, what would it say?

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/jean-chatzky

Follow Hilary on:

LinkedIn

Instagram

YouTube

Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

Welcome to the first Ask Hilary episode, where we dive into real-world questions about money and mindset from listeners like you!

Today, we’re leaning into the conversation we started last week with Jeff Willmore about living true to your calling. We’re going to talk about what happens when you hit your financial goals, but something still feels… off.

These questions center around calling, career pivots, and permission to want more than just security. They are the kinds of conversations that move us from autopilot to intention, to help you make wealth-building choices that actually reflect who you are and what matters to you.

If you’re craving clarity, ease, or meaning in your money life, this one’s for you.

Here’s what you’ll learn in this week’s episode of Love, your Money:

• 02:07 What if I’ve built financial stability—but don’t feel fulfilled?
• 09:26 Can I pivot careers without starting over financially?
• 16:09 Is it lazy to want more space and ease in my business?

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-purpose-pivots-permission

Follow Hilary on:

LinkedIn

Instagram

YouTube

Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.