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:

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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.

If you’ve ever felt like the business you built is running you—or that your professional success doesn’t quite match the personal fulfillment you imagined—you’re not alone.

In this episode, Hilary sits down with Jeff Willmore, founder of The Autonomy Course, to explore how ambitious business owners and professionals can align their work with their deeper calling.

Jeff’s journey started with a business he built alongside his brother fresh out of college, and evolved into a life-changing exploration of purpose-centered entrepreneurship.

Together, Hilary and Jeff discuss what happens when your company’s mission reflects what you do instead of why you do it, and how it’s never too late to change the path you’re on if it isn’t taking you where you want to go.

They dig into callings, regrets, money stories, and the power of language to help you reconnect with purpose and joy in both business and life–something that we hope this conversation unlocks for you. 👇

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

• 04:12 How Jeff and his brother launched their first business after college, and the early vision that shaped his path
• 07:20 What it means to design a business that reflects your authenticity—and how Jeff helps entrepreneurs do just that
• 11:15 Why understanding your personal calling is more powerful than just having a mission or vision statement–and how it can impact your own end-of-life regrets
• 16:13 The role of language in expressing your essence, and how moments of profound inspiration shape a life
• 23:11 The inherited beliefs Jeff carried about money and work, rooted in the labor movement—and how they’ve shifted
• 29:24 Why slowing down your thinking can be a superpower for leaders and decision-makers
• 35:28 What makes The Autonomy Course different from other entrepreneurial coaching approaches
• 39:08 How our company Blueprint and the team’s individual callings are woven into HWM’s client experience, and other real-world stories of people who’ve integrated purpose and profitability

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/jeff-willmore-calling-in-business

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.

We’re excited to introduce a new episode format on Love, your Money® called “Ask Hilary”—short, relaxed, unscripted episodes where Hilary answers real questions from listeners like you.

These episodes are conversational, honest, and focused on connection, because that’s one of the superpowers of our team here at Hendershott Wealth. We don’t just manage money, we build relationships–and we want to make Love, your Money® more of a two-way conversation.

So if you’ve got a question about taxes, investing, retirement, relationships, or securing your financial future and freedom—we want to hear it!

Email your question to hello@hendershottwealth.com, or send us a message on Instagram @HendershottWealth.

No topic is too small, too complicated, or too personal—and yes, you can submit your question anonymously if you prefer.

We’ve got some incredible episodes coming up–hit subscribe to stay in the know when they go live.

Until then, take care of your money… so it can take care of you!

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

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.