Many people who work hard to build and protect their wealth assume that once they "make it," everything will finally feel good, secure, calm, and settled. But most people don't discover the truth until they're already successful: money doesn't quiet the fear. It often makes it louder.

The pressure gets higher, and the decisions get heavier. The same stress, anxiety, and old beliefs they carried before wealth simply move with them into a larger life.

That's the part no one prepares high earners for: the emotional weight that grows alongside the net worth. And it shows up everywhere: in the urge to hold money tighter, in the guilt that makes generosity feel risky, and in investment choices that look diversified but are actually fragmented and scattered.

For more than 30 years, financial advisor Shannon Ryan has seen this up close. She's worked with founders, professionals, and ultra-wealthy families who have everything they once wanted, yet still feel overwhelmed, afraid, or ashamed of how they handle money. Not because they lack discipline or intelligence, but because their emotional relationship with money never evolved as quickly as their wealth did.

In this conversation, Shannon and I explore the hidden side of wealth: why financial milestones don't automatically create peace, and what it actually takes to feel free when the numbers say you should already be there.

About the Guest

Shannon Ryan is a Certified Financial Planner CFP®, behavioral finance advocate, speaker, and the author of the upcoming book Your Money Has Feelings. With over 30 years of experience guiding individuals and families, Shannon blends clear financial knowledge with a heart-centered approach to help people heal their money stories, transform their financial behavior, and build lasting confidence. She's been featured on Good Morning America, CNBC, and TEDx, and is known for making personal finance feel relatable, empowering, and deeply human. To work with Shannon, visit https://shannon-ryan.com/.

Buy her book, "Money Has Feelings," on Amazon.

About Your Host

From pro-snowboarder to money mogul, Chris Naugle has dedicated his life to being America's #1 Money Mentor. With a core belief that success is built not by the resources you have, but by how resourceful you can be. Chris has built and owned 19 companies, with his businesses being featured in Forbes, ABC, House Hunters, and his very own HGTV pilot in 2018. He is the founder of The Money School™ and Money Mentor for The Money Multiplier.

His success also includes managing tens of millions of dollars in assets in the financial services and advisory industry and in real estate transactions. As an innovator and visionary in wealth-building and real estate, he empowers entrepreneurs, business owners, and real estate investors with the knowledge of how money works.

Chris is also a nationally recognized speaker, author, and podcast host. He has spoken to and taught over ten thousand Americans, delivering the financial knowledge that fuels lasting freedom.