Episode Summary

After returning from Europe, Tony Bailey walks straight back into an industry storm — shifting markets, family pressure, and emotional decisions that begin to unravel the life he built.

In this episode, Tony opens up about his years in the insurance and financial-services world, what it means to lead with heart over strategy, and the personal cost of holding everything together for everyone else.

It’s a story about pressure, image, accountability — and the moment one phone call changed everything.

In This Episode

Intro: The illusion of control

Disclaimer & Reflection: Owning every part of the story — the good, the bad, and the fallout

Inside the Industry: What it really means to be a broker and how the business world operates behind the polished image

Building the Business: Legacy, debt, and believing hard work would equal security

Family Tensions: “To keep it in the family” — when success creates conflict

The Facade: People-pleasing, exhaustion, and the cracks beginning to show

The Tony’s: The 30th birthday that looked like success but felt like goodbye

The Call: A lifeline — or the start of the fall

Cliffhanger: When help isn’t help at all

Key Themes

• People-pleasing and the cost of emotional decision-making
• Leadership, pressure, and burnout
• Family expectations and financial legacy
• Accountability, shame, and owning your story
• The illusion of control in business and life

Tony’s Reflection

“This episode took everything to make — anger, shame, guilt, and truth.

I’m not a victim in this story.

I made the choices. I live with them.

But if we’re going to talk about accountability, it should apply to everyone — no matter your title or the size of your balance sheet.”

Follow & Connect

🌐 Website → wwwthebaileysupport.com

📸 Instagram → @thebaileysupport

📘 Facebook → bit.ly/4hWBaOi

🎧 Listen to the full series → Fall From Grace

Fall From Grace is a space for honest conversations, lived experience, and the kind of stories that remind us we’re not as alone as we think. Each episode dives into the messy, human, often painful parts of life — and the strength it takes to rise again.

Hosted by Tony Bailey, a Counselling student and this show explores resilience, trauma, rebuilding your life, and turning your lowest moments into a foundation for something better.

Here, we talk openly. We heal loudly. We make room for the people who’ve been through hell and are still standing — even if they’re standing on shaky legs.

Whether you’re starting over, fighting your way back from rock bottom, or just trying to understand your own story a little deeper, this podcast is your reminder that healing is possible and growth is inevitable.

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