The Illusion of “I’ll Be Happy When” - Jerome Myers

Your Next: A Guide to Finding Fulfillment After Your Exit Hosted by Jerome Myers

You sold it. You won. So why does it still feel hollow?

In this deeply emotional and life-changing solo episode, Jerome Myers dismantles one of the most seductive lies in high performance: “I’ll be happy when…”

Through the raw and revealing story of James, a founder who reached the summit only to find it silent, Jerome explores the emotional collapse that often follows external success. This isn’t just about exits. It’s about identity, meaning, and the quiet ache of disconnection.

This episode is your invitation to pause, reflect, and realign. If you've ever said, “I’ll be happy when…” this conversation will challenge everything you thought you knew about success and might just change your life.

[00:00 – 03:00] The Happiness Horizon Trap

• “I’ll be happy when…” - the emotional illusion
• Why milestone-chasing masks deeper emptiness
• The horizon always moves until you stop chasing
  

[03:01 – 06:30] The Exit Paradox in Action

• Why freedom often feels like invisibility
• The emotional fallout after success
• What founders truly miss after the deal closes

[06:31 – 08:30] Timing vs. Readiness

• When market windows close before you’re “ready”
• How waiting for happiness can cost you more than money
• A lesson from 2021–2023 exits you can’t ignore

[08:31 – 10:30] Stop Chasing. Start Aligning

• Why alignment is the new definition of wealth
• The emotional safety in clarity
• 3 powerful questions to reconnect with what matters

[10:31 – End] The Path to Real Fulfillment

• From exit strategy to life strategy
• The tools that create emotional stability post-exit
• Design a legacy rooted in influence, not just income

Key Quotes:

“I've seen founders who waited for the exit to fix everything, only to wake up with money in the bank and the emptiness in their hearts.” - Jerome Myers

“Happiness doesn't live in the next milestone. It lives in clarity. It lives in alignment, and it lives in the influence you create every day.” – Jerome Myers

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