This High-Earning Pilot was Losing Sleep Over Money at 3 AM (Here's How I Coached Him)

The Full Frontal Living™ Podcast with Lisa Carpenter

In this powerful episode, Lisa shares an unedited coaching conversation with Greg, an airline pilot who has significant wealth on paper yet still wakes up at 3 AM worried about money. This is context coaching in action—addressing the story problem, not the money problem.

What you'll hear:

• The "Just Enough" Identity Crisis Greg has substantial assets and multiple properties, but his relationship with money is still governed by childhood stories like "money doesn't grow on trees." Despite his financial success, he operates from scarcity and wakes up anxious about lack. This disconnect between his actual wealth and his emotional experience with money is more common than you might think among high earners.
• Context vs. Content Coaching in Action Rather than coaching Greg on budgeting or cash flow management, Lisa immediately identifies that this isn't a money problem—it's an identity problem. She coaches to the pattern underneath his words, not the surface-level content he's presenting. This is the difference between treating symptoms and addressing root causes.
• Real-Time Transformation You'll witness the exact moment Greg has a visceral reaction to Lisa calling him "wealthy" and how she uses that as a gateway to help him step into a new identity. Lisa introduces the concept of pattern interrupts and gives Greg specific homework to retrain his brain out of scarcity thinking.

The conversation reveals how Greg's scarcity mindset isn't just affecting his sleep—it's preventing him from doing more good in the world. He and his husband have already established endowments at his alma mater, but his "just enough" identity keeps him from fully stepping into his role as a wealthy person who can create positive impact.

Lisa helps him see that holding onto lack mentality is actually a disservice to those who need him to show up in his full financial power. The shift from victim to steward of wealth becomes not just personal growth, but moral responsibility.

Lisa gives Greg specific assignments: calculate his total net worth and use that number as a pattern interrupt whenever scarcity thoughts arise. She also challenges him to define what wealth means for him personally and plan how he wants to give back from that place of abundance.

The homework isn't about managing money better—it's about managing his identity and relationship with wealth completely differently.

Why This Episode Matters

This isn't theory or feel-good advice. It's real coaching happening in real time with someone who has significant financial success but is still trapped by old stories. If you're a high achiever who feels financially stressed despite your success, this conversation will show you exactly how those patterns operate and how to break free from them.

You'll hear how quickly transformation can happen when you address the right problem. Greg doesn't need more money—he needs to step into the identity of someone who already has more than enough.

Ready to examine your own money stories? Head to lisacarpenter.ca/wwm to apply for coaching and discover what's really keeping you stuck.