In this episode of Simple Success, John Brandy and Doubting Thomas challenge you to lean into the unfamiliar—because often, the path to financial independence (and happiness) lies just beyond your comfort zone.

Blending financial life coaching with a happiness perspective, the conversation draws on lessons from Pablo Picasso and personal reflections to show how uncertainty isn’t the enemy—it’s the opportunity. By embracing what you think you can’t do, you unlock new financial paths, deeper purpose, and more fulfilling success.

Key Takeaways

• Doing the unfamiliar leads to growth—fear is often just a sign you’re onto something transformative.
  

• Your passions are your compass: Financial strategies rooted in joy are more sustainable.
  

• Start with what you know—then stretch: resilience is built through action.
  

• Uncertainty isn't a stop sign—it's an invitation to experiment, learn, and adapt.
  

Quote of the Episode

“I’m always doing things I can’t do—that’s how I get to do them.” – Pablo Picasso

Recommended Reads

• Think and Grow Rich – A timeless guide to success and wealth-building
  

• Jonathan Livingston Seagull – A powerful fable about self-discovery and pushing limits
  

• Dictionary of Finance and Investment Terms – An essential reference for understanding financial jargon
  

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