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#373: Three Rules For Turning Obstacles into Opportunities

High-Income Business Writing

Release Date: 06/04/2025

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Episode Summary

Looking back on the past 30 years of my career, I’ve faced challenges, doubts, and moments of pure grit. Through all of it, I’ve realized there are three core rules that have guided me — rules that I didn’t define at the time but, in hindsight, have made all the difference.

These aren’t just feel-good ideas. They’re battle-tested principles that have helped me push through fear, uncertainty, and roadblocks. And if you’re looking to build a meaningful, successful freelance career, these rules might just change the way you approach your work.

What You’ll Learn in This Episode

·       Why obstacles often contain hidden opportunities... if you’re willing to see them.


How belief in your goal can override doubt and fear.


Why bold action always beats overthinking.


How these three rules can create real, tangible success in your freelance career.

Key Takeaways

1. Obstacles Are Opportunities in Disguise

  • Most people see obstacles as stop signs, but they often hold the seeds of greater success.
  • The key is how you respond. Do you stop in your tracks or look for the opportunity within?
  • Every major breakthrough in my career started as a challenge that I chose to push through.

2. Belief in Your Goal is More Powerful Than Doubt

  • We’re constantly told to “be realistic” and lower our expectations.
  • But our perception shapes our reality; if we believe in the obstacle more than the goal, the obstacle wins.
  • A little bit of “crazy” is necessary to achieve big results. If you’re going to believe in something, believe in your vision.

3. Bold Action Beats Overthinking Every Time

  • The perfect plan doesn’t exist. Progress happens when you start moving.
  • Clarity, creativity, and solutions emerge when you’re in motion, not when you’re stuck analyzing every possibility.
  • The biggest breakthroughs in my business didn’t come from waiting for the perfect moment. They came from taking the leap.

Actionable Exercises

·       Reframe an Obstacle: Think of a challenge you’re facing right now. Instead of focusing on what’s stopping you, ask: What hidden opportunity does this contain?


Challenge Your Own Doubts: Identify one area where you’ve been playing it safe because of fear. What’s one small, bold step you can take today?


Take Imperfect Action: Stop overanalyzing and commit to one meaningful action this week that moves you forward.

Listener Challenge

This week, take one bold action... even if you don’t feel fully ready. See what happens when you stop waiting and start moving.