
First You Fear Losing, Then You Fear Winning.
Most people expect the fear that shows up early in a big goal, when the finish line still feels far away. Almost nobody expects the fear that shows up right at the end, when success is finally within reach. In this episode, I break down both, and give you the exact questions to cut through each one.
What You'll Learn From This Episode:
- Why every "should" statement you tell yourself is a judgment dressed up as a fact, and how to catch it.
- Two questions that cut straight through your inner judge's drama and back to the facts.
- Why self-sabotage most often shows up right before you get what you wanted, not just in the hard middle.
- What it means when success starts to feel scary instead of exciting, and why that's actually a sign you're on the right track.
- A real client story of someone who used to pump the brakes on his own success, and what changed.
Whether you're deep in the hard middle of a goal or standing right at the edge of getting what you wanted, I hope this episode helps you recognize the voice trying to talk you out of it.
Resources:
- Start Here: Free Leadership Playbook for career-critical moments
- Read: Weekly Leadership Insights and join 1,000 subscribers
- Watch: Take Charge Of Your Career Masterclass In 3 Vital Steps
- Meet: Schedule a complimentary Career Strategy Consultation
- Learn More: How 100+ Leaders Have Benefited from my Executive Coaching
Recommended Related Episodes:
- Episode 11 - Self Sabotage
- Episode 27 - Fail Fast To Succeed
- Episode 34 - Follow Through
- Episode 62 - Initial Resistance - When To Ignore It & When To Honor It
- Episode 83 - Risk & Success Intolerance
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Information
- Show
- FrequencyUpdated Weekly
- PublishedAugust 14, 2026 at 9:00 AM UTC
- Length24 min
- Episode103
- RatingExplicit