Why We Self-Sabotage and WTF To Do About It

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Have you ever accomplished something remarkable, only to immediately rob yourself of joy by focusing on all the ways it could have been better? That crushing cycle of achievement followed by self-criticism is what Greg and I unpack in this raw and vulnerable conversation.

Together we explore:

• Why we get in our own way right after achieving goals
• The mountain climbing analogy: celebrating each plateau instead of dismissing it because it isn’t the summit
• How perfectionism fuels a never-ending cycle of dissatisfaction
• The power of reframing self-sabotage as protection rather than defeat
• Practical tools that actually work:
  • Naming your inner critic to create distance from negative thoughts
  • Practicing thought replacement (you can only think one thought at a time)
  • Cultivating gratitude—even if it’s simply for the breath in your lungs
• The importance of giving yourself space to recenter after self-criticism
• A reminder: self-sabotage isn’t proof you’re broken—it’s proof you’re human

This conversation isn’t just philosophy—it’s therapy in real time, with tangible ways to reclaim the joy that comes from acknowledging how far you’ve come.

If this resonates, share the episode with someone stuck in their own head. Sometimes the most healing thing is knowing you’re not alone.

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