How to Stop Delaying Happiness While Pursuing Big Goals with Jess Ekstrom

Creating Confidence with Heather Monahan

What if “making it” doesn’t solve your problems, it just gives you new ones? In this episode, I sit down with Jess Ekstrom, the founder of Headbands of Hope and Mic Drop Workshop, to break down the belief that once you “make it,” everything will finally feel easier, happier, and complete. We talk about the pressure of constantly chasing the next goal, the illusion that success will solve your problems, and how to stop tying your happiness to future outcomes. Jess also shares the idea of choosing problems you actually want to solve, defining your own success fingerprint, and shifting from achievement-based thinking to mission-driven living. Get ready to rethink what success means and start creating a life that feels good now, not “someday.”


In This Episode You Will Learn

  • How to STOP chasing outcomes that promise a problem-free life.

  • The PURPOSE TEST to evaluate if your goals are aligned with you.

  • How to define your SUCCESS FINGERPRINT based on your values.

  • How to shift from singular goals to a MISSION that keeps you motivated.

  • Why attaching your happiness to a FINISH LINE keeps you stuck in a cycle of delay.

  • How to ZOOM OUT and evaluate if your daily actions align with your life.


Check Out Our Sponsors:

  • Quince - Refresh your spring wardrobe with Quince. Go to quince.com/confidence for free shipping and 365-day returns.

  • NerdWallet - Don’t risk your business on unreliable lenders. Go to nerdwallet.com/confidence to find the funding you deserve.


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More description

What if “making it” doesn’t solve your problems, it just gives you new ones? In this episode, I sit down with Jess Ekstrom, the founder of Headbands of Hope and Mic Drop Workshop, to break down the belief that once you “make it,” everything will finally feel easier, happier, and complete. We talk about the pressure of constantly chasing the next goal, the illusion that success will solve your problems, and how to stop tying your happiness to future outcomes. Jess also shares the idea of choosing problems you actually want to solve, defining your own success fingerprint, and shifting from achievement-based thinking to mission-driven living. Get ready to rethink what success means and start creating a life that feels good now, not “someday.”


In This Episode You Will Learn

  • How to STOP chasing outcomes that promise a problem-free life.

  • The PURPOSE TEST to evaluate if your goals are aligned with you.

  • How to define your SUCCESS FINGERPRINT based on your values.

  • How to shift from singular goals to a MISSION that keeps you motivated.

  • Why attaching your happiness to a FINISH LINE keeps you stuck in a cycle of delay.

  • How to ZOOM OUT and evaluate if your daily actions align with your life.


Check Out Our Sponsors:

  • Quince - Refresh your spring wardrobe with Quince. Go to quince.com/confidence for free shipping and 365-day returns.

  • NerdWallet - Don’t risk your business on unreliable lenders. Go to nerdwallet.com/confidence to find the funding you deserve.


Resources + Links


Follow

2026-04-21 54 min
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