
How to Stop Delaying Happiness While Pursuing Big Goals with Jess Ekstrom
From Creating Confidence with Heather Monahan by Heather Monahan | YAP Media
April 21, 2026 · 55 min · Episode 618
About this episode
Heather Monahan and Jess Ekstrom discuss the misconceptions of success and how to find happiness in the present rather than delaying it for future goals.
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…
People in this episode
Host: Heather Monahan
Guest: Jess Ekstrom
Topics covered
- happiness
- goal setting
- success
- personal development
- mission-driven living
Keywords
- happiness
- success
- goals
- personal growth
- mission-driven
Sponsors
Quince, NerdWallet, Whatnot
Mentioned in this episode
Organizations: Headbands of Hope, Mic Drop Workshop
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