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

EPISODE · Apr 21, 2026 · 54 MIN

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

from Creating Confidence with Heather Monahan · host Heather Monahan | YAP Media

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. Whatnot - Visit whatnot.com/sell to start selling. Upwork - Visit upwork.com right now and post your job for free. Resources + Links Pre-Order Jess Ekstrom’s new book Making It Without Losing It and get the FREE audiobook + BONUSES: https://jessekstrom.com/makingit/ Check out Headbands of Hope and support their mission: headbandsofhope.com Learn how to become a paid speaker with Mic Drop Workshop: micdropworkshop.com Call my digital clone at 201-897-2553!  Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/  Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com  If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Jess Instagram & LinkedIn

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. Whatnot - Visit whatnot.com/sell to start selling. Upwork - Visit upwork.com right now and post your job for free. Resources + Links Pre-Order Jess Ekstrom’s new book Making It Without Losing It and get the FREE audiobook + BONUSES: https://jessekstrom.com/makingit/ Check out Headbands of Hope and support their mission: headbandsofhope.com Learn how to become a paid speaker with Mic Drop Workshop: micdropworkshop.com Call my digital clone at 201-897-2553!  Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/  Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com  If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Jess Instagram & LinkedIn

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

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MG Show MG Show The MG Show, hosted by Jeffrey Pedersen and Shannon Townsend, is a leading alternative media platform dedicated to uncovering the truth behind today’s most pressing political issues. Launched in 2019, the show has grown exponentially, offering unfiltered insights, comprehensive research, and real-time analysis. With a commitment to independent journalism and factual integrity, the MG Show empowers its audience with knowledge and encourages active participation in the political discourse. French Your Way Jessica: Native French teacher founder of French Your Way Boost your French listening skills and test your comprehension with this one of a kind series of podcasts. Get the chance to listen to a real conversation between native speakers talking at normal speed AND customise your learning experience through carefully designed sets of questions (2 levels of difficulty) available for download at www.frenchvoicespodcast.com. All interviews also come with the transcript. French teacher Jessica interviews native speakers of French from around the world who share a bit of their life and passion. Where else would you meet in one same place a French yoga teacher based in Melbourne, a soap manufacturer from Provence, or a couple cycling around the world? That Hoarder: Overcome Compulsive Hoarding That Hoarder Hoarding disorder is stigmatised and people who hoard feel vast amounts of shame. This podcast began life as an audio diary, an anonymous outlet for somebody with this weird condition. That Hoarder speaks about her experiences living with compulsive hoarding, she interviews therapists, academics, researchers, children of hoarders, professional organisers and influencers, and she shares insight and tips for others with the problem. Listened to by people who hoard as well as those who love them and those who work with them, Overcome Compulsive Hoarding with That Hoarder aims to shatter the stigma, share the truth and speak openly and honestly to improve lives. The Small Business Startup School – Business Notes | Financial Literacy | Retail Psychology – For Professionals & Entrepreneurs The Small Business Startup School Inc. Starting or buying a small business? While personal circumstances may vary, business patterns remain timeless. On The Small Business Startup School, we explore strategies, insights, and practical solutions to help entrepreneurs confidently navigate their journey.Hosted by Ola Williams—a retail entrepreneur, fintech founder, and financial coach with over two decades of experience—this podcast marries financial awareness and retail psychology with optimism to deliver actionable takeaways.Join us to learn, grow, and connect as we uncover the keys to business success.Let’s continue to learn together and be encouraged to keep on connecting!

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How long is this episode of Creating Confidence with Heather Monahan?

This episode is 54 minutes long.

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This episode was published on April 21, 2026.

What is this episode about?

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...

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