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

Creating Confidence with Heather Monahan

Heather Monahan

Self-improvement, Education, Business, Entrepreneurship

4.8 • 1.1K Ratings

🗓️ 21 April 2026

⏱️ 58 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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

Transcript

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0:00.0	It's free to sign up and posting a job is easy.
0:03.8	Visit upwork.com right now and post your job for free.
0:06.9	That is upwork.com to connect with top talent ready to help your business grow.
0:12.9	That's upw-w-rk.com, Upwork.com.
0:19.5	Whether you need help covering payroll, managing cash flow, or investing in growth,
0:23.9	you deserve better. That's why I recommend the small business marketplace Fendera powered by
0:28.5	NerdWallet. It's free, easy-to-use platform that lets you compare real financing offers from
0:33.6	trusted lenders all in one place. Go to nerdwollet.com slash confidence
0:37.8	to find the funding you deserve.
0:41.1	Refresh your spring wardrobe with quince.
0:43.2	Go to quince.com slash confidence
0:45.1	for free shipping and 365 day returns.
0:48.4	Go to Q-U-I-N-C-E.com slash confidence
0:52.7	for free shipping and 365-day returns.-E.com slash confidence for free shipping and 365-day returns, quince.com
0:57.0	slash confidence. On What Not, you go live and sell directly to people in real time. You go live,
1:03.3	show off products, and turn what you love into real income. Visit whatnot.com slash sell to start selling.
1:12.2	Don't try to achieve things to have
1:14.9	zero problems. Do things that have problems you're excited to solve. And once I realize that, like,
1:23.2	oh, there are not these like thresholds that launch you into like a zero inbox no problems.
1:30.0	It's all about like, do you like the problems you're solving?
1:33.1	Do you like the people that you're with?
1:35.6	Do you like the lifestyle that it affords?
	...

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