10 Jun 456: You’re Successful…So Why Does It Feel So Empty? An interview with author, speaker & founder of Headbands of Hope Jess Ekstrom
What if the dream you worked so hard to build… is now also the thing slowly draining you?
DREAM THINK DO favorite Jess Ekstrom returns to the podcast for her THIRD appearance – and this might be our deepest conversation yet.
You probably know Jess as the founder of Headbands of Hope, the company she launched out of her dorm room that went on to impact millions of lives around the world. Since then, she’s launched other successful businesses, become a bestselling author, and sought-after speaker.
But this conversation goes beyond business growth, productivity hacks, or hustle culture.
Because Jess’s new book, Making It Without Losing It, tackles a tension so many high achievers quietly wrestle with:
What happens when you finally achieve success… but still feel anxious, exhausted, restless, or strangely unfulfilled?
If you’ve ever:
Felt successful on paper… but empty in real life
Wondered if your ambition is costing you too much
Struggled to slow down because success feels tied to safety
Or felt pressure to keep achieving… even when you’re tired
…this episode is going to hit home.
If one of the things YOU’VE been noticing lately is a pull toward coaching, speaking, or sharing your story in a bigger way – Mitch would love to talk.
The Authority Bridge™ is a proven, done-with-you coaching program designed for mid-to-late career leaders, executives, and experts who are ready to turn their wisdom into a profitable, purpose-driven coaching and speaking business – without starting from scratch.
Book a free Strategy Call at authoritybridge.com
In this conversation, Mitch and Jess talk about:
- Why so many high achievers start “playing not to lose”
- The hidden cost of constantly chasing the next milestone
- How to redefine success for the season you’re actually in
- Why changing paths doesn’t eliminate problems – it simply gives you new ones to solve
- The difference between external validation and internal peace
- How to pursue big dreams without losing yourself in the process
- And why fulfillment is found more in the journey than the finish line
Jess also shares some incredibly honest stories about motherhood, ambition, identity, burnout, and the pressure that can come with building something meaningful.
This is one of those conversations that feels equal parts inspiring, grounding, and freeing.
CONNECT WITH JESS:
Website: jessekstrom.com
Instagram: @jessekstrom
Book: Making It Without Losing It
Previous DREAM THINK DO episodes with Jess:
YOUR CALL TO ACTION:
If this episode resonated with you… don’t just listen to it alone.
Send it to a friend, teammate, spouse, or fellow dreamer who’s been carrying a lot lately.
Because sometimes the people who look the most successful on the outside… are the ones most in need of this conversation.
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