In this episode, Dr. Amna Shabbir sits down with bestselling author, speaker, and entrepreneur Jess Ekstrom to explore how we can pursue meaningful success without losing ourselves in the process.
Jess explains why reaching the next milestone rarely creates the lasting fulfillment we expect, how the “post-achievement letdown” keeps high achievers chasing more, and why deciding what is enough is essential for sustainable ambition.
They also discuss perfectionism, imposter feelings, motherhood, and Jess’s experience with postpartum depression. Jess shares how becoming a mother changed her identity, priorities, and relationship with productivity, and why successful women should be more transparent about the support that makes their work possible.
Jess also reflects on her entrepreneurial journey, the importance of leading with clarity instead of trying to be liked, and her mission to help more women share their ideas from the stage.
This conversation is an honest reminder that ambition itself isn’t the problem. What matters is who you become along the way, and whether you view the space between where you are and where you want to be as a painful deficit or an exciting experiment.
In this episode, you’ll learn:
- Why accomplishments don’t always create fulfilment
- What causes the post-achievement letdown
- How to define what “enough” means in your current season
- Why caring less about others’ perceptions can improve your work
- How motherhood can reshape identity and ambition
- Why clarity is one of the kindest qualities a leader can offer
- How to view your ambitions as an experiment rather than a deficit
About Jess Ekstrom
Jess Ekstrom is the founder of Headbands of Hope and Mic Drop Workshop, investor in women, best selling author, Forbes Top Rated Speaker and mom.
Her first brush with success was selling all of her toys on eBay when she was twelve. Since then, Jess and her companies have been featured on the TODAY Show, Good Morning America and more. More importantly, her companies have helped millions of women and girls around the world.
She’s the bestselling author of Chasing the Bright Side and Making it Without Losing it. Her hobbies include writing, hiking, board games with her husband,
Connect with Jess Ekstrom
Instagram: www.instagram.com/jess_ekstrom
Facebook: www.facebook.com/jessekstrom
X: www.twitter.com/jess_ekstrom
TikTok: https://www.tiktok.com/@jessekstrom
LinkedIn: https://www.linkedin.com/in/jess-ekstrom-59160342/
Mic Drop Workshop: https://micdropworkshop.com/
Website: https://jessekstrom.com/
About the Host
Dr. Amna Shabbir, MD, NBC-HWC, CPC is a Dual Board-Certified Physician and TEDx Speaker with advanced training in Integrative Well-being, Performance, and Leadership Development. She speaks, coaches, and consults on Workplace Wellness, Perfectionism, Sustainable Success, and the well-being of High Achievers.
✅Want to explore Corporate Wellness Consulting and Fractional Well-being Officer work With Dr. Shabbir?
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Connect with Dr. Shabbir
📸 Instagram: https://www.instagram.com/dr.amnashabbir/
💼 LinkedIn: https://www.linkedin.com/in/amna-shabbir-md/
📹 Watch Dr. Shabbir's TEDx Talk
Perfectionism Has A Solution - It is Not What You Think: https://www.youtube.com/watch?v=oNIzzM4Vg3s&t=3s
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❌ Disclaimer
This podcast is for educational purposes only and does not constitute medical or therapeutic advice. The views expressed are personal and do not reflect those of any employer or institution.
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