Podcast Summary: Creating Confidence with Heather Monahan

Episode: How to Stop Delaying Happiness While Pursuing Big Goals with Jess Ekstrom
Date: April 21, 2026

Overview

In this uplifting and insightful episode, Heather Monahan sits down with repeat guest Jess Ekstrom—entrepreneur, bestselling author, and an advocate for women’s voices—to dig deep into what it really means to “make it” without losing yourself along the way. Together, they explore the dangers of delaying happiness until after achieving ambitious goals, how to embrace joy in the process, and the importance of re-examining our definitions of success. Jess shares powerful strategies from her new book Making It Without Losing It, and both women share personal stories about period of change, chasing purpose, and finding fulfillment both in business and at home.

Key Discussion Points & Insights

Building Social Capital and Asking for Help

• Lead with Generosity:
  Jess and Heather discuss the importance of helping others and leading with generosity when building relationships, rather than only reaching out when you need something.

  • Memorable Quote (03:03, Jess):
    "You don't talk the talk, you walk the walk. A lot of people are quick to give encouragement, and not a lot are quick to give opportunity. You're so willing and generous with giving opportunity."

• Do Your Homework When Asking:
  Jess emphasizes the importance of showing you've done your research before asking for favors or introductions, making it a partnership rather than a transaction.

  • Notable Practice (09:24, Heather):
    “Before you ask someone for something, do the homework. ...I'll write up three different options of potential [endorsement] just to make it easy for them.”

Transforming Ambition & Scaling Up

• Chasing Purpose over Titles:
  Jess shares her journey from founding Headbands of Hope in college—donating millions of headbands to children with illnesses—to launching Mic Drop Workshop, supporting women to become professional speakers.

  • Story Highlight (17:34, Jess):
    “Headbands of Hope went on to get acquired during the pandemic... I didn't realize how emotional that was for me. Saying goodbye to something you built.”

• The Post-Achievement Letdown:
  Both discuss how achieving long-held goals brings a relief, but often not the permanent happiness expected. Jess calls this the “post achievement letdown” and explains its prevalence—even among Olympians (32:34).

Redefining Success & Enjoying the Journey

• Personalizing Your Success 'Fingerprint':
  Jess introduces the concept of a "success fingerprint": realizing success is individually defined and evolves with life’s seasons.

  • Memorable Exercise (22:13, Jess):
    “Success is redefined by each person in each season. ... Audit what you’re chasing. Would you still want it if no one knew it was you? If yes, it’s in your fingerprint.”

• Avoiding the Delay of Joy:
  Both speakers challenge the idea that happiness comes only after a goal is reached, emphasizing the need to enjoy the process.

  • Quote from Jess (12:01; repeated at 49:19):
    “Don’t try to achieve things, to have zero problems. Do things that have problems you’re excited to solve.”

Practical Strategies for the Process

• Making Asks into Offers:
  Instead of asking “Can I speak at your event?” say “Would my session on [X] be helpful for your audience?”—framing your approach as adding value.

• Zooming Out for Perspective:
  Jess shares a visualization exercise from a silent retreat: viewing your daily life from above to ask, “Do I like the dots I’m painting on the canvas?” (41:15) This helps realign daily actions with your deeper values.

Handling Life’s Uncertainties

• Embracing Uncertainty:
  Heather and Jess discuss the challenge and necessity of being at peace with not knowing when (or if) key personal and professional milestones will occur.

  • Relatable Moment (30:36, Heather):
    “I could enjoy it more if I knew the when... But the not knowing is what kills me.”

• Presence in Parenting, Work, and Relationships:
  They reflect on being told to “enjoy the moment” in tough times—an oft-resented cliché—acknowledging it’s both hard and fleeting, and reframing the narrative to accept multiple truths at once.

Connecting Work to Meaning

• Infusing Purpose into Any Role:
  Any job can become meaningful when intentionally connected to serving others. Jess encourages listeners to make this connection consciously, even if the work isn’t their “passion” (54:09).

Notable Quotes & Memorable Moments

• On social capital:
  “I'm putting my social capital on the line for you. ...If someone does the homework, that is something I can consider.” — Jess, 05:09

• On letting go of needing universal approval:
  “The minute you let go of that outcome—because it's none of our business how others feel—it's just so much easier mentally.” — Heather, 48:09

• On the myth of a finish line:
  “I was kind of putting this making-it label on things I thought would solve problems... There are not these thresholds that launch you into a zero inbox, no problems.” — Jess, 49:19

• On the success fingerprint:
  “Today my version of success is to do enough at work so I have the flexibility outside of it.” — Jess, 22:13

• On meaningful work:
  “Any work can be meaningful work if you take the time to connect it to a human... It takes an extra effort but is worth it in the long run.” — Jess, 54:09

Timestamps for Important Segments

• [03:03] Building true social capital and leading with generosity
• [09:24] Tips for making “asks” easier and more thoughtful
• [17:34] Jess’s entrepreneurial journey: founding, scaling, and selling Headbands of Hope
• [22:13] Creating a personal “success fingerprint” and auditing your ambitions
• [30:36] Navigating uncertainty and the “delay” of happiness
• [41:15] Gaining perspective through stepping outside routine and visualization
• [49:19] Shifting from singular finish lines to ongoing, meaningful problems to solve
• [54:09] Finding meaning in any kind of work

Who Should Listen/Read This Book?

Jess’s Making It Without Losing It is aimed at anyone (not just women) who feels caught between the yearning for future achievement and finding joy in the present. If you struggle with balancing ambition, fulfillment, and well-being, these insights and exercises are designed for you.

Resources Mentioned

• Success Fingerprint GPT (Available for pre-orders at JessEkstrom.com/makingit; pre-orders also receive the audiobook free before May 5)
• Making It Without Losing It by Jess Ekstrom

Final Thoughts

Both Heather and Jess model a candid, authentic conversation about ambition, setbacks, personal evolution, and purpose. Their advice is actionable and compassionate, focusing on creating joy while in pursuit of success—not just after you arrive. You’ll walk away with practical mindset shifts and reflections for enjoying your own journey, no matter where you are on the “path to making it.”