When Career Success Feels Unfulfilling | Megan Hellerer Artwork

Work For Humans

Too often business leaders are forced to choose between the needs of their company and the needs of their employees. It’s a lose/lose scenario leaving managers burned out and workers seeking other opportunities. At Work for Humans, we believe work can be designed differently. When you design work like products people love, your company wins. Work becomes irresistible, employees passionately buy into their roles every day, and your company takes measurable strides towards your vision.

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Work For Humans

When Career Success Feels Unfulfilling | Megan Hellerer

August 11, 2026 • Dart Lindsley / Megan Hellerer • Season 1 • Episode 195

0:00 | 1:08:21

Megan Hellerer had done everything she was supposed to do. She went to Stanford, graduated with a 3.9, and dutifully climbed the ladder at Google. But the life that looked great on paper felt terrible inside. A panic attack on the floor of a public restroom forced her to confront a bigger question: what if the problem wasn't choosing the wrong destination, but the idea that we need a destination at all? In this episode, Dart and Megan explore how we move from “destinational living” to “directional living,” and what it means to build a life and career by following curiosity, experimenting, and learning as we go.

Megan Hellerer is the author of Directional Living and the founder of Coaching for Underfulfilled Overachievers. She spent eight years at Google in Strategic Partner Development before leaving to help other underfulfilled overachievers rethink work, success, and fulfillment.

In this episode, Dart and Megan discuss:
- The underfulfilled overachiever
- Why success can still leave you miserable
- Where our “shoulds” come from
- Destinational vs. directional living
- Why certainty can be so seductive
- Curiosity over purpose
- Using “warmer” and “colder” to find your direction
- The value of small experiments
- Designing more directional work
- Can fulfillment become another destination?
- And other topics…

Megan Hellerer is the author of Directional Living: A Transformational Guide to Fulfillment in Work and Life and the founder of Coaching for Underfulfilled Overachievers. She has spent the past decade helping high-achieving people who feel unfulfilled rethink their relationship with work and success. Before becoming a career coach, she spent eight years at Google in Strategic Partner Development. She graduated from Stanford University with a degree in International Relations and is a Certified Professional Co-Active Coach.

Resources Mentioned:
Megan’s book: Directional Living: A Transformational Guide to Fulfillment in Work and Life: https://www.amazon.com/dp/0593299272
Designing Your Life, by Bill Burnett and Dave Evans: https://www.amazon.com/dp/1101875321
Bill Burnett on Work for Humans: https://podcasts.apple.com/us/podcast/designing-your-life-how-to-use-design-principles-to/id1612743401?i=1000738307337
Margaret Heffernan on Work for Humans: https://podcasts.apple.com/us/podcast/the-hidden-cost-of-certainty-at-work-margaret-heffernan/id1612743401?i=1000754431168

Connect with Megan:
Website: https://meganhellerer.com/
LinkedIn: https://www.linkedin.com/in/megan-hellerer-6868326/

Work with Dart:
Dart is the CEO and co-founder of the work design firm 11fold. Build work that makes employees feel alive, connected to their work, and focused on what’s most important to the business. Book a call at 11fold.com.

Dart Lindsley

Host