Jennifer Tosti-Kharas & Christopher Wong Michaelson on Is Your Work Worth Doing?

What makes work truly worth doing in a life worth living? In this episode of Passion Struck, John R. Miles sits down with Jennifer Tosti-Kharas and Christopher Wong Michaelson, celebrated professors and co-authors of the powerful new book Is Your Work Worth It?: How to Think About Meaningful Work. Together, they unpack some of the most important questions we face in our careers and lives: Should you work for love or for money? How do you balance happiness, purpose, and earning power? Can you find meaning in jobs that don’t feel glamorous—or even lovable?

Drawing from decades of research, philosophy, and real-world stories, Jennifer and Christopher challenge conventional wisdom and reveal what it truly takes to align your work with your values, avoid burnout, and design a life that feels worth living.

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Listen to the episode on Apple Podcasts, Spotify, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Listen Notes, Amazon Music, or on your favorite podcast platform. You can watch the interview on YouTube below.

The Hidden Trade-Offs of Meaningful Work: Redefining Success and Purpose

In this thought-provoking conversation, John R. Miles explores the paradoxes of modern work with Jennifer Tosti-Kharas and Christopher Wong Michaelson. From 9/11 to Enron to personal family legacies, this episode unpacks how crises, culture, and personal values shape the meaning we attach to our careers.

Together, they dive into the hidden trade-offs of passion, the exploitation of purpose-driven workers, and why some of life’s most important meaning may come from work that society often undervalues. With stories ranging from sanitation workers to David Bowie’s final album, this episode challenges the myths we tell ourselves about success and fulfillment.

In This Episode You’ll Learn:

• Money and happiness don’t always align — earning power peaks often coincide with the lowest levels of life satisfaction.
• Passion can be exploited — employees who deeply love their work are often expected to sacrifice pay, time, or well-being.
• Work takes many forms — job, career, and calling are all valid orientations, each offering different routes to a meaningful life.
• Unrecognized work still matters — caregiving and domestic labor remain undervalued, despite being deeply purposeful.
• Legacy outlives labor — like David Bowie, the impact of our work can extend far beyond our lifetimes, shaping how others find belonging and meaning.

WHY IS THIS EPISODE A MUST-LISTEN?

This episode goes beyond surface-level career advice to ask the questions most of us avoid: What are we really working for, and at what cost? If you’ve ever felt trapped in a high-paying job that leaves you empty, or wondered whether following your passion is worth the risk, this conversation offers clarity and perspective. It’s a guide for rethinking the stories we tell ourselves about work—and how to align them with a life worth living.

Key Takeaways We Discuss

✔️ Why the idea of “founder as hero” is toxic—and what real leadership looks like
✔️ The moment Kass asked Mike to fire her—and how that reshaped their marriage
✔️ How to build a culture that doesn’t collapse under pressure
✔️ What cancer taught them about slowing down and prioritizing what matters
✔️ The difference between startup survival and startup success
✔️ Why choosing the right partner—in business and life—might be the most important decision you ever make
✔️ How emotional awareness, humility, and vulnerability scale better than ego ever could

PLEASE SCROLL DOWN FOR FEATURED RESOURCES

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David Bowie and the Legacy of Work That Outlives Us

One of the most powerful moments in this episode is the discussion of David Bowie’s final album, Blackstar, which he recorded while knowing his life was coming to an end. As Christopher Wong Michaelson and Jennifer Tosti-Kharas explain, Bowie’s choice to spend his last months creating art reveals something profound about the nature of work. When faced with mortality, he didn’t retreat into comfort—he leaned into contribution, leaving behind a piece of art that many consider his greatest work. Released just days before his passing, Blackstar became a symbol of how work, when aligned with passion and purpose, can outlast the worker.

Bowie’s story also highlights the transformative role of identity in work. Throughout his career, he was a “shape shifter,” reinventing himself again and again. His creativity wasn’t just about music—it was about challenging norms and giving people permission to belong. As Michaelson noted, Bowie once quipped that he’d like to be remembered for his haircuts, but those very haircuts became a lifeline for outsiders who saw in his strangeness a mirror of their own uniqueness. In this way, his work didn’t just entertain—it created a cultural space for inclusion and belonging.

In their book, Is Your Work Worth It?: How to Think About Meaningful Work, Jennifer and Christopher argue that meaningful work is not just about how it feels in the moment—it’s also about the legacy it leaves behind. Bowie’s story exemplifies this truth: even as he faced death, his work lived on, shaping how others see themselves and the world. For listeners, it’s a reminder that while not all of us will leave behind an album or a cultural movement, the choices we make in our work can ripple far beyond our lifetimes.

Thanks, Jennifer Tosti-Kharas & Christopher Wong Michaelson

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RESOURCES FROM THE SHOW WITH JENNIFER TOSTI-KHARAS & CHRISTOPHER WONG MICHAELSON

Please note that some of the links on this page (books, movies, music, etc.) lead to affiliate programs for which The Passion Struck podcast receives compensation. It’s just one of the ways we keep the lights on around here. Thank you so much for being so supportive!

1. Christopher Wong Michaelson’s Website
2. Publisher’s Book Page
3. Jennifer Tosti-Kharas’ LinkedIn
4. Christopher Wong Michaelson’s LinkedIn
5. BUY Chris and Jenn’s book ‘Is Your Work Worth It?’
6. APA’s recognition of mattering as critical to child mental health
7. Passion Struck Core Value System: https://passionstruck.com/the-passion-struck-core-belief-system/
8. Listen to Passion Struck’s interviews with New York Times bestselling authors Gretchen Rubin and Seth Godin.
9. Check out Passion Struck’s Episode Starter Packs on Spotify or Passion Struck starter packs to get started with the podcast.

About Today’s Guests, Jennifer Tosti-Kharas & Christopher Wong Michaelson

Jennifer Tosti-Kharas is the Camilla Latino Spinelli Endowed Term Chair and Professor of Organizational Behavior at Babson College. Her award-winning research explores meaningful work, work as a calling, and career development, and has been featured in leading academic journals and major media outlets. She is the co-author of several books, including Organizational Behavior: Developing Skills for Managers and The Meaning and Purpose of Work. A former strategy consultant with Accenture, Jennifer brings both practical and scholarly insights to how people build fulfilling careers. She lives outside Boston with her husband and two children.

Christopher Wong Michaelson is the Opus Distinguished Professor and Academic Director of the Melrose and The Toro Company Center for Principled Leadership at the University of St. Thomas, as well as a member of the Business and Society faculty at NYU’s Stern School of Business. A philosopher by training, he has over 25 years of experience advising leaders on business ethics and the pursuit of meaningful work. His career spans consulting at PwC, teaching at Wharton, and serving as President of the Society for Business Ethics. He is also host of the podcast Work in Progress with Christopher Michaelson. Christopher lives in Minneapolis with his wife, three children, and two dogs.

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