Is Your Work Worth It? Rethinking Purpose, Money & Meaning with Authors Christopher Wong Michaelson and Jen Tosti-Kharas

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What makes work truly worth it? Is it the paycheck, the prestige, or the purpose behind what we do every day?

In this episode, I sit down with authors Christopher Wong Michaelson and Jen Tosti-Kharas to dive into their book Is Your Work Worth It? We unpack the big questions around why we work, what keeps us going long after we “have to,” and how to think differently about love versus money in our careers. From rethinking autopilot routines to exploring how work shapes our legacy, this conversation will have you reflecting on your own motivations in a whole new way.

Together, we also explore the tension between career demands and personal life, the myths about turning passions into professions, and how leaders can shape meaningful work for others. Whether you’re building a business, leading a team, or simply wondering what your next career move should look like, this episode offers fresh perspective on finding fulfillment and redefining success.

Topics We Cover in This Episode:

• The surprising truth about why most people really keep working

• Why “autopilot” is the hidden enemy of career satisfaction

• A simple way to test if your work passes the “seven-year-old” explanation test

• The overlooked connection between love, money, and fairness at work

• What entrepreneurs often love most about their work (and it’s not what you think)

• How to use “seasons of life” to plan your career with more intention

• Why the most worthy work is often undervalued—and what to do about it

• A framework to uncover your deeper purpose that goes beyond surface-level goals

Ready to rethink your relationship with work? Tune in now and walk away with new questions to ask yourself, your team, and your organization. And if this episode sparks something for you, share it with a colleague or friend because these are conversations worth having.

Resources Mentioned:

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