The Rethinking Work Show
The Rethinking Work Show
Podcast Description
Rethinking Work is a show hosted by Rishad Tobaccowala about how work is changing and how we can change with it. In each episode, Rishad sits down with bold thinkers, builders, and leaders to explore the future of work across industries. From remote work and AI to purpose, creativity, and culture, we uncover the ideas reshaping how we live, lead, and grow in today’s world. Subscribe to hear fresh, human conversations about what work can and should become.
Podcast Insights
Content Themes
The show addresses topics related to the future of work, focusing on remote work dynamics, the role of artificial intelligence, and the significance of creativity and organizational culture, with episodes such as discussions on how remote work can boost talent and innovation through insights from experts like Dr. Prithwiraj Choudhury.

Rethinking Work is a show hosted by Rishad Tobaccowala about how work is changing and how we can change with it. In each episode, Rishad sits down with bold thinkers, builders, and leaders to explore the future of work across industries. From remote work and AI to purpose, creativity, and culture, we uncover the ideas reshaping how we live, lead, and grow in today’s world. Subscribe to hear fresh, human conversations about what work can and should become.
Are we preparing students for the world of work or a world that no longer exists? Authors Alexandra Levit and Stephanie Loeck explore how work-based learning can close the gap between education and employment, and why real-world experience, not just classroom instruction, may be the key to building adaptable, future-ready talent.
Purchase and learn more about their book Make School Work here: https://makeschoolwork.org/
Alexandra Levit is the founder and CEO of Inspiration at Work, a futurist consulting firm dedicated to helping organizations and their employees thrive in a rapidly evolving business landscape. A former nationally syndicated columnist for The Wall Street Journal, Alexandra is the bestselling author of They Don’t Teach Corporate in College, Humanity Works, and Make School Work, which addresses the American youth employment crisis through work-based learning. She holds a certificate in strategic foresight from the University of Houston and advises leading organizations including Deloitte, American Express, Adecco, and Upwork on leadership, workforce transformation, technology adoption, and skills development. Alexandra has collaborated extensively with U.S. government agencies, including the Department of Labor and Department of Defense, and her work has been featured in outlets such as The New York Times, Forbes, CNN, and NPR. Recognized by Thinkers50 and the American Management Association, she lives in Chicago.
Stephanie Loeck is Vice President of Strategic Development at GPS Education Partners, where she leads national growth initiatives advancing work-based learning and expanding career-connected opportunities for students. A passionate workforce and education advocate, Stephanie brings expertise across strategy, policy, communications, and economic development to help modernize the transition from school to work. At GPS Education Partners, she shapes long-term growth strategies, builds partnerships, and drives thought leadership around learner-centered program design. She played a key role in developing GPS Ed’s signature six-part work-based learning framework, which supports program implementation, continuous improvement, and sustainable impact. Previously, Stephanie served as Vice President of Partnerships at America Succeeds, engaging business leaders in education reform initiatives such as Durable Skills and Age of Agility. She has also worked in economic development and with technology startups. Based in Colorado, Stephanie serves on national advisory boards championing authentic, career-connected learning aligned with the future of work.
EPISODE CREDITS
Produced, edited and mixed by Ria Tobaccowala
Artwork designed by Ben Damiano
Additional music licensed through Premium Beats
LINKS
Explore more about the new frontiers of work at Rethinkingwork.io
For more actionable insights that inspire subscribe to Rishad Tobaccowala’s free weekly substack: The Future Does Not Fit In The Containers Of The Past.
This show is also available on YouTube which includes visual supplements.
Rishad’s Book Rethinking Work is available in print and audio. Click here for where to buy.

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