Leading Up: The Work Shift

Change is constant, but the right insight at the right moment can make all the difference. In this season finale compilation, we're revisiting the hard-won lessons, unexpected turns, and honest conversations that defined Leading Up: The Work Shift. The incredible guests featured in this episode — Krista Chism, Pat Flynn, James Whitmore, Lorraine Lee, Ahyiana Angel, Zak Brown, Terrin Lawrence, Simone Stolzoff, Deborah Grayson Riegel, and Dorie Clark — remind us that navigating the future of work is about staying curious, keeping your eyes on the horizon, and always leading up.  

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Production by Pod People 

Professional uncertainty can be as damaging to our health as actually losing a job. So why do we keep white-knuckling for certainty—and what happens when we finally let go?

This week, Elizabeth sits down with Simone Stolzoff, author of The Good Enough Job and the forthcoming How to Not Know: The Value of Uncertainty in a World That Demands Answers, to explore why our instinct to seek certainty may be the very thing holding us back. Simone shares what years of researching ambiguity taught him about reframing uncertainty—not as a threat to manage, but as an opportunity to collaborate with. Plus: why the human skills employers want most are exactly the ones AI can't replicate. 

Follow Leading Up: The Work Shift on Apple, Spotify, or wherever you listen. New episodes drop Tuesdays. 

If you’re trying to skill up, head to Udemy.com 

Find out more about Leading Up: The Work Shift at business.udemy.com/leading-up-podcast

Production by Pod People

What if the habit that's made you successful is also holding you back? Meg Josephson, therapist and author of the New York Times bestseller Are You Mad at Me?, joins Elizabeth Weingarten to break down the psychology of people pleasing and its hidden cost on leadership. Drawing on her research and clinical work, Meg explains the "fawn response," the lesser-known survival mechanism that drives us to appease rather than assert, and why high achievers are especially susceptible. People pleasing erodes trust, keeps relationships shallow, and quietly undermines your authority — and Meg explains what to do about it. 

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If you’re trying to skill up, head to Udemy.com 

Find out more about Leading Up: The Work Shift at business.udemy.com/leading-up-podcast 

Leading Up: The Work Shift is produced by Udemy in partnership with Pod People. 

More than half of Americans say job insecurity is crushing them with stress. So how do some people look like they've always had it figured out? Spoiler: they haven't. 

Host Elizabeth Weingarten traveled to the World Economic Forum in Davos, Switzerland to pull aside C-Suite leaders, entrepreneurs, and founders from companies like BetterUp, Zoom, Bain & Company, and more to talk about the moments when work inexplicably shifts—the layoffs, the pivots, the feeling of being completely stuck. 

From Dr. Becky Kennedy discovering that admitting "I don't know" was actually the path to knowing herself, to Ray Wang's father asking him "what are you worth?" before he started his own company, to Josh Kallmer's "happiness matrix" that pulled him out of his darkest professional period, these leaders show that navigating uncertainty is what makes great leaders.

Follow Leading Up: The Work Shift on Apple, Spotify, or wherever you listen. New episodes drop Tuesdays. 

If you’re trying to skill up, head to Udemy.com 

Find out more about Leading Up: The Work Shift at business.udemy.com/leading-up-podcast

Subscribe to our Substack: workshifthappens.substack.com 

Leading Up: The Work Shift is produced by Udemy in partnership with  ⁠Pod People⁠.

In a world of consistent career pivots and shifts, mastering how you show up and speak up isn’t optional—it can be your superpower. So how do you go from nervous novice to powerhouse presenter? 

Host Elizabeth Weingarten sits down with Deborah Grayson Riegel to reveal the secrets from her 30 years as an international keynote speaker. As a corporate trainer and instructor at top business schools like Duke Fuqua, Wharton, and Columbia, Deborah coached thousands to communicate with polish, professionalism, and authentic power. In this episode, we unpack her battle-tested tools for conquering public speaking fears, crafting messages that stick, and using presentation skills to accelerate career shifts—whether you’re pitching for a promotion, negotiating a raise, or rebounding after a layoff.

If you’re ready to start leading the conversation, this episode is your script.

Subscribe to Leading Up: The Work Shift on YouTube. 

Follow Leading Up: The Work Shift on Apple, Spotify, or wherever you listen. New episodes drop Tuesdays. 

⁠Subscribe to our Substack.

For courses from Deborah Grayson Riegel, head to Udemy.com

Find out more about Leading Up: The Work Shift at business.udemy.com/leading-up-podcast 

Leading Up: The Work Shift is produced by Udemy in partnership with Pod People.

Doing great work isn't enough to get promoted. You need presence. In this episode, Lorraine K. Lee, author of Unforgettable Presence and former LinkedIn editor, shares why she stayed stuck at the same level for six years despite working hard and being well-liked. She explains the 80/20 rule of career advancement, how to optimize your video presence with the TEAM method, and why introverts have hidden superpowers in the workplace. Host Elizabeth Weingarten helps you learn actionable strategies for standing out in virtual meetings, networking without feeling transactional, and building a LinkedIn presence that opens doors. Plus: the feedback questions that actually get you useful answers, and why small talk might be your secret weapon.

Subscribe to Leading Up: The Work Shift on YouTube. 

Follow Leading Up: The Work Shift on Apple, Spotify, or wherever you listen. New episodes drop Tuesdays. 

⁠Subscribe to our Substack.

If your new year’s goals include learning a new skill, head to Udemy.com

Find out more about Leading Up: The Work Shift at business.udemy.com/leading-up-podcast 

Leading Up: The Work Shift is produced by Udemy in partnership with  Pod People.

How do we know when it’s time to leave a job? Or completely reinvent your career? In this episode, we explore what it really takes to make a major career change, and the fear that comes with stepping into the unknown. 

Ahyiana Angel, former NBA publicist turned published author and host of the hit podcast Switch, Pivot or Quit, shares her journey from sports PR to entrepreneurship. We’ll hear the moment she knew it was time to pivot, how she navigated shifting industries, and what lessons helped her find her footing lessons she learned along the way. She shares what it takes to navigate uncertainty, find clarity and take your next step with confidence.

Follow Leading Up: The Work Shift on Apple, Spotify, or wherever you listen. New episodes drop Tuesdays. 

If you’re trying to skill up, head to Udemy.com 

Find out more about Leading Up: The Work Shift at business.udemy.com/leading-up-podcast

Subscribe to our Substack: workshifthappens.substack.com 

Leading Up: The Work Shift is produced by Udemy in partnership with  Pod People.

James Whitemore, Chief Marketing Officer at Indeed, shares insights from billions of job searches on how to navigate career transitions in today's challenging market. He discusses the power of reframing your skills, why focus beats quantity in job applications, and how to discover non-obvious career paths that match your experience. James also reveals the mindset shifts that matter most after a layoff, why sales roles can be strategic career moves, and how to build a profile that shows adaptability and lifelong learning: the qualities employers value most.

Follow Leading Up: The Work Shift on Apple, Spotify or wherever you listen. New episodes drop Tuesdays. 

⁠Subscribe to our Substack ⁠.

If you’re trying to skill up to land a new job, head to Udemy.com

Find out more about Leading Up: The Work Shift at business.udemy.com/leading-up-podcast 

Leading Up: The Work Shift is produced by Udemy in partnership with  Pod People.

How do you make a quick decision when the stakes are high? Zak Brown, CEO of McLaren Racing, shares hard-won lessons from his journey from professional driver to marketing entrepreneur to Formula One executive. Zak reveals why asking questions matters more than having all the answers, how he learned to control emotional reactions that could have derailed his racing career, and what Formula One can teach anyone about decision-making under pressure. He discusses the parallels between driving at 200mph and leading 1,400 people, why sleep and attention to detail are underrated skills, and how embracing failure accelerates learning. 

Follow Leading Up: The Work Shift on Apple, Spotify, or wherever you listen. New episodes drop Tuesdays. 

If you’re trying to skill up, head to Udemy.com 

Find out more about Leading Up: The Work Shift at business.udemy.com/leading-up-podcast

Subscribe to our Substack: workshifthappens.substack.com 

Learn more about Zak’s new book: Seven Tenths of a Second: Life, Leadership and Formula 1 

Leading Up: The Work Shift is produced by Udemy in partnership with  Pod People.

From being laid off to spinning your wheels in a position with no momentum, getting to the next step in your career can take a lot of energy. And resources, too, if you decide to hire a career coach. This week’s guest has been focused on building a learning culture wherever she goes, and as the Senior Director of Leadership Development at Udemy, Rebecca Stern has applicable ideas on how to use AI as a thought partner to assist you in achieving your goals.This episode covers how human coaching can be inaccessible and how AI models can serve the same purpose, from identifying and contextualizing your career strengths and areas for improvement to facilitating learning through small experiments or tests of a new skill. Turning the page to the next chapter in your career will take a bit of planning. This episode will leave you with small, actionable steps to regain your confidence and find the motivation within.

Follow Leading Up: The Work Shift on Apple, Spotify, or wherever you listen. New episodes drop Tuesdays. 

⁠Subscribe to our Substack ⁠.

If you’re trying to skill up, head to Udemy.com 

Use code SHIFT25 for 20 percent off your first month on Udemy and turn today's inspiration into actual progress. 

Find out more about Leading Up: The Work Shift at business.udemy.com/leading-up-podcast 

Leading Up: The Work Shift is produced by Udemy in partnership with  Pod People.