In 15th century Florence, the Medici family was well-known for patronizing great artists, scientists, engineers, and writers. This investment in cross-disciplinary thinking planted the seeds of the Renaissance, a time of extraordinary growth and enlightenment in Europe.

Today, we have other words for this practice: Diversity & Inclusion. Author, speaker, and consultant Frans Johansson wrote "The Medici Effect," about how expanding your "surface area" of perspectives can help companies, families, governments, and any organization benefit from the alchemy of diversity. And he has the stories and data to prove it.

Frans' book was originally published in 2004, and has exploded in popularity as D&I and social justice conversations move to the front of our culture. In this fascinating conversation, Frans and Whitney unpack the philosophy of intersectional diversity, and focus on very practical ways to activate it in your organization.

Getting your "big break" rarely comes down to luck. But it's also hard to engineer a breakthrough moment. Anne Chow believes it's a combination of science and serendipity: Planning ahead so you can seize a lucky moment when it appears. Her career embodies that philosophy.

Anne is the CEO of AT&T Business, and a 2nd generation American. As the daughter of Taiwanese immigrant parents, their outlook on success was tremendously formative for her.

She's a Julliard-trained musician who became an engineer before one mentor suggested she try sales as a path to leadership. Despite being rejected multiple times, she credits that unlikely S Curve jump as the key to her long-term success as an executive.

Anne and Whitney discuss the resilience it takes to stay with one organization for so long, how to make our inherent human biases work for us, and why it's time to re-think what retirement looks like in the 21st century.

When we spend 50-60 of our waking weekly hours at the office, our "work family" sometimes eclipses our actual one. Companies capitalize on this. Our jobs become our identities. Our work becomes very personal. And this can lead to emotional disaster during career changes, layoffs, and other transactions.

What if we valued work differently? What would the world look like if we stopped treating work itself as our purpose, but as a means to enjoy a more important purpose: Family, relationships, hopes, dreams, and love?

That's just the starting point of Sarah Jaffe's book, "Work Won't Love You Back." Sarah is a journalist who covers labor issues and social movements, and she's observed a major shift in the way we view our jobs.

She profiles teachers, interns, programmers, and professional athletes to identify which kind of work is valued, and which is not. And as "The Great Resignation" has hinted, many people want out — but where are they actually going?

Any career contains thousands of S Curves, large and small, and Russ Wheeler's journey certainly embodies this. He's the CEO of BBQGuys, a retailer for all things grilling, smoking, and camping, but he's worked as an executive in the home improvement business for decades. That means many tough decisions about how to balance the needs of his employees, customers, and himself.

But Russ' core values keep him grounded, even when he's not sure if his decision is right. As he explains in this candid conversation with Whitney, "sharing the gains" with every member of the team was a way for him to take leaps he was initially skeptical about.

Russ shares the difficult choice to not take the company public, despite years of work to do so, and why he loves hiring people at the beginning of their careers so they can grow into mastery on the job.

Nobody wants to be sad. We actively avoid it, and use all the technology in our power to distract ourselves from it. But Susan Cain says, maybe we should seek sadness out.

She knows a thing or two about it. Her books about introversion and quiet reflection are New York Times bestsellers, and her TED talk has been viewed 40 million times.

Her latest book, "Bittersweet: How Sorrow and Longing Make Us Whole," is about what we miss when we stop confronting sad feelings. Susan explains that reflecting on pain -- including the pain of others -- is something we need more of in our lives, especially in a digital world, where we increasingly only see vacation photos, smiling kids, and job promotions.

This practice can be about deep personal connection, or simply seeking a sad song or choosing a heartbreaking movie once in a while. After all, there's a reason history's most enduring art is about longing and loss.

This episode references Whitney's recent newsletter, which you can read (and subscribe to!) here:

"The way we've always done it" is often not the best way. This is the very definition of disruption, but getting "stuck" on old habits can sneak up on us — in our personal lives, and our companies.

That's what Roger Martin explores in his latest book, "A New Way to Think." Roger has built his career as an author and professor studying disruption, mainly identifying business models that we've relied on for decades, and then asking, "Does this really work?"

Roger returns to the show for another rousing discussion about career satisfaction and employee retention, especially in the wake of "The Great Resignation." He also contends that we've structured modern knowledge work too rigidly, and why that can stifle innovation.

He also shares the single most discouraging phrase you could ever say to a member of your team, and how to avoid it.

Achieving something that's important to you: That's probably a big reason you're listening to this podcast. But what is it about success that drives us? Do we achieve for its own sake, or is there something more?

That's what Marshall Goldsmith is exploring. He's one of the most recognized thinkers and writers on the topic of leadership, but in his latest book, "The Earned Life," he asks: Why are we doing all this? Does success really make us happy? And what if those two things were not so deeply connected?

Whitney and Marshall sit down for a conversation that turns traditional Western views of success and happiness on their head. He notes that some of the most successful leaders are great at delaying gratification, only to look back on what they missed out on in life. In fact, after we accomplish something great, we should stop expecting more, but default to a new beginning.

"Fear of Missing Out" or "FOMO" is wired into our brains for a reason. When our ancestors flocked to greener pastures, it was advantageous to follow. FOMO can inform modern, strategic decisions as well, but Patrick McGinnis says we should be vigilant against its more dangerous sibling, FOBO: "Fear of Better Options."

This is a kind of decision paralysis that's catastrophic for personal well-being and companies. Patrick has studied it closely. After all, he invented the term "FOMO" back in 2004, written multiple books on the topic, and hosts the podcast FOMO Sapiens.

He and Whitney discuss how the breakneck speed of 21st century FOMO can trick us into "fear-based decision making," and why outsourcing low-stakes choices to Siri or a coin flip can be incredibly liberating.

John David Mann is a writer and the co-author of more than 30 books. Ana Gabriel Mann is a professional therapist, speaker and coach. Together, they've been married for more than 25 years, which also happens to be the subject of their latest work.

The Go-Giver Marriage is rooted in a framework of gratitude, kindness and self-disruption that John has been writing about for years. When Ana thought to apply this to relationships, it was a "light bulb" moment for both of them.

They join Whitney to discuss the 5 secrets that don't just apply to relationships in trouble, but can help an already good relationship (marriage or professional) become great.

Running a marathon, writing a book, or learning piano. These are big undertakings that require discipline and practice. The harder we work each day, the faster we'll succeed, right?

Wrong, say authors and podcasters Jami and Jeffery Downs. Biting off more than our daily chew can lead to a cycle of discouragement. Instead, commit to laughably small steps: Write one sentence a day. Practice for five minutes. These micro goals are much easier to sustain, and when you keep the streak going, you'll find that sentences turn into pages, and minutes turn into skills.

A revelation in their personal lives lead this husband and wife team to develop "Streaking," a philosophy of personal accountability that applies to anything: Learning, personal relationships, and health.

Jami and Jeffery speak with Whitney about the myths of habit forming, and why some tasks — no matter how often you repeat them — will never become automatic.