In this episode, Bobbi Brown, founder of Bobbi Brown Cosmetics and Jones Road, speaks openly about the challenges of building her businesses, and what it felt like when a major change turned her world upside down. She shares how she navigated the shock, the anger—and the unexpected freedom—of starting over.

She and Leah explore what it takes to navigate sudden change, trust your gut, and start over in a way that feels true. If you’re facing a “now what?” moment, this episode is for you.

Bobbi’s journey began as a young makeup artist breaking the rules, creating natural, authentic looks in an industry dominated by heavy trends. What started with testing lipsticks on nannies at the playground grew into a global brand she built from scratch and ultimately sold to Estée Lauder.

But after decades at the helm of her namesake brand, Bobbi suddenly found herself facing a moment she never planned for: her work contract was canceled. Suddenly, life went quiet. No overflowing calendar. No endless demands. No clear next step. Just… herself.

You can find her book ”Still Bobbi: A Master Class in Resilience and Reinvention” here.

If you liked this episode, you’ll also love this one: On the Clock: A Working Mothers’ Roundtable on Parenthood and Ambition.

Follow Leah Smart and Bobbi Brown on LinkedIn. 

Are you feeling stuck in a career you find meaningless, wondering if you’ll ever find your true calling?

This week on Everyday Better, Leah Smart sits down with Sister Monica Clare — an Episcopal nun, spiritual counselor, and the creator behind the TikTok account @nunsenseforthepeople. Her path to the convent was anything but direct. For decades, she chased one career after another in Hollywood — acting, advertising, comedy, PR — all while ignoring the quiet truth she’d known since childhood: her true calling was to become a nun.

In this powerful conversation, Sister Monica shares how she learned to stop listening to the world around her and finally start listening to herself. She opens up about the values exercise that changed everything, the somatic signals that told her she was on the wrong path, and why “plan A” doesn’t have to mean certainty — just courage. Together, she and Leah explore how any of us can uncover our calling, navigate fear, build self-esteem, and make meaningful changes one small step at a time.

If you’ve ever wondered whether you're on the right path — or worried that you’re not — this episode will help you reframe failure, tune into what moves your heart, and get clearer on the life you’re truly meant to live.

You can find her book ”A Change of Habit: Leaving Behind My Husband, Career, and Everything I Owned to Become a Nun” here.

If you liked this episode, you’ll also love this one: Exploring the Universe: NASA’s Michelle Thaller’s Guide to Everyday Awe
Follow Leah Smart and Sister Monica Clare on LinkedIn.

Today, we’re bringing back one of our favorite episodes of Everyday Better, where Leah walks us through one of her essential personal growth exercises: defining your core values. When you're facing a tough decision and unsure which path to take, a clearly defined set of values can equip you with the clarity and confidence you need to move forward. 

After explaining her own approach to uncovering what truly matters, Leah revisits some powerful moments from her previous conversation with personal growth educator Amanda Hilton. Together, they discuss prompts for identifying which values resonate most deeply with you and how to apply those values to make better decisions in your life.

Listen to Leah’s full conversation with Amanda Hilton here.

Download Brené Brown’s List of Values here.

Follow Leah Smart and Amanda Hilton on LinkedIn.

Have you ever been in a high-stakes conversation where you tried to communicate clearly only to have the other person talk past you? Or maybe you’ve noticed yourself zoning out when others speak because you’re doing mental math on how you’ll respond. 

When it comes to difficult or sensitive conversations, so many of our grievances could be solved with deep listening. It’s a way of listening that encourages each person to hear what’s underneath the surface level conversation. It enables people to be curious, empathetic and respectful so that they can engage more meaningfully and truly understand each other. 

Emily Kasriel, an accomplished journalist, editor and media executive formerly of the BBC, has developed a clear approach for how to listen deeply. In her conversation with Leah, Emily guides us through how to use each of the eight deep listening steps, where deep listening is most useful, and how it can help us improve all of our relationships. 

You can find her book, Deep Listening: Transform Your Relationships with Family, Friends, and Foes here. 

If you liked this episode, you’ll also love this one: Are You Abandoning Yourself to Avoid Conflict?

Follow Leah Smart and Emily Kasriel on LinkedIn.

Nicholas Thompson is a writer, a father, a CEO, and a champion long-distance runner. Nick says that running has taught him how to navigate the hardest things in life. This conversation is about running, but it’s really about what changes when we commit to doing hard things.

Running has been a part of Nick’s life since his childhood, but it wasn’t until his forties that his running career skyrocketed. Even as he took on the demanding role as CEO of The Atlantic, Nick continued to break records as an elite runner.

Together, Leah and Nick discuss the cumulative effects of discipline, why you should challenge yourself outside of work, and how developing strong habits will impact every area of your life.

You can find Nick’s new book ‘The Running Ground’ here.

If you liked this episode, check out our conversation with Michael Gervais, one of the world’s top high performance psychologists.
Follow Leah Smart and Nicholas Thompson on LinkedIn.

Before she became a TikTok star, Eli Rallo had a clear vision for what her post-grad years would look like: she’d have a fulfilling career, fabulous friends, and would finally "feel like an adult." Instead, she found herself struggling with social anxiety, a directionless career, and a nagging fear that she’d never figure it all out: enter the 'quarter-life crisis.'

Eli started sharing her unfiltered experiences online, building a community by being open about the highs and lows of her twenties. And now, in her new book of essays, she’s unpacking the lessons learned and unexpected moments of joy she discovered through embracing life’s uncertainties.

Eli and Leah sat down to explore how Gen Z is coping with “adulting” and what you can learn from the other side of a big life transition. Plus, Eli talks about the unique challenges Gen Z faces and together, they unpack how cultivating real human connection offline confronts the strains and pressures of living in a digital world.

You can find Eli’s new book ‘Does Anyone Else Feel This Way?’ here.

If you liked this episode, check out our conversation with professor Erin Cech on the problem with passion.

Follow Leah Smart and Eli Rallo on LinkedIn. 

We all want to be happier. But how do we get there? 

Former professor of the most popular course at Harvard, Tal Ben-Shahar is a world-renowned positive psychology expert and author who has dedicated his life to understanding how we can become happier, both individually and collectively. Research reveals something surprising: chasing happiness directly is the wrong strategy.

This week on Everyday Better, Tal shares the science-backed tools and mindsets that actually lead to higher overall levels of happiness. He explains how we can build sustainable motivation instead of relying on willpower and why difficult periods in our lives aren't as damaging to our well-being as we might fear.

If you liked this episode, you’ll also love this one: No Regrets Living: Designing Your Life Brief With Brand Strategist Bonnie Wan

Follow Leah Smart and Tal Ben-Shahar on LinkedIn.

We’ve all heard of “fight, flight, freeze,” but there’s a fourth survival instinct that’s harder to spot. “Fawning” can look like people-pleasing, and it’s often applauded in society. But over time, it can wear down your ability to feel safe when someone close to you feels unhappy, disappointed or upset. And it can lead to overly focusing on what other people think, instead of being in-tune with yourself. 

So how do you know when you’re fawning? Today’s guest, psychotherapist Meg Josephson suggests asking yourself, “Am I abandoning myself to keep the peace?” In her conversation with Leah, Meg explains where the fawn response comes from, how it can impact your relationships and day-to-day life, and solutions for how to deal with it in different contexts. 

Order Meg’s book Are You Mad at Me? How to Stop Focusing on What Others Think and Start Living for You here. 

Follow Leah Smart and Meg Josephson on LinkedIn. 

Oliver Burkeman is a journalist, author and former “productivity geek.” His bestselling book Four Thousand Weeks: Time Management for Mortals outlines a saner approach to managing your time in a world of never-ending demands and distractions. 

On this week’s episode of Everyday Better, Oliver explains why all of the tools and techniques meant to save us time and maximize our productivity ultimately make us feel more stressed and short on time. Oliver argues that the only time management technique that works involves recognizing that you’ll never feel on top of things. But once you accept that, you can actually start crossing things off of your to-do list—and he has strategies for how to do that as well.

If you liked this episode, check out Leah’s exercise for taking control of your calendar through “time crafting.”
Follow Leah Smart and Oliver Burkeman on LinkedIn.

In honor of Back-to-School season, throughout September, Everyday Better is sharing conversations inspired by the essential life skills we didn’t learn in school… but should have. This week on the show, Gretchen Rubin—best-selling author of The Happiness Project—lets us into one of her secrets of adulthood: how to make decisions. 

We’re all constantly making decisions, big and small. As we get older and become the “adults” in the room, we’re more often the ones who have to choose one way or another on some big life decisions.

So when the stakes feel high, how are we supposed to pick the right thing? Is there even a “right” and a “wrong?” And how do we make sure we have no regrets and make a decision that will make us happy? 

Spoiler alert: we can’t. 

But! There are things we can do to make better decisions. In this episode, Gretchen shares some of her hard-won wisdom and helpful tips on how to make decisions that are right for us. If you’ve ever wondered how all the other adults are choosing their paths, and whether or not you’re on track, this conversation is for you. 

If you liked this episode, you’ll also love this one: Case Kenny: How to Become an Optimist.

Follow Leah Smart and Gretchen Rubin on LinkedIn.

In honor of Back-to-School season, throughout September, Everyday Better is sharing conversations inspired by the essential life skills we didn’t learn in school, but should have. This week on the show, mindfulness educator Case Kenny explains how we can change our mindsets and find a more optimistic outlook.

If you watch the news, you won’t find much to be optimistic about. To realists, optimism might seem like denying reality. But in this conversation, you’ll hear why optimism isn’t about burying our heads in the sand; instead, it’s a learnable skill you can use to find more agency amidst chaos and build trust in yourself, your community, and the world.

In this week’s episode of Everyday Better, Case shares what optimism really is and how we can authentically cultivate it in ourselves. He explains why changing our mindsets starts with addressing our self-talk and how we can learn to challenge negative beliefs.

You can find Case’s new book The Opposite of Settling here.

If you liked this episode, check out our conversation with cognitive scientist Maya Shankar on navigating life’s biggest transitions.

Follow Leah Smart and Case Kenny on LinkedIn.