What happens in the gap between updating your LinkedIn title and actually knowing how to do the job? Caitlin sits down with Deborah Caulet—leadership coach, former VP of People at Blinkist, and someone who's spent 15 years helping leaders figure out what they're doing (and why they feel like they aren't doing it right!). Deb works with first-time managers and founders at growing startups, coaching them through the messy, humbling transition from high-performing individual contributor to someone ...
May 18, 2026•52 min
What happens in the gap between updating your LinkedIn title and actually knowing how to do the job? Caitlin sits down with Deborah Caulet—leadership coach, former VP of People at Blinkist, and someone who's spent 15 years helping leaders figure out what they're doing (and why they feel like they aren't doing it right!). Deb works with first-time managers and founders at growing startups, coaching them through the messy, humbling transition from high-performing individual contributor to someone ...
May 18, 2026•51 min•Ep. 109
What if the part of you that knows what's actually wrong isn't your brain? This week on Simplify, Caitlin sits down with Dr. Arielle Schwartz—clinical psychologist, somatic therapy expert, and author of more books than seems reasonable for one person—to talk about what your body has been trying to tell you for years. Arielle has been working in somatics for thirty years, long before TikTok turned it into a buzzword, and her gift is making something that can feel slippery and slightly woo-woo fee...
May 04, 2026•47 min
What if the part of you that knows what's actually wrong isn't your brain? This week on Simplify, Caitlin sits down with Dr. Arielle Schwartz —clinical psychologist, somatic therapy expert, and author of more books than seems reasonable for one person—to talk about what your body has been trying to tell you for years. Arielle has been working in somatics for thirty years, long before TikTok turned it into a buzzword, and her gift is making something that can feel slippery and slightly woo-woo fe...
May 04, 2026•47 min•Ep. 108
Episode Notes What if the stories running your life aren't really yours? This week on Simplify, Caitlin talks with Angela Natividad: a mythologist, writer, and advertising veteran—a trifecta that turns out to be the perfect preparation for the argument she makes in her book Remember His Name: Unmasking the Faceless God of the West. That argument, put simply: capitalism isn't an economic system. It's a religious one. We get into what that actually means—the hidden god at the center of it all, the...
Apr 20, 2026•54 min
A loss isn't always a loss—sometimes, it's one of many stepping stones towards winning big. When you change how you think about what succeeding looks like, the long game of changing the systems we live in seems infinitely more doable. This week on Simplify, Caitlin speaks with international human rights lawyer and author Nani Jansen Reventlow about her book Radical Justice—and about what real, systemic change actually looks like from the inside. Nani founded two nonprofits, the Digital Freedom F...
Apr 13, 2026•42 min
Most of us have gotten up on a Monday morning and thought: I simply cannot do this today. Our job is grinding us down in that slow, invisible way that work does when we're not managing it well. Psychotherapist, author, and podcast host Guy Winch has spent his career sitting with people who have experienced this for a passel of reasons from sabotaging coworkers to unrealistic goals. His new book Mind Over Grind is a practical, science-backed guide to surviving your job—even when it really, truly ...
Mar 26, 2026•56 min
What if getting back at someone isn't as satisfying as we think—and what we're really trying to avoid is grief? This week on Simplify, Caitlin speaks with psychotherapist, teacher, and author David Richo about his book Sweeter Than Revenge, which makes the case that there's a better way to respond when people hurt us than the one our brains (and basically every movie ever made) are wired for. Dave has spent decades sitting with people in their messiest, most wounded moments. What he's found is t...
Mar 09, 2026•39 min
Most of us have no idea what it means to repair harm, not just apologize for it. We also regard rage as frightening and out of place in loving, connected relationships. It takes a special person to demystify these staticky aspects of human relating—and we found her. This week on Simplify, Caitlin speaks with relational skills teacher Christabel Mintah-Galloway about repair: why it’s so difficult, why most of us avoid it, and why real accountability requires more than just good intentions. In a c...
Feb 24, 2026•48 min
What if the United States wasn’t just influenced by cult-like thinking, but shaped by it from the very beginning? This week on Simplify, Caitlin Schiller speaks with journalist and author Jane Borden, whose book Cults Like Us: Why Doomsday Thinking Drives America explores how cult dynamics show up across U.S. history, politics, consumer culture, and self-help. From Puritan theology to superhero movies, Borden argues that cults aren’t fringe phenomena—they’re extreme versions of patterns baked so...
Feb 09, 2026•53 min
Strategy. It can sound abstract, intimidating, and vaguely corporate. So who better to help demystify it than Seth Godin? Seth returns to Simplify to talk about his book This Is Strategy, and to reframe strategy not as a rigid plan or a set of tactics, but as a philosophy of becoming. In this conversation, Caitlin Schiller and Seth Godin explore what strategy really is, why tension is not only inevitable but necessary, and how pricing, trust, and generosity fit into long-term thinking about work...
Feb 03, 2026•41 min
Simplify is back! When you leave the doctor with a protocol for what ails you, do you wonder where the knowledge behind your prescription came from? In fact, we know how to treat today's woes thanks to the bodies of people who suffered—and nowhere is that data more inexact and editorialized than in women's health. Feminist cultural historian Dr. Elinor Cleghorn, who specializes in women’s health and its history, is just the person to set the story straight. Her book, Unwell Women, demystifies my...
Jan 12, 2026•54 min
Today, our guest is an award-winning beauty reporter and critic whom you might have stumbled upon while reading her super popular newsletter, The Unpublishable, which, as HuffPost says, "basically gives the middle finger to the entire beauty industry." Writing about what the beauty industry won’t tell you, Jessica DeFino has built an identity as a reporter on a mission to reform it. It all started, however, in a place as opposite as it could be: a few years back, Jessica was a product-obsessed e...
Mar 28, 2024•37 min
This week's episode of Simplify brings you a special collaboration: a conversation with Dhiraj Mukherjee, who is not only the entrepreneur behind Shazam (the app we all love and use so much!), but also a devoted impact investor focused on social good. Drawing from his experience at Shazam, Dhiraj learned firsthand that the best way to predict the future is to create it. That’s why today, his work mostly focuses on investing in mission-driven companies aiming to create a better future for the pla...
Mar 06, 2024•41 min
Although we're at the tail end of 2024's symbolic new beginning, we're still confronted with the flood of discounted "detoxes," "cleanses," gym promotions touting a "New Year, new you," and the latest buzzword, "resets." Despite our desire to think that fad diets are relics of the past and that we have collectively moved away from diet culture, we may instead have fallen for a wolf in sheep's clothing. Drawing from her personal narrative and investigative reporting experiences, Cole Kazdin, an E...
Feb 21, 2024•38 min
Today, we bring you Simplify's first ever crossover episode with the #1 Technology show on Apple Podcasts and Spotify: Acquired! For nearly 9 years David Rosenthal—today's guest—and his co-host Ben have been sharing the strategies and history of 200+ of the world's most successful businesses. From Sequoia to Sony, through to TSMC, Amazon, The New York Times, the NBA and Oprah, Acquired's hosts go deep—sometimes 3 hours deep!—into the details of each business's ups and downs. In this episode of S...
Feb 08, 2024•55 min
In 1971, Joni Mitchell released Blue, an album teeming with stories of a life shaped by romance, desire, longing, and the default path of sharing life with another person. The ideal might persist to this day, but what happens if the romance we are told will give life meaning... never shows up? How gorgeous and fulfilling can we make our lives, sans romantic partner? Amy Key, the celebrated British essayist and poet, sets out to explore exactly these questions in her memoir, Arrangements in Blue,...
Jan 25, 2024•33 min
We might say that “age is just a number,” but if we're really honest with ourselves, a lot of us still think of “old” people as stubborn hoarders who eat dinner (too) early and are forever talking about their aches and pains. Why is that? And could there be another way? These questions prompted Steven Petrow, an award-winning journalist and author to begin compiling a list of things he won’t do when he gets old shortly after his 50th birthday. The list, which included “You won’t have to shout at...
Jan 22, 2024•26 min
What do people mean when they say, 'I'm a perfectionist'? The colloquial and widespread opinion would sound like this: A perfectionist is someone who desires everything to be perfect at all times and becomes upset when things aren't perfect. This definition is often followed by the (generic) advice that the best way for them to set themselves free is to get rid of their perfectionism. According to Katherine Morgan Schafler, a psychotherapist and a former on-site therapist at Google, this is not ...
Dec 15, 2023•36 min
When we experience a traumatic event or decide to pursue healing, what often follows is the tendency to isolate and hide from the world. Shame, exclusion, and the feeling that no one understands remain intertwined with the term "healing." However, this can and should be different—and that 's the message licensed social worker and therapist Minaa B. is here to spread. "Owning Our Struggles," Minaa’s first book, as well as her work in general, stands out for its unique approach and strong emphasis...
Nov 30, 2023•36 min
In the post-pandemic era, the debate over whether or not to return to the office seems far from settled — and yet, the push to bring employees back to the office is growing more aggressive. Amazon issued a warning to staff not long ago. Google is factoring employees’ in-office attendance into their performance reviews. And ironically, working from home has been officially replaced by a return to the office by Zoom. So is returning to the old structured schedule really the best way to optimize ou...
Oct 27, 2023•37 min
Our obsession with beauty and appearance may be deeply rooted, but at this moment, things seem to be reaching a whole new level. Facetune and features like skin smoothing, jaw reduction, and eye enhancement that are standard on social apps like Snapchat, TikTok, and even Zoom, as well as the ubiquitous advertisements for a flawless face and body, are turning our bodies into projects to work on forever. This and much more prompted American journalist and podcaster Elise Hu to research and write h...
Oct 12, 2023•33 min
You were probably hired for your expertise in a certain domain: engineering, product management, paid marketing, or something else. But to be successful in an organization, there are other, secret skills outside your domain that nobody really teaches you—things like effectively communicating your ideas, assessing the business environment, collaborating with leadership, or deciding to leave your current role (and what to say when you do!). To fill in these gaps and create your own stability in a ...
Sep 21, 2023•31 min
The systems we live in suggest that a successful human life depends on denying pain, endless hustle, stress, and sustaining trauma—and making it all look easy. The only problem is that human nature objects. Psychological and physical suffering seem to be increasing while illness and trauma continue to define how we live. But, what's in it for our culture? Why and how do we breed disease—and why do we call that normal? Educator, mental chiropractor, musical theater pro, and co-author of The Myth ...
Sep 07, 2023•42 min
It's a rarely questioned societal norm: feeling bad/mad/disappointed/scared/anxious? A substance (like alcohol) will give you the courage to face it. This is even more true for dating and sex, where we use alcohol as our first line of defense to find the liquid courage to open up to someone. But what happens when we step away, get sober curious, or simply start being more mindful with alcohol? Who might we be? And who might we connect with? In this episode, Tawny Lara, author and speaker, also k...
Aug 24, 2023•42 min
So, what does it take to make the best working relationships? The same ingredients in any relationship, really: a big helping of bravery and the will to dig into deep conversations.There's more to it than that of course, and on this episode, Simplify favorite Michael Bungay Stanier takes Caitlin through it. This is a gentle-but-probing conversation in which you'll learn about the sweet spot between safety and bravery, how to make your colleagueships safer and more vital, and what psychological b...
Aug 11, 2023•41 min
We are delighted to present a conversation with Stephanie Chandler, founder and CEO of the Nonfiction Authors Association and a successful author of several books, including The Nonfiction Book Publishing Plan and The Nonfiction Book Marketing Plan. In this episode, Stephanie shares her remarkable insights into all phases of the book-writing process and offers a sharp view of the publishing industry. By exploring assets and liabilities of traditional publishing and self-publishing, we dive deepe...
Jul 27, 2023•37 min
We're delighted to present a conversation with Natalie Lue, author of the wildly popular blog Baggage Reclaim (baggagereclaim.com) and five books, including the latest, "The Joy of Saying No," that will help you not only identify your people-pleasing style and habits, but also finally leave them behind. In this episode, Natalie shares her unmatched insights on the importance of boundaries and saying no, and the destructive effects a lack of them can have on your body and mind. By exploring the f...
Jul 14, 2023•41 min
We're thrilled to present a dynamic conversation with Robert Glazer, bestselling author and transformative leadership expert. With deep insights drawn from his revolutionary book, 'Elevate Your Team', Glazer demystifies the four capacities essential to extraordinary team performance. In this episode Glazer shares his unique take on the 'work smarter, not harder' philosophy, offering fresh perspectives to drive both personal and professional development. We challenge common preconceptions around ...
Jun 30, 2023•38 min
Have you ever listened back to a recording of your voice and cringed at the amount of 'um's' 'uh's' and 'like's' you use? In this episode, Valerie Fridland, linguist, researcher, and author of the book, 'Like, Literally, Dude' delves into the intricacies of speech habits and argues for the inherent value of these often-demonised words. We explore why women are linguistic trend-setters, why some words carry deep-seated prejudices and what can we learn from the social function of language. You can...
Jun 30, 2023•37 min
