Megan Hellerer on Directional Living and How That Can Lead to Fulfillment in Both Work and Life

We’ve got such a fun one for you today—we’re chatting with Nora Princiotti about her new book Hit Girls: Britney, Taylor, Beyonce, and the Women Who Built Pop’s Shiniest Decade, which comes out on June 17. This book is being billed—rightfully so—as “the ultimate love letter to pop music,” and in this book Nora takes us on a deep dive into how female pop stars broke through the music industry in the 2000s and changed the game forever. Nora covers so many women in this book—Britney Spears, Christina Aguilera, Jessica Simpson, Mandy Moore, Rihanna, Taylor Swift, Beyonce, Avril Lavigne, Katy Perry—and that’s just for starters. She talks about how these women redefined the role of the pop star, not only within the music industry, but within culture, more broadly. Nora writes that “the aughts were a harrowing but magical time in music for women,” and she tells us all about why in today’s episode. Nora is a staff writer at The Ringer, where she covers culture—everything from Taylor Swift to the NFL. Speaking of the NFL, Nora was previously a reporter for The Boston Globe, where she covered the New England Patriots dynasty. Nora currently co-hosts the Every Single Album podcast, which just hosted Miley Cyrus—so covering female artists is a specialty of hers. She writes in Hit Girls that, “though the aughts were over, they certainly left a mark.” We’re going to dig into what that mark is right now.Hit Girls: Britney, Taylor, Beyonce, and the Women Who Built Pop’s Shiniest Decade by Nora Princiotti

So excited to be back with you and our guest today, Megan Hellerer, author of Directional Living: A Transformational Guide to Fulfillment in Work and Life, which came out last September 24. In this book, Megan introduces us to the concept of the underfulfilled overachiever—and I bet there are many of you listening, like myself, who will completely resonate with that term. Underfulfilled overachievers, Megan writes, have been taught the concept of destinational living—but through her book, as the title suggests, Megan is introducing a new way forward, a more fulfilling way forward: directional living. Of course, Megan talks all about what that means in today’s episode, and why this is the better way. We talk about how to begin this paradigm shift and the five phases it takes to do so; what a “fulfillment ache” is; the difference between a fear self and a true self; and so much more. Megan is a career coach and the founder of the appropriately named Coaching for Underfulfilled Overachievers. She has worked with hundreds to transform their lives by transforming their careers, and she is a Stanford graduate, a former Google executive, and sees her mission and purpose now to provide others with the support and guidance that she needed when she was struggling. She has been featured everywhere from Vogue to The Wall Street Journal, CNBC, New York, and The Times, and I’m really excited for you to meet her.Directional Living: A Transformational Guide to Fulfillment in Work and Life by Megan Hellerer

One of the most popular books of 2025 so far is Dr. Judith Joseph’s High Functioning: Overcome Your Hidden Depression and Reclaim Your Joy, which introduces us to the concept of High Functioning Depression—where you may look fine on the outside but don’t feel fine on the inside. When people think of depression, they most likely think of “can’t get out of bed” depression—but what about the lesser-known side of depression, the one that mostly stays hidden? If you are going through a time in your life where everything feels off, if you’re struggling to find joy in happy moments, if you’re walking around feeling numb, if you feel restless when you aren’t busy or empty when you’re sitting still—this book and this conversation might be for you. Today, Dr. Joseph and I talk about anhedonia—a word I had never heard of before she introduced me to it—and her five Vs, which are the crux of the book: validation, venting, values, vitals, and vision. The five Vs are our way out of High Functioning Depression, which I call HFD throughout the episode. Dr. Joseph talks about how trauma plays into HFD and so much more—it’s such a rich conversation. Dr. Joseph is a board-certified child, adolescent, and adult psychiatrist and researcher who specializes in mental health and trauma. She is the founder and chief investigator at Manhattan Behavioral Medicine, New York City’s premier clinical research site, a clinical assistant professor in child and adolescent psychiatry at NYU’s medical center, and chairwoman of the Women in Medicine Board at Columbia. She’s extremely popular on social media and holds an undergraduate degree from Duke as well as a medical doctorate and a master’s in business administration from Columbia. All of this, and the one and only Mel Robbins wrote the foreward for this book—further proof that it’s such an important read. High Functioning: Overcome Your Hidden Depression and Reclaim Your Joy by Dr. Judith Joseph

Today on the show I’m thrilled to have Sophie Gilbert, author of Girl on Girl: How Pop Culture Turned a Generation of Women Against Themselves, which came out April 29. This book looks specifically at the late 1990s and early 2000s—when both Sophie and I were coming of age—as an inflection point, when the energy of feminism collapsed and regressed into a period of hyper-objectification, sexualization, and infantilization. This book examines the era across movies, music, fashion, television, tabloid journalism, the ever-present paparazzi and more and paints a picture of a vicious attack against women in the spotlight and damaging trickle down effects for those who weren’t. Not shockingly, what happened in the early 21st century still has consequences today, and Sophie and I are digging into it. We talk about a great many things in this episode, and I want to fill you in on a bit about Sophie: she is a staff writer at The Atlantic, where she writes about books, television, and pop culture. She is the winner of the 2024 National Magazine Award for Reviews and Criticism and was a finalist for the 2022 Pulitzer Prize in Criticism. Girl on Girl follows 2023’s book of essays, On Womanhood: Bodies, Literature, Choice, and I’m excited for you to hear from her and all she has to say. Girl on Girl: How Pop Culture Turned a Generation of Women Against Themselves by Sophie Gilbert

I am thrilled to have Amina AlTai here with me today to talk about her new book The Ambition Trap: How to Stop Chasing and Start Living, which is out May 13. Here’s what I love about this book, among many things, honestly—it is billed as “the anti-hustle guide to getting what you really want,” and it delivers. If you are experiencing or have experienced burnout, overwork, and stress when it comes to your ambition, then this book is for you. This book helps us escape the ambition trap—and don’t worry, Amina tells us in this episode what that is—and step instead into joy-filled work. This is such a great book and a great conversation! She has taught me that we can be ambitious and not sacrifice ourselves in the process. Hallelujah! It turns out that maybe we’re not looking for money or status but really acceptance and belonging. I know I’ve outsourced my self-worth externally for a great many years, and spoiler alert—that doesn’t work. If you, like me, are ready to reconcile your ambition, let’s heal our core wounds and get to the other side together, escaping the ambition trap once and for all. Today Amina and I talk about why ambition is complicated, especially for historically excluded people; how ambition is not up and to the right and isn’t a linear journey; why being an ambitious woman is somehow still not acceptable, even in 2025; the difference between painful ambition and purposeful ambition; how hustle culture became so pervasive, anyway; what the resentment line is—trust me, you’ll want to know all about that; and what healthy ambition looks like and a microstep we can take even as soon as today to get there. Amina is an executive coach, leadership trainer, and chronic illness advocate that has been featured everywhere from The New York Times to NBC, CBS, Forbes, and more. She’s an expert-in-residence at Entrepreneur Magazine and was named one of Success Magazine’s Women of Influence, and she’s partnered with companies like Google, Snap, Roku, and Outdoor Voices. I not only enjoyed this conversation, but I deeply appreciated it. The Ambition Trap: How to Stop Chasing and Start Living by Amina AlTai

Once again, we don’t often have fiction picks on I’d Rather Be Reading, but usually every year I leave you with a fiction book of the summer around this time of year—and here is one for you: Hotter in the Hamptons by none other than Tinx, who is my esteemed guest today! In case you’re in the 1 percent of the population who isn’t familiar with Tinx, she is an influencer that has become known as “TikTok’s older sister” because of her advice about relationships and mental health. Her name is Christina Najjar, and her content focuses on celebrity commentary, dating advice, and so-called “starter packs for rich moms.” She attended Stanford and Parsons School of Design, and she too is a podcaster, hosting the It’s Me, Tinx podcast. She has written a nonfiction book that came out in 2023 called The Shift: Change Your Perspective, Not Yourself, which tackles topics like self-confidence, friendships, dating, and more; now she’s got a novel, Hotter in the Hamptons, coming out May 6, and it is as juicy as it gets. Tinx is already a New York Times bestselling author from her first book, and I fully expect her to become one again with Hotter in the Hamptons. There’s so much in the book that is compelling—love, sex, friendship, fashion, influencer culture, the Hamptons—it’s difficult for me to cover fiction because I just want to give it all away, but I refuse to do that. I found Tinx to be absolutely lovely; her calming, soothing voice will instantly relax you. I hope you enjoy this conversation and this book. Take a listen!Hotter in the Hamptons by Tinx

Today we are talking about a topic that will resonate with each and every one of you—waiting. Every last one of us has walked through a waiting season at some point in our lives, and I bet that most, if not all, of us are waiting on something to happen for them right now. Be it a marriage, a child, a job, a home, on and on and on, it’s not so much that life is made up of waiting seasons, but life is one big wait. The question becomes—how will we live in the wait? How can we be happy even when we’re waiting on a deeply held dream to come to pass? Today on the show we have the dynamic DawnCheré Wilkerson for a faith-filled conversation about her new book Slow Burn: The Work and Wonder of the Wait, which is out April 29. Today we talk about why humans don’t instinctively wait well; how to live well while we wait; how our waits can transform us and allow God to shape us into the people we were called to be; what her waiting has taught her; and what she’d say to someone—maybe you—in the darkest corner of their wait. DawnCheré is a speaker, singer, songwriter, author, and pastor who has also struggled with infertility, which she beautifully opens up about in the book and this conversation. Spoiler alert—they now have four children, the youngest of which was born just as this book was about to come out! DawnCheré is the wife of Pastor Rich Wilkerson, and together they’ve built a ministry, VOUS Church, that brings so many people closer to God in Miami. We talk about her faith today, and it is such a blessing to see the Lord working through DawnCheré’s powerful story. Surely the presence of the Lord is in this place, and in this episode.Slow Burn: The Work and Wonder of the Wait by DawnCheré Wilkerson

Today on the show we’re talking about the beauty of staying put, and we’re talking with Annie B. Jones, author of the new book Ordinary Time: Lessons Learned While Staying Put, which comes out April 22. Annie is a podcaster herself—her books podcast, From the Front Porch, is a huge hit—and she is the owner of The Bookshelf in Thomasville, Georgia, one of the most well-respected bookstores in the U.S. Annie writes in Ordinary Time that she had dreams of moving to New York City, but instead stayed put, planting roots in the small town of Thomasville. This book combats the notion that one has to have a “loud” life to make a difference, and argues we don’t always have to leave the lives we have to live the lives we’ve dreamed of. Annie describes herself in the book’s very first line as “someone who stays” and, as she writes, “I have not lived the adventurous life I envisioned for myself as a teenager; I have, against all odds and dreams to the contrary, chosen to stay, and in the staying, I believe there is a story to tell.” Maybe you, too, are someone who stayed—as Annie writes in Ordinary Time, among young adults, 80 percent live within 100 miles of their hometown. But it’s not just about staying put in a geographic location: it’s about staying put in a job, in a marriage, in a faith. Annie and I talk about so much in this episode, including our shared love for books; she also tells me what she’d tell the younger version of herself, and so much more. Sometimes, it turns out, staying put can bring forth a life better than you ever imagined. Annie is a writer, a podcaster, and a bookstore owner whose work has been featured in Southern Living. She lives in Thomasville with her husband Jordan and their dog, Sam Malone, and she has quite the story to tell. Ordinary Time: Lessons Learned While Staying Put by Annie B. Jones

I am delighted to have on the show today Chris Guillebeau, here to talk about his latest, Time Anxiety: The Illusion of Urgency and a Better Way to Live, which is out April 15. You may know Chris from his popular newsletter “A Year of Mental Health” or for his books, including 2010’s The Art of Non-Conformity, 2012’s The $100 Startup, 2014’s The Happiness of Pursuit, 2016’s Born for This, 2017’s Side Hustle, and 2023’s Gonzo Capitalism. In Time Anxiety, Chris examines our relationship with the clock, and in our conversation today defines time anxiety; tells us what a cognitive distortion is, including time blindness; how to cultivate a healthier relationship with time; how many of us have bought into the “magical thinking of time management”; how staying busy might be a way of staying avoidant; how our perception of time changes as we age; how a light schedule can be more psychologically challenging than a full one; and so much more. I learned so much from this book and this conversation. Take a listen!Time Anxiety: The Illusion of Urgency and a Better Way to Live by Chris Guillebeau

Whether you are decidedly a Swiftie or decidedly not, I promise you’re going to get something out of this conversation. It’s hard to believe that we’ve never, to my knowledge, spoken about Taylor Swift in her own episode in the nearly four years and 300-plus episodes of I’d Rather Be Reading, but now, she gets her due. Here today I have Kevin Evers, a senior editor at the Harvard Business Review who has written the brilliant book There’s Nothing Like This: The Strategic Genius of Taylor Swift, which comes out April 8. We look at Taylor today from many perspectives—a business perspective; a music perspective; and a personal perspective, focusing on her Eras Tour, which wrapped last year, and its impact; her fan-centric approach; and her drive, determination, and vision. Kevin and I talk about why Taylor decided to go the pop music route after her country music beginnings; what “that” moment with Kanye West at the 2009 VMAs did to her career, and to her personally; where she is most in her element—as a singer, a songwriter, and a performer; and what gives Taylor the “it” factor that has catapulted her to unparalleled levels of fame. We also talk about Taylor’s long-term strategy; her moment of backlash and how she rose up from it; and what her most strategic business decision is. We also talk about her legacy, although, at 35, her story is most definitely still being written. Here to walk us through it all is Kevin Evers, who, as previously mentioned, is a senior editor at the Harvard Business Review. He has edited bestselling and award-winning books on high performance, creativity, innovation, marketing, strategy, and digital disruption, and he has written popular articles on Hollywood blockbusters, brain science, the unpredictability of success, and the art of persuasion, among others. He is fantastic, and I can’t wait for you to hear what he has to say.There’s Nothing Like This: The Strategic Genius of Taylor Swift by Kevin Evers