Megan Gorman on U.S. Presidents, Their Personal Money Stories, and How They Built Wealth — Or Didn’t

What if I told you that, when it comes to managing your time and your life, you were never going to get it together — and that was okay? Continuing the thread from our last conversation with Kendra Adachi, today on the show we have the incomparable Oliver Burkeman, who wrote the book Meditations for Mortals: Four Weeks to Embrace Your Limitations and Make Time for What Counts, which came out October 8. Literally from the opening page of the book — page one of the introduction, which is called “The Imperfect Life” — Oliver had me hooked with the words “This is a book about how the world opens up once you realize you’re never going to sort your life out.” The hard truth? There will always be too much to do. We will never win the unwinnable battle of conquering our time. But the good news? We will be okay, and Oliver’s book teaches us how. We will, in his words, never reach the end of the trouble-free phase. Our culture has a productivity and busyness obsession, and it all comes down to grasping for control in an uncontrollable world. The book is broken up into bite size chunks — daily offerings over four weeks. Those four weeks are Week 1: Being Finite; Week 2: Taking Action; Week 3: Letting Go; and Week 4: Showing Up. Today on the show Oliver talks to us about why he decided to organize the book this way and teaches us about a concept called strategic underachievement and what he calls JOMO, which is the JOY of missing out, as opposed to FOMO, the fear of missing out. We talk about embracing “imperfectionism” and why people pleasers may struggle with this more; a major fallacy about time that Oliver thinks we’ve gotten terribly wrong; and so much more. Oliver is also the author of 2021’s Four Thousand Weeks: Time Management for Mortals, the title of which roughly represents the length of a human life. Oliver wrote the weekly column “This Column Will Change Your Life” for The Guardian from 2006 to 2020 and, in addition to Meditations for Mortals and Four Thousand Weeks, is the author of two other books, HELP!: How to Be Slightly Happier and Get a Bit More Done and The Antidote: Happiness for People Who Can’t Stand Positive Thinking. You’re going to love him. If you’re looking to be liberated from your to do list, explore a more meaningful life, and take a four week “retreat of the mind” (unless you’re like me and gobble his book up in one sitting), take a listen. Meditations for Mortals: Four Weeks to Embrace Your Limitations and Make Time for What Counts by Oliver Burkeman

I said I was going to take this month off from the show, but then, Kendra Adachi’s brilliant book The PLAN: Manage Your Time Like a Lazy Genius found me, and I couldn’t be selfish to you lovely listeners and keep it to myself. I really do believe books meet you where you are, and The PLAN certainly met me where I was (and still am). I am obsessed with time management, productivity, life hacks, life optimization — but I was shocked to learn in Kendra’s book, which came out October 8, that a full 93 percent of time management books are written by men! In today’s conversation, Kendra explains why that matters, and why we need a different voice at the table. Kendra writes in the book “The problem isn’t you” when it comes to time management, and that “It’s not your lack of dedication, consistency, or motivation. It’s not because you haven’t started the right habit or taken the right online course. It’s because the current productivity paradigm doesn’t work for women. It’s that simple. The advice you’re getting is for men by men, and women are just expected to make it work.” In today’s episode we talk about the productivity industrial complex, her method of compassionate time management, what a “Lazy Genius” is anyway, the four components of the PLAN (which is an acronym!), and perhaps most meaningful for me, how time management looks different in different seasons, and to embrace the season we’re in and what time management in this particular season looks like. There’s so much good here, and here to walk us through it all is Kendra Adachi, who is a New York Times bestselling author of The Lazy Genius Way, The Lazy Genius Kitchen, and now, The PLAN, which is a New York Times bestseller! And rightfully so. She hosts the Lazy Genius Podcast and, through her compassionate time management philosophy, believes that we should stop doing it all for the sake of doing what matters. She has a husband, three kids, and a great message.   The PLAN: Manage Your Time Like a Lazy Genius by Kendra Adachi

Election Day is on Tuesday, November 5, and I could think of no better book to tee that up than Bill Haldeman’s new book Meeting the Moment: Inspiring Presidential Leadership That Transformed America, which is out November 1. This book about presidential leadership takes a specific leadership quality of a certain president and shows readers how the combination of that quality and that president transformed America. Case in point? Bill writes that for Thomas Jefferson, his transformative leadership quality was ingenuity; for George Washington, it was his judgment; for Teddy Roosevelt, his courage and fearless, daring spirit; for Franklin D. Roosevelt, his confidence; for Ronald Reagan, his optimism. As Bill writes, when a president’s defining leadership quality met their action, America was advanced. We talk today about how presidential leadership has transformed America, as Bill writes, “it was not one leadership quality that made America stronger and better—it was many.” Bill, like me, has long been interested in the American presidency, and this is a fresh, compelling take on presidential leadership that inspired me to ask myself the question, “What is my transformative leadership quality that I might be remembered by?” Bill also talks about speeches of import and tells us about a powerful one in today’s episode, which presidents maybe didn’t meet the moment, and about the “second term curse” for presidents. I love studying the presidency and I love studying leadership, and this book combined both subject matters brilliantly. Let me introduce you to our fantastic guest today: Bill Haldeman is a veteran public servant and is the Vice Chancellor and Chief Strategy Officer at the University of Pittsburgh. He has also served the White House Domestic Policy Council, two U.S. Secretaries of State, and is a senior staff member to a state governor. I’m excited for you to hear our conversation.   Meeting the Moment: Inspiring Presidential Leadership That Transformed America by Bill Haldeman

Today on the show we have Wright Thompson here to talk about his latest book, one of the most powerful books I’ve ever read — The Barn: The Secret History of a Murder in Mississippi, which came out September 24. Though it’s not mentioned in the title or the subtitle, the book is about the brutal, absolutely depraved murder of 14-year-old Emmett Till on August 28, 1955 in Mississippi. I have a deep connection with Mississippi, as does Wright, who was born and raised there, and who grew up just 23 miles from the barn where Emmett lost his life (and where the book’s title comes from). Though Wright grew up so very close to where this atrocity took place, he never found out about this awful murder until he went to college out of state. As he writes in The Barn, the erasure of Emmett’s murder “was a collective effort, one that continues to this day.” It has been nearly 70 years since this unspeakable crime, and The Barn is an effort to reverse that erasure. William Faulkner has been quoted as saying, “To understand the world, you must first understand a place like Mississippi,” and I must admit, it’s difficult to understand this senseless murder. The two men accused of murdering Emmett, Roy Bryant and J.W. Milam, were acquitted in a mockery of justice. The four-hour torture and murder of a young man who was barely a teenager for allegedly whistling at a young white woman was depraved, even for Mississippi at the time. In today’s episode, Wright sets the scene for us of what August 1955 was like in Mississippi, especially in terms of race relations. He also tells us about that terrible night and what precipitated it and tells us more about Emmett’s brave and courageous mother, Mamie Till, who insisted that her son’s badly damaged body be on display in an open casket at his funeral after his body was returned home from Mississippi to Chicago because, in her words, she wanted to “Let the world see what I’ve seen.” Emmett’s death essentially launched the civil rights movement — for context, Rosa Parks refused to give up her seat on a Montgomery bus on December 1, 1955, just over three months after Emmett’s senseless killing. When asked why she didn’t give up her seat, she said, “I thought of Emmett Till, and I just couldn’t go back.” Just as the book is overwhelmingly powerful, so too is the fact that, as we recorded this episode, Wright was at the barn, working on a project that will eventually be announced with those who knew and loved Emmett. I got to see the barn on our Zoom call, and I’m forever moved and impacted by it. After Bryant and Milam were acquitted and therefore protected against double jeopardy, the two men admitted in a 1956 interview with Look magazine (which Wright references in this episode) that they had, indeed, tortured and murdered Emmett. To a point we later make in the episode, they both died young of cancer. Here on the show today is the incomparable Wright Thompson. He is a senior writer for ESPN.com and ESPN the Magazine, and his 2010 article “Ghosts of Mississippi” inspired the 2012 ESPN 30 for 30 documentary film The Ghosts of Ole Miss, which he narrated, about the 1962 Ole Miss football team’s perfect season and the concurrent violence and rioting over the integration of the university by James Meredith. He also narrated the ESPN 30 for 30 film Roll Tide/War Eagle. Prior to writing The Barn, Wright also published the book Pappyland: A Story of Family, Fine Bourbon, and the Things That Last, which came out in 2020. Take a listen to our conversation — and please be forewarned it contains deeply disturbing subject matter, but subject matter that is absolutely necessary to hear.   The Barn: The Secret History of a Murder in Mississippi by Wright Thompson

Today on the show we’re talking about a woman you all have long known I admire — Jacqueline Bouvier Kennedy Onassis. I have read every book I can get my hands on about this former First Lady, American (and, really, global) icon, and one of the most famous women to ever live. We have even had many episodes of the show about her in the past. But today we’re talking about the new book Our Jackie: Public Claims on a Private Life by Dr. Karen M. Dunak, which is out November 12, and instead of just looking at this remarkable woman’s life, we’re looking at this remarkable woman’s life through the lens of how she represented American womanhood more broadly. As Karen writes in the book, “Jacqueline Kennedy Onassis was a person, but she also served as a symbol of broader cultural expectations.” And what Karen found through her research here was totally fascinating. Jackie's designer Oleg Cassini called her “a powerful symbol for the United States,” and she held power as a public figure, both domestically and internationally. It goes without saying that American womanhood changed dramatically from 1960 and John F. Kennedy’s election to the presidency and 1994 and Jackie’s far too soon death. Jackie’s life is examined through her time as a campaign wife to First Lady to widow to a wife again after remarrying Aristotle Onassis to becoming a career woman and an icon. As Karen writes in the book of Jackie, “She often followed a path of her own choosing, enduring the ebbs and flows of assessments about her much as she did the transition from campaign wife to first lady and then beyond. Response to her may have reflected broader ideas about American womanhood. But she was just being herself.” This book specifically zooms in on media coverage of Jackie and how that framed her narrative, and I gobbled it up. Here on the show today we have the pleasure of hosting Dr. Karen M. Dunak, professor and Arthur G. and Eloise Barnes Cole Chair of American History in the Department of History at Muskingum University. Prior to Our Jackie, Karen was the author of As Long as We Both Shall Love: The White Wedding in Postwar America, and she is a contributor to Of the People: A History of the United States. Her research interests include post-World War II U.S. history, American women’s history, gender and sexuality, and social movements, and celebrity and media in U.S. history, and her work has appeared in many academic journals. I can’t wait for you to hear what she has to say.   Our Jackie: Public Claims on a Private Life by Dr. Karen M. Dunak

What an episode we have for you today, listeners. Today on the show we have the phenomenal Terri Cole, whose work about boundaries I have so resonated with in the past. She has a new book out on October 15 called Too Much: A Guide to Breaking the Cycle of High-Functioning Codependency, and it examines what we thought we knew about codependency. We have had the godmother of codependency, Melody Beattie, on the show, and Melody introduced the concept to the world. Now, in Too Much, Terri is taking the concept to the next level, introducing us to high-functioning codependency. In today’s conversation we define what high-functioning codependency, or HFC, is, what it looks like, some common behaviors exhibited by those who have it, and how those with HFC got to this place. You also might have heard this called “overfunctioning.” You’ll hear me say this many times throughout this episode, but I identify as a recovering HFC, and Terri writes that these behaviors are “highly programmed and largely unconscious.” Terri, too, is a recovering HFC, and writes in Too Much that “prioritizing the wants, needs, and outcomes of others over my own well-being was my default setting.” She talks about the moment she knew she couldn’t go on this way, and the book is a deeply personal one to her. We also talk about how we draw the line from being caring and a high-functioning codependent — and when we know, as the book’s title suggests, that it’s too much. By the way, when it comes to romantic relationships, codependents are attracted to narcissists, and the reverse is true, as well. The book talks about how we can prevent this deeply unhealthy combination. In our conversation today, we talk about the cost to a life if one doesn’t address their high-functioning codependency, and how the key to getting to the other side is boundaries. Now, Terri is an expert in boundaries; her book prior to Too Much, which I also highly recommend, is called Boundary Boss: The Essential Guide to Talk True, Be Seen, and (Finally) Live Free. I do think it’s important to note that reversing high-functioning codependency is absolutely possible, but it isn’t a linear path or a straight line, and that those working through this should expect setbacks. You know what? People could probably live their whole lives with high-functioning codependency, but because of Terri’s book, they won’t want to, and they don’t have to. Terri Cole, MSW, LCSW, is a licensed psychotherapist and global relationship and empowerment expert and has been doing this work for over 25 years. She is the host of a podcast I love, “The Terri Cole Show,” and inspires over 600,000 people weekly. She has a deep gift for making complex psychological concepts actionable and accessible so that clients achieve sustainable change. This conversation with Terri meant a lot to me, and I bet it will to you, too. Take a listen.   Too Much: A Guide to Breaking the Cycle of High-Functioning Codependency by Terri Cole   Check out Terri’s HFC Toolkit at terricole.com/hfc and visit hfcbook.com/ for more information!

Today on the show we are talking about Victoria’s Secret, the retail giant that, as my guests Lauren Sherman and Chantal Fernandez write in their new book Selling Sexy: Victoria’s Secret and the Unraveling of an American Icon, “defined a generation’s idea of sexy.” Selling Sexy is out October 8 and tells the story of a company that, at its peak, pulled in $8 billion in annual sales. We talk in today’s episode about Les Wexner, what Victoria’s Secret was like at its apex, its ubiquitous presence in malls, its revolutionizing of bras and underwear, its Angels, and its fashion show. We talk about how Victoria’s Secret fit into the business conversation (including a look into its business model), how Victoria’s Secret fit into the fashion conversation, and how Victoria’s Secret fit into womanhood and girlhood for a generation of women, including myself. We also talk about its downfall, from an American icon to where it is today. How is Victoria’s Secret doing today, you may ask? Well, you’ll have to listen to find out. Here to guide us through it all is Lauren Sherman, who hosts one of my favorite podcasts, “Fashion People.” Lauren has been reporting on the fashion industry for more than 15 years and is a special correspondent at Puck. Prior to that appointment, she was Business of Fashion’s chief correspondent, and before that a reporter at Forbes. You may have seen her work in The Wall Street Journal, Fast Company, Women’s Health, or The New York Times. Chantal Fernandez is a writer that covers fashion, retail, luxury, and beauty with a focus on business and culture. She is currently a features writer at New York Magazine’s The Cut, which I am completely obsessed with and read every day. She, like Lauren, is a Business of Fashion alum, where she was a former senior reporter. You may have read Chantal in The New York Times, Elle, Harper’s Bazaar, or The Financial Times, and these two women are just about as knowledgeable and impressive as it gets. I enjoyed this book and this conversation so much. Take a listen.   Selling Sexy: Victoria’s Secret and the Unraveling of an American Icon by Lauren Sherman and Chantal Fernandez

We have a legend on I’d Rather Be Reading today, friends. None other than Malcolm Gladwell is here to talk about his latest book, Revenge of the Tipping Point: Overstories, Superspreaders, and the Rise of Social Engineering, which is out October 1. Revenge of the Tipping Point comes nearly 25 years after Malcolm’s 2000 book The Tipping Point: How Little Things Can Make a Big Difference, a bestseller that took his career to the next level and ushered in a new genre of books. Today on the show we talk to Malcolm about what made him want to return to the concept of The Tipping Point and if there was unfinished business there; what a tipping point is, exactly; and how, as he writes in Revenge of the Tipping Point, “the very same tools we use to build a better world can also be used against us.” As he puts it, Revenge of the Tipping Point is a study of the underside of possibilities he explored a quarter century ago. We talk about social engineering, social epidemics, monocultures, overstories, his process, and how we can use tools necessary to control an epidemic to build a better world. So much here, and I’m excited to dig into all of it with you listeners today. Malcolm Gladwell is someone I’ve mentioned on the show before — I’ve read all of his books, and I’m a big fan. He is a journalist, author, and public speaker who has been a staff writer for The New Yorker since 1996. In addition to publishing seven New York Times bestselling books (and I have no doubt his latest, his eighth, will become a bestseller, too), he is a podcaster — his show “Revisionist History” is a must-listen. His work is in the realm of sociology and psychology, social sciences, and after the success of The Tipping Point in 2000, books like Blink, Outliers, What the Dog Saw, David and Goliath, Talking to Strangers, and The Bomber Mafia followed. His books are massive bestsellers, he’s one of the forefront thinkers of our time, and has even been named one of TIME’s 100 most influential people. Revenge of the Tipping Point marks Malcolm’s eighth book, and I’m thrilled to chat with him about it today. I also want to throw this in here for good measure — he has a cat named Biggie Smalls, so that’s absolutely amazing. Take a listen.   Revenge of the Tipping Point: Overstories, Superspreaders, and the Rise of Social Engineering by Malcolm Gladwell

We are back today with another fantastic episode, and for my 38th birthday today, I’d like to give you a gift — a conversation about a book that really touched me. We’re chatting today about Dr. Mary E. Anderson’s book The Happy High Achiever: 8 Essentials to Overcome Anxiety, Manage Stress, and Energize Yourself for Success—Without Losing Your Edge, which came out September 24. She writes that we are experiencing an epidemic of high achievers anxiety, which Mary explains in today’s episode. In the book, she writes “The bad news is that right now, you are likely not feeling your best. You may be overwhelmed and tired and frustrated by what feels like an insurmountable mountain of effort, and the truth is, if you continue on this track, you will burn out.” Sometimes achievement becomes a problem and becomes as much of an addictive behavior as maybe some of the more traditionally destructive behaviors. Mary writes of those with high achievers anxiety that they are “plagued with a feeling of inadequacy, no matter how high they soared” and I self-identify as one of these people. But Mary gives us hope, writing that “You can be happy and high achieving,” and that one can move from being an anxious high achiever to, as the book title alludes to, a happy high achiever. Today on the show we chat about Mary’s eight essentials to overcome anxiety, manage stress, and energize yourself for success, which are the roadmap to being a happy high achiever. We also talk about the “Troublesome Trifecta,” and what life as a happy high achiever looks like — and how, with this great book, we can get there. Here to guide us through it all is Dr. Mary E. Anderson, known affectionately as “Dr. A” by her clients, who is a licensed clinical psychologist and sought-after speaker with over a decade of experience helping patients become happier, healthier, and sustainably high achieving. I truly hope that you get as much out of this book and this conversation as I did. Take a listen!   The Happy High Achiever: 8 Essentials to Overcome Anxiety, Manage Stress, and Energize Yourself for Success—Without Losing Your Edge by Dr. Mary E. Anderson

I’m so pleased to have on the show today Megan Gorman, who wrote a very compelling book called All the Presidents’ Money: How the Men Who Governed America Governed Their Money, which is out September 24. Before we get into the book — which isn’t that such a great idea and such a great title? — let me tell you a little more about Megan: she is the founder and managing partner of Chequers Financial Management, a female-owned high-net-worth tax and financial planning firm. Her clientele ranges from entrepreneurs to corporate executives to inheritors of family wealth. She is an attorney by training and is passionate about the problem solving required to work in the world of complex financial planning. She has been named to Forbes’ list of America’s Top Women Wealth Advisors and was a vice president at Ayco, a Goldman Sachs company, and BNY Mellon Wealth Management prior to launching her own firm. Megan is a senior contributor at Forbes, where she writes about personal finance and income tax, and she is frequently cited across prominent financial media outlets, including The Wall Street Journal, The Washington Post, and CNBC. She has now written the brilliant All the Presidents’ Money: How the Men Who Governed America Governed Their Money, where she dives deep into the personal finances of the presidents. As she writes, “most of their money problems are just like ours.” In the book, Megan teaches readers what president is the best at money (and he may surprise you!), and who is worst with money. Interestingly, Megan writes that, when it comes to solid financial advice, “if you ever asked me what is the best thing you could do financially, my answer would be quite succinct: get married and stay married.” We talk about First Ladies, too, and about financial advice for the presidents and for us; Megan writes about financial fragility and financial resilience, and how “In many of the presidents’ stories, financial fragility is a common theme.” We talk about what grit has to do with wealth, how the American dream is still there but much harder to attain in present times, and so much more. Studying the U.S. presidents and their personal money stories and how they built wealth — or didn’t — is incredibly fascinating. Take a listen.   All the Presidents’ Money: How the Men Who Governed America Governed Their Money by Megan Gorman