Permission with Dr. Sherry Walling

Britt is the co-founder of Dow Janes, a financial education company that started in her living room and has since taught more than twenty thousand women. We get into the night in the bottom bunk when she was six, convinced the family was about to run out of money, and handed her dad her entire piggy bank. The shame cycle that keeps smart people stuck in debt, and why she insists you’re not bad with money, you just were never taught it. Why money is power inside a relationship, and what happens to the partner who stays out of the numbers. And her own definition of rich, which turned out to be friends within walking distance, a house manager named Meg, and a backyard sauna she’s building for the whole neighborhood instead of putting the money into crypto. It’s an episode about giving yourself permission to be good at money, to want more of it, and to decide for yourself what rich actually means. Learn more about Dow Janes at dowjanes.com

At the top of his career, seven or eight companies in, seven figures, an Aston Martin with “Secret Agent Yanik Silver” stamped on the door sill, Yanik Silver asked his journal a plain question. Am I happy, and would I be happy doing this in ten years? The honest answer was no. Yanik is the founder of Maverick1000, a global collective of entrepreneurs, and the author of Evolved Enterprise and the Cosmic Journal. We get into what came next: selling the Aston Martin (but keeping his ticket to space), driving a beat-up family SUV until he felt real gratitude for it, and sinking four hundred thousand dollars into a new venture before it became anything. The 108 straight days of making art at two in the morning that became a book he never planned to publish. And why, after all of it, he still hesitates to call himself an artist. It’s an episode about the inner voice Yanik calls the cosmic alarm clock, the one you can keep hitting snooze on, and what happens when you finally answer it. Yanik runs Maverick1000 (maverick1000.com) and created the Cosmic Journal (cosmicjournal.com).

A note before you listen: this conversation is about suicide and the loss of a spouse. If you' or someone you know is struggling, the 988 Suicide & Crisis Lifeline is available in the US by call or text at 988. When Kim Witczak's husband died, the official story didn't add up, and she refused to accept it. That refusal turned a grieving thirty-seven-year-old who had never thought her voice mattered into a drug-safety advocate who took on the FDA and helped change the warning label on every antidepressant in the country. Kim is a globally recognized drug-safety advocate, speaker, and former FDA Consumer Representative. Woody died by suicide five weeks into an antidepressant he'd been given for insomnia, a risk that was known and had never been disclosed to him. We get into what it actually takes to fight a system when everyone tells you to sit down, the scripts she had to put down first ("someone competent is in charge," "no one is coming to save me"), "borrowed hope" and how she held onto it in the days she couldn't feel any of her own, and the line she borrowed from Woody that still drives her: "I'd rather try like hell and lose." Sherry, who lost her own brother to suicide, meets her on shared ground. It's an episode about giving yourself permission to fight, for the truth, for your own voice, and for a life worth living after the one you planned falls apart. Kim is on Instagram (@kimwitczak), LinkedIn, and Substack, and her book The Cost of Trust is out later this year.

Derek Coburn thinks we're in a fun recession. His words: 99% of adults aren't having anywhere near the amount of fun they should be. Derek is the founder of Cadre, a community for entrepreneurs, and the author of Networking Is Not Working and Let's Retire Retirement. We get into the research that stopped him cold (the time we spend with friends collapses from about 150 minutes a day as teenagers to almost nothing by our thirties), a term he loves called "collective effervescence" and why he goes to twenty-five concerts a year, how a busy middle-aged adult actually makes new friends when the kids' bus stop is no longer doing it for you, and the money reframe underneath his book: if you're going to work longer than you planned, you can stop over-saving and spend more time and money on the people and the fun that matter now, instead of deferring all of it twenty years. It's an episode about giving yourself permission to have more fun now, not someday. Derek's community is at cadredc.com, and his book Let's Retire Retirement is at derekcoburn.com.

I've been married to Rob Walling for almost 24 years, so I went into this one already knowing the plot. Rob was raised to follow the rules, with a whole career mapped out as an executive at his family's electrical construction company. Then he got into the management training program, realized he was miserable, and walked away with no connections and no plan except that he liked writing code. Rob is the founder of Drip, co-founder of TinySeed, and the host of Startups for the Rest of Us. We get into the years he built on nights and weekends before he'd let himself quit the day job, the tattoo he got of a hand drawing a map, and the arrival fallacy that left him restless three months after getting everything he'd worked for. He makes the case that the buck stops with the founder, which means you're allowed to do far more than you think. Mostly, it's an episode about giving yourself permission to make bold, imperfect decisions and act before you feel ready. Rob writes at robwalling.com and hosts Startups for the Rest of Us.