Episode 408: 5 Traits Entrepreneurs Share with Artists

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.

Mia Sundstrom is a CEO who swims in the middle of the workday, on purpose, and can tell you exactly why she gets that hour back. She runs the National Institute for Play, she's a lifelong gymnast, and she's on a mission to reach ten million people with play by 2030.We get into play as both a state (the thing you're doing) and a trait (the way you show up), the neuroscience that play lives in the oldest part of the brain and is something we're born knowing how to do, and the six play styles (I took the quiz and came out mover and explorer.)We talk about why play is productive, from the $10 trillion cost of disengagement to the fact that nobody's best idea has ever arrived while staring at a monitor, and how to tell real play from the scrolling that only looks like it. Mia's grandfather, the psychiatrist Stuart Brown, built this field after noticing that people who commit serious violence tend to be starved of play, and she carries that work forward.It's an episode about giving yourself permission to play, and the science that says you'll get the time back. Take the Play Styles assessment and discover your unique play spark (https://playstyles.nifplay.org/). Stay up to date with the latest play science information by subscribing to their Substack @NIFPlay. And check The Live Playfully Journal: 90-days of reflection and practice to a more playful, joyful you.

Jason Cohen has founded two unicorn companies, WP Engine and Smart Bear, and written at asmartbear.com for almost twenty years. His new book, Hidden Multipliers, opens with a founder lying awake at 4 a.m. feeling like a fraud — which tells you it isn't a normal growth-tactics book, and this isn't a normal growth-tactics conversation. We get into why the people who love your work often love it for the things you'd call weaknesses, why Jason would rather have fewer followers who actually care than ten times the audience and a version of himself he'd have to fake, the three-word question he keeps on his daily note to save himself in meetings (does this need to be said, by me, right now), and the night a board member named the real reason he didn't want to step down as CEO: "You want the credit." Underneath all of it: build a company, and a life, in the shape of you. Jason writes at asmartbear.com. His new book, Hidden Multipliers, is at hiddenmultipliers.com. New here? Welcome. And if you've been with me since the ZenFounder days, you're in the right place — the whole back catalog is still here. Follow Permission wherever you listen.

After more than a decade and a few hundred episodes, ZenFounder is becoming Permission. I'm Dr. Sherry Walling — clinical psychologist, and the voice you've been listening to all along — and this is the next chapter of the show we've built together. Somewhere along the way, most of us started waiting for permission: to rest, to change our minds, to want a different life than the one we built. Permission is a podcast for people who've done the hard thing — built the company, hit the number, raised the kids — and found themselves wondering what it was all for. Each week I sit down with founders, entrepreneurs, scientists, artists, and creatives, and we go where most business shows won't. Some weeks it's permission to admit you got everything you wanted and you're still not happy. Some weeks it's permission to be led by pleasure instead of productivity, or to stop earning your worth and simply have it. And every single episode ends the same way — with a permission slip: one thing you didn't know you were allowed to do. If you've been here since the ZenFounder days: thank you. You've sat with me through hundreds of conversations, and I don't take that for granted. This is the version of the show I've been growing toward for years, and I think it's about to get really good. I can't wait for you to hear it. If you're new: welcome. This is a good place to land.

In this intimate conversation, Dr. Sherry Walling explores our relationship with fear and why it is not something to override or dismiss. Drawing from both psychology and her experience as a circus aerialist, Dr. Sherry explains how fear functions as a warning system in the body signaling potential danger, asking us to slow down, and inviting attention.  Rather than treating fear as a weakness or obstacle, this conversation reframes fear as information, a signal worth listening to.  This episode is an invitation to develop a more mature relationship with fear, one that allows it to inform decisions, clarify priorities, and protect what matters most, without letting it run the show. What You’ll Learn in This Episode: Why fear is often misunderstood as weakness instead of wisdom The difference between listening to fear and letting fear run the show Why emotional fears (shame, failure, rejection) deserve attention, not avoidance The role of fear in helping us prioritise what truly matters #ZenFounderPodcast #DrSherryWalling #FearAsInformation #NervousSystemWisdom #EntrepreneurMentalHealth #EmbodiedLeadership #Presence

Entrepreneurs are great at leading teams, making decisions, and optimizing time. But what happens when those same skills show up at home—and start to hurt your closest relationships? In this episode, Dr. Walling shares the 4 entrepreneurial mindsets that often cause trouble at home—and what you can do differently. Self-importance around time – why treating family moments as “below you” creates distance. Productivity over presence – how chasing efficiency can crowd out play. Reviewing family members like employees – why constant appraisal kills safety and connection. Expecting instant implementation – what happens when you “CEO” at home. And last, the best lessons you can actually learn from family life — lessons that will make you a stronger, more human leader.

Entrepreneurs are keen to push themselves to grow and become the best version of themselves. As early adopters, they’re often open to immersive experiences that accelerate their personal and professional development. But when it comes to non-ordinary state experiences like psychedelics, deep retreats, even personal breakthroughs, too many skip the most essential part: integration. In this episode, Dr. Sherry Walling breaks down exactly what it means to integrate a transformative experience into your daily life. Whether you're navigating a psychedelic journey or simply returning from an immersive retreat, this conversation offers practical tips for slowing down, listening in, and making your growth real. You'll learn: How to decipher the kinds of “messages” you receive during a journey How to build a 4-month plan around new values, habits, or intentions Why busyness is the enemy of growth—and how to build in space for listening Subscribe to Sherry’s newsletter: tinyurl.com/ZenFounder

Is Entrepreneurship a Creative Act? In this episode, Dr. Sherry Walling shares what producing a full-scale circus show taught her about the creative process of entrepreneurship. From the vulnerability of putting your work in public to the emotional risk of innovation, Sherry explores how the mindset of an artist can unlock better products, deeper audience connection, and long-term fulfillment as a founder. #Entrepreneurship #CreativeLeadership #MentalHealth #Startups #Founders  #Vulnerability #CreatorEconomy

Did you know that 27% of Americans are actively estranged from at least one family member?In a world where ideological division is high and screens are the most consistent recipient of our attention, our families are quietly fracturing. In this special episode, clinical psychologist Dr. Sherry Walling reflects on the beautiful, painful, complicated terrain of family life.  Inside this episode: – Why family can be our deepest source of pain—and our greatest opportunity for healing – The psychological dynamics of individuation, estrangement, and reconciliation – A radical practice for staying close: becoming a neutral observer Whether you're in the thick of parenting, navigating loss, or redefining what family means to you, this episode is an invitation to reflect, feel, and begin again. Learn more about the Familia circus show: https://www.touchingtwoworlds.com/familiaRead the book: https://www.touchingtwoworlds.com/free-chapters Get support o...