Permission with Dr. Sherry Walling

Episode 403: Feeling Alone in Business? How to Find Your People

Permission with Dr. Sherry Walling

Show Notes

Entrepreneurship is lonely—but it doesn’t have to be. In this video, Dr. Sherry Walling dives into one of the most overlooked challenges in the entrepreneurial journey: finding your people. Starting, growing, and even exiting a business can be incredibly isolating. That loneliness can quietly erode both your mental health and your ability to lead. In this episode, you'll learn:

The difference between networking and true friendship Why proximity, attention, and shared play are essential to adult friendships How relationships are foundational to both mental health and business success

Whether you’re craving deeper connections, wondering why your friendships feel thin, or simply looking to feel less alone in your work—this one’s for you. Learn more about Sherry’s upcoming Touching Two Worlds: Familia circus show—an original performance about the power of relationships: www.touchingtwoworlds.com/upcoming-shows

More from Permission with Dr. Sherry Walling

Oct 20, 2026

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.

Oct 13, 2026

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.

Oct 6, 2026

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.

Oct 6, 2026

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.

Sep 29, 2026

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.

See all episodes →