What if the person who always makes things sound fun is actually doing the hardest work of all?

What does it cost to be the bridge that connects people to their next true thing—knowing you might get walked on, knowing they might never come back, knowing you have to keep showing up anyway?

Annie F. Downs has built a New York Times bestselling writing career, launched an award-winning podcast, and created a network that reaches millions. But beneath the joy she's known for is a woman who's learning to hold grief in one hand and hope in the other—and not let go of either.

As an Enneagram 7, Annie's wired to chase joy and avoid pain, to keep moving, to make everything sound fun. But life doesn't work that way. And in this conversation, she opens up about what happens when the fun runs out and you're left sitting in the hard stuff alone.

Annie reveals the true cost of being a "trusted bridge"—a person who connects others to what matters most, even when it means they'll walk right past you to get there. She shares about the loneliness that comes with public life, the parts people don't see: grieving alone, making impossible decisions, carrying financial weight, and the exhausting work of showing up when you'd rather disappear. She talks about losing someone who believed in her, about learning to sit in grief rather than run from it, and about why she's planning to shut down her entire company for the summer of 2027—a radical sabbatical practice inspired by biblical wisdom about letting fields rest.

This is a conversation about what it means to make joy and grief roommates, to trust your calling when it gets hard, and to keep showing up as yourself even when yourself isn't always fun.

In this conversation, you'll learn:

• How to Be a Bridge Without Getting Walked All Over
• How Your Enneagram Type Shapes Your Relationship with Pain
• How to Hold Joy and Grief in the Same Moment
• How to Lead a Public Life Without Losing Your Private Self
• How to Know Your Calling When Everything Feels Hard
• How to Rest From What You've Done and Toward What You're Building
• How to Build Community When You're Deeply Lonely
• How to Sit in Grief Instead of Running From It
• How to Make Peace With What You Can't Control
• How to Trust Your Voice Even When People Walk Right Past You
• How to Practice Sabbath in a World That Never Stops
• How to Build Things That Don't Exist Yet
• How to Be "Both/And" in an "Either/Or" World
• How to Keep Going When Your Why Gets Heavy

Welcome to Human School, where we learn what matters most.

- Miles Adcox

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What We Discuss:

00:00:00 - Intro: Welcome to Human School

00:01:29 - Why Annie Calls Herself a "Trusted Bridge"

00:05:30 - The Parts of Public Life People Don't See

00:09:42 - How Enneagram 7s Avoid Pain by Chasing Joy

00:12:15 - When the Fun Person Has to Sit in Grief

00:17:28 - Learning to Hold Joy and Grief at the Same Time

00:24:56 - When Community Feels Far Away Even When You're Surrounded

00:36:55 - When Your Mission Means Losing Your Audience

00:46:09 - Making Peace With What You Can't Control

00:53:42 - Planning a Full Summer Sabbatical in 2027

01:12:29 - Breaking Into New Areas of Media

01:28:34 - Making Faith Attractive and Invitational Instead of Activating

01:36:06 - Final Thoughts: We're Going to Make It