Living Dangerously

June 3, 2025

There’s a scene in Gossip Girl, a show I greatly enjoyed while living in New York City during and after law school as a mental break from all that law—and which made me, in its portrayal of the emotional and relational challenges of my city’s super wealthy, grateful for my ordinary life, and in full disclosure, a show which I’m enjoying again years later, watching through a second time, distractedly, in five minute intervals while kneading dough, still a mental break, from all that laundry, and dishes, and yes, sometimes still law—

there’s a scene where the humble Brooklyn kid, Dan, half broken into the Manhattan elite crowd by virtue of his private school attendance, but ever the outsider, discusses his short stories with his advisor, a famous writer. All boring, the advisor declares. Iterations of the same thing on repeat. Brooklyn kid obsessing over a girl.

“But aren’t I supposed to write what I know?” Dan asks.

The advisor considers this and replies with an anecdote about his younger days as a writer: Charles Bukowski blowing a glass of whiskey off the advisor’s head with a pistol. “When your writing is too safe,” he advises, “do something dangerous.”

So Dan pursues what he thinks is a door to a life of glamorous danger, the good life that will equip him to write the kinds of stories that can assure his success. He goes out with the show’s bad boy for a night, taking drugs and narrating incessantly. He’s ultimately deposited on a rainy sidewalk, alone, with no shoes. “Shoeless and clueless,” as the narrator puts it. So this is what it looks like to have an adventure for the sake of art?

But his next story is still junk. Dan has changed boroughs, but he took his same self to Manhattan. His perspective, his vision, never shifted. Perhaps looking for something exciting out there failed to give him a a good story, because nothing changed in here.

But there was plenty of danger he could have embraced right where he was.

What about taking a risk to stop projecting so much judgment at your on and off again gorgeous girlfriend as a self-protection mechanism, derailing your relationship drama of Greek theater proportions?

Or the risk of being curious about learning what it’s really like to be your younger sister, spurned by the private school queens?

Or the risk of being honest with your aging rock star dad for whom it is clearly not the first rodeo, and who clearly cares and is ready to listen, instead of bunkering down and thinking you can fix everything alone?

What if you had stayed in Brooklyn, but chosen to see it differently, to see people around you differently, to bring a sense of wonder to your ordinary life instead of grasping for a fictional, romanticized world?

There are countless opportunities to live dangerously within the confines of ordinary events and relationships. Danger I regularly see my kids encounter, and still feel as an adult. There is danger every time you try, risk, face things beyond your control, are vulnerable. Live examples from the last week in our family life:

• It can be dangerous to tell someone the way they talk to you hurts your feelings
• It can be dangerous to invite a friend to play when last time she said no
• It can be dangerous to make a phone call you’re dreading, knowing you may not have all the answers even though you’ve done your best to prepare
• It can be dangerous to share something you’ve created
• It can be dangerous to venture into a new place

I bet you can think of some of your own. Living dangerously is a way of life for anyone who is willing to embrace the routine challenges of not staying safely stuck. Of being who they really are while staying connected to people who are different. In other words, endless possibility.

Dan, you had all the source material you needed right in front of you. But enamored with rich Manhattanites and an anecdote about a pistol, you remain blind to the potential. You just weren’t paying attention.

This persistent belief that we need something else, and the radical counter practice of finding what matters most in what we already have, is why I’m hosting storytelling workshops + a fall party to help us practice seeing our ordinary lives anew, no pistols required. The first one is a week from tomorrow, and there’s still one or two spots left. Maybe one of them is yours? Not too late to sign up!