✍️ Friday, July 1
I’m hiding in the bathroom at a Fourth of July barbecue at sunset on the Upper West Side. Everyone else is in the backyard, milling about as people do. Tomorrow, I leave for a week of family vacation. I said yes to my mom’s invite in May as a magical thinking Hail Mary.
Maybe if I get out of New York City to spend time with people I love, I will have a nonlinear breakthrough—a paradigm shift revealing how to dig my business out of this anxiety hole.
When I booked my flights, I hadn’t gotten The News from The (Former) Client yet. I just couldn’t take the mounting dread any longer around whether they would renew or not without doing something—anything.
Now, at the barbecue, I’m finding it hard to focus on making conversation.
I got The News three weeks ago, and desperately need a new sign. What’s next? Where do I go from here? Someone should write a book on that 😭
I have already eaten three star-shaped holiday cookies—each of the red, white, and blue sprinkles (one must know if they all taste different), and poured myself a second glass of sparkling rosé.
My small talk allergy started flaring up, as I repeatedly tried and failed to find conversational threads that could lead toward more engaging big talk.
It wasn’t their fault, it was mine—these were wonderful people.
I know that everyone is interesting, and that in social settings it is my job to ensure that’s the case, yadda yadda. If I’m bored (look in the mirror!), I must be the boring one. As the saying goes, “When you point the finger, there are three more pointing back at you.”
Speaking of mirrors . . .
I back away slowly, excusing myself to the bathroom so I can ponder my conversational failures in peace.
It had been a long week. I was exhausted. I probably shouldn’t have left the house, but this was for Michael and hosted by his friends. It seemed like I should for him; after all, I was leaving for eight days the next morning. Relationships, etc.
I sigh in deep relief as soon as I enter, settling into my little paradise within the party, lights off like a cocoon. There it is, that sweet sound of silence. Oxygen.
Thank goodness I can stop trying for a moment.
Trying what? You ask. What kind of grinch can’t enjoy a friendly neighborhood barbecue?
Trying to be friendly when all I really want to do is collapse on the couch.
Years ago, I remember optimistically heading out on a chilly Tuesday night to a book launch party at the swanky Crosby Hotel in SoHo, where I didn’t know anyone but the author.
Within minutes of walking through the thick wood doors, after bumbling awkwardly around the plastic cups and conversation at the drink station, I beelined for the bathroom and locked the door behind me.
Pro tip: You can stay in there, unnoticed, for as long as it takes the next person to jingle the door handle, testing to see if the little paradise is occupied. Be right out! You call, smiling at the fact that fifteen minutes has passed.
By the time you’ve locked yourself away from the crowd, the writing is on the (bathroom) wall: Some nights you’ve just gotta call it early.
I used to love playing business as a kid—it was way more fun than playing house.
In one iteration, I’d pocket extra carbon copy forms that we filled out to rent skis during our annual sojourn to Lake Tahoe. Then I would sit at a desk and ask family members to step up and fill them out with a black ballpoint pen, delighting in the fact that writing on the top white sheet would produce identical ghost-like copies in yellow and pink behind the original. I took a certain thrill at tearing the perforated edge, handing them their copy, then filing what remained of the packet away in a manila folder. Next!
Back in the UWS bathroom, I sat (you know where) sending a Marco Polo voice memo to my friend. We had traded passing parallel fantasies of Burn It All Down Mode in our businesses several years prior, an exchange that serves as the opening story of Free Time.
Earlier in the week she said something powerful in passing:
“I’m ready to start designing experiences in my business that I look forward to; not just for my clients, but ones that are fun for me too.”
She was dreaming about events that were outside, in person, away from the computer, with delightful touches sprinkled throughout.
Along these lines, we noted a mutual friend recently launched private strategy sessions over dinner, although that time window is past my bedtime. (See also: hiding in the bathroom at an evening barbecue.)
This started a brainstorm we half-jokingly dubbed Business Bestie Brunch, which transformed into cohosting a half-day mastermind together in a gorgeous space with beautiful views, followed by a delicious buffet and a few weeks of follow-up coaching.
I had become self-conscious in recent months about my role as a cheerleader for non-traditional business values. Was it still The Responsible Thing™ to encourage fellow Free Timers to pursue business activities at the intersection of revenue, ease, and joy? What if that feels impossible, or you need the money more?
When my projected income nose-dived mid-year, it yanked my confidence away with it.
But suddenly, seeing an idea so joyful take shape instantaneously, with one of my business besties—even while hiding in a bathroom—made it all feel like play again.
Business Bestie Brunch already had stirrings of joy, ease, flow, freedom, and fun. It remained to be seen if we could fill all five seats, but we decided it would be a fabulous use of time for the two of us, even if no one else joined.
“Jenny!” Michael called from the backyard. “Where’d you go?”
“Coming!” I replied.
I looked at my watch: I bought myself twelve glorious minutes.
The sun had fully set into the milky night; New York City is never truly dark. Strings of holiday lights formed a lattice over a large planter in the middle, illuminating the party, with citronella candles burning. As I emerged from the magic portal, smells of grilled sausage, burgers, and ribs started wafting my way. I was grateful for the food and for the company.
I smiled. My little paradise provided what I entered for: peace.
That’s the thing about work that feels like play: it’s out there.
Don’t stop looking for it.
❤️
Maybe undefine what work is, how it feels, what reward you look to get from being successful at it. Maybe think of it all as self-expression-in-the-moment. What magical things might emerge from "free time" that's not business-related? Saturate with those activities and you reach that shift/catalytic point where you realize you could make money with some possibly "silly" indulgent activity. Like Rolling in D-Oh! Love you.
Oh the beauty of a mid-party bathroom retreat! Sanctuary and source of breaks to restore sanity. 💥 Love learning more about the origin story of business bestie brunch too! ❤️