It’s Come To This: Procrastination Nannies Are Now A Thing

How much is the idea of finally finishing that screenplay worth to you? Does $40 and giving up your Sunday sound fair?

It’s Come To This: Procrastination Nannies Are Now A Thing
Cave Day co-founder, Jeremy Redleaf [Photos: Phillip Van Nostrand]

At a little before 9 a.m. on a Sunday in late March, a small group of people stood sheepishly eyeing each other in a lower Manhattan office building. Their friends, it’s safe to say, were sleeping in, sipping mimosas, and walking their dogs at this hour. Meanwhile, this group of bleary-eyed professionals—most in their twenties and thirties—would be spending the next eight hours hard at work. And they’d each paid $40 to do it.


Today was “Cave Day,” an event series that’s sort of like a pop-up coworking space; rather than sign up for a weeks- or months-long membership, you register for a single day. The price of admission includes two meals, snacks, coffee, and a handful of work-related services doled out by a briskly energetic group of facilitators—whose sole job is (as the program’s website puts it) to help you “GET STUFF DONE” with “NO DISTRACTIONS.”

Getting stuff done with no distractions is a challenge many fail to overcome on their own, especially when it comes to passion projects. There’s no shortage of reasons (or excuses) why—work got really busy, you had to travel for that wedding, your cat got sick, Veep started up again—and before long, you realize you’ve been procrastinating on that one thing you’ve really been meaning to do, whether it’s finally drawing up that business plan or banging out the next chapter of that novel. It’s long put-off solo projects like these that Cave Day’s organizers seem to believe are best tackled together.

Related: How To Finally Stop Procrastinating (For Real This Time)

Can Beating Procrastination Be A Team Sport?

“Greetings cave dwellers!” the email confirming my reservation had said. “We’re so excited to cognitively spelunk with you!” The email had also urged me to install the internet-blocking application Freedom (one of the day’s sponsors), and recommended, a service offering “music designed by scientists for focus.” I had followed the email’s instructions to the letter, bringing my water bottle, work materials, and flat shoes.

Molly Sonsteng

The lobby elevator doors opened to reveal Molly Sonsteng, one of the day’s organizers, who had a bat-shaped name tag on her black turtleneck and a spelunker’s lamp cheekily strapped to her head. Inviting us to pack into the elevator with her, Sonsteng held out a bowl filled with little strips of white paper and told us to choose one. She asked us to imagine that our strip of paper represented something we didn’t want to bring into the “cave” (which on non–Cave Days is the coworking space ImpactHub), something we feared might stifle the productivity binge that awaited each of us.


“Mine, for example, is Facebook,” said Sonsteng.

“Can it be an emotional thing?” a woman asked.

“It can be anything.”

“Great, okay. I’ll make mine self-doubt,” said the woman.

Upstairs, we were greeted by Jeremy Redleaf, another Cave Day creator, outfitted similarly to Sonsteng. Redleaf gestured to two lit white candles on a blue table. “Step right up, one at a time, drop the paper onto the flame.” And so we did. Goodbye, Facebook. Goodbye, self-doubt.


Next, Redleaf furnished a large lockbox. “Phone check?” One by one, we “cave dwellers” surrendered our iPhones and Androids.

We were officially lashed to the mast of productivity.

A little while later, Redleaf, Sonsteng, and their third collaborator, designer Jake Kahana, convened the entire group of some 40 participants, asking them to go around the circle and share what they’d be working on through the day, and how far along they were. “Molly, short stories, 10%.” “Cesar, blog posts, 15%.” “Lily, wedding planning, 60%.” Then the group broke, a low-tempo remix of “Eye of the Tiger” came over a set of nearby speakers, and everybody made their way to a workstation.

At 9:49, Sonsteng took a microphone and announced: “The first sprint begins in three . . . two . . . one.” Our heads were down. It was time to work.


As Redleaf explained, the idea for Cave Day was borne of desperation. Last November, he turned up in his therapist’s office noting that while he was excited about many creative projects, none of them were “crossing the finish line.” So, countered his therapist, what would it take for him to make real progress on any one of them?

“I think I just need a kind of cave day,” Redleaf blurted out. He needed to turn off his devices, get off the grid—just shut the world out for a full day.

So he did, and it was marvelous. He finally made the progress he craved on a screenplay he was working on. The only problem? “It was lonely, being in this cave by myself,” he recalls. So Redleaf began hosting small gatherings of friends to share in his productivity. They loved it, too. Soon, he looped in Sonsteng and Kahana, theorizing the idea could grow. They hosted a first Cave Day on January 15 this year and called it a success.

Now, more than two months later, they were hosting their second. And I was staring down a blank sheet of paper, trying to make progress on a play I’d barely been able to make time for in many months. I looked to one side: A woman eagerly scribbled in a notebook. I looked to another: A man tapped away on his laptop. I reached reflexively for my phone—then remembered it wasn’t there. I had coffee, I had snacks, I had community, I had time, I had a pen and a paper and my brain. What excuses did I have?

Over the course of the morning, punctuated by occasional stretching and doodling breaks led by Sonsteng, I found myself steadily plugging away at it—and proceeded to make more progress than I had in months.


No Excuses Not To

For Cesar Kuriyama, the founder of a video app called 1 Second Everyday, Cave Day was an excuse to “work on a couple of blog posts I have been putting off literally for years.” As more of a technical thinker than a literary mind, Kuriyama said he felt Cave Day freed him up to try something new and challenging.

Margo Aaron, a marketer, said the experience helped her get comfortable saying no to social invitations from friends, coworkers, and family. Ever since she’d bought her ticket, Aaron had made it known she wouldn’t be available this Sunday, which she said now felt liberating.

And for Michael Berwin, a freelance designer knocking out some pro bono websites for friends, it was the imposed structure of the day that brought him value. “If I were just told to do 45-minute ‘sprints’ alternating with stretching, I probably wouldn’t do it. But to have them actually instigate it is great.”

At 4 p.m., in a rear break room Sonsteng had littered with Legos and snacks, I dropped in on a 15-minute “design thinking session,” as a bearded man named Carl Collins coached a fashion entrepreneur who was wrestling with her website’s workflow issues. Across the workspace, other participants dropped in on 15-minute mindfulness sessions with another coach.


An hour later, Redleaf’s voice came over the loudspeaker as the theme song from Rocky began to play: “Cave dwellers, you have seen the light at the end of the tunnel.” Once more the cave dwellers coalesced into a giant circle to share their experiences. “I did everything on my to-do list!” exclaimed one woman. The room erupted into applause. Then Redleaf declared Cave Day over, and the group dispersed—looking more exhilarated than exhausted—with many decamping to a nearby bar where Cave Day’s organizers had wangled happy hour specials.

“I feel like I’ve actually earned a happy hour drink,” Kuriyama remarked on his way out. He was trying to figure out why the experience had worked so well for him. He could’ve gone to a café, library, office, but said that something about the combination of features—the structure, the food, the camaraderie, the weird sense of ritual—had made it uniquely valuable.

I heard similar reports from other participants, many of whom said they planned to attend the next event, on May 21, for which the ticket price has risen slightly, to $45.

It wasn’t easy to explain, Kuryiama admitted. When he’d told a friend about his plans earlier in the week, he said, “She was like, ‘So you paid . . . to work?’” What else could he say? “I was like, ‘This is true. This is accurate.'” But he’d do it again.

About the author

David Zax is a contributing writer for Fast Company. His writing has appeared in many publications, including Smithsonian, Slate, Wired, and The Wall Street Journal