My first day coworking: A moment that changed my life forever


Last updated: June 6, 2016 at 6:10 am

March of 2007, Long Island, NY, Age 22

I thought I’d invented something new. I was standing around the kitchen table at my parents’ home, where I’d just completed my quintessentially Millennial boomerang by calling it home again after college. We were brainstorming about the paradox of working from home versus working for someone else in an office.

The idea arose naturally: If working from an office feels oppressive and forced, but working from home feels lonely and isolated, then what would it look like to have something that could be the best of both worlds? Could there be a place where people could go that would have all the good parts of an office, but none of the bad parts?

A quick search on Google confirmed that we were not the only people contemplating this. There was a small but growing global movement, not even two years old, around the notion of “coworking,” which was for all intents and purposes the very thing my stuck-working-from-home self so badly needed.

I love my parents. I didn’t mind living with them. But being 22, living on Long Island, and not having a good reason to leave the house for days at a time was wearing on me.

In New York, the first coworking group I found was called Jelly. It took place once every other week in a how-is-this-legal five-bedroom loft in midtown Manhattan. You didn’t have to know anyone to attend; you could simply add your name and what you were working on to a wiki RSVP page and away you went.

I had to email the organizer, Amit Gupta, to be sure this was for real.

He assured me that, yes, even though I was a total stranger to him, I was welcome in his home.

It was hard for me to believe.

So on March 14, 2007, I packed up my recently purchased laptop and a special headset I could use to make and receive calls through my computer. I purchased it specifically so I could take client calls from a stranger’s bedroom. Little did I realize how often I’d be doing that sort of thing over the years.

For the first time since my internship at Time Inc the summer before I went to college, I commuted by train to New York City to go to work.

I was, almost certainly, the only one on the train who was going to work in the city when I could have worked at home. I felt like an interloper. It was kind of fun.

I bought a box of pastries from a nearby bakery I’d found online the previous day. I got to the apartment way earlier than the designated start time, but Amit buzzed me up anyway before hopping in the shower.

Suddenly, I was in this apartment.

Well, apartment doesn’t really do it justice. This was House 2.0, a five-bedroom communal living project borne of a close-knit cadre of recent Amherst college graduates who wanted to carry the spirit of their dorm life into adulthood.

There was art on the walls. The decor was a hodgepodge of things found and reclaimed. The kitchen area was wallpapered with large sheets of paper, each one packed with handwritten quotes and notes from friends and visitors.

I was on 39th Street in Manhattan, sitting on a couch in this crazy loft apartment, and I didn’t know anybody. Where the hell was I?

People started to trickle in. Two brothers with a tee-shirt company and an eye for great design. A guy designing a new kind of teapot. A fuzzy-haired developer. A bright and upbeat web designer.

I picked a spot on a cozy-looking big blue couch and got to work. I did, after all, have a job to do.

I felt like a total poser. Everyone there had their own business, and here I was, the sucker with a salary!

They were independent. I was only able to join their ranks because I could telecommute, making me technically eligible to spend a day working on Amit’s couch, but I certainly didn’t feel worthy.

These people around me were bright. They were happy. They were creative. They had fun carving out their own paths for a living. And, for some reason, they accepted me as one of their own.

Work led to lunch. We talked. Those conversations continued as we returned to work in the afternoon.

I ended up talking with two of the guys about a new mobile payment service. The site was offering five dollars for every new referral, so we made a site called and proclaimed that anyone who put their number on our site would be sent a dollar through this new service, then get the five dollar signup bonus, and… voila. Six bucks for free.

We would, in turn, net four dollars.

I’ll cut to the chase: we didn’t end up taking home any money. We got shut down in a matter of days.

But the fact remained that on my first day of coworking, I met two guys and built and launched a new web site.

Those guys, Jaime and Adam, are super neat guys.

After launching the site, later in the evening after most of the other Jellyers had gone home, I was invited to join some of the House 2.0 crew to go bowling.

Enamored with this group, I of course went along with them.

By the time I took my train ride back home after 10:00, I was hooked. I wanted to go to every Jelly I could.

The only trouble was that Jelly was only once every two weeks, and that wasn’t nearly enough for me. I wanted to be able to have an experience like this every day.

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