Work environments used to be a settled question. In the forties and fifties you dressed formally, you sat where you were put, and the building told you what kind of company it was. Then people like Jobs showed that comfort and output weren’t opposites, and the whole convention fell apart.
I have run companies from four very different kinds of space, and my opinion about which one mattered has completely reversed.
1982: a desk in a truck center
I started the freight brokerage at twenty-three with my younger 18-year-old brother and 16-year-old brother-in-law, operating out of a truck center. It was not impressive. We went from ten thousand dollars a month to a hundred and thirty thousand inside the first year anyway.
We also invented a small piece of theater. When a client rang and asked for a different department, whoever answered would wheel their chair across to another desk, wait a beat, and pick up in a slightly different voice. Everyone did it. It worked because the clients cared whether the freight arrived, not how many rooms we had.
1994: an office with a door
After a couple of years away in the entertainment business I took a suburban unit — twenty-five hundred square feet, near a café run by Tom Cruise’s sister. The culture stayed casual. People played computer games; we played basketball; it felt like a family with invoices.
It was more organized than the truck center. I am not sure it was more productive.
1997: the thing I had been chasing
Then I got it. Two hundred thousand square feet of warehouse on seven acres with its own rail access, seven thousand square feet of designed office attached, and a forty-foot sign with our name on it.
I had wanted that sign for fifteen years. I want to be honest about what changed: the rent.
An animator in a coffee shop
Around the turn of the century I got talking to a young South African animator in an East Village coffee shop. I asked where he was based. He said, “Home is wherever my computer and my backpack are.”
I had heard versions of that before and dismissed them. This time it landed, partly because I was reading Rolf Potts around then, and his argument that attaching a cash value to every hour of your experience is precisely what keeps you from being free.
I have since worked remotely since 2003. I run a digital agency from cafés on beaches and restaurant terraces in India. The company is as successful and far more enjoyable than the one that needed the warehouse.
What the answer actually is
There is no correct work environment, which is an unsatisfying conclusion for an article that has just spent nine hundred words on the subject. There is only the intersection of what the company genuinely needs to function and what lets the people in it do good work without resenting it.
For a freight brokerage in 1982, that was a room with phones. For a digital agency now, it is a laptop and a decent connection. The forty-foot sign was never operational. It was a monument to a vision of success I had accepted without examining, and the useful thing about getting it was finding out it was empty.
These days the question I ask about a working arrangement is whether it leaves room for the rest of the life. Mine currently includes a motorcycle expedition through the Himalayas, cross-country travel through Argentina, and life in the Caribbean. The warehouse wouldn’t have allowed the time away for that.