Remote work: some personal history

Remembering when it was unusual to be a remote worker

Until the early 2000s, I had a relatively conventional work arrangement. I commuted to an office, where I had meetings with my colleagues and where most of my work-related equipment like computers could be found.

That said, even in my graduate school days (late 80s and early 90s), I did some work from home over a ridiculously slow (300 baud!) dial-up modem to MIT. That enabled me to do certain chores from my apartment, late at night or early in the morning, rather than having to go into the lab. However, there was no sense in which working from my apartment was a substitute for being in the office.

Likewise, after I went to work at Lotus in 1994, I was in the office pretty much every day. Although I now had a laptop, and although we dealt with research issues relating to remote work and collaboration, there was not much likelihood that we would try to go fully remote. The technology just wasn't ready. When I jumped to a startup called SightPath during the internet bubble, the destination of my commute changed from Cambridge to Waltham, but nothing else really changed in terms of the work structure.

Beginnings of remote work

With the 2000 acquisition of SightPath by Cisco, things started to change for me. I was now part of an organizational unit that had a substantial presence on the west coast, as well as me and my former-SightPath colleagues on the east coast. To a first approximation, everyone who thought they were in charge was on the west coast, while everyone who knew what they were doing technically was on the east coast. Accordingly, I got used to being on many conference calls as the counterpart to the in-person meetings that had been a mainstay in my previous jobs.

At the same time, my office kept moving further and further northwest in the Boston metro area, which meant it kept being further and further from where I lived, just south of the city. This was understandable as a cost-saving move by Cisco, since these far-removed office parks were no doubt much cheaper than office space that was closer to the city. If I had been a true company man, with fewer connections to where I lived, I might well have reacted to this shift by moving myself to follow my office. However, my family and I liked our house and liked the schools, and I was not a person who was particularly ambitious to rise within Cisco. Accordingly, it was not hard to decide to stay where I was, with an ever-increasing commute.

At some point, I realized that it was bizarre to spend almost two hours driving each way (!) so that I could sit in a cubicle and be on conference calls with people in California. So, in an informal way, I simply spent more days at home doing those conference calls and fewer days driving out to the boondocks.

All of that meant that I had laid the groundwork for my eventual move to being fully remote. When Cisco bought the wrong startup in a particular technology, I then joined the right one – the one they should have bought. At that point, Riverbed was quite a small company, with 40-ish employees and no presence in the Boston area. As the cofounders told me at the time, they had not planned on having anyone in Boston at that point in the company's growth. But to their credit, they recognized the substantial advantage of having me join them: I “knew where all the bodies were buried” in the Cisco business unit that would almost certainly be their most important competitor.

Fully remote

So, I joined Riverbed in 2004, and for a time my house was the corporate nexus for Massachusetts state taxes and similar bureaucratic details. Happily, the technological focus of Riverbed was improving the user experience and network performance for remote offices. I was able to put Riverbed products into my house and use them to accelerate my network traffic exchanged with our headquarters. That arrangement made for marvelous anecdotes when talking with prospects, since I could tell them about my personal experience as a one-person office on the other side of the country from corporate HQ.

It was less fabulous that the initial implementation involved a hefty Rackable server that sounded like a jet engine during takeoff. The fans on a serious server make a noise that is not necessarily objectionable in a data center, where everything is making a noise like that, as well as the data center’s own air movers making similar noises. However, my situation was quite different. I could really tell when the box was turned on, and there were multiple occasions on which my wife asked me to turn it off. Even behind a solid wood door in a network closet, it was pretty damn loud. Fortunately, the company soon produced smaller, home-focused units that were much quieter.

Part of my practice from my first days at Riverbed was to travel to headquarters roughly once a month, and certainly at least once each quarter. The travel ensured that people remembered that I existed and invited me to relevant meetings, as well as getting some face time in which people would confide the kind of anecdotes and gossip that just don't get shared in remote meetings.

I was lucky that I had been part of a research team thinking about remote work and collaboration, long before I tried to do it myself. One of the things that I had learned when I was doing workplace research at Lotus is that in organizational terms, meetings don’t work the way that a lot of people think they do. The meeting itself is not actually all that important. Certainly, a good meeting is trying to solve some problem or achieve some goal, so I’m not claiming that every meeting is useless. However, the meeting itself, from when it starts to when it ends, is arguably less important than what happens as people are assembling and as people are dispersing. It’s all the little get-acquainted, check-back-in, or what-just-happened side conversations in which all the really important information sharing happens. One of the as-yet-unsolved problems in remote work is that there is no remote counterpart to that informal assembly and the corresponding informal dispersal.

In it for the long run

Since I first joined Riverbed, I've never had a conventional office job. I've always been remote: about 10 years with Riverbed, a little less than two years with Dropbox, and five years so far with Netskope.

When the pandemic started, many other people started to work in the way that I had become accustomed to working. I was able to reassure people that it was possible to get work done despite remoteness, while also being realistic about the limitations of the approach.

Remote work has been very congenial for my personal situation. One part of the benefit has been the elimination of commute time. Another part of the benefit is a reduction in the social anxiety I sometimes experience when meeting strangers or engaging in small talk. It's pleasant to be in a situation where I can do face to face meetings when they're required, but they are not an ongoing, uncontrolled part of everyday work.

Remote work has also allowed me to customize my work environment in ways that would have been impossible in a conventional office. I work in a large high-ceilinged space with light on three sides, with dark wood and ornamental wallpaper. I have two desks, each with a different kind of chair, and a third easy chair. My usual work process causes me to cycle among the chairs as I write, or mark up previous writing. I suppose that I might have been able to have a similarly plush office in some kinds of fancy companies, but I think the prevailing ethos in most companies is to save money… so it would have been difficult to have a space as nice as the one that I work from now.

I take some of my inspiration from Richard Feynman, who apparently used to hang out drinking in exotic-dancer bars, while working on scientific papers. In some ways my work setup is more eccentric than his, in other ways it's less eccentric; but in both cases it feels like we figured out what works well for us, however odd it might seem to other people.