Reflecting on 2.5 Years as a Remote

February 27th was my last day at Etsy, concluding 2.5 years as a remote employee (more on what's next in a future post). A lot has been written about remote work, including a recent book, but I wanted to talk about my own experience and some of the lessons that I learned over the past few years.

Overall Etsy does a great job with remote employees, and it continues to get better. During my last couple of weeks at Etsy they were rolling out a new policy that added a number of additional benefits for remotes (including the ability to bring your spouse with you to the main Etsy office in Brooklyn for a week once a year). All that said, at the end of the day I believe that how much you enjoy working remotely is more a function of your personality than the perks that your company provides.

Generally I think there's a correlation between how introverted you are and how much you enjoy remoteness. Here's how I put it in my last lecture at Etsy, discussing how my expectations matched reality.

Why the mismatch? A few reasons:

  • Being remote makes you want to get out more
  • I like having close friends at work, and this is harder as a remote
  • The pace of learning is slower as a remote, and a big reason why I came to Etsy was to learn from the amazing engineering team that Etsy has
  • Fear Of Missing Out translates to the Reality Of Missing Out. There are always activities, free food, and get-togethers that are happening in the office, and as a remote you can't take part in these things
One thing that really stuck out to me throughout my time at Etsy and from reading a lot about remote work is that really successful remote companies/teams have one thing in common: they are mostly remote. For a long time I was the only remote on my team, and part of a company that has roughly 10% remotes. While Etsy does a great job with their remotes, it's tough when you are a small minority at the company or on your team. 

Alright so it's challenging, but what are some specific things that companies can do to make remote life more enjoyable?

Team Off-Sites

My team came up to Boston for a week, stayed in an Airbnb near my house, and generally just hung out with me and got work done. This was a great way to make me feel like a true member of the team, get to know the folks on my team a little better, and interact socially as opposed to only communicating in a work context. I highly recommend doing team off-sites if you have remotes at your company. 

Communication Tools

You need to have some sort of real-time chat application with remotes. Etsy uses IRC, many companies these days are using Slack. Pick something and have as much conversation as possible there. 

You also need to have outstanding A/V setups in all of your conference rooms. Every time I was part of a meeting with 6+ people huddled around a laptop trying to video chat with me I died a little bit inside. It's ineffective, frustrating, and makes remotes feel like they aren't valued members of the conversation. Luckily Etsy recognized this, upgraded all of their conference rooms, and for the past year or so that I was there this wasn't a problem.

Buy high quality webcams for your remotes. The difference between a $100 webcam and the built in one in a Macbook is incredible, and the cost is negligible. This should just come as part of the package when a remote starts. Here's your computer, here's your webcam. 

Remote Bootcamps

If your company is serious about having remotes, every employee should have to go through a "remote bootcamp", where they work from home for 2+ weeks straight. This will uncover all sorts of small barriers that are likely easy to fix, and will help everyone understand the challenges of remote work. 

Trips to the Office

During my time at Etsy I came to the Brooklyn office roughly once every two months, for a full week. Really successful remotes tended to come more often, up to once every month. This meant that they were in the office 25% of the time, which can be pretty disruptive to your home life, but definitely helps work relationships. I have a lot going on in Boston, so it was tough for me to come to the office more often. I think it's great that Etsy encouraged frequent trips and paid for all of them, but the solution to being a great remote can't simply be "come to the office more". 

One big takeaway from these trips was that from my perspective the trip was special - something fairly unusual where I got to spend a lot of time with my coworkers and feel like I was a true part of the team. For everyone else in the office, generally it was just another day at work. My team did a great job planning lunches, dinners, and in person meetings when I was there, and I think it's really important to have a pretty structured week when remotes are in town. Without deliberate planning, you might spend 80% of your week sitting at a desk in the office coding away with headphones on - not the best way to spend your time. A big part of the responsibility for this planning rests with the remote employee, but anything you can do to facilitate that as a team member is beneficial. 

Wrapping Up

I'm glad that I had the opportunity to spend a couple of years as a remote. I learned a lot about the benefits and drawbacks of remote work, and how to do it effectively. I saw first hand what works and what doesn't, and what companies can do to make remote work as enjoyable as possible. I think my personality is slightly better suited to working closely with other people in an office environment, so I am unlikely to take another remote job in the near future, but I think having remotes can be a great way to access the best talent from around the world. If you are going to take a remote job, just be aware of the challenges and make sure that you are working for a company that takes remote work seriously (to reiterate, Etsy is a great fit in that regard).


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