Working remote: one year on

May 06, 2019 // Lessons learned from a year of hacking at home.

There was a talk at PyCon 2019 from Lauren Schaefer about working remotely and the challenges and opportunities it presents. It was well-prepared, well-presented, and made me reflect on my own experience. I've always savored the idea of working from home, and I never saw a good reason why our employers shouldn't let us at least dabble in it. So now that I've been working remote full time for almost a year with Skiplist, I thought I'd compile some of my thoughts on the experience.

As expected, the biggest benefit is the flexibility & freedom offered by working from home. So long as the work gets done and I attend meetings, my day is my own. Want to take a long lunch? Go for it. Start early or stay late to finish up on a feature? I can go to the office anytime by just walking into the room and putting on headphones. Want to travel to France for a few months? Sure thing, just keep pushing your cards across the board and checking in with the team. I have better control over my work environment, and I can make it exactly what I need it to be. There's no commute to wrestle with, which alone lowers your stress, enables you to live wherever you want, to change jobs without moving across states or countries, and is significantly better for the environment.

Most importantly, working remotely has allowed me the opportunity to spend all day with this little dude.

The major drawback I've found is the lack of socialization. My first job in software came with a move to a new city. For me, going out to coffee, lunch or happy hour was critical to building a network of friends and contacts. This is significantly harder to do in a remote company. I've made up for that by being more intentional about making time to see friends outside of work, and I could probably join some meetup groups if I were so inclined. Work-wise, remote also means team and company communication has to be much more intentional. Instead of coming across info by just walking around the office, knowledge can end up in silos unintentionally. This means harder work for everyone involved. We've made extensive use of apps to close the communication gap. We use Zoom, Slack and VS Code with the Live Share extension to make everyone feel more like we're sharing the same space, and we use Asana, Slite, and Office365 to keep our knowledge as centrally located and minimally siloed as possible.

Working remote works for me. I have always been able to manage my own time well & work independently. I am vocal; whether in an office or remotely, if I'm stuck on an issue I'm going to verbalize it rather than spin my wheels for too long. I communicate well and raise up issues when I see them. Also, our company, while being remote-first, is mostly located within 45 minutes of each other. This means we can still do weekly meetups for breakfast or happy hour, meaning that the socialization still happens.

This doesn't mean that working remote is the answer to everything. One thing I didn't consider until recently is some people don't have adequate spaces to set up a home office. I have the privilege of a decent-sized 3-bedroom house and can afford allocate a whole room for my office. People living in studio apartments, with roommates, or have children might not have that same flexibility. We need to make sure we as employers provide solutions so we aren't discriminating against potential employees by being remote-first.

At the same time, offices can also be discriminatory. San Francisco office jobs discriminate against people who can't afford their outrageous housing prices or move across the country. Any office job can be difficult on those with limited access to vehicles, live in an area poorly served by mass transit, or have families with complicated schedules.

There's no one size fits all solution, but I recommend you look at the slides posted above to learn more. Schaefer's talk was very in-depth and can help you decide whether to pursue remote work further and some tips for convincing your boss if it sounds appealing. It's been an enjoyable time so far and it will be a hard sell to get me back into an office anytime soon.