Remote Life at WonderProxy: Transitioning

I've been working remotely as a software engineer for six and a half years, with three different companies. At the first company, I had been an on-site employee for four years, and I was their first full-time remote employee.

Caroline and Allison have already covered coworking and juggling two remote jobs, respectively. I'm going to talk about transitioning from on-site to remote work environments.

Your Company

Your employer and your team both have to be all-in on this remote work thing. When I worked in an office, hallway conversations were frequent, and folks "just dropped by" every hour or so. When I started working remotely for the same company, I was isolated from those interactions. I missed out on the ad-hoc brainstorming sessions, the quick status updates, even basic logistical information like my boss leaving early that day. At the same time, I still got those company-wide emails about extra pizza in the kitchen, or the lack of toilet paper in the bathroom. If your team doesn't adjust, you'll be seen less as a team member, and more as a team extra. If you're going to work remotely, or have a remote member on your team, the entire team needs to "go remote".

• Find a team chat system you like, and move the watercooler stuff there. Make sure people keep their "online" status updated, so everybody knows who's around. (I'm terrible at this. Sorry, Paul!) Make mentioning somebody in chat your new "drop by the cube", and be liberal with the cat pictures in #random.
• Find a video chat system that works for teams, and push your meetings out of meeting rooms and into video chat.

At WonderProxy, we like IRC and Slack for chatting, and Google Hangouts for video. (Google Hangouts won't work for huge teams, but other services will. We have the technology, folks! Use it!)

Side note about meetings with remote team members: If you can help it, don't bundle up your local team members into a meeting room with a camera and a screen (or worse, a speakerphone) and call it done. You'll spend the first ten minutes of each meeting fighting with tech, the actual meeting will be spent trying unsuccessfully to hear the remote person, and you'll all end up mildly annoyed at the inconvenience of supporting those entitled remote workers. Instead, have everybody on equal footing: at their desks, with webcams and microphones!

Communication

The obligation isn't only on your company to get into the remote work mindset. You're in a new environment too, physically removed from your team and your boss. Being out of sight means nobody can glance over to see where you are or what you're working on. It's an entire line of silent communication that no longer exists.

You can compensate for that lost information channel by over-communicating. Broadcast what you're working on in chat. If you get up to walk your dogs, tell people you'll be right back. If you're working over a gnarly problem in your head, think "out loud" with your keyboard. Be liberal with comments and status updates in whatever issue tracker you use. Don't make your team members guess at how you're spending your time, or feel like they have to ask you. (Again, full disclosure, I'm terrible at this too. Sorry again, Paul!)

At WonderProxy, we track our work with Trello, and we use WorkingOn for day-to-day status updates. WorkingOn integrates into our Slack instance, so logging an update is as lightweight as typing /on writing a blog post about remote work in chat.

Scheduling

For all the praise remote work gets for allowing flexible work hours, my own hours are pretty vanilla: I work weekdays, 8am-ish to 5pm-ish with an hour-ish break for lunch. My schedule lets me sync up with family and friends for evening or weekend activities, and keeps my work time predictable. It also gives everyone (me, my team, and my family) a clear distinction between work and non-work time.

Allison already explained her WonderProxy schedule, and how the nature of her work (and her day job) pushes her into different hours. Some people are night owls and work best in the afternoon and evening. Others might have family obligations mid-afternoon, and want to work mornings and evenings. Maybe you work best in two-hour bursts with naps in between. Find a schedule that works for you, and then be as consistent as you can for the sake of your team.

Balance

Caroline talked about how she uses a coworking space as a "work environment", and Allison has a designated space in her home that she uses exclusively for her day job. Both my colleagues maintain a physical separation between work area and non-work area. That's a common recommendation in "how to remote work" articles: have an office, have a desk, have a separate space dedicated to work and nothing else.

I don't have separate locations for work and play. I use the same desktop PC for gaming and working, and I can't really haul the whole thing back and forth every day. I will occasionally take my laptop to a coffee shop and work there, but I'm too accustomed to my big desktop monitors for the laptop to be a long-term workspace.

Instead of maintaining a physical distinction, I maintain a virtual distinction: I dual-boot Linux and Windows. When I work, I boot into Linux; when I play, I boot into Windows. I'm sitting in the same chair and using the same hardware (I mean technically I'm using different SSDs, but you get the idea), but the difference between the two OSes is enough to mentally shift myself to and from "work mode". (Any virtual environment change would have the same effect: If I had to work in a Windows environment, I could create a separate user profile just for work.)

Pyjamas

Until lunchtime, folks. If you talk to me in the morning, I'm wearing pyjama pants.