Cate Huston

Mobile lead at Automattic

Cate Huston has a different morning routine for each time zone. She works remotely as a mobile lead at Automattic, and how she kicks off her day can depend on whether she happens to be in Bogotá or Barcelona. “When I’m in Europe, my mornings are a bit more chill,” she says. “I’ll go for a walk, have breakfast, head to a café, and that’s when I’ll get focused and work, mainly by myself. But my afternoons will be much more crazy, [my work] often going into the evenings.” When she’s in South America, she wakes up and dives straight in. “Sometimes it’s just crawl out of bed, put on day pajamas, and work as I eat breakfast,” she laughs.

Cate works as part of an entirely distributed company. Her team is mainly spread throughout North and South America and Europe, with Cate splitting her time between Europe and Latin America. “It doesn’t really matter where I am; I’m happy to just put on some music and work anywhere.” She’s part of a growing number of remote engineers who, thanks to tools like Slack, Google Docs, and GitLab, can stay connected to the office without having to actually go there. Or, in Cate’s case, can work for a company with no office at all.

There’s a manager on my team I had never had a voice or video chat with before he became a manager.

Automattic—whose products include WordPress.com, WooCommerce, and Simplenote—is often cited as one of the most successful examples of a fully distributed workforce. They place a huge amount of value on the written word; text-only stand-ups (with people keeping to their own local office hours) and one-to-ones over Slack are a common occurrence. “There’s a manager on my team I had never had a voice or video chat with before he became a manager,” Cate says. “We just talked by text.”

Cate initially decided to look for remote work as a way to remove herself from male-dominated environments that “weren’t particularly welcoming towards women,” where she often experienced uncomfortable microaggressions. “I was thinking, ‘It would be so much better when I cry at work if I could cry in my own living room,’” she recalls grimly. “I didn’t know what it would be like to go to an office where I felt psychologically safe. Thankfully I do work in a much more welcoming environment now.”

With the increasing ubiquity of open-source projects, Cate thinks engineers have become accustomed to asynchronous collaboration and can find it easier to adapt to remote work. “The open-source ethos is an important foundational principle of remote work. For example, you don’t have projects arbitrarily located in San Francisco,” Cate says. “For people working in other job functions, working remotely can be a bit more of a culture shock.”

Cate's work week, by the numbers

Simon McDonnell

Game client developer at Digit Game Studios

Although many programmers can and do make the transition from an in-house role to remote work, those who are suddenly thrust from one into the other can find it difficult to adjust. Most of the employees at Digit Game Studios, where Simon McDonnell works as game client developer, work out of the studio’s Dublin offices, but personal circumstances led McDonnell and his partner, Laurel, to relocate to Edinburgh, Scotland. “I was literally getting out of bed at 8:58 a.m. and walking to my desk in my pajamas,” he says. “If you’re not working remotely, you might think it sounds great, but it really wasn’t; it was demoralizing.” Wearing the same sweatpants and going days without showering isn’t the stuff #DigitalNomad Instagram captions are made of, but it is the reality for a lot of remote developers.

Having to work away from your team can be challenging, though in many ways, Simon admits, he has it easier than most. He’s in the same time zone as his colleagues, which can make stand-ups, real-time feedback, and pairing sessions more accessible, and he frequently flies back to reconnect with his team, spending a week or so in house. Like most technical teams, Simon’s team uses digital tools that make it easy to communicate and collaborate, and he has the shortest commute imaginable—about 90 seconds from his bedroom to his home office.

Wearing the same sweatpants and going entire days without showering isn’t the stuff #DigitalNomad Instagram captions are made of, but it is the reality for a lot of remote developers.

These days, Simon makes a point of getting up early every morning, showering, and doing a few chores before starting his day. Work kicks off with a daily stand-up that Simon’s team dials him in for. But aside from an hour-long weekly team meeting and fortnightly sprint planning sessions, most of his days are spent solo.

“You do get left out of small things,” he notes. “The big stuff gets communicated, but the casual conversations in which you might go, ‘Oh, hey, I was working on that thing, what’s that?’ or somebody is just bored so they come by your desk and you end up talking to them about a problem… That doesn’t really happen.”

On the plus side, Simon isn’t as susceptible to the late nights that tend to creep in as dev teams approach big deadlines. “I still have to do crunch sometimes, and I work late when my projects are running late or I’m set on hitting a goal, but I don’t feel the same ambient pressure.”

Unlike many companies with remote developers, Simon is very much in a minority, one of only a handful in his company, and he reckons he would return to work in house if he had the option. “It’s strange, because I’m kind of an introvert and I like my solitude very much, but I also like hanging out with people and I get few opportunities to,” he says. “I’ve realized I like being around people; it can be hard to just be in your flat all the time.”

Simon's work week, by the numbers

Dana Lawson

VP of engineering at InVision

Dana Lawson says many people are surprised to discover that being an introvert doesn’t necessarily mean you’re well suited to working remotely. “Introverts struggle a little more,” she says. “They’ll apply for remote jobs because they might not like office dynamics, but they won’t know where to start or how to ask questions, whereas extroverts just dive right in.”

InVision has employees on “every continent except Antarctica,” with Dana managing team members in Argentina, Colombia, Spain, and Canada. She believes having a fully distributed workforce is key to a happy, healthy working environment. “When you have that squad-type concept [of being in a shared office] there’s always this feeling of being left out,” she says. And she echoes some of the challenges Simon’s experienced: “If you have a couple of people remote and everybody else is in the same location, that typically really sucks for the remote worker, because things will happen in real life that won’t get communicated.”

Being an introvert doesn’t necessarily mean you’re well suited to working remotely.

This role was Dana’s first 100 percent remote job. “When I started, I don’t think I left the house for two weeks!” she laughs. “There’s this fantasy that [with a remote role] you get to work less, but actually, if you’re not disciplined, you’ll finish dinner and go right back in or just get out of bed and start your workday right away.”

While she enjoys getting everyone together every now and then for some face time, Dana relishes the amount of focus and flexibility working from home has afforded her. “As an executive, a lot of people like to just cruise by [in the office] and shoot the shit,” she laughs. “Which I love! I’m into it. But it would push me into 12 or 13-hour days. Now, being remote, I can just turn off my calendar, turn off Slack, and get to it.”

When Dana first started at InVision, the company had about 100 employees; eighteen months later it had grown to 400 and counting. “With that kind of explosive growth, you have to learn to keep alignment across the company,” she says. “I always tell people to be explicit and really think about establishing a written culture, especially as you grow, because things move so fast.” Dana also stresses the need for mindful, accessible communications across distributed teams: “Don’t use metaphors or language that doesn’t translate well, as English will no doubt be a second language for a lot of your colleagues.”

If you’re not disciplined, you’ll finish dinner and go right back in or just get out of bed and start your workday right away.

Her advice to any programmers new to remote work is to err on the side of over-communication, rather than sweating it out solo and unsure. “Don’t feel like you’re annoying someone, and don’t feel like you’re asking stupid questions,” she says. “You’re sitting in this space by yourself and you probably don’t have any work yet, which will bring a lot of anxiety and imposter syndrome. So just explore. Talk to people, Slack people, spend time getting to know people.”

Her role also involves helping her department navigate learning, advancement, and growth, which can be tough for remote workers. “One of my biggest tasks was to define the career development path,” she says. “In my experience, a lot engineers tend to [think in] black and white—they need checklists, validations, and to have a goal to reach. For us, it comes to back to defining what success looks like and having a consistent conversation.” Regular one-to-ones, quarterly reviews, budgets for online learning, and conferences are all key to ensuring people don’t stagnate in their roles and continue to make progress while working remotely, whether on a technical track or in managerial leadership.

Dana firmly believes remote work “is the way of the future,” as it empowers people to build a working environment that suits them. “We’re adults—we know what we have to get done, so let us get it done and we will give you our best,” she says. “It’s about breaking that traditional mindset of butt-on-seat office culture.”

Dana's work week, by the numbers