Working remotely for extroverts

I got a DM from my friend Matt the other day.

“Yo!” he wrote. “I’m about to start working at a company that’s fully remote and thinking about joining you at Workbar a few days a week… I think commuting will be good for me to feel connected to the city / not go nuts.”

Matt and I are pretty similar in that we are both extroverts. We very randomly met at a Ruby on Rails workshop nearly three years ago and literally the next afternoon he and his girlfriend (now fiancee!) were at my house hanging out. When Matt told me he was thinking about working remotely, I realized that I had to write this blog post for him, because working remotely can be a tough adjustment for hyper-social weirdos like us. :)

Of course, there are a lot of structural things your company needs to do to help make a distributed workforce work. Things like not treating remote and non-remote workers differently, and having a really robust internal communication system.

However, as an extrovert, there are things you need to do to take care of yourself and make your new remote gig successful. Extroverts get energy from being around people, and working exclusively online can be exhausting. I’ve been a distributed worker at Automattic for a little over two years now. For Matt and any other distributed extroverts out there, here’s what I’ve learned:

1. Don’t move right away.

A mistake that people often make is that working remotely means you can immediately pick up and live anywhere. For an extrovert starting remote work, your existing support network is even more important than ever. Your new co-workers are hundreds (if not thousands) of miles away, so they’re not going to be the people joining for drinks after work, or random brunches on a Sunday morning. Your existing network of friends and old co-workers will continue to be your social support network, because a remote job can’t provide that for you.

2. Schedule your social life. 

When you work in an office, there are a lot of random interactions that we take for granted. It’s someone’s birthday so we gather around for cake. It’s the end of a project sprint and we celebrate with a team lunch. It’s a bizarrely cold Tuesday, so we all go out for drinks. For an extrovert like me, I love office culture stuff like this (to the point where I organized an Office Olympics at my old job).

When you work remotely, those sorts of unplanned social interactions don’t take place, so you have to be proactive in making sure they happen, because for extroverts these are little energy boosters that keep you going throughout the week. This means planning lunch with people who work close by, scheduling dinner or drinks with friends, or even planning 15-20 minutes a day to just putz around your co-working space and chitchat. Speaking of co-working spaces…

3. If possible, get a co-working space.

Choosing a co-working space that was within walking distance of my house was one of the best decisions I made in ensuring a happy work environment. On Twitter, Matt had asked me: “How do you like Workbar?”

In my opinion, Workbar is the best co-working space in Cambridge. Here are two things I would look for in choosing a co-working space:

The space caters to whatever work-style you need. The designers of Workbar Cambridge were extremely thoughtful in creating different types of workspaces, because everyone works differently. If you want to be around people, there’s a cafe space that mimics a coffee-shop. If you want to be heads-down, there’s a study space that has traditional desks. There’s also a variety of seating types: office chairs, standing desks, benches, bean bags, couches, picnic table (outside!), even a treadmill desk.

Also, make sure the staff truly, genuinely cares about the co-working community. The Workbar team does lots of little things I appreciate, like making cold-brew coffee in the summer, having informal after-work happy hours, random karaoke parties, sometimes having a teddy bear do my work for me… They don’t have to do any of this stuff, but it’s all these small interactions that keep me going and make office life fun.

Just remember that with any community, you only get as much as much as you give. It wasn’t until I started going regularly and making an effort to attend Workbar events that I started seeing the value of the co-working space. Simply just dropping in once a week just wasn’t enough.

4. Get out of the house.

Without a commute or a mandatory office, my morning “get out of the house” routine is critical to maintaining my sanity. Every morning I take a full hour to eat breakfast, listen to podcasts, putz around the kitchen, and get dressed. And then I have to leave the house to work — whether it’s a walk to a coffee shop or to my co-working space.

I won’t open the laptop before I leave, otherwise I will get sucked in, and the next thing I know it will be 6 p.m. and I haven’t left my apartment or seen anyone else. Don’t get lazy about your “get out of the house” routine — it’s happened to me a few times and I absolutely hated it, and I was drained and bummed at the end of the day. And poor Emily, she had to come home to a stir-crazy roommate.

5. Go offline. I’m serious. 

Working remotely, you’ll quickly start to notice that your entire life will revolve around your laptop. Instead of chit chatting with your colleague at your desk, the conversation will be entirely through direct messages. Instead of brainstorming in a meeting room, it will be through video and text chat. Instead of watercooler chats in the hallway, there will be a Slack channel named watercooler.

The problem with all of this laptop-based communication is that you are quietly living in your head all day long. As an extrovert, not only does this drive me crazy, but it’s exhausting. Processing information over text is so much harder for me than processing a face-to-face conversation. So, in your off-hours, it’s super important to go offline, give your brain a break, and get out of your head. Put your phone away, go out to dinner, go see a show, go see a movie, go to a bar, go be social in an offline kind of way. It’s important for your sanity. And when you go on vacation, leave your laptop behind. Really.

6. Recognizing non-social cues of affirmation.

Social cues of affirmation are really important to an extrovert. Little things like a smile, nod, laughter, hug, a hello in the hallway, a random joke — all of these cues tell an extrovert that they are accepted into the community and are doing okay.

Those cues don’t exist in a distributed environment, and, depending on how much feedback your colleagues tend to give, there might not be a whole lot of “good job!” messages floating around your chat room. For a long time, I was convinced I was terrible at my job, until I realized that I wasn’t registering cues of affirmation, or positive feedback, because they were being expressed in a way I wasn’t used to. I know it sounds ridiculous, but someone saying “good job!” on text chat didn’t register in my brain as much as someone saying “good job!” to me in person.

Failing to internalize accomplishments can lead to something called “Imposter Syndrome,” a fear that you don’t deserve to be part of the group because you were hired or invited by accident. My colleague Allen blogged about this, and this sentence in his post really stood out to me:

… months after starting, I still feared that any day might be the day I finally “got caught” and that I “didn’t belong.”

Feeling like you “belong” to an organization or a team of people while working remotely is exceedingly difficult. You don’t get peripheral, contextual workplace chatter that helps you settle in and get to know your co-workers – the hallway conversations, the chit chat about weather, the random “Nice haircut!” comment (online that becomes, “Nice new avatar!”). You also don’t get non-verbal cues of affirmation – eye-contact, a smile, a nod. This is tough for everyone, and it’s even harder if you’re an extrovert who requires that sort of communication to keep you going.

I don’t have an easy answer to this other than to make sure you recognize what you need to feel good about your job and your team, whether it’s more video calls, more travel to see your teammates, or training yourself to adjust to different types of affirmation. Either way, just be sure to keep an eye on how you’re feeling about work and why, because it will help you figure out ways to be successful at your job. That’s actually true for any job, extrovert or introvert, remote or not.

At the end of the day, I love working remotely because there’s an incredible amount of autonomy to tailor a work environment that works specifically for you. That’s a lot harder than simply adapting to a pre-existing office environment, and it requires a lot of trial and error (hey, it’s two years and I’m still working on it). But, in finding a solution that works for you, you’ll learn a ton about what makes you successful. Not only will your productivity skyrocket, but it will make your day-to-day work a heck of a lot more rewarding.

p.s. If you want even more excellent advice on working remotely, check out my colleague Sara’s post on “10 Lessons from 4 Years Working Remotely at Automattic.”