Remote Extrovert

I’ve worked from home for over ten years. I started working this way out of necessity, eventually preference, then both. The first thing I noticed was how utterly lonely I felt. Conflicting emotions are my specialty. So, while I was so grateful to be able to make this transition a reality, I couldn’t help but mourn the loss of real” human interaction. The interactions that, for the most part, I found very fulfilling and energizing.

The concept of a contractor feeling lonely doesn’t generally surprise anyone, and this is how I got started. Since I’m well aware of the harmful impact isolation can have on me, I quickly set out to try and figure out how to make this doable. I got an office out of the house. But the office building was more silent than a library. I suppose this may be why some people chose it, but there were no events, no chatting in the halls, nothing. It was like showing up at a storage facility each day, waiting for inspiration and friends to manifest.

I tried some events, but they were all so rooted in traditional networking that I felt out of place, exhausted, and empty–not at all what I was looking for. Eventually, I stopped leaving the house and began to assume this loneliness was just part of it, and I had to try to suck it up and keep working. I kept working on contracts, keeping my head down, and getting by. I didn’t understand how to translate what I needed into a remote context, so I settled into a mindset that it didn’t exist. I needed to learn to ignore this innate need.

Eventually, I signed up for CodePen to experiment with some new CSS stuff I was learning. I was having fun with this work in itself, but this thing happened when I was working in the open. Eventually, people started reaching out. We were talking! They were down-to-earth! We were helping each other and really rooting for each other! We were learning together! This was when I gained insight into the idea of non business-bear online communities, spaces that had more substance and direct interaction than social media but also not as intimidating as trying to openly exist on Reddit. I met someone through CodePen all those years ago who is now also in Wiggle Work today. That’s very powerful and longer than any in-office friendship I’ve had.

Once I started working as a full-time employee at a startup, I thought this would all get easier and even better. I mean, these are super cool, in-the-know people, and I’m sure if anyone can make a remote work environment feel warm and welcoming, it’s them–they are well-funded, smart, and know all the right words so far. And, of course, I was hilariously wrong. Through this experience, I learned one of the most essential things about remote human connection: everything has to be more deliberately crafted and nurtured than when in person. Nothing can be left to happen organically, especially in the beginning stages.

Tone is more challenging to decipher. Reading” a remote room” takes a different level of insight and abilities than reading a room irl. Adding a Giphy bot to Slack (or whatever the big thing was at the time) and calling it a day is not community, and it’s not work culture. It’s lazy, shortsighted, and ignorant. Here, I initiated coffee chats on Fridays. We’d chat about non-work stuff and show off our favorite mugs. People even bought unique mugs for these occasions. More people joined each week. I set up what was somehow the first instance of video call-based one-on-ones to get a sense of how each person was doing but also who they are.

Choosing video calls over Slack was a rare thing until then, and it made a huge difference in everyone feeling closer. Eventually, we started setting up these calls to talk work stuff out, too, over just typing at each other all day through avatars, where gaps in communication and misunderstandings happened more easily. We got more comfortable with each other, understood each other better, and appreciated each other more–we felt less lonely, more invested, and less likely to default to frustration. I learned that occasional face-time is essential for me to experience the level of connection I was looking for.

I had been making great progress in fulfilling my itch for remote friendships and interactions, but it still wasn’t quite enough. I tried out different events and communities again, mostly learning more about what I didn’t want than finding the right fit. There was a heavy, disingenuous tone to much of what was out there. When I eventually started Ela Conf, I brought these lessons and observations to how we conducted our events and managed our Slack channel, and it made a profound difference.

From a code of conduct that we actually enforced to regular events and intentional space for daily discussion, I had finally found the space I had been looking for all this time. We talked shop, but we also talked about our weekends. We shared struggles and successes and were always quick to want to genuinely help one another. It was like finally finding a space to belong, finally finding my people.” I had helped create the very thing I had thought I would have to accept didn’t exist and wasn’t possible. I was happier and did better work. I now had things to look forward to, people to check in on about kids’ soccer games, and new people to get to know. There was a lot of nothing to talk about with friends, which is everything.

While Ela Conf didn’t last forever, it wasn’t from a lack of sincere and friendly engagement. Again, I took what I learned from this experience and applied it to my next effort: the move from Twitter to Mastodon and to where I now happily spend all my time, Wiggle Work. Wiggle Work was built on the insight I had to gather the hard way. It’s small, cozy, very approachable, genuine, fun, smart, delightfully weird. What you’ll find here are friends that provide a sense of hope and recharging. You can laugh here, vent here, ask for help, or offer help here. What you won’t find here are empty link-dropping bombs, tech celebrity worship, and a sense of competition. This is by design. Now I have truly found a place to belong.

Working remotely doesn’t have to be isolating if you don’t want it to be. There are good, real communities out there, and companies should be hiring the right people to create these necessary experiences instead of defaulting to ramblings about remote not working. These things take thoughtfulness, attention to detail, empathy, strategy, observation, flexibility, and deliberate action. Anyone saying remote setups fail because of a lack of team bonding or isolation doesn’t want to do this work. I’m glad I didn’t give up since the payoff of these efforts has been immeasurable, professionally and personally.

See you tomorrow over breakfast.

February 14, 2024

A tiny project byJoni Trythall inspired by friends at Wiggle Work.