Rebuilding Digital Relationships

The power of friendly non-transactional connections

February 29th, 2024

It’s funny how what’s old can be new again.

When I was thinking about the topic of digital relationships, I thought of a funny juxtaposition. The rest of the world seems to be catching up to how techies have communicated for decades. And in return, the way regular civilians are using tech are helping techies to humanize their own circles.

There’s an interesting boomerang of communication tools and patterns between two usually distinct cultures: nerds and normies.

The Great Flip

It seems like ages ago that my work involved going into an office and collaborating with people in real life. I’ve been working from home on fully distributed remote-only teams since the pandemic started. A handful of years later and this is all the new normal. The routines feel like muscle memory.

The omnipresent thrumming of Slack, Zoom and gCal has replaced the footsteps and voices in the hall between conference rooms. Focused alone time with Figma now comes with snoring little dogs as a soundtrack, instead of whatever loud repetitive techno I needed to block out idle chatter from coworkers.

When I step back to compare working life in both scenarios, it’s easy to see a flip in the ratios of interaction types:

  • Pre-pandemic, at least 90% of my most important communication and collaboration was face-to-face, with the digital tools filling in the last 10% as a sort of glue.
  • Now it’s the other way around, working on teams where digital tools take at least 90% of the interactions and there might be an occasional 5-10% of real life component that acts as a social mortar between the bricks of work.

What occurred to me only recently is how much the latter feels exactly like how I made friends in the early days of my career.

Back during the heyday of blogging, user groups and the explosion of both the commercial and non-commercial web, you’d follow plenty of people online and get to know them through their writing, forums, mailing lists and the like. Then occasionally you’d be lucky enough to meet them in person at a local meeting or big industry conference. Then it’s back to the digital spaces to the maintain and deepen those relationships.

Digital relationships that were 90% online, with a crucial 10% in person.

Now, it’s like a good chunk of the world took an intensive course on online communication in the last 4+ years and decided that well what do you know? Those geeks were on to something.

I’m glad they came around.

I’m not saying remote work is perfect but holy hell did I use to daydream about the kinds of focus and convenience that I take for granted now. I spent 15 years riding the San Francisco startup rollercoaster and loved it immensely, but it used to kill me that so much of my work there was so inefficient. It got harder and harder to ignore the irony of creating tools and services to help people around the world run their businesses, all while crammed together like a pool of typing secretaries from Mad Men.

Still shot from the TV show Mad Men, depicting a row of secretaries working at their desks.
Open office = productivity nightmare

But once Zoom became as ubiquitous as email for our daily work, the change didn’t stop there. It ricocheted right through the office and back into our social spaces, exactly like the way geeks used tech to blur the lines between work and play.

Normies started Zooming for fun. They took the digital relationship-making tools from work out into their private spaces.


Just before the pandemic started, I reconnected with a theater buddy from my college years that now works in entertainment in LA. He welcomed me into his circle of other theater geeks and movie buffs and we all fought the cabin fever of the lockdowns together. We did weekly Zoom parties to watch TV and movies, staying up late for premieres of shows like Wandavision and The Mandalorian. In between seasons, we did an epic full rewatch of the entire MCU movie library. Plus there were the occasional game nights too.

All that time spent together turned into ongoing digital relationships to this day. The friends-of-friends eventually became my friends too as we all got to know each other’s quirks, interests and senses of humor. I followed along with their podcasts and even made a few guest appearances, first with a Q&A interview and then in a group panel about Dune.

In fact I’m hoping we can do another Dune show again before the next movie. I read all seven of the books in the original arc and totally loved them.

Those digital relationships bled over into the real world too, as we got annual passes to Disneyland (a great spot to practice photography) and went to movie premieres.

This would’ve sounded so far-fetched before. We even had complicated words for it like “video teleconference” that sounded about as inviting as an accountant’s convention. The idea that you’d try to use a complicated enterprise app like Webex just to say hi to a few friends sounds like a setup for one of those old Mac vs PC ads. I can almost picture John Hodgman doing a bit about how piecharts and spreadsheets can capture the essence of a family vacation on a tropical isle.

Now all that has been brushed away. My elderly mom uses Zoom to sit in on painting classes at the local community college and never once needed to ask for my help in getting set up.

My mom’s an artist and a life-long learner. She’s taken art classes for decades. Her friend circle is almost exclusively through these meaningful connections.

Now I wouldn’t be surprised if 90% of her interactions are through Zoom. Whether it’s taking a guitar class, getting a guided tour through a museum, learning a new illustration style or what have you, these digital relationships are as real as any other she’s had.

Full Circle

And here’s the kicker, the last boomerang.

Once people started using these tools in this way and normalized the use of work apps for social occasions, that fun spirit worked it’s way back to exactly the same types of tinkering web creatives that made me first fall in love with tech in the first place.

The Homebrew Website Club was my first gateway drug to the larger IndieWeb community and is still my favorite part of it. Meeting new people regularly over Zoom and even occasionally locally is the crucial 10% that humanizes all of the remaining 90%. Busy IRC chats, immensely comprehensive wikis, active Mastodon conversations, following each other’s blogs… it all feels like the 90’s and early 2000’s again.

What I love most about that is that I didn’t realize how much of that maker’s spirit was missing in my life, how much the intrinsic fuel of personal web sandboxes was getting used up at work, until these communities became a regular part of my social life the last few months.

I stopped going to user groups ages ago. Understandably so – I got sucked into the hamster wheel of startups, first as an early employee and then a founder. It’s draining for the same reason it’s so exciting: it takes everything you have. Being entrepreneurial is a double-edged sword in that way. Every hard skill, soft network connection and drop of energy gets fed into the machine.

This is getting a bit confessional, but I just didn’t make time for the kinds of friendships that got me into this racket in the first place. The in-person nature of meeting up felt like too big a commitment. If there was a choice between an industry event or unplugging completely from the tech scene, I chose the latter almost every time, for years in a row.

Until digital relationships outside of work became as fun and easy as firing up a Zoom. That’s the boomerang that I’m grateful for.

Speaking of IndieWeb…

This post is my first time making an entry for the IndieWeb Carnival, a monthly writing prompt for bloggers and online creators. February’s topic is “Digital Relationships” and is hosted by Manuel Moreale - read his kickoff post here.