12 May 2020

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2013 Marissa Mayer bans work-from-home at Yahoo
2020 Jack Dorsey permanently institutionalizes work-from-home at Twitter.

Working remotely: not just for COVID-19 anymore.

From academia to the Open Source movement, remote collaboration is not exactly novel. From Github to DuckDuckGo, remote-first successful businesses are no longer rare.

Remote work occupied the cultural relevance of something those whiz kids do, working on a beach in Thailand. Until today.

Actually, we took this photo in Vietnam. Hi Luka!

What has prevented remote work adoption?

  1. Inertia. I have a job and a system that “works” for me. Don’t change what isn’t broken.
  2. Status. I have a “real job” at a “real company.” Working remote is for weirdos and loners.
  3. Productivity. Real decisions happen in elevators on the way to lunch. We know how to be efficient and innovative in-person. How the hell do you build a team remotely?

COVID-19 addressed inertia. Twitter, a Legitimate Tech Company™️, addressed status. Productivity is still pretty hit-or-miss, but it’s early days yet.

Trust me, I’m an expert guinea pig

I came to the Bay Area like a moth to the flame of start-ups after college.

Lacking an H-1B, I left in 2014, and started Hacker Paradise, a boutique travel business catered to remote workers. During that time, I worked remotely as a software engineer for an SF client for over a year.

In 2016, I came back to San Francisco. I did it for the same reason I came in the first place - the quality of the jobs and the community.

I don’t love working remotely. I miss the energy I get from a well-run office environment. COVID-19 has taught me that I’m an extrovert, and shelter-in-place has sucked.

And yet.

Reality is that which, when you stop believing in it, doesn’t go away

- Philip K. Dick.


1. Remote work is about to do to San Francisco what San Francisco did to the South Bay.

Techies have been leaving San Francisco for cities like Portland, Austin, Denver and Seattle (PADS) for over a decade. We seek a place to settle down and improve cost-to-quality-of-life ratio.

This is how you know they appreciate us.

As it becomes easier than ever to keep your job while moving, this trend will pick up. The microkitchens at Twitter are nice, but not “an extra $2k/mo in rent” nice.

As ambitious millennials realize they can optimize for quality of life, expect businesses like Culdesac and Hacker Paradise (see what I did there) to blossom.

San Francisco will neither be abandoned quickly nor completely. It’ll retain a “city emeritus” status, like London, Philadelphia or Palo Alto.

2. We’re going to learn to run remote organizations.

We are, as an industry, pretty clueless at remote company building.

In fairness, we’re not even that good at regular company building. We just figured out 1:1s were a good idea and are still deciding who dotted-lines to whom in the matrix org structure.

You can’t just slap “remote friendly” on your jobs page and decide you’ve done a “heck of a job.”

Should team sizes change? How to you measure and manage morale? What about onboarding and knowledge sharing?

There’s some knowledge to be gleaned from the Basecamp folks; they wrote a book about remote work. That book is the COBOL of remote work; it works, but we can do better.

3. We’re about to enter a renaissance in remote collaboration tooling.

Slack is doing phenomenally well during COVID-19, but it still kind of sucks, right? At least when people emailed you, they didn’t expect a response right away. Etiquette around Slack usage is still pretty immature, am I right @channel?

Also. Software engineers use Github, and it’s a pretty mature way to collaborate on shared work. Every other industry is still sending around Presentation Final Final [2].pdf. Some of my favorite former co-workers are building companies in this space. expect more businesses like Figma and Loom to blossom.

PS. You’re wrong, Alexey. Offices are here to stay.

That’s true. They will.

We tend to overestimate the effect of a technology in the short run and underestimate the effect in the long run

- Amara’s Law

The move to remote-as-mainstream-option will take a good decade or two. The inflection point, however, was today, on May 12, 2020.

I for one look forward to kids asking what it was like when I had to leave for work every day.

Tags: #remote work #productivity