Jacob Kaplan-Moss

Coworking With a Friend to Write More

This post was co-written by Sumana Harihareswara, and you’ll understand why in just a moment.

In the early years of this blog, I wrote a fair bit. That started to trail off around 2009, and by 2012 I only managed two posts that year. In 2013 I wrote about wanting to write more but that didn’t happen: I averaged less than half a dozen posts per year from 2013 - 2020.

You may have noticed that changed this year: I’m publishing about twice a week on average, including a week when I posted a substantial article each day.

What changed?

In early January, I started regular co-working sessions with a friend, Sumana Harihareswara. She read that post from 2013 about wanting to write more, and emailed me to see if I wanted to form an accountability team to work on our writing together. She’s making progress on her book, and I’m writing more here: we’ve been able to get a lot more done together than trying to work solo and power through.

This model of coworking together on separate-but-related work has been terrifically successful and valuable. The fact that we’ve made so much progress on our goals despite the pandemic, an attempted coup, and various other personal and professional pressures shows how valuable this structure is.

I think this sort of thing is a great model for anyone who’s feeling stuck on something big and needs a bit of extra help and structure to make progress. We wanted to share details of what we’re doing to encourage other folks to give it a try.

Big picture

I’ll get the details of our structure, but from a high level the idea’s pretty simple:

  • Find a partner who also wants to make progress on something. We think someone you’re friendly with, with similar-ish goals, is best (more on that below).
  • Try it out by working together once. If that works, at the end schedule a few more sessions. If it’s still feeling good, then…
  • Agree on a regular cadence and structure for work, and explicitly block time on your calendars, maybe a few months’ worth. Almost any cadence can work, but having specific scheduled time is key.
  • On that cadence, get together and work, mostly silently, on your respective projects.
  • Regularly check in with each other on your progress, goals, and how the working-together system is working for you.

Details of our structure and process

A screenshot of our Whereby session, with both our videos and text editors shared.

Working together. I'm working on this very article.

  • We meet four times a week (weekdays except Tuesday), for an hour, 9-10 a.m.

    For us, this 9-10 am block gets the morning routine off right, with a block of productive making-stuff time.

  • Most days, our agenda is:

    • 5 minutes: catch up, share goals for the day
    • 30-45 minutes: writing silently
    • 5-10 minutes: check in how we did and talk about next steps, and sometimes chitchat about other stuff
  • Once a week (Wednesdays), we have a longer check-in where we talk about our longer-term strategy and goals. We also use this as a time to do a meta-checkin, where we talk about how the process itself is working and see if we need to make any adjustments.

  • We use video chat (Whereby).

  • We usually leave cameras and mics on even during the “work silently” part – something about hearing each other’s keyboards clacking away seems to be really nice. The ambient noise reminds me a bit of the quiet hum of a good calm coffee shop, and helps me focus.

  • We frequently screen-share our text-editors1. Whereby can show both our faces and both of our screens, which some other video sharing platforms can’t.

    A 60 minute dial timer

    Sumana's timer

  • Sumana sets a timer for the writing portion. It ticks loudly enough that I can clearly hear it through my headphones, adding to the nice ambient noise. It also buzzes quite aggressively at the end of our session. When I’ve made good progress that buzz feels like a victory air-horn to me.

  • Sometimes we collaborate more directly: Sumana sometimes proofreads my posts or suggests edits and/or new topics2.

Why this is working

In reflecting on this partnership, we think there are a few reasons this works so well:

  • Blocking out time works. Putting priorities on your calendar is a well-known “trick” for making sure you have time to work on your priorities. It works here, too: explicitly blocking four hours a week means we actually make sure we have time in the week for writing.

  • Soft pressure helps with accountability. There are days when I don’t feel like writing, but I don’t want to let Sumana down, so I show up anyway3. This pressure is mild - we’re not explicitly pressuring each other to show up, and we’ve definitely skipped a day or two when we needed to. But just this light amount of social pressure to show up for a friend really helps on those days that feel uninspiring.

  • We’re friends, with a good deal of trust in each other. This means the time spent is genuinely enjoyable, and not a chore. It also means we can easily give each other feedback, and discuss how things are going overall.

    However, we’re not coworkers in the same team/organization, so there’s far less pressure for us to use this time to catch up on work we owe each other, or be dishonest about what’s interesting or challenging right now.

    This model certainly can work within the context of a working relationship, but the dynamic would be different.

  • We have similar, but not identical, expertise. Because our knowledge overlaps substantially, we can “talk shop” – use jargon, chat about current events, discuss specific projects – without needing to get each other up to speed. Sumana can say “well, Karl writes…” without having to pause and explain to me who Karl is and why his writing matters to her work4.

    But, our work doesn’t completely overlap, which means there are genuine moments of interest and surprise. For example, when Sumana first told me about performing SWOT analyses for open source projects, I had a legit “whoa” moment. I know open source well, and I’ve used SWOT any number of times, but I’d never thought about combining the two. We know enough to follow each other’s work, but not so much that we don’t learn from each other.

    (Want to know more about SWOT analyses for open source? Check out the sample chapters from Sumana’s upcoming book!)

  • We check in about the process itself, not just our work. About once a week, we double-check with each other that the process we’re using is still working, and make adjustments if needed. Continuous improvement: it’s not just for agile software development!

Sumana agrees, and adds:

I work for myself and my schedule is very flexible, and mostly-quiet coworking is a tool I’ve loved for years. Before the pandemic, I’d often co-work for a day (informally and formally) at shared offices or with friends at our homes. Now, I have regular co-working videocall sessions with 6 friends. I haven’t tried Focusmate or other similar services which set you up with strangers for randomized sessions, but I’d predict they are not likely to give me the same sense of commitment, the shop talk benefits, and as joyful a shared sense of accomplishment when my friend and I use our time together well. Plus, these work sessions provide little regular, timeboxed checkins with people I want to stay in touch with, but aren’t as socially intense as dedicated conversation calls.

Failure modes we’ve seen

Speaking of adjustments, we’ve made a couple around some small failures we’ve observed:

  • I’ve noticed I tend to talk more during the “chat” portions. This is a common failure mode for me – not just here. I’m trying to pay attention to how much I’m speaking, and make sure to hold space for Sumana more.

    Lesson: social dynamics exist within friendships, too - pay attention to them!

  • We noticed - when working on this article! - some asymmetry in feedback: Sumana has so far given me more feedback on my work than I have on hers. Part of this is because we’re working on different things: I’m writing (relatively) short blog posts; she’s working on a book. So I have more opportunities for feedback, and that’s fine. But, also, once we realized this, we did adjust slightly (I read her sample chapters with an eye towards feedback), and it’s something we’ll be watching more closely going forward.

    Lesson: asymmetry isn’t, in and of itself, problematic – “fair” is different from “equal” – but it does represent something that has the potential to become a problem. So it’s important to check in and make sure everyone’s feeling good.

Try it yourself!

I used to go to a coffee shop when I was feeling inspired to write. That worked, but I didn’t do it frequently enough to make writing a habit. And, of course, that ended last March.

This works so much better - and is pandemic-friendly, to boot. If you’ve got priorities you’re struggling to make progress on, or a big project you want to tackle, or even just want that bit of light social pressure around a side-project or day job: why not give coworking a try? I think you’ll like it – we do!

  1. Sumana: Emacs; Jacob: VS Code. ↩︎

  2. This blog is a private GitHub repo, which Sumana has access to, so we can use PRs and issues to work together in a way that is quite comfortable for us. ↩︎

  3. Surprisingly, I find I write about the same amount regardless of whether I’m “feeling it” or not! Sometimes it even ends up seeming easier to write when I’m less inspired because I pay less attention to trying to be “good” and just write. ↩︎

  4. That’s Karl Fogel, author of Producing Open Source Software, a book that’s been terrifically influential to both of us. ↩︎