Organizing Developer Writing Retreats

One of my biggest and scariest projects of 2022 was co-organizing the first-ever DEV | WRITERS | RETREAT in Miami!

• I’ve been an admirer of the Writing Excuses community for a while, and how they primarily serve their community as a podcast but every so often bring people together for the Writing Excuses Retreats.
• I’d also been accumulating “How to Write” style notes for v2 of my book (subscribers only link) for the past 2 years and realized I needed a push to get it out, and probably that the pressure of organizing a writing retreat would both set a deadline and provide valuable feedback.

TL;DR: This post is a brief recount/review of my experience co-organizing the first DEV | WRITERS | RETREAT in Miami, sharing lessons and opening up for others who might be interested in doing the same for their own circles (I’ll help you!).

2023 Update

The sizzle reel for the writing retreat is now live!

Superfans can find the playlist of the all the workshops if you know where to look.

The Magic of Writing Retreats

I noticed that:

• Developers routinely talk about the importance of writing to their careers, and
• the regular writing world regularly improves their craft through writing retreats…
• …But developers do not.

This seemed like an inefficiency and I realized that if developer writing retreats were ever to be a thing, I would probably be one of the few people to try leading one to produce proof-of-viability.

My hypothesis was that a writing retreat would provide one or more of these services for attendees:

• Time to focus on writing and writing alone
• Ephemeral, curated, in-person community of fellow writers
• Break routine (from normal environment, calendar, etc) to do something new
• Consecutive days of immersion to start a writing habit
• Exposure to new techniques and ideas
• Official excuse to take time off work to write (as in regular writing retreats, attendees often sign up for retreats but miss all the workshop and social programming to do their own thing)

Challenges

I had just come off a streak of manifesting meetups in NY, SF, and London this year, and was looking to showcase Miami to more folks during the cold winter months. But I knew I needed a partner to help with organizing, so my first port of call was to Michelle who pulled off a fantastic React Miami in April. She said yes, we picked a date 3 months out (yes a tight timeline! but we wanted to do it before Thanksgiving) and announced it with a lu.ma waitlist:

The format we landed on was as stated on the invite:

​Each day from Monday to Thursday, we will follow a semi-structured program:

​Morning: Talks, workshops, brainstorms (full schedule coming soon!)

​Afternoon: Free (for focused writing or remote work, up to you!)

​Monday: Goal setting, inspiration, aspiration
Tuesday: Topic choice + Formats
Wednesday: Editing + Craftsmanship
Thursday: Marketing your Work + Tactics

​Friday is graduation day - a mass publish event and an Unconference where we share what we worked on, what we learned, and what's next.

We figured the morning on/afternoon off format would give people flexibility in the afternoon if they had to work remote, or if they wanted to just write, while providing enough content in the mornings that people could learn and discuss something in a more formal setting. Friday we figured would open up for a freestyling Unconference, which has fallen out of style in recent years but we had seen be successful enough to want to try for our group (Jeremy Howard also recently held an Unconference in Brisbane for the Fast.ai group if you want to use his format).

I also guesstimated (correctly) that November would be a period when people would be looking to catch up on their writing and have some education budget leftover.

Costs

The hardest part was estimating costs.

• The nature of all in person events is that the organizers take a massive financial commitment upfront with no real knowledge of what attendance will be like (particularly for a first instance of an event)
  • The commitment is not even fixed - venues are step function changes where if attendance goes beyond a certain amount you have to book a totally different space!
  • Venue choice was an interesting subproblem in itself as you are optimizing for attractiveness, suitability for writing and workshops (Wifi, A/C, etc), proximity to other interesting locations, and of course costs.
• On top of that, you have to pick pricing upfront, but pricing will be inversely correlated with ticket sales, with a totally unknown price elasticity
  • To make things more fun, most ticket sales will be last minute, somewhat mitigated by early/late bird pricing

So in the interest of helping others do event planning in future, here were the rough budget splits for our 22 person Writing Retreat + 52 person Unconference:

• venue + food: $14k (hotels come with an annoying minimum food spend per each venue)
• swag + signage + materials + organizer expenses: $2k

We were standing by for extra Accessibility and AV expenses if needed but we ended up not needing them. Ticket sales ($500 for the 5-day full retreat, $100 for the 1-day Unconference) + sponsorships from Hashnode and Third Web (thanks to prior work/contacts) ended up covering most of it and I covered the small shortfall (making a profit was a non-goal).

For the future organizer: We’ll review lessons on costs and venue down below, but in case you’re worried, I do believe you can significantly bring costs down from where we had it.

Marketing

Once we were announced, we were committed and had to do marketing. The venue somewhat sold itself, Michelle’s and my prior event work built some trust, I managed to personally invite two dream attendees Philip Kiely of Writing For Software Devs and Monica Lent of Blogging For Devs with their own following, and finally some of our own attendees kindly spread the word for us after booking their tickets.

Part of our goal was also to help build up the Miami tech scene, so Michelle also did an interview with Refresh Miami and reached out to local student contacts and tech companies. Ultimately these weren’t as successful as we hoped but fortunately our online reach was sufficient for us to not really have to worry about the marketing side of things (though it felt a lot shakier going thru it than it does now typing this).

For the future organizer: Marketing is important, but know that there are many people who are keen to help you even if they personally can’t attend (like me!). Building your way up from organizing smaller meetups can help, but also getting a partner like Michelle with large event (400-800 people) experience can help make up for your lack of organizational expertise (or credibility for that matter).

Content

The part that was my sole responsibility was the workshop content. I’ve done 2-4 hour workshops before on technical topics for groups of 20-50, but this would be my first time teaching on writing for 2-4 hours a day for 4 straight days 😱 .

For the future organizer: If you are reading this looking to organize a writing retreat, this might scare you, but you should know that this is also optional. There are writing retreats that have no “content” whatsoever, and leading the retreat just means communicating what the common schedule is and facilitating discussions.

Part of what helped with the impostor syndrome was the framing of this thing as a “retreat” rather than a “workshop”. I would be a draw and an authority people can lean on, but far from the final word on things, and people could work on things their way if they wanted and still be a success.

Still I wanted to give it my best shot. I set a daily theme, and came up with prereadings and exercises for each day. That’s really it (well we also came up with extra topics on AI writing, conference speaking, and hiring virtual assistants! based on attendee interest)

You can see all the exercises and reads on @Nutlope’s repo: https://github.com/Nutlope/devwriting

(but unfortunately for you and beneficially for attendees, the exercises were definitely more fun and interactive in person! Probably my best decision was to kick off the retreat with “flash writing exercises” and no preamble, and then later on to doing interactive quizzes, which I think everyone liked.)

The point of the Unconference was that the attendees would come up with their own topics or go deeper on anything we had done during the week, so I was “off” on the Friday though I still made a point to bounce around if people wanted my input. Fortunately there were attendees like Mark who ended up just leading his own impromptu sessions on open source :)

Outcomes

We did an optional post retreat survey of attendees and there were a lot of learnings, but I am most proud of this:

The qualitative responses were also great:

I was also happy that some attendees got started with their first blogs ever (on Hashnode!), others pumped out half a dozen in a week, and yet others overcame very specific challenges they were running into at work (too many to shout out, but peek the #devwriters hashtag on Twitter).

We also hung out for a bunch of social stuff in and around Miami which is perhaps the intangible part of the retreat :)

My colleague Justin kindly volunteered to record all the sessions and so we hope to have some form of video recording up for attendees.

Misc Lessons for Future Organizers

From a mix of survey feedback and personal reflection:

• Venue choice: This is the biggest lever for costs. We chose to go big and splashy in Miami Beach which was pretty much the highest cost decision you could make. Wifi and food were good, and people enjoyed the retreat-ey vibe, and the open air cabanas helped with Covid concerns, but there was unforeseen construction and background music that proved to be very distracting during the workshops. I made pains to point out the many quieter areas in the hotel that people could work, but almost no-one took advantage of them and just stayed where we met. I still don’t know if it was a mistake, as some folks would definitely have enjoyed this over an indoor environment that they might have at home/work, but I do know that the choice of venue directly led to the $500 ticket price and having to stress out about getting sponsors. If we had just booked a large Airbnb for like $4k instead, that would have completely realigned our economics at the cost of slightly less awesome photos.
• Communication: Multiple people called out that I only opened up the Discord and sent the pre-readings the weekend before the retreat. People need time to chat and coordinate and get situated, and I kept things to the last minute out of a combination of busyness and indecision and procrastination. So… next time give it 2-4 weeks (more if you want people to coordinate travel and activities together).
• Expectations: Related to the above
  • people were unsure about whether to have started a blog prior to arriving (something I simply assumed everyone would have or could easily set up)
  • people were unsure about whether they should have prepared stuff for me to review and give 1:1 feedback
  • people were unsure about whether or not they should be working on 1 broader piece throughout the week (they were, but I didn’t do a good enough job of saying so often enough)
  • A couple of technical writers wanted to see other forms of writing, whereas I am (evidently) very content-marketing/thought-leadery heavy. I agree these are important but also covering all kinds of developer writing in one week would probably spread time too thin and not allow enough depth; so just set the expectation of what kind of writing will be featured and everyone will be aligned.
  • let’s call this “Company sponsorship eligibility” - quote

    “we had different expectations e.g vacation vs bootcamp. It would’ve been helpful to know how serious it was and how much content we were going to deliver. My company may have been interested in sponsoring my trip if I’d described it as more structured.”

• Assigned Peer Review Buddies: People wanted more structure for their afternoon free sessions.

  “I had expected more peer review in the afternoon…a lot of us just kind of wandered off. Maybe more explicit like here are two peer review buddies, sync either face-to-face now or offline to make a review plan.” I actually avoided this because I feared that a mismatch in a buddy system would cause a poor experience for attendees. I think this could have been mitigated if I asked for a smaller group of people opting-in for afternoon peer reviews and then rotating them around each day.

• Improving Relevance of Workshop Exercises:

  ""Start a newsletter” is not a great CTA as it is way too big of an investment to make on a whim. Starting a newsletter is easy, maintaining it is hard. I think a content calendar exercise would be much more effective.”

  “I would have liked if the titles were more focused on topics that we would actually publish as part of our jobs vs. general interest.”

  “The writing genres that we learned most about seemed very promotional. It might be interesting to have a little more focus on other types of writing we often do, such as technical writing, corporate comms, etc.”

• Guest Speakers/Attendees: I had about 6 people holding their own and talking about their areas of expertise at some point in the week. People LOVED these as they get leverage from being in the community of multiple experts rather than just hearing my crappy voice all the time. Recommend actively looking for these folks and making space for them where possible.
• Social: You as the organizer and workshop leader do -NOT- have to stay out each night with the attendees. Everyone will understand if you need to turn in early to prep for the next day or simply recharge.

On a personal angle, perhaps the hardest part of organizing was juggling this with my day job. My team and I gained responsibility on two major projects that I hadn’t anticipated when embarking on this retreat in June/July, and most importantly it meant that we would be running our company conference (virtual, not in person) just 3 weeks after the writing retreat, with all the requisite speaker and marketing prework. That was quite stressful and definitely could have been planned better but shit always happens and you just roll with it (it gets easier over time).

Any other questions I can answer for you? Toss them into the comments below :)

But most importantly YOU can host one too!

As for the post-retreat wrapup, Michelle and I met once more to go through every item of the survey responses, settle the retreat finances and discuss future plans. The biggest question was “will we do this again?” We were both interested but with major changes possibly coming in 2023 we could not commit to a Miami date yet (though I love the play of getting everyone to come someplace warm while it’s cold). I’ll definitely host one again at some point, perhaps with an online component for broader accessibility.

I got interest from friends on doing London and Bali versions of Dev Writers Retreat, but I don’t think I could host them all - it’d be terrible for the planet, and it’d take a bunch of time away from other things I want to do in 2023 (I’m not aiming to be a writing influencer!).

Still, writing retreats are awesome. As you can tell, they are challenging to pull off, but it was definitely one of the projects I’m proudest of in 2022 because it stretched me in so many ways, and benefited others as well.

Now that Dev|Writers|Retreat has demonstrated proof-of-viability, I write all this in the hopes that -YOU- could host one! I’ve laid out the blueprint for you here, and of course you can tweak and adjust to your needs!