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Lessons Learned from the First Writing Retreat Sampler

I held the first Writing Retreat Sampler on February 27th and 28th. The idea sprung up from a conversation I had with one of my brothers in October. The Writing Retreat Directory website was still in the works and I was excited to start connecting writers and writing retreat hosts.

Without a website or an email list, just one contact in the writing retreat space, and a total of 107 followers total across Facebook, Twitter, and Instagram, though, I wasn’t sure what I could realistically do.

In a conversation about the future Writing Retreat Directory with my one writing retreat contact, Kent Sanders, he mentioned people hosting virtual summits to build an audience and get to know people in the industry.

When I floated the idea of a virtual summit aimed at writing retreat hosts by my brother on that October day, he suggested a twist. What if instead, I hosted an event where writers could learn more about writing retreats directly from the hosts.

I thought that was a brilliant idea, so right after we hung up I bought the domain for and searched the internet for online virtual events. I came across Summit In A Box, that shows you how to create and host a virtual summit.

The model wasn’t a perfect match for what I wanted, but the program gave me all of the templates, swipe copy, and detailed instructions to host a virtual event, so I used that as my baseline and made adjustments.

Getting Event Speakers

Kent agreed to present his next writing retreat. I was hoping to get between 8 and 10 speakers for the event, so locking in one felt like a huge step forward.

Since I had no other connections to ask, I searched online for any writing retreat coming up in 2023 and cold pitched the hosts through email, social media DMs, and their website contact pages.

It never crossed my mind that I couldn’t do this. Of course, I had moments of “what did I get myself into?” but once I committed to the idea I knew I’d see it through even if only a few writing retreat hosts took a chance on me.

However, I was pleasantly surprised to get positive responses and within a month I had eleven writing retreat hosts willing to prerecord a presentation/interview and commit to being available during the chat when their presentation would air in February.

What Went Well

  1. Getting wonderful writing retreat hosts to be a part of this. Many of them have won writing awards, are adjunct professors at universities, on the boards of writing related nonprofits, and highly engaged in the writing community, so having them at my first event relieved a lot of anxiety.
  2. Many people, some who I just met, helped me promote the event on their own social media and email newsletters. Everyone was generous with their time to help get this new concept off the ground.
  3. The website, graphic, and swipe copy templates as well as the detailed plan that came with the Summit in a Box program was invaluable to putting this together by myself. It was a lot of work, but I never had to guess at what needed to be done.
  4. I ended up with 81 people registering. And after the event, only three people unsubscribed from my email list.
  5. The positive reactions from both writing retreat hosts and writers for this is new concept helped overcome any nerves I had about hosting a Writing Retreat Sampler. I heard phrases like “fills a void,” “so needed in the writing community,” and “I had no idea the writing retreat I needed was out there.”

What I Didn’t Like

  1. Although the Summit in a Box model was helpful for the first iteration, I didn’t like the prerecorded videos with the live chat box for questions during the “air” time. It was so impersonal and not the vibe I wanted when connecting writers and writing retreat hosts.
  2. Waiting for the scheduled air time for each presentation was a bit confusing. If you got to the presenter’s webpage too early, you had to remember to refresh the page at the scheduled time to view the video.
  3. Since people played the video once they arrived on the page, everyone was looking at them at different times. There was no shared experience.
  4. People asked questions and comments in the chat boxes, but without some verbal prompting, I think people weren’t as engaged as they would be at a live event.
  5. In the Virtual Summit model, videos are only accessible for 48 hours to encourage attendees to purchase an All-Access Pass (AAP) for a small fee to access them for longer. They also get great bonuses in the AAP, so the value was there, but I hated cutting off access to those who didn’t pay.

What I’m Doing Differently Next Time

I still believe 100% in this concept of writing retreat hosts presenting their retreats virtually and giving writers tips and ideas on making the most of one, but I’m ditching the prerecorded model.

Here’s the rough plan going forward:

  • Live presentations on 1st (8:30am US EDT) and 3rd Wednesdays (3:00pm US EDT) of every month to catch different time zones. Starting in June.
  • Continue with the interview-style presentations, but have the guests control the slides.
  • 20-minute presentations with the same info as the first Sampler: helpful tips for writers, benefits of a retreat, info on the retreat, walk through of first day, and how to keep momentum after back home.
  • Chat will be open throughout the presentation for people to comment
  • 30-minute Q&A 
  • Ask businesses who cater to writers to pay to sponsor episodes
  • Post videos and transcripts to Writing Retreat Sampler blog and on YouTube for greater reach
  • Post audio as a podcast for greater reach

Since I’m set on making the experience for the attendees, speakers, and sponsors as great as possible, I’m exploring a variety of virtual event platforms. I’m leaning towards Airmeet, which I think is going to be amazing. I’ll post more about that after I have a demo next week.

Right now, I have a landing page where people can sign up to be notified when registration opens for the next Writing Retreat Sampler event.