Reflections on running a weekend retreat

First published:

At the start of this month I co-organised Saddle Point, a three-night & 30-person retreat. (Duncan, my co-organiser, reviewed this post before I published it, but all opinions are mine alone.) Overall, things were a success! Average satisfaction was 8/10; no participant thought they would have preferred to do their counterfactual activity instead; the median willingness to pay was 50% higher than the price (£300 vs £200); we generated around £10,000 of surplus (excluding costs of organiser time).

When preparing for the weekend, I tried searching for blog posts about what running a retreat is like, but couldn’t find much that was relevant. I’m hoping that this somewhat fills the gap – it’s a mixture of practical details about the way we did things, personal reflections on how the experience differed from my expectations, and what I’d change next time. You can also read a Claude-written summary of the anonymous feedback we received after the event here (we managed to get a 93% response rate, mostly thanks to individually messaging people who we thought hadn’t filled it out) – it’s interesting to see which aspects were criticised in both directions (e.g. too much & too little structure, price too low & too high).

Outside of the weekend of Saddle Point itself, organising was actually quite a bit easier than I was expecting – I estimate that I spent around 15 hours total working on it pre- and post-event, and we were in a position to start accepting applications only five days after I first had the idea (which was six weeks before the weekend took place).

If you’re considering organising a retreat or other event like Saddle Point, I’d be more than happy to chat, so do feel free to reach out! Kristi has put together a very handy list of things to bear in mind – and look into getting event liability insurance too.

Advertising, applications, attendee diversity

Communication and structure

Culture

Observations from during the retreat

Food

Venue and equipment

Activities

How it felt

All of that said, I am glad that I organised Saddle Point. It feels extremely gratifying to know that without me taking the initiative and putting things in motion, none of it would’ve happened. I really like being busy, especially when what I’m doing seems valuable, which the positive feedback helped a lot with.

Other changes for a future iteration