#97 How To Plan Your Self-Organized Retreat
I was in Nashville this week with two of my best friends that are entrepreneurs. We rented a house, co-worked together, cooked meals, and read Onyx Storm (the new Fourth Wing book). Only one of us finished the book, and it wasn't me, so no spoilers please. 🤣
We helped each other with our businesses, worked through challenges together, and had deep conversations that are just better in person.
I'm a HUGE fan of self-organized retreats. Don't get me wrong – I love a paid retreat with facilitated workshops. I'm even co-hosting one in May.
Personally, I like to attend 2 paid retreats per year, and a couple of self-organized ones as well. Self-organized retreats are awesome for building relationships, a looser agenda, and for keeping expenses low!
In 2023 I attended a self-organized retreat with six other creators and we still meet every two weeks as part of a mastermind. Hanging out for a few days in-person can create really special bonds in your business.
Whenever I share on my Instagram story that I'm meeting with our retreat mastermind I get two questions: (1) I'm so jealous. Can I join? and (2) How do you self-organize a retreat?
Let’s get into it –
I've done this a few times so I'm pulling together all my tips for you. If you decide to self-organize a retreat from this please share that with me! And if you have any tips you'd add, I'd love to hear them.
(1) Put your invite list together
For my 2023 group we originally had a list of ~12 people we invited. There were 4 of us that organized it, meaning we made sure we'd be able to attend and whoever else could join would be great. We chose the date and location before opening it up.
We sent them an invite email that said we were organizing a retreat, keeping it at-cost, and shared the dates and location. We kept track in a spreadsheet of our Yes/Maybe/No responses. We ended up having 7!
(2) Pick a central location
Your goal isn't to pick somewhere awesome for sightseeing, it's to find an affordable place that will have a couple great restaurants, outdoor space, and is central to everyone attending.
For one trip we chose Scranton, PA because it was driving distance for most of us, and one of our attendees was an alumni of the University there so he knew the town which was convenient.
For this past week we stayed in Franklin outside of Nashville. It had a super cute downtown area to walk around and eat at, but the Airbnb was super affordable.
(3) Write a survey
You saw this one coming right? You need to understand what everyones shared goals and interests are. For example, find out if attendees want to do workshops, mastermind sessions, co-working, etc.
It's also good to check for things like dietary restrictions or any special requirements they might have.
(4) Stay in an Airbnb
It might feel weird to stay with a bunch of internet friends in a house together, but it's the best way to maximize your time together, and I promise it's super fun.
Be picky about the Airbnb you choose and make sure everyone has a bedroom (or agree ahead of time if anyone is bunking). Make sure it has good shared space like living room spaces and big tables.
(5) Share planning responsibilities
If one person is planning then they should be compensated for that. So instead, share the responsibilities.
We had a planning meeting and volunteered for planning tasks. At our Scranton retreat, I planned a workshop for the group. One of our attendees owned choosing and booking the Airbnb.
(6) Plan to cook meals
There will definitely be a cook or two in the group. Have people raise hands to organize a meal for everyone.
This week we did 2 dinners out and 2 dinners where we cooked at the Airbnb which was super fun and affordable!
Not every meal needs to be had together, people can get items for their preferred breakfast or lunch, but its nice to organize having dinner together.
(7) Include co-work time in your agenda
Even if you're the person that would put on your out-of-office and plan to not work, there will be people that aren't able to do that.
Make sure you don't jam-pack the agenda so that you have free time where people can work or explore.
(8) Plan for meaningful discussions
One night in Scranton, we went around the living room taking turns sharing something that was a challenge for us. It ended up being a very meaningful conversation for each of us, and super vulnerable.
Building a business can be so hard and lonely and to have a chance to get feedback from others, or just talk about the daily struggles and pressure means the world.
(9) Take photos & videos
I never do a good job at this and always have regrets. Take lots of photos and video clips together – it makes for great content creation!
You can even organize a photoshoot if that is fun and aligned for your group. I did this with a couple friends in Portugal last fall and we had a blast hyping each other up when it was our turn.
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