How to run a mastermind retreat

At the start of October, I headed out to Sussex for our annual mastermind retreat. It’s amazing how spending a few days away with other like-minded business owners can really focus the mind and get you fired up.

Why host a mastermind retreat?

I’ve written about mastermind groups before. This is how I described a mastermind group:

A mastermind group is a group of like-minded people who share a common goal. They meet (physically or virtually) on a regular basis to discuss what they’re working on and what problems they’re facing.

You could think of it as a circle of professional friends. They might not be people you know to start with but over time you will become friends. You’ll help each move forwards by holding each other accountable and by providing support.

A mastermind retreat is spending time with your mastermind group in an inspiring location for a few days.

Here are some of the benefits of a mastermind retreat:

Time to step away and think

A retreat is a great excuse to get away from the day-to-day grind. I don’t do any client work and I’ll only check emails once or twice a day. As far as my clients are concerned, I’m off-the-grid on vacation. This frees up the time and space to think about the bigger picture. (Note to self: you should really get away from the day-to-day grind more often.)

You get valuable feedback

Most of us, especially those of us that work remotely, find getting honest feedback a challenge. A retreat fixes that problem: it’s time to put your ideas on the line. The group will ask questions and offer new ideas and perspectives. Talking through your ideas with people you trust and respect is something we should all do more often.

You build deeper connections

Chatting to your mastermind group on Skype is all well and good, but meeting in person is different. Even Matt Mullenweg, CEO of the fully-remote company Automattic, has recently written about the importance of meeting in-person. Spending a few days together gives you time to get to know each other, and helps you better understand their businesses.

Rekindle the groups energy and motivation

Our mastermind group has been meeting on Skype every 2 weeks for a few years but over time things can become repetitive. A retreat is a way to bring everyone together again. It’s an incredibly motivating place to be. You come away wanting to execute on your ideas.

What’s more, a retreat is easy to organise. Here are a few things to consider:

The logistics of a mastermind retreat


It’s important to have to the right group of people on the retreat. For this reason, you’ll likely want to make it application or invite-only.

You’ll want everyone to be in roughly the same position. On our retreat, we were all self-employed and had a focus on moving our businesses to the next level. We also had a good cross-section of skills, which meant we could all contribute different ideas to the discussion.

You don’t have to know each others businesses before attending to get a huge amount of value. You have enough time to learn about each other while you’re there.

You’ll want to keep the group relatively small. There were 5 of us on our retreat, which worked out great. There were just 3 of us on the first retreat I attended. I could imagine groups of up to 8 working just as well. Any bigger and you risk not having enough time to chat to everyone.


Finding the right location is key. We used Airbnb to book a lovely 8-bedroom home in Sussex. It was likely overkill for just 5 of us, but the extra space is often worth it.

Once you split the cost with everyone, it doesn’t work out too expensive. All in, for accommodation and food, it worked out to just under £400 each. You could, of course, run a retreat for much less. Airbnb also lets you split the cost with other attendees, so you don’t have to foot the bill yourself.

When looking at a venue, here’s a few things to consider:

  • Does it have a well-equipped kitchen so you can prepare meals?
  • Is there a table big enough for you all to sit around and run sessions from?
  • Are there enough bedrooms/beds to get a decent nights sleep?
  • Does it have a garden with a seating area?
  • Are there things to do and places to walk in the surrounding area?


You’ll need to plan food ahead of time. Good quality food that everyone can enjoy is essential to running a good retreat.

Here’s a few things we did:

  • We went out for a pub meal on the first evening
  • We used Gousto for two evening meals (which made it easy to organise and cook)
  • For lunch, we prepared salads and pizza
  • We created a shared shopping list for additional things like tea, snacks, etc.


You’ll also want to plan the schedule before arriving. You don’t want to be thinking about what to do when you arrive.

We arrived Tuesday afternoon and left on Friday morning, leaving 2 full days. Here was our itinerary:

Arrival day (PM): Pick bedrooms. Round of introductions. Unpack. Pub meal for dinner.
Day 1: Sessions in the morning and after lunch, leaving a space for an activity in the afternoon and evening.
Day 2: Same format as day 1.
Final day: Pack. Check-out. Breakfast at a café to wrap-up.

The first day looked something like this:

Pre 9am: wake, shower and breakfast
9am: Session 1 – Darren
10am: Session 2 – Francesca
11am: Session 3 – Andy
12am: Lunch
1pm: Session 4 – Nazz
2pm: Session 5 – Marc
3pm: Afternoon activities
6pm: Evening meal

Each session was roughly 45 minutes with a 15 minute break. For the session, we each presented something we were working on or thinking about for 10 minutes. The next half an hour was spent in group discussion. Have someone with a timer to keep things on track.

Plan the list of sessions prior to the retreat. This will give everyone time to prepare for their session.

Andy Henson shared the document template we used to organise our retreat in his write-up on mastermind retreats.

Tips for getting the most out of a retreat

  • Keep it small. 3-8 people feels like the sweet spot. Any bigger and you risk changing the dynamic of the group and it becomes more difficult to organise.
  • A retreat is for work. A solo retreat might be about rest and recovery, but a mastermind retreat is about getting and providing as much value as possible. It should be intense.
  • No client/project work. Set an out of office on your email. Let your clients know you’re away. Client/project work is out-of-bounds. It’s time to focus on your business.
  • Know what you want to get out of the retreat. Do your homework before attending. Know what you want the group to help you with. The better you can come prepared, the more you’ll get from it.
  • Plan in advance. Have an itinerary and meal plan ready before you arrive at the retreat.
  • Setup a Slack group. Get to know each other first. A Slack group is a great way to plan and chat before and after the retreat.
  • Hold an event wrap-up. Share what you’ve learned and what your next moves are. Keep everyone updated on your progress.

And a few final tips, courtesy of Seth Godin:

  • Must be off site, with no access to electronic interruption
  • Don’t serve boring food
  • Here’s the goal: new friends… here’s the output: a new and better to-do list