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Masterminds Retreat: How To Run One

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Does anyone even really know what masterminds are? It’s kind of a weird word (and it sounds SLIGHTLY wanky in my opinion) but what it means is a bunch of business people or solopreneurs who band together in a group to support each in their businesses/cry together in a corner while drinking heavily.

Running a business or being a solopreneur seems like the dream but its weirder/wilder/scarier than you can describe to anyone who hasn’t done it.

And don’t even start me on the loneliness. If you ever want to test the boundaries of your sanity, work by yourself from home for a week straight without talking to another living soul. By Friday, you’ll be wearing tissue-boxes for shoes and getting sad that your friend Barry The Pidgeon hasn’t visited you today.

This is why masterminds exist. So when a client complains, another company tries to sue you, your email funnel shits itself for no reason or your Facebook ads stop working, you’ve got a collective of people you can turn to and say ‘I SHOULD HAVE FINISHED MY LAW DEGREE LIKE MY PARENTS TOLD ME TOO!’

Most masterminds are run online, usually in Facebook groups. The very best ones I’ve seen have several in-person retreats per year. Yes, it’s lovely to have people on tap online, but it’s not the same unless you see people in person.

If you have a masterminds group and you’re keen to run a retreat, here are some tips to get you sorted.

1. Run a poll on which dates work best for people

Choosing the date is hard, but the best way to do it is run a poll on your Facebook group. Say something like this –

Hey Masterminds!

Just looking for some dates for the next retreat, please pick which dates work best for you.

13/06/18 to 15/06/18

20/06/18 to 22/06/18

25/06/18 to 27/06/18

Happy for other suggestions too just let me know!

Pick whichever date gets the most votes. Der. Hot tip: Try to avoid picking dates at peak-crazy business times like end of the financial year and December. The purpose of these masterminds is to refresh and replenish the attendees, not give them extra work to do at an already busy time.


2. Sort out location/accommodation

Run another poll in your Facebook group asking about accommodation preferences. Say something like this;

Hey Masterminds!

Some accommodation/location ideas for the retreat. Pick your preferences.

1. Cheap and cheerful near a major city
2. Cheap and cheerful somewhere coastal/rural
3. Something a bit fancy near a major city
4. Something a bit fancy somewhere coastal/rural

This way you can cater to the feel of the group and see how much people want to spend and where they can travel to. In every Masterminds group, there will be a variety of income levels so make sure you keep it accessible to most people in the group. It’s a bit of a dick move if you’re raking in multiple six figures a year and you’re all ‘Let’s chip in $20k each to get Richard Branson as a guest speaker!’.

No one likes the person who does that.

3. Plan a food roster

You NEED to plan food, especially if you’re going to a place that’s out of a major city with limited supermarket and restaurant options. Put together a roster that looks like this.


Lunch – Salads and sandwiches made by Rachel and Monica

Dinner – BBQ chicken and potato salad and made by Grace and Karen


Breakfast – Omelettes made by Blair and Serena

Lunch – Quiche and salad made by Rory and Lorelai

Dinner – Booking at Tom’s Restaurant


Breakfast – Cereal, fruit and yogurt made by Samantha and Carrie

Lunch – Deli platters made by Meredith and Christina

Get a few people to do a big shopping trip and split the bill. Make sure the food roster includes kitchen clean up as well. If anyone has any dietary requirements, make sure they have their food covered if you’re unable to cater for them. Although I don’t know too many female solopreneurs who eat gluten or dairy, so definitely ask the group first. You might discover that the majority of the group only eats quinoa blessed by unicorns, in which case cater for the majority.


4. Create a schedule

A Masterminds session without a schedule can turn ugly quickly. And by ugly, I mean picture a room full of a dozen people who work alone and seldom get to hang out with other 3-dimensional people. It’s like locking twelve puppies in separate boxes for a week and then releasing them all at the same time. I mean it’s adorable, but it’s also complete chaos.

Put together a schedule that looks something like this.


Afternoon session – Welcome and intention setting


Morning session – Guest speaker

Afternoon session – Break out hot seat sessions


Morning session – Goal setting and implementation sessions

Depending on the vibe of your masterminds you might like to run some other activities like group bonding or meditation. Read the room and see what people might be interested in. A paddle boarding session might be great for some groups while others might prefer a tarot card reading session. If you’ve been in your masterminds group for a while, you’ll know the vibe.

5. Allow for rest time

It’s tempting to pack in a full schedule but make sure you allow for lots of socialisation time. A program is essential, but most human-contact-starved soloprenuers are mainly interested in having a few glasses of wine with real people so make time for that to happen. Evenings are suitable for this, and long lunches are also beneficial, so everyone can adequately recharge and have enough energy for the afternoon session.

6. Run a Hotseat Session

Get into groups of four and give each person 30 minutes to talk about whatever they want about their business and the others will provide feedback. Don’t skip this bit; it’s one of the most valuable things that can happen at a Masterminds retreat. Hot tip: Tell everyone you’ll be running these sessions so they have a chance to prepare and think about what they’d like to workshop. Try to make the selection of these groups as random as possible. Otherwise, people will choose their friends is terrible for two reasons. One; they’ll often get distracted and chat the whole time and two; friends already know what’s going on with friends, so it’s usually a bit of a waste.

7. Finish with next steps

Just before everyone leaves, go around the circle and have everyone state their intentions and takeaways and what they plan to do from here. If you have a chance, try to get some feedback about the retreat so you can make positive changes for next time or keep in the bits everyone felt worked.

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