How To Plan A Mastermind + Mastermind Retreat

I just got back from a mastermind retreat in New York and I’m excited to share more about my mastermind, how we organize it to suit our needs and the things we discussed while at our DIY retreat in New York City. We met up in New York to talk about our businesses, our goals and plans for the new year and to brainstorm together. There is just something about the last quarter of the year that makes me want to plan all the things. Hopefully this post will give you some ideas on how to start your own mastermind group or how plan your own mastermind retreat.

How we started our mastermind + what we discuss monthly

My mastermind group is with two other creative business owners. We met on Instagram and have become good real life friends since. Even though we all started as handletterers, our businesses each went in different directions with course creation, private lessons, paper products, workshops and more. So we didn’t let the fact that we’re all “calligraphers” and maybe have overlapping audiences or whatnot stop us from mastermind-ing together. Is that a verb?

Just because we’re each very different so how we approach our businesses is different. And those different opinions and ways of doing things helps each of us learn from each other.

When setting up a mastermind it is important to have some ground rules and set topics in place.

  1. Having the same meeting time is of course important (we meet monthly over a Google Hangout). Before we decided to form a group, we got on a call to discuss what we wanted the mastermind to include and what we wanted to discuss every month. We also shared our Strengths Finder results with each other because we’re nerds and love taking tests like that. That helped us see how we could better work together and support each other.
  2. Before our monthly calls, we also fill out our shared goal document where we each list out 3 goals we’re working on. it helps keep us accountable.
  3. On our monthly calls we discuss the goals we set the previous month, if we achieved them or not and why, what went well and what we might need help on or advice on. That could be how to handle a client situation, maybe pricing questions since we’re all very comfortable with sharing that with each other, and just general advice.
  4. We also share new resources with each other like books or articles, or maybe a new podcast we think would benefit the others.

Why DIY a retreat vs attending a conference

We decided almost immediately after starting the mastermind that we wanted to meet up in person. We all live in major cities so it was basically up to those three - San Francisco, LA or NYC. I’d definitely suggest agreeing on a city where it’s not only easy to fly into, but also easy to get around. We booked an Airbnb (after our 1st place cancelled on us 3 days before coming to NYC) because we wanted to have one space we could all stay and hang out for the first part of the trip. We ended up at a hotel because we discovered Airbnb-ing in NYC wasn’t our thing. No thanks 4th floor walkups.

Truthfully attending a conference together never crossed our minds. I think because we’re all introverted and knew that it would be more cost effective to plan our own retreat. Plus, we’ve all been to conferences where we loved some things but not others. So we wanted to make sure we controlled what we did, ate and discussed on our own retreat.

What we discussed at our retreat

So in-between eating and exploring, we organically spoke about our businesses. But we did also set aside a topic each day that we made sure to discuss. We also set aside time each morning to kind of slowly get ready for the day, journal, maybe letter or sketch. It was our alone time, which was important for the three of us because we’re all extroverted introverts.

Every evening, we made it a point to be home at a certain time to sit down and really dig into that day’s topic. That worked out for me because I’m not 23 living in NYC anymore guys - so you know, I just can’t hang anymore :)

We spoke about things like

  1. Reflecting on 2017 and what worked well and what didn’t. We set our intentions for the trip on the first night and just talked about what we were hoping to get or achieve out of our time together.
  2. Another day we took turns sharing our projects we wanted feedback on - whether that be a new service or product or revamping a current service or product. We basically came with our big ideas that we weren’t quite sure how to execute on and brainstormed together.
  3. The third night we spoke about each others businesses and ideas we had for the other two people’s businesses. Sometimes it helps to have another set of eyes.
  4. And on our last night together, we shared our 2018 goals and laid out steps for those goals and for the remainder of 2017.

I’m a major planner because - Virgo? - and my mastermind buddies also big on planning. So this was actually really fun for us. We mapped out our goals backwards. We wrote down all the steps we needed to do to achieve those large overarching goals and assigned due dates to those smaller steps.

It’s so easy to say “I want to earn X amount from my etsy store” or “I want to start a course about X” but how will you do that and when? So we took those large goals and planned out steps throughout the year.

Check out more NYC footage below. Hope that this post and video give you that push you need to set up a likeminded group, or maybe just to step our of your comfort zone and connect with others in your industry.

Being a solo biz owner can be tough and lonely at times, with your “real life” friends maybe not understanding as much - so I really encourage you guys to make connections online and see if it can foster into real life friendships and in person meetups - but you know, like be safe and keep your stranger danger guard up :D