Mastermind Retreat 2019: Full Weekend Recap & Takeaways

Mid-October 2019 I spent an incredible, action-packed weekend with my “Mastermind Girls” as I call them & received such a huge response from the community to share about it that I decided to write a blog post.

In this post, I’ll briefly share the impact having a mastermind has had on my business, how you can start one of your own (fo’ free) & what we did each day during our in-person retreat + my key takeaways.

First, let’s talk about what the heck this MASTERMIND thing is.

I’ve been in this online-business-world for many years now (read: 2015) – even though I didn’t start SMC until January 2017. All of my mentors & the online gurus talked about being a part of a “mastermind”.

There are paid masterminds and free masterminds – and there is value to each, for sure.

A mastermind, when you get down to the nitty-gritty, is a group of focused individuals collaborating, holding one another accountable, learning together & growing together.

I mean, you could technically have a mastermind about anything (spear fishing, sci-fi-reading) but I’m specifically talking about business masterminding.


How did we start our Mastermind?

After an in-person event we all attended, my girls (I’ll tell you about them later) & I decided to join together and start our own Mastermind.

Although a paid mastermind may give you access to materials & people you otherwise wouldn’t have access to, you can always start with a free mastermind you create on your own with a group of peers.


Top Tips for Starting a Mastermind (brief)

I really want to dig into the mastermind retreat we put together, so I’m just going to be brief here.

My top suggestions are:

  • Find people that treat their business the same way you do (all full time, all part time, all side-hustlers, all work from home parents, etc)
  • Find people who either serve a different ideal client with the same service, or the same ideal client with different services (this was Valerie’s suggestion!)
  • Get organized. Figure out how you will communicate, how often and also set up video calls to check in – then stay on topic.


Our FIRST Annual Mastermind Retreat

First, I should tell you…our Mastermind consists of the following stellar business owners:


Now let’s break down what we did every day during our retreat & some of my KEY takeaways!


✨ Before We Left

Before we actually went to our in-person retreat, we did the following:

  • Worked together to find a central-ish location (Chicago, IL was what we chose this year!)
  • Booked an Airbnb
  • Shared a Master Retreat Google Doc with:
    • Things we wanted to accomplish
    • Flight information (for carpooling, duh!)
    • A loose itinerary to keep us focused


✨ Day One: Cultivating Friendship & Celebrating Wins

Our first day was all about catching up with each other, enjoying our company, buying snacks for the weekend & hanging out.

This was really important because if we didn’t make time to do this – it was definitely going to interrupt our work time!

We also celebrated wins that night which I absolutely loved – as entrepreneurs (often the CEO of our businesses) we sometimes have to pat ourselves on the back, which is great but it’s also lovely to have a group of ladies who respect & love you lift their glasses to your accomplishments!

My Mastermind Retreat 2019 - My tips for starting your own mastermind, plus a full recap and key takeaways from my 2019 mastermind weekend.


✨ Day Two: Finances ($$$$$) & 2020 Goals

One thing that is easy to neglect when you’re the wearer of all or most of the hats in your business, is that from time to time you DO have to wear the CEO hat.

That’s what we did on Day 2.

We looked at finances through many lenses:

  • We did a complete expense audit – what are all of our yearly and monthly expenses? What did we need? What could we cut? What could we combine?
  • We talked about investing + retirement accounts (pssst, that’s important!)
  • We made “Good, Better, Best” financial goals based on our previous year and what we wanted to accomplish in the next year

Then, after starting with finances, we created GOALS, HABITS, & TARGETS for 2020. We focused on Q1 and Q2, leaving Quarters 3 & 4 a little more “obscure”.

Here are some of MY goals, habits & targets for Q1 and Q2:

This was so helpful to see – and to REALLY calculate numbers (if we want to make $X we need to sell X).


✨ Day Three: Action Plan

Day three was actually surprisingly tough. We went through and mapped out our exact client journeys for each of our businesses.

We all wrote down exactly how clients would flow through our businesses, what services we offered, everything.

It was so helpful to hear people who KNOW your business give feedback about what does / doesn’t make sense – and where improvements could be made.

Here were my key takeaways from Day Three:

  • I removed my “free consultation call” as it wasn’t serving my business or my time well
  • I created a strategy call offer that is now the start of the 1:1 client project process (it’s AMAZING)
  • I streamlined what I offered, cut things I didn’t need to do anymore, and figured out how it all flowed together.


✨ Day Four: Goodbyes & Reflection

I left crazy early on our last day, but it was actually perfect for me. I needed space to reflect on the weekend (and as an introvert, that looks like popping on my headphones and sitting on a plane evaluating everything alone).

I reflected on the pages and pages of notes and brainstorming from the weekend, the goals I had created and my business map.

Then I did the most important thing for my business. I created a full plan for the end of the year & 2020.

I listed out in my planner exactly when things would launch, when sales would happen, when work would be complete.

This has been invaluable already & it’s only been 2 weeks!

Knowing exactly what needs to be done and when puts into perspective when I need to push and when it is okay to rest (I will run myself into the ground if I don’t have boundaries for myself, seriously).

The rest of the 2019 year looks like:

  • Finish up final client projects
  • Book 2020 Projects
  • Celebrate the holidays with a sale on my limited Strategy Calls for 2020
  • Brainstorm all of the topics + content for 2020
  • NO MORE WRITING CONTENT (other than this post!)
  • Resting, Resting, Resting
  • Spending time with my family

& Next year you already know my goals – so just imagine what my planner looks like (#details).

My Mastermind Retreat 2019 - My tips for starting your own mastermind, plus a full recap and key takeaways from my 2019 mastermind weekend.

This was one of the most inspiring & action-oriented business trips I have ever taken. I walked away with:

✅Pride & confidence about what I accomplished this year

✅A sense of sisterhood sharing some tough stuff with my girls

✅Clear financial goals, rooted in my “WHY”

✅Clarity around building more wealth in my life and business

✅Booked 2020 projects

✅More simplified offerings

✅Less expenses

✅A full action-plan for 2020 goals and how I will achieve them

✅A notebook full of content ideas

✅A landing page for my new strategy call offering

…and honestly probably more I can’t think of!

If you’ve been thinking about starting a mastermind + you also want to do an in-person event, I say DO IT. My biggest advice is to: have a plan & stay on track…but give yourselves time to connect, because that is invaluable.

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