Planning a Mastermind Retreat - Society for Creative Founders_0436


2018 has started off beautifully! This year, we held our first ever Alumni Mastermind Retreat for eight women who had joined us in previous years for the Conference, the Course, or the Intensive. To those who didn’t come this time, don’t worry! This will now will be an annual event.  We had such an amazing time and so of course, we wanted to share the experience with you!  



Planning a Mastermind Retreat - Society for Creative Founders_0450 Planning a Mastermind Retreat - Society for Creative Founders_0436


We want this to be a post that you can use if you want to plan a mastermind retreat of your own too, so we have included a few tips and suggestions included throughout this post as well.  Having a mastermind can be pretty beneficial for yourself and your business friends, so even if you don’t know each other well beforehand, take the leap and plan one!  Every single one of us did different things in our businesses for this Retreat in particular, which we found was incredibly helpful in providing feedback and suggestions as we worked through things together.


Planning a Mastermind Retreat - Society for Creative Founders_0436

We kept the group really small with only eight of us total, which allowed each person to really spend time focusing on their business both individually and in a group setting.  We rented a beach house so that we could have our own space and community together, but on the same side, have our own spaces.  Additionally, we were only steps away from the beach.  The beautiful white sand beaches of Pensacola, Florida.  And since it was January, we pretty much had the whole beach to ourselves, which of course is always a bonus if you’re wanting to spend some time simply doing some soul searching or good thinking without any distractions.

Everyone arrived on late Friday afternoon, checked in to the beach house, and all got comfortable.  We opted to have dinner catered in on Friday night since all of us were arriving at different times, and so that we could relax from the moment we stepped foot into the house.   We started the evening with a goal setting + 2018 planning session, which really got the ideas flowing and we all learned more about each other’s businesses as well.


Planning a Mastermind Retreat - Society for Creative Founders_0434 Planning a Mastermind Retreat - Society for Creative Founders_0440

Probably one of the most beneficial things was setting a schedule beforehand – it was a loose schedule, but everyone knew what to expect coming in.  We blended in both a mix of feedback sessions (which we lovingly call ‘Hot Seat Sessions’) where each person could offer what they were working on, what they were thinking about, what they were planning or what they were considering and receive feedback from everyone in the group, along with make a plan on what to do.  We had it set up in a way that there were breaks built in, time for both group planning and individual worktime, and of course, fun built in as we went too!

Saturday was the day we did the most “work”.  Each person spent time going over their business and started to plan out the details of what they wanted to come from or work on over the weekend.  We also had lunch catered in on Saturday so that we could stay focused on the topics at hand and extend conversations while keeping our mindset business related, particularly on Saturday.  

Planning a Mastermind Retreat - Society for Creative Founders_0439
On Sunday, the day started quietly with everyone having their own time to work on what they wanted to, and we came back together mid-day where everyone shared what their plans would be moving forward, setting goals, action steps, and of course, setting rewards along the way as well!  That afternoon, we had a photographer come and join us so that everyone could receive updated headshots, working shots, and a few new photos for SCF that you’ll see sprinkled into the pages more in the weeks ahead.  Saturday and Sunday evening we went out to local restaurants to celebrate the weekend, share wins from each day, and simply to relax and enjoy each other’s company.  

We headed home on Monday morning, all leaving at the same time, with new friendships and camaraderie with each other and ready to take on the year.  Overall, the weekend was an incredible way to start the year!

So, do you want to plan your own Mastermind Retreat? Here are a few things that we found incredibly helpful.  Pin this image below so that you can have it to refer back to in the future!

Planning a Mastermind Retreat - Society for Creative Founders_0436


1. Have a schedule or a plan in place ahead of time.

Communication is Key!  Each day, we knew what to expect, and we all knew it beforehand.  This helped us so that we didn’t wake up each day without knowing what would come from the day. We knew what was happening, when we would have planning time, when we would have time to chat with each other, and what to bring. 

2. Have one person go grocery shopping beforehand.

This may sound like a strange one, but we didn’t want to use any of our time together for our Mastermind Retreat at the grocery store.  The beach house was a house, but there wasn’t any food or beverages there for us for the weekend.  So, we created a list together beforehand and I went to the store beforehand so that once Friday arrived, we could spend just a few minutes stocking the pantry and the fridge with all of our individual wants and needs (and on that note …. You may not need as much food as you think you do, we found we didn’t eat nearly as much as we thought we would!)

3. Keep it small.

I am all in favor of having big get-togethers, but there is something about being able to connect with each and every person you spend time with over a weekend.  By keeping it small, each person was able to have individual time on their business where they were the focus and also be able to pour their talents and knowledge into their fellow retreat buddies.  Especially because we all came from different backgrounds and offer different products and services, we found it incredibly beneficial to blend everyone together in one group!

 4. “Schedule” Relaxation / Stop Time Each Day

If we hadn’t set times to work and time to play, I’m pretty sure every one of us could have spent all weekend working.  Once you get into a zone, it’s really easy to stay there for hours. By changing locations (in our case, piling together into my minivan and heading out each night) and having reservations in place at each restaurant ahead of time where we all went together, it literally forced us to stop working at a certain time each day.  

During the day, our schedule was loose so that it allowed for wiggle room as well – if people wanted to see local sites or spend time the beach watching the waves, they had time to do so. If they wanted to sleep in, get up early, or stay up late, they could do that too without missing out on anything.  I put schedule in quotes above because you don’t want to have every minute planned ahead of time, but you definitely want to have a general flow of how you all can expect the weekend to go before you arrive.


Planning a Mastermind Retreat - Society for Creative Founders_0448


 5. Book a Photographer for Individual Sessions

In our businesses these days, we are all in continual need of media to share.  Whether it’s new headshots or images you can use for your website or specifically for blog posts (like these you’ve seen here), this is probably something that we all say we need to do more often, but we simply don’t.  We booked Anna beforehand with time built in for everyone so that each of us had photos they could use for their businesses. A few even brought props personal to their business as well, resulting in a great combination of images for them to have.

Planning a Mastermind Retreat - Society for Creative Founders_0431 Planning a Mastermind Retreat - Society for Creative Founders_0451 Planning a Mastermind Retreat - Society for Creative Founders_0436 Planning a Mastermind Retreat - Society for Creative Founders_0449



6. Go in with open expectations

It’s really easy to think, “okay! I’m going to work on X, Y, and Z.” But, sometimes when you get into a group setting, and you really start thinking about things you want to do, you may come out with an entirely different outcome.  We found that some of us walked in with one thought and walked out with an entirely different one.  Permission to let things go, the courage to start new things, and friendships that grew stronger over those few days.  Don’t go in with set opinions of how the weekend is go, leave it open to new possibilities too!

 7. Open Up and Ask Questions

It’s really easy to keep to yourself, but in a Mastermind Retreat environment, it is best if you share open and honest thoughts with each other.  This not only helps you to really be honest with where things are, but it also helps others to help you where you really need it.  If you keep things to yourself that are weighing on your heart especially in your business, and if people don’t know, it limits how much they can truly help you to make things better.

8.  Have a Way to Follow up with Each other After

It’s easy to keep in touch these days – especially if you have a private Facebook group set up where everyone can stay connected.  Check in, share wins, share challenges, and continue to nurture the relationships with each other long after the weekend has come and gone.  You will grow relationships with each other that weekend, it’s important to continue to build them throughout the year!

Planning a Mastermind Retreat - Society for Creative Founders_0436

9. Have FUN.

And of course, have fun.  Relax, enjoy yourself, and build new friendships.  Take snapshots of the weekend. Have conversations that you may not otherwise have with people you just met,  let your guard down and simply have a good time! Community is something that can easily built and formed with people when they all know they are there to have fun – yes, we are all there to work on our businesses too, but this is definitely a time to mix the two. Talk about things that you’re wondering about, let your personality shine through, and simply have fun!



Planning a Mastermind Retreat - Society for Creative Founders_0441

Planning a Mastermind Retreat - Society for Creative Founders_0437Planning a Mastermind Retreat - Society for Creative Founders_0446

{from left to right:  Steph of Duffy Design Co., Brittany of Farmstead Design Studio, Erin of Erin is Creative, Janet of Paper and Spark, Kristin of Creative Founders and Grace and Serendipity, Jenn Elwell, Mallory of MalWest Design, and Kelsey of Paper and Oats. Thank you so much to Anna Filly Photography for capturing these images from our weekend!}



We want to hear from you!  Would you go on a Mastermind Retreat? Do you have additional questions? Share with us in the comments below!