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How to Plan A Creative Mastermind Retreat // Part TWO!

May 29, 2019

It’s time for another round of Creative Retreat Planning!  If you’ve ever dreamed of creating a space where you and others in your industry can laser focus on your goals and plan out the big dreams of your business, a creative retreat is for you!  It’s a little bit soul-searching retreat, a little bit mastermind event, and a whole lot of space to create!  It’s perfect for photographers, wedding planners, florists, videographers, and others in the wedding industry, but I believe that any small business owner could benefit from this type of retreat!  If you missed my first posts on it, check out Part One of the Creative Retreat Planning Blog Series here, and you can also check out how my own retreat went down earlier this year here.  AND, I’m super excited to offer you a free 12 page Creative Retreat Planning Workbook that you can get right here!  It even comes with a sample timeline so you can get down to planning your own retreat right away!

Now that you’re all caught up…let’s dive back in to the next planning steps.  Last time, we talked about setting intentions for your retreat and getting some general ideas about who, when, and where.  It’s time to get specific now and talk logistics!  What will you do, exactly?  And how will you organize it all?  Keep on reading!

dream bigger retreat behind the scenes

Pre-Event Planning // Logistics


If you’ve gone through the first steps blog post, you should have a general idea of your goals for the retreat, as well as what your attendees are expecting.  If you haven’t yet, brainstorm and crowd source this NOW! This is an essential step to give your retreat direction. Without this step, you’ll be pulled in a million different directions either in the planning process or once everyone arrives and you’re all on different pages about your goals.

Your goals will inform your activities.  Do you want to come away with a ton of new images for your portfolio?  Then you’ll want to focus on incorporating a variety of hands on shooting (and possibly editing and critique) time.  Do you want to come away with new knowledge? Then plan to have several different types of educational events like speakers, videos, and roundtable discussions.  Are you just hoping to have a low key, rejuvenating weekend with some goal setting? Then maybe you’ll be focused on scheduling a few relaxing activities like yoga or massages and then lead (or hire someone to lead) a short goal setting workshop.  

There are two main things you want to ensure when you’re dreaming up activities:

  1. Every activity serves one of the goals of your retreat.  There might be multiple goals: business growth and relaxation, for example.  In that case, as long as an activity is serving ONE of those goals, and there’s a good balance between those two goals, it’s a winner!
  2. There’s a variety of types of activities: active/passive, group/solo, doing/learning, downtime/social.  You’ll have a ton of different personalities at your event, and your goal is to serve each of their different learning modes.  Introverts might prefer solitary shooting opportunities, while extroverts might love a roundtable discussion. Within each goal, schedule several different activities that address that goal in different ways.  At our retreat, for example, we had four different types of hands on shooting opportunities: a structured styled shoot with models, an opportunity to shoot flat lay details independently, a small group headshot exchange, and late-night time to edit photos during casual hangout time!  So while not everyone might benefit from all of those opportunities, there really was something for everyone!

So what types of activities should you plan?  This will look different for everyone depending on what your industry is, but here’s a list of starter ideas that you can tweak!

  • Speakers
  • Workshops
  • Peer led teaching talks (5 minute presentations from attendees on whatever one thing they’re super knowledgeable about!)
  • Roundtable discussions on a specific topic
  • Presentations and hands on activities based on a pivotal book you read
  • Educational video movie night
  • Downtime fun activities–maybe a photo booth set up in a corner or a drop in craft table
  • Demonstrations
  • Mastermind Hot Seat Sessions–spend time problem solving for one person for a set amount of time
  • Portfolio or website reviews
  • Headshots
  • Goal Setting activities like vision boards or planning worksheets
  • Opportunities for journaling
  • Icebreaker games or conversation starters


No matter the length of your retreat, at some point…people have to eat!  Plan to incorporate this into the cost for each attendee if you’ll be providing the food or having it catered.  If you’re doing a more low key event, plan a few restaurants you’ll be visiting and suggest attendees set aside a budget for eating out.  We chose to do breakfast and lunch potluck style since we had a kitchen in the home we stayed in. Everyone brought simple foods that didn’t really need to be cooked and we ate family style for those meals.  Fruit, bagels, croissants, chips, salsa, and cheese and veggie platters were all big winners. Cleanup was super easy and no one person got stuck with cooking. We had a restaurant within walking distance for dinners and enjoyed a few dinners as a group that were really fun!  If you’re planning to have food at your event, remember to check beforehand for any food allergies from your attendees.



Maybe it’s just me, but I love to make things just a little more special by making it PRETTY!  I stuck to a consistent and pretty font for any signage. I also chose some colors which I stuck to whenever I bought stuff like cardstock, paper plates, and gifts.  It won’t make or break your event, but it sure will make it more Instagrammable! If it’s overwhelming, choose two colors and just stick to those whenever you have to buy something for the retreat!  

Dream Bigger Retreat - Creative mastermind retreat for wedding photographers in Oregon

The gift I gave each attendee!


I also chose to make a little welcome gift for each of the attendees that they received when they arrived at the retreat.  I think it sets the tone for a weekend of gratitude and abundance, plus it’s another thing that is just super cute! Mine was simple and also useful: pencils with inspirational sayings on them and a legal pad, topped with a printed sign and wrapped with a pretty ribbon.  And chocolate. Always chocolate.

You could also reach out to connect with potential sponsors, and see if they’d like to include something in a little swag bag.  What types of business might be interested in reaching the people who are attending your retreat? Do they have coupons or pens or lip balm they want to give away?  Get that in a swag bag and make sure to give them a shout out on social media!


Timeline and Lists

Down to the nitty gritty…once you’ve gone through all the steps above, you should have a pretty solid idea of what you’d like your retreat to include.  List it all out, meals, activities, fun things…ALL of it. I used one giant list for this.

Then, write down each hour from the time people will arrive to the time they’ll leave.  Block off time for sleep, getting ready in the morning, and meals, and then you’ll see the available times you have to work with.  Start by plugging in the activities that are MOST important to you. Add in activities that are different from those first ones to make sure there is balance.  If you realize there are almost all solo, hands on activities, schedule some group, passive learning events like a speaker. And don’t forget downtime! I totally overscheduled activities for us and we ended up dropping some on the fly to make time for connecting with each other and relaxing.  As long as you’re flexible about this and attendees are on the same page about it, that’s totally fine!

Last, once you’re satisfied with your timeline and it has plenty of space for wiggle room and downtime, make one more big giant list.  On this list, you’ll want to go item by item on your timeline and write down any materials you’ll need for that event. Notebooks, paper plates, tape to hang up signs, nametags, bowls for snacks, worksheet printouts, clipboards….literally: EVERYTHING!  Especially if you’re travelling to your retreat and can’t just run home and grab a pair of scissors, you’ll need to pack them in your box of supplies! This list will be your shopping list and packing list, so take time to think through every single hour of the retreat and anticipate all the needs!

Coming up next time is the final installment in the Creative Retreat Planning Series…what to do right before, during, and after the retreat to make sure that everyone (including you) gets the most out of it!  Stay tuned!

In the meantime, are you stuck on a timeline?  Click here to get the Creative Retreat Planning Workbook HERE, which includes a sample timeline!  I also walk you through all the steps of planning a retreat, and it’s totally free!  Just sharing my Leslie-Knope-like planning abilities with the world!

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how to plan a creative mastermind retreat on a budget

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