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How To Plan A Creative Mastermind Retreat // Part ONE!

May 22, 2019

The desire to do a creative retreat starts small–the realization that your daily to-do list has overtaken all of your time, the unfinished big business projects, the constant feeling of running the hamster wheel that all small business owners run to keep things GOING!  A retreat won’t instantly solve all those problems, but it’s the perfect way to press “pause” on your daily life. You’ll spend some time regrouping and reworking your business. You might do creative projects that feed your soul. You’ll connect with people in a similar season as you.  All of these things can drive you to create your own Creative Mastermind Retreat!

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For me, I saw some fabulous big-name conferences out there.  I was energized and inspired just by the THOUGHT of going! At this point in my life and business though–balancing mom life with two small kids and a business that’s growing but definitely not GROWN–it just wasn’t practical to spend the money on conference fees PLUS the travel cost to get to them.  (Is it just me, or are all the best conferences always on the other side of the country?) And spending a week away from my kids the first time I’d ever be away from them? I just wasn’t ready! For my business and my family, what really worked best was a weekend away somewhere local. I was ready to book myself a Motel 6 in the next town over and curl up with a cache of my best CreativeLive videos and a stack of business books, and maybe for you that’s enough!  But I really craved a bigger experience, one where I could sit with other business owners and pool our resources and knowledge to create a space to really, I mean really, DREAM. And so, the Dream Bigger Retreat was born!


In this 3-part blog series, I’ll be guiding you on how to create your OWN retreat!  There wasn’t a lot of info out there when I was researching how to organize the Dream Bigger Retreat–this wasn’t completely a soul-searching wellness retreat, or 100% a photography workshop, or a business mastermind retreat.  It was a little bit of all of those! So I hope that this series helps guide you to create something that fits your needs!


First Steps // Brainstorming


Vibe / Size

Your very first step is to think about what lights you up about the idea of a retreat.  What are you envisioning? Is it a spa weekend in wine country with two or three of your best girlfriends?  Is it camping out at a mountain lodge with 50 local business people you admire? Is it a conference-style teaching event at a downtown hotel?  


Give some thought to what type of space and vibe will be most beneficial for you.  Specifically:

  • the size of the event
  • the general type of location: ocean? Forest? Country? City? Mountain?
  • What about the overall vibe?  Is this an edgy retreat for modern wedding industry pros?  Or a soft, soul-searching retreat for film photographers?  


At this point, you might consider making a mood board on Pinterest as you get ideas about what you’d like your retreat to feel like.  Pin 10-15 images that can help guide you as you “brand” your retreat.



What about your goals?  What, specifically, are you hoping to come away with from this weekend?  If you already have a group of people you know you’ll be with at the retreat, this is a great thing to crowdsource so that everyone will be able to come away with something useful.  Are they hoping for opportunities for content creation? A chance to do something creative with no pressure? Soul searching activities to figure out the next steps in their business?  Speakers who can teach on business, leadership, or technical aspects of your specialty? Knowledge sharing between peers? Critiques? There are SO many possibilities, so it’s important to start nailing down the types of goals you have for the retreat as soon as possible.


Find Your Tribe

And what if you don’t have your people yet?  Who will be joining you on your retreat? For some, a smaller retreat is ideal–just two or three people that you really trust to help grow each other’s businesses.  Others might want a larger scale retreat. Look to your network–business networking groups are a perfect opportunity to meet people interested in investing time in their business.  Before diving into a retreat, take the time to get to know them in a small group setting!  I lead the Professional Women Photographers of Yamhill County, and I knew I wanted the retreat to be about connecting with them!  Our group met monthly for about a year before we did our retreat. Try to get a core group of about 3-5 people committed to the retreat idea before moving into the next planning stages.


Nailing Down A Date and Location

Okay, you’ve got your goals, your 3-5 core people invested in the idea, and a general sense of the feeling you’d like at the retreat.  It’s time to get down to some planning! Start with the date–you’ll want to make sure that whatever you book, those core people will be able to make it.  I’d aim for about 2-3 months out, longer if you’re thinking the retreat will be larger scale (20+ people), or if you are planning to book in-demand speakers/teachers.  


Season will also effect your date.  If you’re planning to camp outside, you might not want to schedule it during the winter.  If you’re in an industry that has a “busy season” (like wedding photographers in June), then you should avoid that season so that more people are able to attend.  Ideally, the season just before the busy season would be best, because that’s when people have had a little break to recover from any burnout, and they’re pumped and ready to head into the new season but still available.  As wedding photographers, we chose early March for our retreat–well before the busy season starts here, but long enough after the holidays that we were ready to dig back in to our businesses.


With our location, we were lucky–one of our core members had a family beach house to offer.  Definitely work your resources to see if you have a similar option! The more affordable the retreat is, the more likely people will be able to attend.  I absolutely recommend partnering with other businesses whenever possible–if you’re photographers, then offering professional photography of the venue may come with a discounted rate.  You might even be able to barter other services depending on what your business is. And if you’re a smaller group, there are many Air BnB’s out there that can accommodate you–it’s surprisingly affordable when the cost is divided up!  Even a block of rooms at a hotel could be an option (and often that may come with the added bonus of usable meeting space).


Last, if an overnight retreat is just proving to be cost-prohibitive in your area or for your people, don’t give up!  I truly believe that just dedicating time to yourself and your business is the important thing! A retreat might look different for you–more of a daylong event in a community center, for example.  There are always, always options!


PHEW!  So you have a good chunk of homework here for you as you start to brainstorm what your retreat will look like.  Are you excited yet? GOOD! In the next installment, we’ll talk about activities, meals, and (my favorite) the timeline!  Get out your notebooks and start dreaming bigger!!


{Download the Creative Retreat Planning Workbook HERE!}

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  1. Brit says:

    This is brilliant! I’m encouraged and inspired and looking forward to the next parts!!

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