Thoughts and Tips on Planning A Creative Retreat

 “…..We really must create the experiences we most need. ” – Kelly Rae Roberts

Let me start by saying Kelly Rae Roberts will get her OWN post very soon. Kelly Rae Roberts is my creative & business inspiration since going on FOREVER. Okay, maybe circa 2006. Maybe even earlier than that. Let’s just say I was reading Kelly’s blog when she posted her first drawing and was still working as a social worker. Google her now…and well, she’s something else all together. Although I believe what she offers the world now, is still social work!

In short though, Kelly inspires me EVERY DAY.  She’s the reason my art journals have evolved the way they have. She’s the reason I started Crafts + Cupcakes. She’s the reason why I do NOT believe in the “starving artist.” I want to blame her for my addiction to decorative tape.  Her ecourse, “Flying Lessons” is pretty much my gospel.  (I swear by it and it is WORTH THE PRICE. Also, that last one was an affiliate link!) She’s amazing!

Kelly is also one of the MAIN reasons I began planning and hosting my own yearly artistic gatherings of powerful, creative, Wild Magical Women called “C.R.E.A.T.E.”  A month from now C.R.E.A.T.E., the 2013 edition will be taking place in Wine Country!!!!!

"How to Plan A Creative Retreat"


Don’t die without embracing the daring adventure your life is meant to be. — Steve Pavlina

The story starts with Kelly. Every year I kept reading about her Love Bomb trips and I loved how creative, artsy and crafty they were and I absolutely loved the group of women attending. They were all people whose websites I read or whose books I owned or whose products I couldn’t go a day without.

Then Sarah Humphreys from Real Simple wrote an articled called, “The Magical Mystery Trip” (<– this link leads you to my pdf scan of the article. I have kept it with me all these years. There is an online version of the article but its much shorter. You can find that one here. –> The Magical Mystery Trip)

"How to Plan a Creative Retreat"

So…..I’m reading about Kelly and about Sarah and I knew I needed to experience my own gathering  friends and creative people. Then, of course Kelly then writes, If Your Soul is Calling….Listen. In it she writes, “Jen and i have been getting several emails asking for advice on how to create a gathering of women similar to lovebomb. here’s the quick and dirty of how we did it. of course, you can do it however you’d like, but the most important thing is to do it “

Next thing I know I was on a road trip driving from LA to Santa Barbara  and I was telling a friend about what this trip might look like. And you know what she said? She said, “DO IT!” So I sent an email to my friends. I called it, “Sheena’s Idea for World Domination.”

"How to Lead A Retreat"

 The women said yes and so the planning began.

BUDGETS – Is your gathering a girl’s getaway or a for-profit retreat that’s a part of your business? Depending on that answer, your budget is shaped differently. I have made a habit of budgeting an ALL INCLUSIVE cost for my retreats. Since the trips are both a relaxing vacation AND an artist retreat, I have to factor “cost” in a variety of ways.  Either way, I have found having an ALL INCLUSIVE cost has made it easier on the women. As C.R.E.A.T.E. evolves, this will change. I foresee, All Inclusive except for Flights. This means you have to get creative and resourceful with activities, food and time!

"Creative Retreats"

HOUSING – My retreats are centered around community, so its been important that everyone stays together. Right now, I can’t imagine this intimate gatherings to take place in a hotel and conference room. What we have done each year is rent a house. We have either been lucky enough to rent gorgeous houses from friends & family. (The cost varies depending on who you know, who you ask, length of stay and more.) Or we rent houses using websites like Air Bnb, VRBO, HomeAway, or FlipKey.

What’s important to note is that your housing decision should be based on the experience you want your retreat and guests to have. Renting a few suites at hotel may work perfectly. Finding a campy retreat center in the woods where you build fires may work perfectly, resting on sleeping bags and couches at a friend’s house may work. It depends on you. I want my guest to be in a home. I want everyone to sleep in beds. I don’t want their to be a minibar fee if someone wants to raid the fridge at 2AM.

MEALS – From the beginning, keep a list of everyone’s food preference. Are people vegan, gluten free or do they just HATE mushrooms? I HATE mushrooms. While you may not be able to accommodate everyone, knowing everyone’s eating habits will help you plan your meals. I intentionally prepare dishes where everyone can add what they like. For instance, instead of preparing a soup which may have ingredients three people hate, we might make fish tacos and lay everything out in separate bowls.

"Meal Plans for Retreats"

 Before I get into any other food details, keep in mind for my retreats, we prepare our meals together. There isn’t a catering company. I don’t have kitchen staff. We don’t eat out. We make a list of our food preferences, then we compile a menu for the retreat, then we grocery shop together and we wine shop and then we cook together. And if you aren’t cooking, you’re cutting or doing dishes or taking pictures or setting the table or being the kitchen DJ. You must have a kitchen DJ.

We make fanciful meals from 15 ingredient fish tacos to homemade Thai soups to organic apple pies and this year we’re even having some CAJUN COOKING!

ACTIVITIES – My retreats are two fold. They are a way to relax, hang out and get to know people AND they are, as mentioned, an artist retreat. With this in mind, I keep a loose itinerary and I don’t plan every moment of the day. With this in mind, I intentionally invite guests who are able to lead workshops. (My retreat is invite only. If this were a public retreat, attendees would not be required to teach or lead.)

"How to Host a Retreat"

Even if you are planning a public retreat, when it comes to your activities, invite workshop leaders or speakers who have something cool to offer. Rather than trying to find classes in the city of our retreat, my guests have led us in Negative Space Drawing Classes, Custom Linoleum Stamp Carving, Jewelry Making, Art Journalling, Photography classes and more. This year’s guests will be leading us in Doodling Exercises, Flash Writing Workshops, Guided Meditations, Sensual Movement Classes and the list isn’t even complete! Keep in mind all of these activities require very little supplies of those taking the class. That’s intentional too.

I also lead the group in numerous activities. My favorite thing is leading the group in writing and journaling sessions and well as guided discussion. We once did a journaling session while sitting on rocks in the middle of a river. It cost nothing for us to do that and yet  it was one of the most sensual experiences we had. We were outdoors. We could hear the loud rushing water. We met a set of twin dogs that did tricks for us. We could feel the sun. We were inspired by nature. It’s not skydiving or deep ocean diving but its very in line with the intent of my artist retreat.

"Outdoor Writing Classes"

PLAY – Whether your retreat is for business or just a fun girl’s getaway or something else all together. You must have fun. Remember fun can be low cost and low maintenance. Have a dance party. Tell funny stories around a camp fire. Make smores. Have a picnic. Or in our case, we drink wine and play games right before bed time.

SACRED SPACE – This probably should have been first or second, but as soon as you walk into the space that you’ll be using for your retreat, I’d advise that you conduct a space clearing or do a smudging ceremony. Energy is a very real thing and its important to clear out any lingering energy that was in the space before and to set the intention for the energy of your retreat. If smudging or space clearing is a bit out there for you in the zen, new age, lala category, try lighting a candle. (This also helps the rented homes feel “homey.” By bringing my own candles with my favorite scents, it truly smells like home or whatever you want it to smell like.) This year I’m even bringing a tibetan singing bowl.

"Artistic Retreats"

GIFTS – I love giving gifts. Although I don’t like receiving them. What I like to receive is time and presence. BUT I love to give gifts. Surprise everyone with a gift. A read cute gift and not a bookmarker. I’ve made handmade journals. I’ve given away my favorite books. And once I even gave everyone gift bags full of Sabon products. I love Sabon. Whatever is in your budget, give it away. This year I have a cute surprise in store.

ADMINISTRATIVE ORGANIZATION –You can either use your assistant or a VA to keep track of all of the details. You could even use a travel agent. Or maybe you have an intern or staff. My staff consist of Gmail, Google Drive, Facebook Private Groups, and Pinterest. I make a pin board for EVERYTHING. Here’s the C.R.E.A.T.E. overall pintest board.  Here’s the C.R.E.A.T.E 2013 pinterest board. (I even have one for Crafts + Cupcakes  and Wild Magical Woman. 2 other workshops I do.)

I use social media and online websites and apps to keep me organized. I have a google drive folder for every event, project and client. I have note taking and project management apps and online accounts for every area of my life and its all color coded. I keep lists and matrix and copies of everything important. This is manageable for an intimate gathering and retreat. Next year, when C.R.E.A.T.E. is open to the public….I’m going to have to write a new blog post on how I keep organized.

"How to use Google Drive"

THE LOCALS – Wherever you hold your retreat, find ways to engage with the locals. Is there a farmer’s market? We usually get some of our groceries at local farmer’s markets. The possibilities are endless and it depends on where you are. I’m glad we don’t just stay in our C.R.E.A.T.E. bubble. Because we choose to be a bit adventurous, I ended up discovering PastaMore at a farmer’s market and now their products are a must have in my kitchen.

 COMMITMENT – The biggest challenge I have faced in regards to planning retreats is commitment. People say yes, then they say no. People can be flaky or change their minds. Or maybe some life event happens or maybe they simply missed their flight. Because I PLAN every aspect of my retreat and I make an ALL INCLUSIVE cost AND I have to secure housing that can sleep 5 or 10 or 20, knowing who will show up and who won’t show up is key! One way to combat this issue is to have guests pay upfront for some or all of the retreat. If you give them a year to plan for the retreat, you can easily collect all the moneys needed long before everyone arrives. You can also be forthcoming in your communication with the group. My friends know I’m honest and straightforward. I give them a time frame to live in a “maybe I will attend” mindframe. Then I give them a deadline for when they must say yes. When someone was flaky a few years before, I chose not to invite them the next year. It’s a puzzle really. As mentioned, what may help is people committing with the dollar signs and also communal accountability and transparency helps too.

"Art Retreats"

Guests List – If your retreat is invite only or if your marketing material is intentionally attracting a certain kind of person, you need to take some things into consideration. First, if it truly is an invite only kind of thing, remember that this retreat isn’t for everyone. My retreat is NOT for a woman who has to check her phone constantly. Although its more than okay to check in on foursquare when you get to the top of a mountain! My retreat is NOT for the woman that HAS TO talk about her husband or baby every single moment and has to call them 10 times a day. Or my retreat is not for the complainer. It’s for a woman who is present, curious, creative and open. It’s for a woman who is okay with being outside of her comfort zone. My “retreat” isn’t about “retreating from your life” but moreso about “gathering” with other women to be in community and creating and sharing together. The entire world is not your ideal customer or retreat guests. All of your friends are not your ideal guests. Even if your event is open to the public….you should really think about the kind of person you want attending and intentionally attract that kind of person.

"Hosting Your Own Retreat"

Only those who risk going too far can possibly find out how far they can go. — T.S Eliot

Am I freaking you out? Goodness, this only scratches the surface of retreat planning when you want it to be intimate, intense, artistic with yummy meals and great workshops.  If you’re planning a corporate retreat or a church retreat or a bootcamp or something else…maybe this doesn’t help you. But if you know me or my brand or the energy of my life, this retreat does speak to a certain kind of person. It speaks to the Wild Magical Woman who wants to gather with other powerful and creative women.

The biggest takeaway is to create what you want. I resonated with Kelly’s LoveBomb retreats and Sarah’s Great Mystery retreat. I also have taken all the highlights from every trip and retreat I’ve been on. My retreat is informed and inspired by the 10 day silent retreat I attended and the 10 day dance immersion I attended and the World Domination Summit I attended and all those church/college/corporate retreats I’ve attended. I also use to be a camp counselor too! I take all my best experiences and all the thing I imagine to be awesome and I find ways to create that in my life…. Thus C.R.E.A.T.E., my annual artist gathering of Wild Magical Women.

Now if you want to attend a retreat and not necessarily plan, manage and host one…consider joining us next year for C.R.E.A.T.E. 2014…our first public one. Or join me for a local  2 day workshop in New York called “Wild Magical & Creative Woman”. It’s like my four day retreats and craft parties and everything I know about being authentic and expressive and artistic and creative all mushed into 2 full day workshops with Whitney Freya of “The Artist Within.”

  "How to Plan a Group Retreat"

 Let’s close with some quotes that I love.

I do not want to get to the end of my life and find that I just lived the length of it. I want to have lived the width of it as well. – Diane Ackerman

Always remember, it’s simply not an adventure worth telling if there aren’t any dragons. Sarah Ban Breathnach

 Do not go where the path may lead, go instead where there is no path and leave a trail. — Ralph Waldo Emerson

 If you obey all the rules, you miss all the fun. – Katharine Hepburn

There is no such thing as bad weather, only inappropriate clothing. – Sir Rannulph Fiennes

And forget not that the earth delights to feel your bare feet and the winds long to play with your hair. — Kahlil Gibran

"Creative Retreats"

 You may also want to read two articles I wrote, “ Living On Purpose: A Life of Your Own Design” and “Explore: Choose Your Own Adventure

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Showing 3 comments
  • Nina

    Oh your retreat sounds like fun!

    My pole studio did a retreat last summer, and while I didn’t get to attend (I was visiting my family in Norway), everyone kept raving about how great it was. I think there’s something to getting out of your normal routine and surrounding yourself by creative people, it really does make a difference from talking to people online in a hectic daily schedule.. I will look forward to seeing your details for 2014! :)

    • Sheena LaShay

      @Nina, the retreat for 2013 hasn’t even happened yet and I am already planning next year. That’s crazy. But its so worth it. These retreats are awesome. I personally love retreats. Hence, why I can’t wait for a PDBA retreat/conference!

  • Cynthia Insinna

    OMG Thank you so much. I am exploring a passion and I am quite sure it includes having small retreats in my home, which is quite large with pool, jacuzzi and a pond. I am taking a teachers yoga class, love art, books, etc etc.
    This is the best website I have found.
    Do you have any plans of being in Florida?
    Cynthia Insinna

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