Dreaming Up a Retreat

See that girl in the picture? That’s me. Walking in to my first conference, so excited to be there I was hugging every speaker as fellow attendees flooded in the doors. I was anxious, hopeful, and eager to soak in all the weekend had in store.

In 2015, I started Lettered Grace. I was a stay at home mama to 3 and I took my love of lettering and put my creative genes to work and launched a little side business.

In 2018, I attended my first conference for creative entrepreneurs and absolutely loved every second of it. I learned more than I could’ve ever imagined and met some amazing, talented, brilliant creatives. It changed the small business game for me. (You can actually read more about my experience at that retreat in some previous blog posts.)

I had such an incredible time, I was a return attendee for 3 more and a couple of their alumni retreats. Each time, I had a blast and wished the time hadn’t passed so quickly.

Fast forward to 2020 – the year that everyone felt disconnected. As a stay at home and homeschooling mom of 3 (at the time – 4 now), I was crushed that the one event of the year that allowed me time away with other women in the creative community was on hold until further notice. In fact, no one was hosting any conferences or retreats of any sort. For me, it triggered those “what if” thoughts that creative minds default to – What if other women are feeling this way, too? What if I organized something?

The more I thought on it, the more I realized that I didn’t really want the learning or business-focused aspects of a conference. What I was craving was connection. I missed those moments of sitting around a table and laughing over a meal. Piling up on the couches after a fun day and just following wherever the conversation led – late into the evening. I missed those moments where you feel friendships deepening in the smallest, but significant ways – not because of an awkward ice-breaker game or assigned seating during a breakout session, but just in the natural way that we connect with one another when we take the time to slow down and just BE.

I decided to make it happen. I reached out to friends to gauge interest. I researched rental houses. I vowed to keep the price as affordable as possible so it wouldn’t be impossible for someone to come who really wanted or needed it.

In January of 2021, the first Rest & Play Retreat took place in Seagrove Beach, Florida. It was new and informal and imperfectly perfect. There were 7 women who gathered together and rested and explored and biked and shopped and dined and made memories. Some went to bed early, some stayed up late. Some studied for school, some read books, some worked a little on laptops, and some walked on the beach. We spent a weekend together with no itinerary, no outrageous budget, no early wake up calls just to eat breakfast. It was exactly what we needed after the chaos of the year before. We left filled and grateful and refreshed and I immediately knew I would do it again.

January of 2022, I was all of six months pregnant with our sweetest surprise – our baby boy, Jack. Rest & Play didn’t happen that year, but it was worth it for the healthy son we welcomed that April!

January 2023, Rest & Play was back for round 2 in Seagrove Beach in a perfect rental with our friends at 30A Beach Girls. Seven women gathered for the weekend and we had the most amazing time together! So many similar moments of enjoying great meals and staying up chatting into the night, but also so many new adventures, too. New group, new dynamics, new friends – still the same result. We all came in with our own heaviness from daily lives and stresses and we all left a little lighter, feeling seen and loved and refreshed.

I can’t describe what it feels like to dream up something like this retreat, to watch it come to fruition, and then have the women that attend tell you how it was exactly what they needed, how it’s the only retreat they’ve been to that they leave feeling ready to return home rested and rejuvenated, or how it was life-changing.

Honestly, I can’t take the credit. It’s all totally a God thing. From the desire for community, the spark of an idea, the way it all comes together piece by piece each year, and how there are so many little affirmations that this is what I’m supposed to be doing.

Let me wrap this up with two bits of encouragement:

  1. First of all, If you have an idea that seems crazy or too big or out of reach, don’t hesitate. Don’t wait until everything lines up perfectly. Don’t be distracted by the people who don’t get it or think you’re copying them or don’t have anything positive or encouraging to say. (They’re probably not your people anyway.) You chase that big idea down, step by step, little by little, and you watch it as it unfolds in front of you!
  2. Secondly, if you read this and you’re thinking, “My goodness! That sounds like an amazing weekend! I wish I could’ve been there!” Or maybe you’re wondering when the next one is – just jump on our email list to get all the details for upcoming dates. You can also get an inside peek by following along on Instagram, too. This retreat was created to be a place the weary to find rest, to sink in, slow down, and enjoy the beautiful moments of simply being together. I would absolutely LOVE to have you join us!

Stay tuned for upcoming posts highlighting our past Rest & Play Retreats – full of pictures, comments from attendees, and some of our favorite local 30A spots we shopped and dined at!

© Lettered Grace + Kelli Cross Designs 2015-2022 | Video by LoveTravelfilm | Photos by Kelli cross + Anna Filly Photography | Policies