Have you ever wanted to move away and leave everything you know behind? In today’s episode, I’m joined by Kadie Smith, who did that very thing by moving to Costa Rica. Kadie is the multi-talented art director and branding expert behind Drop Cap Design, who felt called to share her experience of Costa Rica with her followers by hosting her very own retreat. (And fun fact: I was there!)

Her first retreat was nothing short of an adventure, complete with a tropical storm that changed everything she had planned. We chat about the unexpected joys of imperfection, why calculated risks matter, and how the little things (like a stormy beach day) can lead to the most impactful breakthroughs.

Kadie’s experience hosting this retreat is an important reminder that even if plans don’t go as we intended, sometimes they can turn out even better, and help us embrace the ordinary day-to-day things. If you’ve ever dreamed of hosting a retreat or stepping outside your comfort zone, tune in for insights on planning, personal development, and why embracing imperfection is the secret to hosting with heart.

If you’re an educator, coach, course creator, or someone passionate growing the educational side of your business, Creative Educator Conference is the place you need to be! Come join us at this in-person event in Dallas!

Kadie moved from Montana to Costa Rica two years ago, finding inspiration and creativity in the vibrant atmosphere. Her vision of hosting a retreat sparked from her personal experiences, watching wellness retreats take place all around her in Costa Rica, and the desire to share the place she loves with others.

Despite having only ever run her business from behind her screen, with the encouragement and partnership of her fiance, Kadie set out to create a wellness retreat that blends personal development with exploration. This was very different from her actual business of traditional branding and design.

In her business, she helps people craft identities for their business, but they never really  get to the point of helping someone understand who they are as a person. This creates  a huge disconnect in the branding space—people don’t know what their values are and how they impact the brand.

At this retreat, Kadie and her fiance, Addison, curated a schedule that combined yoga, personal development, and one-on-one sessions. Addison took on leading the yoga sessions and managing the schedule—ultimately deciding that people would have the space to make this retreat their own.

Now one of the challenges in cohosting a retreat was that they had to take the other’s ideas into consideration—while one might have a concrete idea of what should happen, that wasn’t necessarily how the other felt. This is especially true when you have different backgrounds and experiences. Finding a balance did take some time to determine what would be best for attendees. In Kadie’s case, it meant aligning her ideas, her fiance’s, and the photographer, Rachael’s ideas.

They opened the retreat up to bringing your partner or a friend so that you could enjoy the time they created for you (yes, I was Sarah Erickson’s plus one). Ultimately, they made the event schedule very flexible, which ended up being a blessing once they arrived.

Things don’t always go as planned—like an unexpected tropical storm. Kadie quickly had to learn to embrace the flexibility that they planned for. It rained the entire time. While on a vacation, this would be terrible, it actually allowed the attendees to connect more and spend quality time together.

At my own retreat, I had my own experience with the unexpected. I found myself with a bad case of vertigo and spent the first two days of Next Level 2025 in bed.

Kadie embraced every challenge, allowing the retreat to unfold naturally. Kadie’s highest highs included watching participants conquer surfing and an impromptu coffee tasting!

Kadie’s retreat was more than just an escape; it was an invitation into her life, offering attendees a glimpse into her daily life in Costa Rica. This level of personal involvement created genuine connections, transforming attendees into lifelong friends. There is power in creating events rooted in authenticity and locality.

Perfection isn’t necessary for a successful event. Instead, it’s about creating an inviting environment where attendees can thrive and explore new facets of themselves.

Kadie believes that people are following you because of your lived experiences—that’s what keeps them interested. Hosting a retreat in her town and sharing her favorite places to go, even introducing attendees to her friends, those are things that connect the attendees to a host.  Inviting anyone into your space creates a greater level of intimacy.

Connect with Kadie:
Instagram: @dropcapdesign | https://www.instagram.com/dropcapdesign/
Website: https://dropcapdesign.com/
The Sunday Edition: https://view.flodesk.com/pages/5fd26577f6bb96e801aefdd9

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The post 186: How Imperfect Plans Can’t Take Away from Perfect Experiences with Kadie Smith appeared first on Laylee Emadi | Coach for Creative Educators.