The Final Chapter: Planting Creative Roots in Costa Rica
One story ends and another begins
On Valentine’s Day of 2025, Anita and I made the boldest decision of our lives. Every great journey starts with a single decision, and on that night we decided to sell our house, and almost everything we owned, to become immigrants in Costa Rica.
We uprooted everything and began a journey that has reshaped our lives in ways we never imagined.
We’ve traded the comfort of familiarity for the thrill of discovery: diving into adventures that challenge us, and lessons we’ll carry for a lifetime. Through this process, I’ve learned so much about creativity, rest, and the delicate rhythms that make life beautiful.
Now, we find ourselves planting the seeds of new dreams. Like this journey, these creative pursuits will grow, transform, and evolve alongside us in our new home. To understand why this move mattered so much creatively, I need to rewind a bit.
Ten years ago I launched my original podcast, Cracking Creativity. I was also helping artists market their work, and I wrote a book on how to be creative.
For four years, I gave everything I had to build a creative business. But when my course launch failed, I walked away from it all.
I’m not saying all this for sympathy. I’m saying this because oftentimes things don’t go as planned. But it’s what you do afterwards that really matters.
Burnout hit me hard. I felt lost in a fog, unsure of how to move forward or rekindle the creative fire that once fueled me.
But by November of last year, I felt a flicker return. I decided to try my hand at building a creatively focused business again. Long before we moved, I knew I wanted to plant new seeds — ideas that could grow into something meaningful.
I was back in the groove and rediscovering my spark as a creative connector when the move disrupted everything. Once again, I hit pause on my projects, and uncertainty crept in. Would the connections I’d built still be there when I returned? Would anyone care?
At first, this fear consumed me, but then clarity took hold. I realized the journey itself was my story. I needed to write about this experience, about the challenges and triumphs of uprooting our lives and beginning again.
The months following our move felt like a constant state of transition. Every day brought new adjustments, and for a while, I struggled with guilt about not adapting quickly enough.
Why wasn’t I working on my podcast?
What happened to hosting Creativity Parties?
Are you going to publish to Substack?
All of that took a backseat for a few reasons.
I knew I needed to write about my experience and share it with the world.
I was in a brand new city where the only people we knew were our lawyer and real estate agent.
There is so much to explore and do around the city.
I am not fluent in Spanish so even every day conversations take a mental toll.
But over time, I realized that the best thing I could do was slow down. I needed to embrace life’s new rhythms with patience instead of shame.
Our Moving Journey
Writing this series has become one of my most fulfilling creative undertakings. It’s given me the space to reflect on what it means to uproot your life, to leave behind everything familiar, and grow roots in an entirely new environment.
Writing about this journey is not only a record of memories but also an exploration of resilience. Through it all, I’ve learned to trust the messy, imperfect process of becoming. And I’ve found peace in knowing that home isn’t just a place. It’s something you create.
Making New Connections
When we first arrived in Costa Rica, Nacho and Lorena were our lifeline. They guided us through every hurdle, from finding a place to live to navigating endless stacks of paperwork. Without their help, the transition would have felt insurmountable.
But once the dust settled, they were no longer part of our everyday lives. That means we needed to make new connections, something that’s never easy in a foreign country and unfamiliar community.
This is where Pookie helped open doors for us. In October, Anita posted in the community chat about Pookie’s 11th birthday party, and the response was both surprising and heartwarming. Eight adults and five dogs showed up to celebrate his birthday. There were unforgettable moments: Pookie trivia, human and dog treats (including a piñata for the pups!), and two cakes. It turned into a joyful gathering that allowed us to meet our neighbors and find some canine friends for Pookie.
Outside of our complex, I’ve also connected with Ticos, an affectionate name for local Costa Ricans, through a language exchange group chat. We’ve met in person a couple of times, and I regularly hop online to practice with one of them. Switching between Spanish and English has allowed all of us to improve in our new languages.
Anita and I hope to meet even more new people through volunteering next year. It’s a chance for her to meet new people, and for me to immerse myself in the local culture and improve my Spanish. Connections take time, but little by little, we’re finding our place in this community.
Exploring Costa Rica
Moving to a new city always comes with opportunities for exploration, but moving to a new country opens the door to truly unique adventures.
Costa Rica has already surprised and delighted us in countless ways.
Avenida 10, our favorite grocery store, always keeps us guessing with its unexpected finds and unique atmosphere.
Oxigeno feels like stepping into the future, with its sleek design and innovative spaces.
And Barrio Chino is an unbeatable spot for mouthwatering food and browsing all kinds of cheap wares.
San Jose also comes alive through cultural events that showcase its vibrant spirit.
At the African Cultural Festival, we celebrated the heritage that ties the country to its African roots.
Costa Rican Independence brought a torrential rain and the streets flooded with people full of pride.
And Festival de La Luz sparkled with holiday joy with its brightly illuminated floats, enchanting music, and a sense of community.
Beyond these celebrations, it’s the small moments that make this new life feel more grounded: catching a show at a local theater, viewing art at the nearby museum, strolling through La Sabana park. These quiet experiences help us feel like true locals.
Orlando was familiar and predictable, while Costa Rica surprises us every day. They remind us how curiosity and exploration are keys to a fulfilling life. I hope this sense of wonder continues to intertwine with our creative journey here.
Navigating Spanish
By nature, I am deeply introverted. When I was a kid talking to strangers felt terrifying. I dreaded restaurants because interacting with waitstaff filled me with anxiety. Even making friends felt insurmountable. The world seemed overwhelming, and for a long time, I kept my distance.
Over the years, I’ve worked hard to step out of my shell. Improv classes taught me to embrace uncertainty. Joining a fraternity connected me to a supportive community. Hosting online events helped me find my voice in new ways.
But moving to Costa Rica, where I don’t speak the language fluently, has tested that confidence all over again. Communication feels daunting, and often I find myself retreating to old habits of silence.
Thankfully, Spanish is becoming less of a stranger each day. Through apps like Duolingo, Airlearn, and Unedo, I’ve kept up streaks that help reinforce my vocabulary.
Watching shows and singing karaoke with Anita makes learning fun. Slowly but surely, I’m at the point where I can understand a lot. Mastering conversations still feels far off, but with each small step, I’m building up my confidence again.
These challenges aren’t obstacles to my creativity. They’re necessary pauses that allow me to grow and adapt.
Before the move, I hit pause on my creative projects — not out of desire, but necessity. Our days were filled with packing tape, endless paperwork, and bittersweet goodbyes. That frenetic energy followed us across borders: new schedules, unfamiliar streets, and the daunting task of calling a foreign place home.
But when the dust settled, a quieter urgency emerged. I felt an aching hunger for creativity. Unlike before, though, I wasn’t trying to fill a void. I became intentional, asking myself not just what I wanted to create, but how collaboration could bring greater meaning to the work.
So I started planting seeds. Small ones at first. I brought back my Substack to write about this journey. Restarted my podcast with less polish and more heart. But the projects that surprised me most were the collaborative ones, the ones where I got to watch something bigger than myself take shape.
I organized submissions for the Global Zine Project, watching artists I’d never met weave their work into a beautiful compilation.
Marc, Nikki, and I hosted a Creativity Summit where the goal was actual connection instead of lectures or presentations. Marc and I also hosted a Book Summit to finish off the year.
And then there’s Standout Authors Unbound, where I get to spotlight writers from underrepresented communities. That one’s been quietly meaningful. I think helping other people tell their stories has helped me understand my own.
What might seem like a mountain of projects fits seamlessly into the steady rhythm I’ve found here. In Costa Rica, I’ve learned to listen to life’s natural tempo: to work when inspired, rest when needed, and know that creativity flourishes in both.
These projects are just the first seeds of what I hope will become an ever growing creative garden.
Through this process, Anita and I have discovered so much about our creativity, and even more about ourselves. The most profound lesson we’ve learned is to trust in ourselves and in each other.
We’ve stopped trying to control every outcome, especially the ones beyond our reach. Plans don’t always unfold the way we plan. So the best thing we can do is trust in our ability to adapt, adjust, and flow with whatever comes our way.
Anita discovered this by becoming her own boss. She built a video/podcast editing business from scratch. And little by little, she went from not knowing where her next gig would come in the beginning of the year to being fully booked by the end of the year.
I’ve stopped fixating on the question of whether my projects will succeed or fail. It no longer holds the same weight. Instead, I pour my energy into what sparks curiosity and joy. Months ago I would have felt disappointed in the fact that we only had 8 attendees to our Book Summit, but now I recognize having such a small group allowed us to create a more intimate and personal experience.
Some things will turn out beautifully, others will fall apart. But embracing both rest and creation has showed me how to balance my life and my work. Giving up the need for control has allowed my creativity to flow freely for the first time in years.
One of the projects I’m most excited about is the anthology of stories inspired by moments that changed us. It’s a natural extension of the work we began earlier this year, and it’s finally taking shape as something tangible we can hold in our hands. It will be filled with stories that move people and remind them of the beauty in transformation.
My second project dives into fiction: the story of Radioactive Raymond, inspired by one of our GrimlyGala dolls. It’s a gritty tale set in a small, forgotten town, and it explores belonging, and survival. Writing it has been incredibly fulfilling, and has me exploring what it means to endure, to hope, and to reimagine what’s possible.
But the most rewarding part of these projects isn’t the end result — it’s the process itself.
It’s about my ability to follow my curiosity.
It’s about my openness to things I don’t feel qualified to do.
It’s my willingness to do things even if they aren’t successful.
That’s the biggest change in me since June. Instead of waiting for the “right” moment to work on what fulfills me, I’ve opened myself to a world of creative possibility. All I need now is the courage to keep pursuing it.
There has been a sense of finality about our move from Florida to Costa Rica. In June we uprooted everything and it profoundly changed our lives.
Remember that first day I wrote about? Pookie snoring, coffee brewing, the cool breeze through the sliding door? Those moments that felt surreal and new?
Now they’re just Tuesday.
And that vision board we made with mountains, creative work and community has transformed from dream to daily reality.
We’ve gone from asking “Wouldn’t it be amazing to live here one day?” to living our answer.
I am filled with new creative purpose. My podcast seeds are sprouting again. The writing flows more naturally here. Even learning Spanish feels like part of the creative journey we came here for.
This journey has been one of countless lessons, and through it all, I’ve learned that when you open your heart to change, the world opens itself up to you in return.
But as one story concludes, another begins. Our creative roots are finding new soil. Our community is growing. Our adventures are just beginning.
I’m no longer amazed that we live here now. I’m amazed at what we’re building here. And I can’t wait to share what comes next.
Pura Vida is not just a greeting anymore. It’s the life we’ve chosen.
I want to end this series by acknowledging all the people and things that made this journey possible. I know every journey requires the help of the people around you and I know I could never have done this alone.
Anita – Anita is not only the rock that holds me up, she is also the partner who has done it all with me. Without her, there is no move to Costa Rica. I am blessed to love her and be on this amazing journey with her.
Pookie – Pookie is more than just our dog, he is a pivotal part of our story and journey. He gives us comfort and joy every single day and he has made this move extra special.
Our Families – This journey would not have been possible without the support of both of our families. They not only helped us pack, move, and store stuff for us, they have also been completely supportive of following our dream and helping us make it happen.
Friends – Our friends were crucial in supporting us with our move. Our business friends have been the constant that made all our creative work possible. And our new Costa Rican friends have made moving here less lonely.
Neighbors – A special shoutout to Aaron and Carolina for helping us every step along the way. They helped take so much stuff off our hands and watched Pookie when we had to make those trips to Tallahassee. I’d also like to thank our new neighbors in Costa Rica who have helped us adapt to our new home.
Bonnie – Bonnie helped me get my first house, helped Anita and I get our home together, and helped us sell our home. She was amazing the entire way. She is not only a fantastic realtor, she is an even better friend.
Mike, Nacho, and Lorena – It’s funny how someone I never met before helped us find the key pieces in our move here. Without my brother introducing us to Mike there would be Nacho and Lorena. Without Nacho and Lorena we would be at a complete loss here. They have made our move here as seamless as possible.
Everyone else who helped us along the way – There are so many unsung heroes who helped make this dream come true. I can’t possibly name them all, but you all know who you are. Thanks for everything you did to make our new lives possible.
If you’re standing at the edge of something, I’m curious what it looks like from where you are. Share your story in the comments below.
Series in Order:
We Weren’t Unhappy But We Left Anyway
Why We Left a Good Life Behind
Letting Go (Pt. 1): The Beginning of a Creative Reset
Letting Go (Pt. 2): Clearing Space for What’s Next
Between Worlds (Pt. 1): The Messy Middle of a Creative Reset
Between Worlds (Pt. 2): Saying Goodbye to Our Old Lives
Final Farewell (Pt. 1): Saying Goodbye to Orlando
Final Farewell (Pt. 2): Our Last Days in Florida
Journey to San Jose (Pt. 1): The Not So Calm Before the Storm
Journey to San Jose (Pt. 2): We’ve Finally Made It
Journey to San Jose (Pt. 3): First Day Adventures
Finding Home (Pt. 1): Our First Big Decision
Finding Home (Pt. 2): The Race For Cash
Finding Home (Pt. 3): A New Start
Settling In (Pt. 1): Early Lessons & Adventures
Settling In (Pt. 2): So Many Curveballs
Settling In (Pt. 3): Everyday Moments That Make This Home
Settling In (Pt. 4): The End of the Beginning
Finding Our Rhythm (Pt. 1): Becoming the Guides
Finding Our Rhythm (Pt. 2): The Reset We Didn’t Plan For
Currently Reading: The Final Chapter: Planting Creative Roots in Costa Rica
Thanks for sharing. I've been thinking of moving out of the USA and I enjoy reading the experiences of others who have made the move
Hi Kevin, just read this and thank you for sharing your journey. It’s inspiring- especially the parts of how you responded to things that didn’t pan out. It’s so true though- that it’s about what we do afterwards. Looking forward to reading more of your posts!