Dear friends,
Second Harvest was born from a simple belief: that the second half of life can be the most creative, connected, and courageous chapter yet.
It began not as a business plan, but as a personal wakeup call. Realizing how easy it is to lose ourselves in achievement, and how hard it can be to pause long enough to notice what’s quietly asking to begin again.
For years, the world told us to move faster, work harder, and never stop producing. We participated in all that until one day, it no longer made sense. After building companies, raising families, and losing people we loved too young, the things we thought defined us began to fall away. And in those endings, we found something unexpected: space. Space to be ourselves, without the armor of titles, résumés, or expectations.
Second Harvest is that space made real.
We are not therapists or life coaches. We’re facilitators, companions, and fellow travelers — still learning, still becoming. This isn’t a self-help retreat or a spiritual bootcamp. It’s a designed pause for grownups that becomes the launchpad for the most meaningful season of your life.
Each gathering brings together remarkable people in beautiful places to slow down, reconnect with what matters, and design a life worth living. Through meaningful conversation, adventure, reflection, and shared meals, we explore what it means to live with clarity, courage, and intention.
Every retreat is built on three simple principles: Pause to step away from the noise and the endless loop of doing, connect with yourself, with others, and with the natural world, and then craft the next chapter of your life with curiosity and care.
We don’t offer generic answers. We create environments that help you live your questions and shape spaces where meaning reveals itself in its own time. As Rilke once wrote, “Try to love the questions themselves… maybe, gradually, you will live your way into the answer.”
That’s what Second Harvest is about. Learning to live your way into a new kind of truth — one defined not by what you achieve, but by how deeply you live.
With warmth and gratitude,
Richard & Devon
Founder Stories
Richard's Story
For decades, I lived by the metrics of achievement: startups founded, books published, clients served. Ticking the boxes of the American Dream. And for a while, it worked, until it didn’t. Losing my wife to cancer and being forced to shut down a business soon after stripped everything down to essentials. What emerged from the smoldering mess was a remembering of what it means to build something from love, not fear. Of how creativity, relationships, and purpose can rebuild a life.
Second Harvest began as a question I needed to answer for myself: What if the second half of life could be better than the first? It’s now become my answer to that question. A living, breathing experiment in meaning-making.
Devon's Story
I’ve spent my life at the intersection of care and creativity—building a portfolio of startups, nurturing a community around that, raising children, navigating transitions with grace and humor. My transformation wasn’t a single moment, but a collection of them: the realization that being fully alive means being fully present. That real leadership starts with the humility to truly listen to others, and to myself.
Second Harvest is where all of that experience comes home. My work is to create environments of belonging—places where people can safely drop the masks, meet themselves again, and rediscover the joy of being seen
Our Invitation
Second Harvest is an invitation to pause. To lay down the script of success and pick up something more honest: wonder, gratitude, courage.
You’ve spent your life building. Now it’s time to harvest.
FAQs
No two retreats are the same but they all follow the arc of reflection, connection, and finding a pragmatic path forward that makes sense for you. Each day is designed to create just the right amount of creative tension between familiar structure and adventurous spontaneity.
Days start with a meditation and yoga session followed by a quiet coffee and gentle conversation.
Mid mornings are all about workshops exploring identity, purpose, or creative reinvention. This isn’t group therapy or drum circle stuff, this is practical and grounded work with a healthy dose of intuitive alignment.
Afternoons open into adventure. We can’t tell you too much about this because they are intentionally mysterious and awe-inspiring. These experiences are designed to reconnect you to your body and your senses (psst, you can see some clues if you watch our videos and browse our gallery of stunning photos).
Evenings are slow and social: long meals, fireside chats, music, and meaningful conversations that can sometimes wander late into the night.
There’s also time to be alone and time to belong. To listen and to be heard. To feel human again. It’s less a schedule, more a rhythm. A design for slowing down so you can finally catch up to yourself.
Second Harvest attracts people who have already “made it” by conventional standards and are asking, “Now what?” Executives, entrepreneurs, and investors. Artists, founders, and athletes. Leaders, makers, and seekers.
People with rich resumes and restless hearts. They’re united by curiosity, not category. By a desire to live the next chapter with more courage, creativity, and connection.
Many come solo, some come as couples. All leave as part of a lifelong circle of peers and friends. They arrive successful. They leave significant.
We’re not a traditional self-help retreat. You won’t find any gurus or shaman here. We’re not here to “fix” you. We’re here to help you remember who you already are. Second Harvest was built as a quiet rebellion against the noise against the endless productivity hacks, dopamine hits, and quick-fix enlightenment weekends.
Everything about the experience is rebelliously analog: long walks, handwritten notes, slow (and mouthwatering) meals, real conversations. No screens, no PowerPoints, no apps to guide your actions. Phones go away. Presence returns.
Each retreat is a curated adventure. We’re blending art, nature, philosophy, and design.
It’s equal parts creative residency, leadership lab, and spiritual sabbatical. Crafted for people who don’t need another program, but crave a place to pause, to breathe, and then to step back into their lives, fully awake.
You’ll leave with something rare: a sense of alignment between who you are and how you live. Aligning the intangible with the practical. Many participants describe a kind of exhale. A new relationship with time. A renewed sense of creativity. And, maybe most importantly, new friends that can support you on whatever path you choose to take.
You’ll return home with a close-knit community of people who speak your new language of courage and curiosity. A clarity that makes decision-making simple again. But don’t take our word for it, read the testimonials, look through the gallery, and see yourself right there.