Magical Year Retreats

A Global Community Navigating The
Mid-Life Journey

Small Group, Nature Based
Yacht, Villa, Equine And
Pilgrimage Based Retreats

 MEMBERSHIP APPLICATIONS AUTUMN 2026

The World's FIrst Membership Based School For Navigating Life's Major Chapters

Seeking a more rewarding next chapter?

Our nature based retreats and unique methodology are designed for you. Magical Year Retreats is a community for accomplished professionals who feel the ground shifting beneath their identity. Members navigating the gap between who they were and who they’re becoming connect through curated correspondence and small-group conversations.

And then, we come together in person.

Learn how to design and build the life you love

01
Retreats, summits, and peer circles for accomplished people designing their next chapter.

International community.

Through private retreats and summits, Magical Year Retreats brings together close cohorts of people ready to step out of the performance and back into themselves. A deliberate pause in a world that rewards relentless forward motion.
Small retreats in locations like medieval Spanish cities, the Austrian Alps, or New England’s coast. This isn’t another exec off-site, self-help or therapy. We’re not here to fix you. We’re here to help you remember who you already are.
Amongst remarkable people and in meaningful conversations, you’ll reconnect to what actually matters to you now. You’ll leave with clarity, steadiness, and practical knowledge you can act on immediately.
Feel like a fit? Apply below.
Join a retreat or summit

Origin Story

Founder, Christopher Baron
I know what it feels like when the things stop working. At 51, within the span of months, I lost my wife to cancer, had to shut down her business, and sold the business I'd been leading for 15 years. Everything I had used to define myself was gone.

What I did next was instinctive: I applied the same design methodology I'd used to build world-class products to my own identity. I mapped my stories, ran small experiments, tested new versions of myself, and rebuilt — not the old life, but something relevant and meaningful. I've now taught this process to hundreds of executives, founders, and leaders navigating their own inflection points.

The methodology works because it treats identity the way great designers treat a hard problem: with curiosity, structure, and a tolerance for iteration. This is the most important design work you'll ever do.

I've been where you are. I've spent over two decades in the room with founders, CEOs, and senior leaders. As a former CEO of a top product design firm and bestselling leadership author, I know the challenges first-hand. I've raised money, built and sold companies, led hundreds of high-stakes product launches, and navigated every kind of transition you can imagine.
Give me 3 days to see the stories that have been running your life, and then redesign your operating system for clarity and peace.

Methodology

A supportive and authentic community with shared values and goals.

Your Classroom: The Most Beautiful Natural Places On The Planet

Our nature based retreats and unique methodology are designed for you. 

Membership

A place where curious and adventurous people are the norm - not the exception.

Does This Sound Like You

You spent decades building. But nobody prepares you for what's next.
Research on executive transitions is clear: while you can plan for your business, you can't answer the question, "who am I?" without inserting a work related title or a role.

You've become your title. You know how to be a CEO. You know how to be a founder. You know how to run the board meeting, close the deal, lead the team through the storm. But when the role ended, whether you chose it or it arrived unexpectedly, your identity ended too.

The calendar cleared. The phone stopped pinging. And the question you've been too busy to ask for twenty years finally surfaced: "Who am I without all of this?" That question isn't a sign something is wrong with you. It's a sign you're paying attention. Congratulations, you're asking the right question.

Your Guide

Christopher Baron
I’ve spent more than two decades helping teams and leaders design high-stakes products, brands, and experiences.

As the former CEO of a top product design firm and the coauthor of best-selling books like Product Leadership and Design Leadership, I’ve led hundreds of workshops and transformations for organizations around the world.

After losing my wife to cancer, burning out, and rebuilding my life from the ground up, I co-founded Magical Year Retreats alongside Devon to help others navigate their own second chapters with more courage, creativity, and humanity. Helping others find their true purpose and identity is my true calling.

Scientific research and behavioral studies support the idea that early, tangible progress (especially repeatable small steps) increases the likelihood of sticking with a behavior change over time. In this course I’ve combined the best of the science-based methodologies with my practical experience teaching transformation to executives, founders and entrepreneurs.

At Magical Year Retreats, we help our participants become aware of their internal narratives, understand how they are influencing their decisions, and rewrite their stories so they can develop a better relationship with themselves, others, money and their life plans.

Don't just take my word for it. See what others have to say about this program below.

What people are saying...

Men's

Virtually Or Aspen Intensives. Our base curriculum tailored to support your physical, mental, and professional thriving.
LEARN MORE

Virtual Workshops

Our signature Memoir For Healing and Life Transitions curriculum virtually. Three one-month sessions.
LEARN MORE

Aspen & Italy Literary Retreats

A beautiful, intimate, and soulful week in Aspen and Italy for our Memoir For Healing and Life Transitions.
LEARN MORE

British Virgin Islands Swim

A swimming and sailing adventure in the magnificent British Virgin Islands for experienced ocean swimmers.
LEARN MORE

1:1 Virtual

Customizable based upon goals, complexity, and urgency. Three months is ideal.
SCHEDULE A 15 MIN INQUIRY CALL

Aspen 5 Day Intensive

Customizable based upon goals, complexity, and urgency. Office, gym, skis, horseback, hiking & more.
SCHEDULE A 15 MIN INQUIRY CALL

Japan

You spent decades building. But nobody prepares you for what's next.
Research on executive transitions is clear: while you can plan for your business, you can't answer the question, "who am I?" without inserting a work related title or a role.

While each gathering is intentionally unique, they all share a commitment to creating an environment for remarkable personal evolution, alliances for support, and practical ways to ensure that change sticks. There are no gurus or dogma, just extraordinary people. We meet in stunning landscapes, to discover fresh perspectives, and engage in meaningful connections so you can forever change your personal journey.

Greenland

You spent decades building. But nobody prepares you for what's next.
Research on executive transitions is clear: while you can plan for your business, you can't answer the question, "who am I?" without inserting a work related title or a role.

While each gathering is intentionally unique, they all share a commitment to creating an environment for remarkable personal evolution, alliances for support, and practical ways to ensure that change sticks. There are no gurus or dogma, just extraordinary people. We meet in stunning landscapes, to discover fresh perspectives, and engage in meaningful connections so you can forever change your personal journey.

Sardinia

You spent decades building. But nobody prepares you for what's next.
Research on executive transitions is clear: while you can plan for your business, you can't answer the question, "who am I?" without inserting a work related title or a role.

While each gathering is intentionally unique, they all share a commitment to creating an environment for remarkable personal evolution, alliances for support, and practical ways to ensure that change sticks. There are no gurus or dogma, just extraordinary people. We meet in stunning landscapes, to discover fresh perspectives, and engage in meaningful connections so you can forever change your personal journey.

Autumn | Winter Cohort 

You spent decades building. But nobody prepares you for what's next.
Research on executive transitions is clear: while you can plan for your business, you can't answer the question, "who am I?" without inserting a work related title or a role.

While each gathering is intentionally unique, they all share a commitment to creating an environment for remarkable personal evolution, alliances for support, and practical ways to ensure that change sticks. There are no gurus or dogma, just extraordinary people. We meet in stunning landscapes, to discover fresh perspectives, and engage in meaningful connections so you can forever change your personal journey.

Are you facing a major life transition, an enticing opportunity or a daunting challenge?

I work with motivated clients in Aspen and remotely to enhance health, well-being, and performance utilizing a multi-faced approach based heavily in stoicism, mindfulness, and physical and mental performance. In Aspen it is heavily nature/activity based (hike, ski, ride). The Aspen cliche of Mind, Body and Spirit is real. My interest is successfully navigating transitions and high-stress situations, moments that shape life trajectories, as well as strategically optimizing life to align with personal responsibilities, passions, values and goals. This isn't a dress rehersal. To do so I utilize a proprietary inquiry-based model. When necessary, I assemble a supportive team of professionals. My approach is informed by a lifetime of experiences in athletics, meditation, expeditions, research, parenting, and business, as well as my experience overcoming significant health challenges.

1:1 Virtual

Customizable based upon goals, complexity, and urgency. Three months is ideal.
SCHEDULE A 15 MIN INQUIRY CALL

Aspen 5 Day Intensive

Customizable based upon goals, complexity, and urgency. Office, gym, skis, horseback, hiking & more.
SCHEDULE A 15 MIN INQUIRY CALL

Magical Year Retreats

You will receive regular emails on living an adventurous, meaningful life.
Terms & Conditions
© 2025 Magical Year Retreats LLC. All Rights Reserved.