Magical Year Retreats

A Global Community Navigating The
Mid-Life Journey

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

 MEMBERSHIP APPLICATIONS SPRING 2026

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

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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...

"I just wanted to say thank you — these last few days at Magical Year Retreats were some of the most meaningful I’ve had in a long time. I came in feeling raw and unsure, hoping to find what’s next, and I’m leaving with not just tools, but a community of people I can lean on as I work through a lot of transition, hurt, and healing."
— Nehal Patel

"I can not express how grateful I am for that weekend. Wow I am totally blown away. I really was soooo stuck and it’s helped me see a bit of a way out. It was incredible - you really were not kidding when you said it was going to be magic. Thank you thank you!!"
— Colleen Zulich

"Thank you so much for having me on this trip. It was such an honor to be part of this journey with you. Would love to connect when you’re back and continue this journey together!"
— Mary Grace Levin

This gave me clarity I did not realize I was missing. From the very first day, it surfaced beliefs I had been carrying for years without questioning them or even being aware of them. Seeing those stories clearly helped me understand how much of my urgency, fear, and pressure were rooted in old narratives about identity, safety, and aging.
— Kristen Shaheen

It was a punctuation in time that was much needed; reminding me to be intentional. I appreciated the experimental mindset vs. goal-driven one - which is usually what happens at the onset of any calendar year with resolutions where you are thinking in absolutes. I found this to be much more forgiving, softer, approachable, and framing it in this way felt like way less of a daunting, scrutinizing task and more like a nudge in the self-love direction.
— Lauren Sozio

By working through the combination of "ID" narratives and "OS" narratives and living in the questions, I've achieved an interesting new state of acceptance and curiosity. Instead of trying to optimize my way into a better self, I can instead pursue a felt-state (beginner's mind) to build around:.. openness, curiosity, presence, expression, humility, freedom from expectation, connection, etc. My freedom of movement seems to have increased. And, coincidentally or not, new doors appear to be opening. Super grateful, thank you!
— Brandon Comstock

The biggest realization for me was stepping back and recognizing how long I’ve been stuck in this uncomfortable space, fully identifying with the unhelpful narrative. I’ve been perpetuating this heavy cloud of despair and ruin—completely at odds with the optimistic, adventurous, "can-do-anything" dreamer version of myself. I’m hyper-aware of this now. And know people around me are noticing.
— Chris Merrill

I did day one [of the 72-Hour Reset} yesterday and was truly saddened by the stories that surfaced and how they’ve shaped me. Excited to reframe a few things in my life so I can move forward.
— JP Tanner

I really love how you two consciously create space for people to be vulnerable. It is quite beautiful and so appreciated - especially in a world that sometimes feels lonely, uncertain and polarized.
— Christine Holland

I really appreciate the continued engagement you’ve been offering after the 72-Hour Reset. The biweekly conversations and the effort you’re putting into keeping the community connected say a lot about what you’re building. All of this is landing at a meaningful transitional moment for me, so I’m grateful for the timing.
— Erik Bettencourt

Thank you for a wonderful overall Spring Summit event. The time and love you put into it was evident, and the positive energy was tangible. I loved the breathwork and visualization. The fireside chats were very inspirational. The vulnerability the speakers showed helped them be relatable.
— John Simonetta

I was observing the Spring Summit participants at all times, which is what I always do, and people seemed so connected and so engaged and really really moved by a lot of the conversation. I was so happy for you guys and so glad to be included.
— Kristin Cabot

I felt like I really needed this and it allowed me to take a step back and just pour into myself. It felt great also having some meaningful conversations and connections. You and Richard make such a great team and are doing something so special.
— Kim G

Thank you so much for the chance to join you all. It was so cool to see what you have built and experience it first hand. I came away with some great nuggets. The breath work and my third crop circle session were so dope!
— Bethany LoMonaco

Shit happens in life. In my case, as a CEO you really aren't afforded the mental space to process and adjust. Magical Year Retreats creates an environment of similar beings with similar journeys. You can pause, reflect and set a new course or at the very least a new mindset allowing you to go forward in a more meaningful way.
— Jeff Dickerson

The anti-conference, that has set me on my path. I want to be part of Magical Year Retreats for years to come.
— Elisabeth B
The synergy, empathy, and openness in the room felt like a warm blanket on a chilly day. I left feeling grateful, encouraged, and connected.
— Steve Woodward

I can't tell you how much I loved today's Spring Summit. Thank you for the thoughtfulness with which you brought us all together and helped us along our winding journeys.
— Angela P

I want you to know what I appreciate that WASN'T there: no scarcity sales pitch to join, no loud music and dancing before each session, no long intros for each speaker, no fist pumping your neighbor telling them "YOU can do this." I loved the space that was created, the invitation to be imperfect, the breath… the magic.
— Sandy A

More details to come, but Magical Year Retreats and the 72-hour reset were the catalyst. I made changes at my company this week Team shuffles, getting stable, rebuilding. Love you, bye.
— Chris M

Richard, I can’t even begin to tell you but our life is changing faster than the trees whip by the window when you look HARD RIGHT out of your car when driving down I-95. I’ve made new friends and I’m just fucking blown away about the fact that I’ve tapped into a whole other stratosphere of life, that I never even knew existed before reconnecting with you and Devon. I really want to thank you.
— Randy B

It was such a pleasure spending a day with you all last month. Such a meaningful and impactful fellowship.
— Tucker Hamilton

“The retreat gave me emotional clarity I didn’t know I needed. I came looking for quiet and reflection, but what I found was connection. I left with friendships and a renewed sense of courage for what comes next.”
— Suzanne Balassone

I had no idea what I'd be walking into, but I was so happy to be a participant. The energy was real, and the impact was palpable for folks. I suspect that's not an easy emotion to create, so kudos. And, I met some very cool humans.
— Peter Zotto

“There is something rare about being truly seen, and that’s what happened at Magical Year Retreats. It wasn’t about performance, but presence. I left with more than memories — I left with allies.”
— Jennifer Linehan

“The biggest surprise was how much laughter and lightness accompanied the depth. I came expecting something serious and got that, but also joy, play, and the power of pausing. It was exactly what I didn’t know I needed.”
— Brad Stanton

“The retreat was a reminder that slowing down is not the same as stepping back. It’s actually moving forward with more intention. I found space to breathe, and in that space, new ideas emerged.”
— Natalie Fernandez

“We often spend our lives talking, but rarely do we spend them listening. In Austria, I was reminded that silence can be the most generous gift. Magical Year Retreats taught me how to be present again.”
— Wouter Oudemans

“I thought I was coming for inspiration. What I received was transformation. A rare gift, not because it was flashy, but because it was simple, human, and true.”
— Nino Maisuradze

“What struck us was the intimacy of it all. Fireside chats, shared meals, quiet walks in the forest — these were not just activities, they were containers for courage and creativity to emerge. It reminded us why human proximity is the real luxury.”
— Bernhard & Kathrin

Men's

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

Our signature Memoir For Healing and Life Transitions curriculum virtually. Three one-month sessions.
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Aspen & Italy Literary Retreats

A beautiful, intimate, and soulful week in Aspen and Italy for our Memoir For Healing and Life Transitions.
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British Virgin Islands Swim

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

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 

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.
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