Reboot: Leadership & the Art of Growing Up
Is a partial scholarship for you?
We believe in making personal growth and education accessible to everyone, which is why we offer partial scholarships on a needs-aware basis for many of our programs.
These scholarships support individuals facing financial challenges, including — but not limited to — members of underrepresented communities. If financial stress might prevent you from attending a workshop, we encourage you to apply.
Partial scholarships, provided through the Association for Growth and Education, are limited to 2–3 seats per workshop and reviewed in the order received. We recommend applying as soon as possible, as scholarship decisions are typically confirmed 90–120 days before the workshop date.
Chip Conley
MEA Founder, Hotelier + Hospitality Entrepreneur, Bestselling Author
Jerry Colonna
Guest Faculty
From Performing Leadership to Embodying It: Radical Self-Discovery with Jerry Colonna & Chip Conley
By most measures, you've arrived. The goals that once seemed impossible now sit in your rearview mirror. But arrival has revealed something unexpected: the destination was never the point.
There's a quieter question surfacing: Is this who I really am, or just who I learned to be?
If you're a leader in your 40s, 50s, 60s or beyond who's achieved success but feels something essential is missing, this is your inflection point. The patterns that got you here may be the very things keeping you from deeper impact and fulfillment.
You have the experience, platform, and influence. What you may lack is the self-awareness to wield that power authentically and create the kind of leadership that transforms lives, including your own.
Meet your faculty: Jerry Colonna, the "CEO Whisperer" whose blend of Buddhism, Jungian therapy, and entrepreneurial wisdom has guided leaders at Etsy, SoundCloud, and Gimlet Media. Alongside MEA founder Chip Conley, who built one of the largest boutique hotel companies in the U.S. and mentored Airbnb's founders through extraordinary growth.
Here’s some of what you’ll explore:
Do the deep work of growing up as a leader with two master practitioners and gain laser-sharp clarity on the impact you're here to build.
Listen to Chip and Jerry Colonna on the Midlife Chrysalis podcast:
From Wall Street to Inner Peace: The Emotional Journey of Jerry Colonna
“Time and again, I’ve watched hearts break open so that true and authentic leaders can emerge.”
- Jerry Colonna
Meet
Jerry Colonna
CEO Whisperer | Executive Coach | Bestselling author of Reboot
Jerry Colonna transforms leaders by helping them grow up.
Known as the "CEO Whisperer," Jerry has guided executives at Etsy, SoundCloud, WME Ventures, Gimlet Media, and more through their most challenging moments.
His unique blend of Buddhism, Jungian therapy, and entrepreneurial straight talk cuts through surface-level leadership advice to address the deeper work of becoming fully human. As author of Reboot: Leadership and the Art of Growing Up and Reunion, Jerry's approach isn't about optimizing performance, it's about leading with humanity and equanimity.
“At the heart of great leadership is a curious mind, heart, and spirit.”
- Chip Conley
Meet
Chip Conley
MEA Co-Founder | NYT Bestselling Author | Former Head of Global Hospitality & Strategy at Airbnb | Host of the Midlife Chrysalis Podcast
Chip Conley reframes what it means to age in the modern world. A three-time TED speaker, Chip is one of the world's leading experts at the intersection of business innovation, psychology, and spirituality.
As creator of the boutique hotel movement and modern elder to Airbnb's young founders, his intergenerational mentoring was instrumental to the company's extraordinary success. That experience inspired him to found MEA and dedicate his midlife years to helping people navigate this life stage with renewed purpose and possibility.
Supported By the MEA Team
Lee Johnson
Head of Land, Livestock, and Mindfulness in Santa Fe
Lee likes to say that he’s as ordinary as dirt but as complex as soil. A former Course Director for the Colorado Outward Bound School and Certified Holistic Management Teacher, he has managed ranches in Nebraska and Tennessee as well as several ranches here in New Mexico. As ...
View BioThis Workshop Is For You If…
What You'll Gain
Authentic Leadership Power
Discover why becoming a better human makes you a better leader, and learn to lead from wholeness rather than just competence and achievement.
Pattern Recognition & Rewiring
Identify the success habits that may be sabotaging your relationships and wellbeing, then develop new approaches that sustain both performance and connection.
Redefined Success Framework
Move beyond accumulation-based metrics to purpose-driven fulfillment, creating meaning that compounds rather than just wealth that accumulates.
Modern Elder Mastery
Step confidently into your role as wisdom-keeper and inspiration source, becoming the kind of leader who elevates people across all generations to show up as their best selves.
Our Agenda at a Glance
Sunday:
4:00 PM: Arrival/Check-in
5:30 PM: Welcome Reception & Dinner
7:00 PM: Orientation Session
Monday:
7:00 AM: Mind + Body
8:30 AM: Breakfast
10:00 AM: Classroom Time
1:15 PM: Lunch
2:00 PM: Free Time
3:00 PM: Classroom Time
5:30 PM: Free Time
6:30 PM: Dinner
8:00 PM: Free Time
Tuesday:
7:00 AM: Mind + Body
8:30 AM: Breakfast
10:00 AM: Classroom Time
1:15 PM: Lunch
2:00 PM: Free Time
3:00 PM: Classroom Time
5:30 PM: Free Time
6:30 PM: Dinner
8:00 PM: Free Time
Wednesday:
7:00 AM: Mind + Body
8:30 AM: Breakfast
10:00 AM: Classroom Time
1:15 PM: Lunch
2:00 PM: Free Time
3:00 PM: Classroom Time
5:30 PM: Graduation
6:30 PM: Celebration Dinner
Thursday:
7:00 AM: Breakfast
10:00 AM: Checkout/Departure
Friday:
Saturday:
*Please note that not all “classroom time” activities take place in the actual classroom.
*Please note all times are estimates as some activities go longer or shorter depending on the group. This agenda is meant to give you an idea of the general flow of activities.
Step into transformation in the high desert
Rising Circle Ranch | Santa Fe, USA.
Our spectacular Santa Fe campus is located on an upscale regenerative ranch featuring traditional Pueblo architecture and nearly 2,600 acres of wildlife, hiking trails in the arroyo, and awe-inspiring beauty. Close to historic Santa Fe, an artisan’s mecca.
PLUS: Gourmet from-scratch meals, snacks, and drinks featuring locally sourced ingredients, made by our in-house chefs
Explore the Ranch
on Horseback
Our Rising Circle Ranch spans 2,600 acres of New Mexico high desert, offering guided horseback riding for all experience levels through diverse terrains under the vast Southwest sky
You’ll experience highlights like:
Horseback riding is an optional add-on activity you can book once you arrive on the ranch. Whether you’re seasoned or brand new to horseback adventures, this guided experience lets you discover the ranch’s natural wonders alongside our gentle horses.
Your Workshop Also Includes:
Turn Your Vulnerability into Your Competitive Advantage: Authentic Leadership Mastery
Most successful leaders live divided lives. There's the polished professional who has it all together, and there's the real person underneath dealing with doubt, uncertainty, and struggle. This split is exhausting and it's capping your potential.
Your team senses the disconnect.
Your relationships suffer.
You're constantly performing instead of leading from authenticity.
The longer you wait to integrate these parts of yourself, the more energy you waste and the more opportunities you miss to create real impact.
Jerry Colonna & Chip Conley help leaders bridge this gap. They've guided countless people through the process of becoming whole, and their methods create lasting change.
You'll walk away with:
This is strategic leadership development that happens to involve the most important work you'll ever do: becoming who you actually are.
Book Your Spot Today
Reboot: Leadership & the Art of Growing Up
Is a partial scholarship for you?
We believe in making personal growth and education accessible to everyone, which is why we offer partial scholarships on a needs-aware basis for many of our programs.
These scholarships support individuals facing financial challenges, including — but not limited to — members of underrepresented communities. If financial stress might prevent you from attending a workshop, we encourage you to apply.
Partial scholarships, provided through the Association for Growth and Education, are limited to 2–3 seats per workshop and reviewed in the order received. We recommend applying as soon as possible, as scholarship decisions are typically confirmed 90–120 days before the workshop date.
The program was spectacular. It really surpassed my expectations. I was really surprised about how the course was curated. There was such a warm intensity and personal touch to it.
I experienced MEA as a newly diagnosed multiple myeloma cancer patient, and as a result of the things I’ve learned - I’ve banished the anxiety of being a cancer victim, am in remission, and living with a newfound energy and purpose.
Just know how grateful I am for the joy fuel you all put in my rocket ship. When I want to feel loved or just need a good smile I can think of my time at MEA, which came at the perfect time to encourage me on my journey. Thank you!
Frequently Asked Questions
Is this therapy or business coaching?
It’s neither and both. Jerry’s approach blends business wisdom with therapeutic insights, but you’re not lying on a couch talking about your childhood. You’re doing practical leadership work that happens to involve honest self-examination. Think of it as strategic personal development – the inner work that unlocks outer leadership effectiveness.
What if I’m already successful? Why would I need this?
Success often creates its own challenges. Many high-achievers find themselves asking “Is this it?” or feeling disconnected from their work despite external wins. This workshop is designed for leaders who’ve achieved significant success but sense there’s more authentic power and impact available to them. It’s not about fixing what’s broken – it’s about integrating what’s split.
I’m not comfortable sharing personal details in a group. Will I be forced to?
Jerry and Chip create psychologically safe environments where vulnerability is invited, never demanded. You’ll share what feels right for you, when it feels right. The power of the work often comes from witnessing others’ courage to be real, which naturally invites your own authenticity. But you’re always in control of your own boundaries.
How does Jerry’s “radical self-inquiry” actually work?
Jerry asks the questions most leadership coaches avoid: What stories are you telling yourself? What are you afraid of? Where are you performing versus being authentic? He combines Buddhist mindfulness practices with Jungian psychological insights and entrepreneurial pragmatism. It’s not abstract philosophy – it’s concrete exploration of the patterns that shape how you show up as a leader.
What makes this different from other leadership workshops?
Most leadership programs focus on tactics and strategies – how to manage better, communicate more effectively, or optimize performance. This workshop goes deeper. Jerry and Chip help you examine the fundamental question: who are you as a leader when you’re not performing? It’s about integration, not optimization – bringing together your authentic self with your professional power rather than compartmentalizing them.
What’s included in the investment?
Everything: four days of sessions with Jerry and Chip, luxury accommodations at MEA’s Santa Fe high desert retreat center, all chef-prepared meals and snacks, materials, and access to the MEA alumni community. The only additional costs are your travel to Santa Fe and personal expenses.
Still deciding or have questions?
Connect with our helpful team of Advisors
Our Advisors are all MEA alumni who can offer genuine insights into our programs. They’re passionate about helping you finding the right fit to make your next chapter the best one.
Daniel Booz
Lucas Erie
Leslie Bartlett