Explore your path
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If you're seeking more
meaning, connection, adventure and joy in your life. Join us. |
Our Programs
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The Traverse; to get through or across
A unique 3-month program harnessing the power of retreats, community and coaching to help you create what's next in your life. In fellowship with a small community of men, make meaningful progress toward the life you imagine while forging lifelong bonds. February 15 Deadline to Join |
The Retreat; a place to connect and reflect
A five day, four night gathering near Jackson, Wyoming. A space to reflect on what matters to you at this juncture in life and to hike, laugh, build new friendships and discover new possibilities for yourself. April 15 Deadline to Join |
Coaching; individualized support
One on one personal coaching to help you clarify your goals and make clear consistent progress toward what matters most to you. Our approach is rooted in genuine listening, optimism, authentic questions and clear accountability. |
"One of the most enlightening, rewarding and amazing experiences."
Heath, September 2022
Heath, September 2022
Which program is right for me?
There's no right (or wrong) answer. The best way to decide is to connect with us and talk through the options together to help you find what fits for you.
Who joins?
Our programs serve a wide range of guys of all ages and life-stages. We have execs and engineers at Fortune 500 companies to stay-at-home dads and retirees. We have small business owners and craftsman, entrepreneurs and creatives. Guys who are single, married, divorced, and separated. Guys with kids, without, and empty-nesters.
What really matters?
The thread that connects us is we're all working on something in our life. For some it's our relationships with our partners, spouses or family members. Or it's our careers, passions and purpose. For others it's our friendships and community or we're in a moment of transition in our lives.
What really matters is you're open to exploring what's true for you, to creating new friendships with other guys, and you're willing to show up and engage.
There's no right (or wrong) answer. The best way to decide is to connect with us and talk through the options together to help you find what fits for you.
Who joins?
Our programs serve a wide range of guys of all ages and life-stages. We have execs and engineers at Fortune 500 companies to stay-at-home dads and retirees. We have small business owners and craftsman, entrepreneurs and creatives. Guys who are single, married, divorced, and separated. Guys with kids, without, and empty-nesters.
What really matters?
The thread that connects us is we're all working on something in our life. For some it's our relationships with our partners, spouses or family members. Or it's our careers, passions and purpose. For others it's our friendships and community or we're in a moment of transition in our lives.
What really matters is you're open to exploring what's true for you, to creating new friendships with other guys, and you're willing to show up and engage.
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"The experience was deep and meaningful in the connections I made with others, myself and with the outdoors" - Keith |
Space is very limited across each program. We keep groups small on purpose.
Our group size creates the space for you to explore what’s relevant and valuable for you given your unique story and life experience. It also supports deeper connection with your fellow guys.
If this approach to learning and growing seems right for you, join us.
Our group size creates the space for you to explore what’s relevant and valuable for you given your unique story and life experience. It also supports deeper connection with your fellow guys.
If this approach to learning and growing seems right for you, join us.
2025 Program Details
The Retreat
A one-time opportunity to pause, reflect, connect and imagine new opportunities with a small group of guys in a beautiful place.
Dates: May 23-27, 2025
Key Elements
Enrollment: Only 10 spaces available
Deadline to Join: April 15
Pricing: $2,995
The Traverse
A 3 month experience to help you move from where you are to where you want to be. Provides individual and group support to make clear progress toward the life you imagine in a defined period of time.
Dates: March 2025 - June 2025
Key Elements
Enrollment: Only 10 spaces available
Deadline to Join: February 15
Pricing: $9,950
The Coaching Program
Individualized one on one coaching to help you clarify your intentions and goals, explore options and support your progress.
Dates: Minimum 5 session commitment.
Key elements:
Enrollment: Ask about availability.
Pricing: $1,245 for 5 sessions
A one-time opportunity to pause, reflect, connect and imagine new opportunities with a small group of guys in a beautiful place.
Dates: May 23-27, 2025
Key Elements
- A 5-day, 4 night in person retreat for you to consider who you are and where you in your life, to do some beautiful hikes, to share your story and listen to others, to work on a dilemma or challenge you're facing and to explore what's possible for your life.
Enrollment: Only 10 spaces available
Deadline to Join: April 15
Pricing: $2,995
- Includes all programming and materials as well as food and lodging on retreat. Doesn't include travel to and from our retreats.
The Traverse
A 3 month experience to help you move from where you are to where you want to be. Provides individual and group support to make clear progress toward the life you imagine in a defined period of time.
Dates: March 2025 - June 2025
Key Elements
- Begins with a 4 day, 3 night in person retreat for you to share your story, build new friendships, get into nature, reflect on where you've been and envision where you want to go next.
- Every other week, you have a 55 minute one-on-one video coaching call to clarify your intentions and goals, explore possibilities, identify options, take action and support your progress.
- Weekly optional 30-minute group meditation calls to cultivate your mindfulness.
- Monthly community calls for you to catch up, check-in and support each other.
- Closes with a 3 day, 2 night in person retreat to reconnect with your brothers, honor your progress, and celebrate our community.
Enrollment: Only 10 spaces available
Deadline to Join: February 15
Pricing: $9,950
- Includes all programming and materials as well as food and lodging on retreat. Doesn't include travel to and from our retreats.
The Coaching Program
Individualized one on one coaching to help you clarify your intentions and goals, explore options and support your progress.
Dates: Minimum 5 session commitment.
Key elements:
- Bi-weekly 55 minute video calls to help you clarify your dreams and goals, explore potential paths, identify opportunities and resources and support you to take meaningful action.
- Grounded in professional training, expertise and extensive experience, Scott and Jerry utilize a range of practices and approaches to build your awareness, responsibility, intentionality and commitment to your goals.
Enrollment: Ask about availability.
Pricing: $1,245 for 5 sessions
"Ooh man, it was incredible. The whole thing. The setting, the people, the structure, the physical and mental stretching and pushing, the organic opportunities to connect and learn and contribute, it was all sort of unexpectedly overwhelmingly good. It impacted me profoundly" - Elliot, September 2022
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"Powerful, game-changing, eye-opening" - Chris, May 2022 |
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"Aside from the birth of my girls, the most influential experience of my life" - Kevin, September 2021 |
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"While it may sound dramatic, it was life-changing" - Neil, May 2022 |
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"It changed me. Improved me. Inspired me. Challenged me. " - Rick, September 2022 |
FAQs
What the hell is a cairn?
A lot of guys have asked this question. It's a man-made pile of stones used to mark a trail or a place of significance. Even though it's not a well-known word, we encounter cairns on hikes in the Tetons and we like how it relates to the metaphorical purpose and value of our retreats.
What's the difference between The Traverse and The Retreat?
There are significant differences. The Traverse is designed to help get you somewhere - move through a transitional phase, a change in career or relationship or lifestage, or to get unstuck and head in a new direction. It's a 3 month program, with an in person retreat to start and end the program, and includes coaching and monthly community calls to help you follow-through. The Retreat is a one-time experience, where you join other guys for 5 days to pause, reflect and gain new insights on particular dilemmas or situations you are facing. It's an opportunity to reset and reconnect with yourself and envision new possibilities.
Who joins your programs?
Guys range in age from their 20s to 70s. You may have stalled, stumbled, strayed, or even become a little lost on our life's path. You may find yourself no longer surrounded by the friends you once had. You are looking for new insights to help you clear the brush and discover new possibilities. The challenges guys bring range from career, marriage or relationship, to family, self-worth, faith or health.
Do you do hikes on all of your programs? How hard is it? How fit do I have to be?
Integral to our approach is to get outside, to have fun and to explore beautiful places. We know -- from our own experience and from all the science that backs it up -- that time in nature and moving our bodies can be profoundly helpful to our outlook on life. Our hikes range in length from about 5 miles to 10 miles each, with some significant elevation change. We think most men who are reasonably fit can handle the hikes. We are happy to talk with you and answer any concerns you may have about your fitness for the experience.
What the hell is a cairn?
A lot of guys have asked this question. It's a man-made pile of stones used to mark a trail or a place of significance. Even though it's not a well-known word, we encounter cairns on hikes in the Tetons and we like how it relates to the metaphorical purpose and value of our retreats.
What's the difference between The Traverse and The Retreat?
There are significant differences. The Traverse is designed to help get you somewhere - move through a transitional phase, a change in career or relationship or lifestage, or to get unstuck and head in a new direction. It's a 3 month program, with an in person retreat to start and end the program, and includes coaching and monthly community calls to help you follow-through. The Retreat is a one-time experience, where you join other guys for 5 days to pause, reflect and gain new insights on particular dilemmas or situations you are facing. It's an opportunity to reset and reconnect with yourself and envision new possibilities.
Who joins your programs?
Guys range in age from their 20s to 70s. You may have stalled, stumbled, strayed, or even become a little lost on our life's path. You may find yourself no longer surrounded by the friends you once had. You are looking for new insights to help you clear the brush and discover new possibilities. The challenges guys bring range from career, marriage or relationship, to family, self-worth, faith or health.
Do you do hikes on all of your programs? How hard is it? How fit do I have to be?
Integral to our approach is to get outside, to have fun and to explore beautiful places. We know -- from our own experience and from all the science that backs it up -- that time in nature and moving our bodies can be profoundly helpful to our outlook on life. Our hikes range in length from about 5 miles to 10 miles each, with some significant elevation change. We think most men who are reasonably fit can handle the hikes. We are happy to talk with you and answer any concerns you may have about your fitness for the experience.
FOUNDERS
Cairn & Sky was born from our desire for more connection, adventure and community in our lives and we thought other men might want more too.
Scott Taylor
Scott has been in the learning and leadership development space for over 20 years and has led programs for men since 2016. He's been an executive in the private and non-profit sectors, an outdoor educator, a Peace Corps Volunteer and a consultant and leadership coach. He has trained in life and executive coaching with Co-Active Training Institute. Scott holds a masters degree from Harvard, loves cycling trips in Europe, a smooth bourbon, the stillness of mornings and his dog Weezie.
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Jerry Casagrande
Jerry is a social entrepreneur and writer. He's launched a couple of organizations, written and produced screenplays, and worked in international development. He's lived in Mongolia and Costa Rica and got his MBA from Stanford back in the day. He has trained in positive psychology coaching with The Whole Being Institute. Jerry is married with three kids and loves spending time on Lake Joe in Canada, dipping into freezing lakes, rivers (or even buckets), and hanging with his dog Lucy.
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Have questions? Want to learn more?
Email Jerry at [email protected] and he'll be in touch within 24 hours.
Or you can call or text to 703-717-3603 and share your name and any questions you may have about Cairn & Sky.
Email Jerry at [email protected] and he'll be in touch within 24 hours.
Or you can call or text to 703-717-3603 and share your name and any questions you may have about Cairn & Sky.