Advancing in a Different Direction: What is a Men's Retreat? And Why Would You Ever Go On One?

A view over beautiful Jackson Wyoming where Cairn & Sky hosts men's retreats...but what the hell is a men's retreat?

by Jerry Casagrande

It was November, 1950. Oliver Smith, a WW2 veteran and multi-decorated US Major General, found himself leading 30,000 troops in sub-freezing temperatures near the Choisin Reservoir in Korea. The People’s Republic of China had just entered the war and Smith and his soldiers were surrounded by 120,000 of the enemy's forces. Smith and his division faced almost certain annihilation.
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Instead, the Major General courageously designed and implemented his division’s retreat to the Port of Hungam, saving his soldiers' lives and enabling them to fight another day. And, more importantly, to simply live another day. 

Smith famously said at the time, “Retreat, hell! We’re just advancing in a different direction!”

And that folks, gets to the heart of what a men’s retreat is:

A men’s retreat is an opportunity for you to step back from the challenges life is presenting--whatever they may be--so that you might advance again in a new direction.
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Some really legit questions about a men’s retreat

​Cairn & Sky is a new effort offering men’s retreats in extraordinary Jackson, Wyoming, so we have a few thoughts about what a men’s retreat is all about and, sincerely, whether or not one is right for you. We set out to answer your very legit questions in this, our first ever blog. Questions like: 
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• What is a men’s retreat? 
• Should I go on one? 
• What might I get out of it? 
• What should I expect?

That first question is answered in the story about General Smith: A retreat is an opportunity to step back from everyday life to find the time and space so that you might advance again in a new direction. 
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"Retreat, hell! We're just advancing in a different direction."
​- 4 Star Marine General Oliver Smith

A retreat can be a powerful experience and we believe that if you are a guy with some questions, challenges, or dilemmas in his life, you will very likely benefit from going on one. If you are the spouse or partner of a guy like that--or the sibling, parent, or child of that guy--we think you will see how the retreat has benefited the man you love.

What are those benefits? There are too many to name and each guy will discover different ones--the chance to destress and reset; the chance to enjoy the outdoors; the chance to reflect, journal, and be quiet; and many more. 

Two of the biggest and most consistent take-aways, however, are friendships and insight.

It’s remarkable the bonds of friendship you can create on an intentional five day retreat and the unexpected insights you can draw--insights that before retreat you may have thought were unrelated to the questions and challenges in your life; but which on retreat, you realize are actually fundamental to those questions and challenges--right at their beating heart.

Deep friendships and new insights
are two of the most consistent take-aways 
from a men's retreat.

Should You Go on a Men’s Retreat?

​A men’s retreat is not for everyone. Let’s talk about whether you should consider joining one.

Let’s face it. Life is complex on so many fronts:

• Marriage or partnership. Maybe after many years of marriage or partnership, your oh-so steady relationship is wobbling. Would you benefit from some time and space to figure out what is going on so that you can reinvest in your most important relationship? 

 

• Divorce. Alternatively, did your marriage or long-term relationship just end and now you find yourself a bit lost, asking what the hell happened to the relationship you thought would take you to the end of your days? Even more importantly, what now? Would the time and space a retreat creates help you lean into those questions and gain new insights?

 

• Career crossroads. Years ago, you set out on your career path and have been successful by all counts. Now, mid-career, you are not sure if your path is still the right one. Perhaps, you see an adjacent path, one that leads to...well, you aren’t sure where it leads. Would the opportunity for reflection and the chance to talk to other men in mid-life help you clarify where you’ve been, where you are now, and where you want to go?

 

• Friendship. Where did all your friends go? Damn, college was fun. Now you live hundreds or thousands of miles from those college buddies and just haven’t connected with other guys in deep friendship ever since. You’d never admit it but you’re feeling lonely. Would the chance to commune with some guys, go hiking, have a beer and a talk around a campfire--would all that not only help you make some new friends but perhaps offer insight on friendships that are elusive back home?

Those are just a few reasons a retreat might be right for you. That said, there are as many reasons as there are men for taking time away to gain insight on challenges or dilemmas you are facing. For example:

• The kids just moved out, or you’re on the cusp of being an empty-nester and find yourself looking at your partner thinking, “Oh shit. It’s just the two of us. Now what?” 

 

• You’ve never been married, even a decade or two after your buddies all tied the knot, and now you’re struggling with the thought that marriage and fatherhood aren’t ever going to happen.

 

• Fatherhood: How is your relationship with your dad impacting you? That’s a question every guy faces once, more, or continually in his life--even after his dad has passed away.

 

• And, also, fatherhood: How is your relationship with your kids? Are you slipping into patterns you swore you’d never adopt? Struggling in relationships with your kids--whether they are in elementary school, teenagers, or grown-ass adults?

That shit you're dealing with? It can be fertilizer to grow something new in your life.

In short, a retreat may be right for you if you’re a man who's got something you are noodling on: a dilemma, a life-choice, a problem that maybe you can’t even quite define, but you know something seems amiss.
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You can allow this irritant to just bother you; or you can go on retreat and, like an oyster, take it as an opportunity for something better, and then nurture it into a glorious pearl. 

Put another way, that shit you’re dealing with? It can be fertilizer to grow something new in your life.
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Comparing Men’s Retreats

So, a men’s retreat is an opportunity to explore your path--your path of relationship, career, friendship, family, faith, health, passions, and more--so that you can clear a new path or at least discover the tools you need to navigate a path strewn with brush.

Given that broad description, it might be useful to know how various retreats differ. 

There are a number of men’s retreat organizations out there. Some offer two day retreats; others like Cairn & Sky offer a 5-day experience to allow time not just to dig deep, but to adventure, to nurture new friendships, to have some fun, and to have time for quiet reflection. 

Some are faith-oriented. There are a number of men’s retreats offered by churches for example. Others, like Cairn & Sky, are completely secular but of course welcome men of faith to share their stories of, and joys and struggles with, faith.
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Grand Teton National Park is a short drive from Jackson and offers incredible hiking opportunities.

Some are urban. Others use nature as a backdrop for the retreat and stop there. At Cairn & Sky, nature is far more than a backdrop. The outdoors is integral to what we do. We believe there is benefit in taking three hours or five hours or even six or seven hours to get out on a hike, in the trees and then above the trees, to feel the sense of accomplishment that comes from reaching a mountain ridge, and to enjoy the utterly unscheduled time to talk freely with the guys around you about whatever you want--whether that is comparing MJ and LeBron, talking about sex after 20 years in relationship, or something else.

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Some retreats are large--40 or 50 guys thrown together for 48 hours. Others are small. Cairn & Sky offers retreats with not more than 12 men at a time. We believe doing so allows men to form deeper bonds than is possible in a big group where time with any given person is necessarily limited. Those bonds are important during the retreat and simply essential afterwards.

Most retreats have some sort of philosophical approach. As mentioned, some are faith-based. Others are led by therapists or psychologists who will download their expertise to guys for you to then try to implement in your life. At Cairn & Sky, our philosophy is that the wisdom you need resides in you and in the small community of men we gather together on retreat. The job of our facilitators is not to download any particular expertise, but rather to create the time and space for you to find your own insights and to gather the wisdom of the men around you.

​What will you actually do on a men’s retreat?
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So, you know the purpose of a men’s retreat, some reasons a retreat might be right for you, and how men’s retreats differ, but still one question remains: 

What the hell do you actually do on retreat? 

Whether you want to get another guy's take on MJ and LeBron, or talk about what sex is like after twenty years of relationship, a six mile hike in the wilderness provides that opportunity.

We are not going to give away all that happens on retreat, but here’s a bulleted overview of the highlights:

• Getting outside. On a C&S retreat, we take three day-hikes ranging in distance from about five miles to about ten miles. We explore mountain ridges and alpine lakes. We invite short dips in the chilly Hoback River. Weather depending, we might get to a natural thermal pool to star gaze. The outdoors is both our classroom and our rec-room.

• Talking and listening. Each day, we take time for carefully facilitated discussions that are led by you, in which you get to talk about whatever the hell you want to talk about. You’ll take your turn to listen to the guys around you talk about what they want to talk about. C&S Guides offer unique structures to enable the group to offer their experiences and ask questions that may guide you to new insights.

• Yoga. Never done yoga? No problem. These are introductory yoga classes, suitable for all guys. Their purpose is to wake our bodies up in the morning and help us come into the present moment, where we can truly pay attention to ourselves and to the world around us.

• Delicious food, campfires, tunes, & beer. We like food and we ensure that the three squares you get each day are delicious. We like fire. Who doesn’t? We’ll jaw around the fireplace and around the fire ring outdoors, listen to some of your favorite tunes, and, if you are in the mood, crack a beer or sip a bourbon.

There’s more of course and, quite predictably, some unpredictable but wonderful things happen when you bring together a dozen men intent on exploring both the dirt paths that lead up a mountain and the experience-strewn paths that form the content of their lives.

Retreat to Advance Again

In the end, getting to Jackson, Wyoming, to meet 11 other guys, hike with them, talk with them, listen to them, and share a campfire with them, takes a big step by you. A sort of leap of faith that the dilemma you are chewing on needs a little something else to get resolved so that you may advance once again on your own unique path. If this doesn’t sound intriguing to you, that’s cool. Maybe we will meet another way. However, if the idea piques a bit at your heart, mind, or soul, take that leap today.​​​

If you're wrestling with a dilemma, a challenge, a big life-choice--maybe even something you can't quite define--then a men's retreat might give you the time and space to move forward again.