Here’s my experience: Life has a way of throwing us into moments of uncertainty. At various times, I’ve had uncertainty around my career, my most cherished relationships, and even that bigger, but sometimes vague “sense of purpose” - you know, “what’s it all about?” "how did I get here?" or, more plainly, "what the hell am I doing with my life and why?" This for sure was true for me back in 2019 and, that year, I took some time to get away with ten guys or so, most of whom I'd never met before. It was a men's retreat. And it was very helpful to me in answering some of those purpose questions as well as questions around what exactly the "story of my life" was and could be. Since that time, I’ve learned to take time more often for myself--as a kind of reset or renewal. I've found that key to those experiences, to successfully resetting and renewing are at least 3 things:
You know, women go on retreat all the time. Many of us guys feel it is not for us–I recently saw a video of a stand up comedian who joked that if you simply say the phrase ‘women’s retreat’ it will instantly be full; for guys, not so much. And yet, I’ve seen first-hand the impact of time away for men, so I am going to say it: there’s value for dudes too in a retreat. ![]() In leading retreats through the Tetons and in Joshua Tree, I’ve seen how these experiences offer guys something rare in our overly-scheduled, always-moving lives—time for real reflection and time for community. Away from the noise of daily life, you get space to think deeply about where you’ve been and where you’re going. And you’re not alone in the process. You’re accompanied by a group of supportive, like-minded men who are also seeking clarity and growth. For some dudes, that might sound like a turn-off: many of us have the idea that we are loners, that we can get through it all by ourselves, that in fact this is the modus operandi of guys: struggle and persist and succeed (or fail) on your own. As Green Day sings, and as many guys see it, “I walk alone.”
But Green Day also sings, just a few seconds later, “I wish someone out there will find me.” So, imagine if you will, the idea of a community of guys that not only laughs and jokes around but that also talks about deep shit - about shared struggles around the most important things in life. It can be eye-opening to see that the dude who you thought of only as the tech-guy, or the small business owner, or the die-hard Cubs fan, or the lawyer, or the fly fisherman, also has some struggles in his marriage, some challenges with his kids or parents, some doubts about what the hell is next in his life. Through conversations, laughs, and genuine camaraderie, you may discover a network of friendships that lets you know that you don’t have to figure everything out by yourself. Be clear: nobody will tell you what to do; but, you’ll gain wisdom and insight from men with shared experiences so that you can make some decisions about your life. We hope to see you on the trail in Jackson.
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AuthorOur blogs are written by Jerry Casagrande and Scott Taylor, Co-Founders of Cairn & Sky. We are also interested in hearing your voice. If you have a topic you'd like to share with the Cairn & Sky community, please reach out to [email protected] and let us know. We'd love to hear the idea and then maybe share it with the world right here. Archives
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