A New Chapter for Dare to Detour
After years of shared adventure, vulnerability, and deep belly laughs, I have decided that this September’s Montana retreat will be my last Dare to Detour retreat. As I stand on the brink of turning 60, I’m taking a cue from my own playbook and truly listening to my intuition—a practice I’ve always encouraged in others, and now, it’s my turn to follow that inner compass.
The truth? The excitement and spark I once felt planning and executing retreats is shifting. I’ve been learning that I don’t have to force it, and I know from experience that when I do, I’m not showing up as my most effective, authentic self. Creating these transformative experiences has been both joyful and sustaining for me through some of my toughest times in recent years. And I’ve heard from so many of you about the real, profound changes you’ve made in your lives after our retreats together. To know that I’ve contributed to those moments, and to this remarkable web of camaraderie, is something I will always cherish.
The WhatsApp groups are still buzzing, the friendships are real, the energy and joie de vivre is alive and well. And if those are the legacies left from this chapter of Dare, that is truly significant. Together, we have built something special, and that makes saying “not right now” to retreats bittersweet. But I also know this is the right Detour for me.
Looking ahead, I am most excited about focusing my energy on giving back in new ways. I’ll be facilitating my first retreat this fall for the Cancer Support Community. And working with this community that supported me through my cancer journey feels deeply meaningful. My approach is evolving: I want to use my experience and skills to support organizations that have supported me, and to help guide and facilitate events and experiences for communities that need it most.
If I’m honest, after pouring so much of my time and resources into Dare retreats, I want to practice what I preach: take more trips with my family, discover new places for myself, and dream big about what this next decade holds. My vision is to spend half the year in Montana (which I will always call home) and half the year abroad. This is a big, brave change, and it will require time, flexibility, and, yes, courage. I plan to shift how I live and work so that by 2027, this dream becomes my reality.
In pausing the retreat arm of Dare, I want you to know that this isn’t a goodbye. I’m not closing up shop, just refocusing. Dare will still be here. Guides, speaking and facilitation, 1:1 calls, and travel planning support—all of that remains. And more than ever, I want your input: What would you love to see from Dare moving forward?
But before all that, this September, we have one last chance to gather in Montana together, and there are just a handful of spots left to jump in and join us. I want to go out with a bang, so you know this one is going to be good!
Thank you. For every story, every moment of laughter, every brave Detour you’ve trusted me with. Permitting myself to shift gears is one of the boldest things I’ve done, and it’s only possible because of the strength and warmth of this community.
Let’s continue to Dare together.
With deep gratitude,
Sheryl
