Walk with Ryan Conklin: Grief, Initiation, and Being With What Is
Episode Summary: I expected this conversation to be about coaching and vision quests.
It became something else entirely.
When Ryan Conklin shared, “There is grief in the gap between who we say we want to be and who we are becoming,” it shifted the direction of our walk.
This episode explores grief not as something to resolve, but as something to be with—and how nature, community, and intentional practices like vision quests can support that process.
Show Notes
What began as a conversation about coaching and vision quests opened into a deeper exploration of grief, initiation, and the quiet work of being with our own experience.
Ryan Conklin is a transformational coach and wilderness guide who leads vision quest experiences—modern rites of passage that invite people to step away from daily life and listen more deeply.
Together, we explore the tension between who we intend to be and how we’re actually living, and the role that grief plays in that space. We talk about the ways modern life often moves us past experiences that are asking to be felt, and how nature can serve as a steady, non-judgmental container for reflection and transformation.
This conversation also touches on integration—the often overlooked phase of change—and why transformation doesn’t happen in the peak experience, but in what follows.
Key Themes
Grief as a natural, often unacknowledged human experience
The gap between intention and lived experience
Nature as a container for reflection and transformation
Rites of passage and initiation in modern life
Integration as an essential part of change
Connection as being with what is, without judgment
Key Takeaways
There is often grief in the space between who we say we want to be and how we are living
Transformation requires a willingness to stay with discomfort rather than move past it
Nature offers a steady, non-judgmental environment to process experience
Initiation is not the peak experience—it’s what follows that shapes change
Integration happens in relationship, not in isolation
“There is grief in the gap between who we say we want to be and who we are becoming.”
Connect with Ryan Conklin
LinkedIn: https://www.linkedin.com/in/ryan-conklin-12947640/
Website: https://www.thebridgercoaching.com/about
Instagram: https://www.instagram.com/thebridgercoaching/?hl=en
Resources Mentioned
Vision Quest / Vision Fast (rites of passage practices)
Men’s work and community-based support spaces
Grief rituals and personal reflection practices
Reflection Prompt
What might be asking for your attention that you’ve been moving past?
Prefer to read?
The full transcript is below.
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Susan
Well, hello Ryan. It’s great to see you today.Ryan Conklin
Yeah, great to be here. Thank you for the invitation, Susan.Susan
I get to see the person who connected us on LinkedIn later this week. I’ll be meeting Matt in person for the first time, so I’m looking forward to closing that loop all in one week.We’ve had one chance to speak and connect. We are both coaches, but you have a backstory that’s different than mine—not surprising.
Since we’re here talking about nature, let’s talk about origin story. I’m curious to hear your background, wherever you want to start, and what brings you to the work as a coach—nature-based coach, or however you might describe that today.
Ryan Conklin
I think, just to be direct about it, what brings me to the work is having had the opportunity to experience the potency of the work.Inherently inside of me, there’s someone who’s always longed for connection and seen the power in connection. Through connection, I’ve really experienced the potential for people’s experience with themselves, with others, and with their purpose to shift in a profound way.
Susan
And how long have you been coaching?Ryan Conklin
Five years now.Susan
And before that—was the work you were doing anything like coaching?Ryan Conklin
Maybe adjacent. I’ve been in love with “aha” moments my whole life.For the beginning of my education, it was elementary school. My degree is in elementary education, and I just loved the idea of watching young minds come to their own discoveries—filter magic through and create from there.
Then the world proposed a different path for me. I started relating to the world through the camera for quite some time—telling stories through adventure, international travel, professional snowboard photography.
And then into hospitality—taking food and beverage seriously and experiencing the world through people’s flavor, their sensory epiphanies, their “aha” moments within that space.
The thread I can track through all of it is a relationship with those “aha” moments.
Susan
I love that. It really is so much fun to be with a young mind—or a non-young mind—discovering something.There’s something really precious about that. And as I think about that idea, what comes up for me is the idea that the young mind is not always present with us as we get older.
There’s this perspective—spoken or unspoken—that we lose that openness to new experiences.
I’m checking myself as I say that, because maybe it’s not just about the young mind.
So I’m curious—from your perspective, which came first, the coaching or the nature?
Ryan Conklin
A lot of it came online at the same time.For me, this was never about doing it for someone else. So much of this was really for me—to be with myself and my journey.
There’s a teaching—I don’t know where it comes from—but it says you can only take people to the places where you’ve gotten yourself.
I don’t think that’s a true academic one-to-one. I think it’s more about: are you willing to be with things in depth and intensity?
Coming through my own job loss and personal identity shattering, I leaned into community. I leaned into a significant amount of men’s work.
That brought me into connection with both the wilderness outside and the wilderness inside. It brought me into connection with coaching. It brought me into deeper listening.
A lot of what came into my field around this came in serendipitously, all at the same time.
Ryan Conklin (continued)
I had a partner who told me, “You’re horrible at listening. You’re not vulnerable.” She left me.At the time, I felt that as hurtful, even if she was trying to be kind.
Fortunately, I was able to hear both sides of that. I took a moment, wrote it down, and really sat with it for weeks.
Then I got to a point where I realized I needed to get out of my head and back into my body.
A friend handed me a book, introduced me to a podcast, and that led me into a men’s group. I leaned in, and it just kept holding me.
I’m still part of that group today. It’s a global group, and I lead a chapter here in Denver.
It’s given me the opportunity to both be held and hold others.
Ryan Conklin (continued)
Through that work, I was introduced to wilderness work. I went out on the land a couple of times.Through that experience, I got a really clear message: “Walk with me.”
At first, I interpreted that as a call to lead vision quests—even though I had never been in one.
And now I do lead vision quests. I’m heading out in late May with a group here in Colorado.
But when I dropped into my first ceremony, I immediately knew this was only part of my work.
The way it was being held felt inaccessible to a lot of people. I knew that the way I show up—whether you call it coaching, guidance, or support—has to be accessible.
Susan
For those listening, I want to pause and define a few things.When people hear the word “coach,” it brings up all sorts of images. For many, it’s a sports coach—directive, telling you what to do.
You and I are both transformational coaches, which is a very different experience.
I’m curious how you help someone understand what it means to be coached as they work with you.
Ryan Conklin
I could tell you what it’s like to be coached by me, but I can’t fully tell you what it’s like—you have to experience it.My work as a coach is to be with people inside of their contradictions.
I relate to my clients as whole and complete. There’s nothing wrong or broken.
Most of the people I work with have thrived their way to the point that I’m meeting them. They’re full of survival mechanisms and success strategies.
And they’re discovering that what got them here is not going to get them to where they’re going.
There’s nothing wrong with getting to a point where it’s not possible to do it on your own anymore.
For me, there’s so much grief in the gap between who we say we want to be and who we’re becoming.
Susan
Grief in the gap between who we say we want to be and who we are becoming.That is… we should stop recording now so I can ponder that.
Not an option—we’ll come back to it later. But that’s powerful.
And part of the work you do is reflecting back permission to be with yourself in whatever state you’re in—without judgment.
Ryan Conklin
Yeah. Interestingly, that’s how you received me.My vision is to empower connection.
And if we’re defining things, the way I understand vision is that it’s the place from which we make our decisions.
My decisions are made from a place of empowering connection.
And the way I define connection is being with what is here, without judgment.
Susan
And you used the term “vision,” which is one of the other terms I wanted to define.When people hear “vision quest,” I’m thinking about all the Gen X listeners who immediately go to the movie version of that idea.
So for those who have either that reference point or just a vague sense of what it might be—how do you describe it?
Ryan Conklin
It goes by so many names. It’s a pan-cultural experience that goes back across time and across cultures.At its core, it’s taking your story to the land, in community, with a willingness to be stripped completely bare.
Bare of any need to do anything.
And to receive what’s there—and to have it mirrored back to you in profoundly life-changing ways.
Susan
That sounds amazing. Does this happen in just a weekend?Ryan Conklin
To bring it out of the transformation space and into logistics—it can take many forms.In the West, a lot of lineages follow a structure influenced by organizations like the School of Lost Borders.
Typically, it’s about a 12-day process.
You arrive and spend the first day getting settled—landing on the land.
Then you have about three days in community with the other participants and guides. It’s a very intimate container—often one guide for every two participants.
During that time, you clarify what brought you there. You name your intention. You draw a circle around a question.
Then you go out onto the land—usually for about four days.
You’re alone. No food. No four-walled shelter. Just essentials—sleeping bag, safety gear, maybe a few ceremonial items.
You take your question with you.
Ryan Conklin (continued)
Then you return.You’re received by the same community that sent you out. You share your story, and that story is mirrored back to you.
And then the real work continues—maybe even begins.
Because it’s about taking that story back into your life.
Ryan Conklin (continued)
One of the biggest challenges I see is integration.People seek peak experiences, but they don’t prepare for what comes after.
They don’t say to the people in their lives, “I’m going to do this thing, and I might come back changed. I’m going to need support.”
That change can disrupt relationships—but in a meaningful way.
Susan
That resonates.I’ve had experiences—not a vision quest—but journeys that changed me.
Coming back from the Camino, I needed someone to help me integrate that experience. And it was hard to find that support.
What you’re describing—preparing people for that before and after—that feels really important.
And I also think about the people who don’t have the language to say, “I might come back different.”
Or the people around them who don’t want them to change.
Ryan Conklin
Yeah. And I want to be explicit—this is also how I relate to coaching.If someone isn’t willing to let their community know they’re doing this work, they’re not my client.
Transformation doesn’t land when it has to be hidden.
If you can’t say, “I’m doing this work, and it may change how I show up,” then there’s a kind of code-switching that happens.
And that limits what’s possible.
Susan
That makes sense.As you’re talking, I’m thinking about something I heard recently—“evolve or die.”
That’s how nature works. Things change.
And I’m connecting that to what you’re describing—the idea of rites of passage.
It feels like, in modern life, we’ve lost those.
There used to be natural inflection points where people would step away, reflect, and mark a transition.
Now, we don’t really have that.
And the phrase that stuck with me was: we have a society of “olders,” not “elders.”
I’m curious what comes up for you when you hear that.
Ryan Conklin
Yeah, that lands.Before I respond, I’m curious—how do you define an elder?
Susan
The first word that comes up is “wisdom keeper.”But I’m not attaching that to age.
I’ve met younger people who feel like wisdom keepers.
But beyond that, I’m not sure how I’d fully define it.
Ryan Conklin
There’s so much access to information right now. People are getting very smart.But for me, eldership isn’t about intelligence—it’s about a willingness to be with.
Specifically, to be with your own experience.
I do think wisdom is part of it, but it’s embodied wisdom.
I think elders are grief-literate.
Our society, in many ways, is grief-illiterate.
Elders know how to be with grief.
They know how to be with all of life’s experiences, and their bodies have been shaped by that.
Ryan Conklin (continued)
There are people who are very intelligent, but if that intelligence comes from inside four walls, without real hardship, there’s a limit.At some point, life will bring an edge—and that’s when the shift happens.
It becomes less about knowledge and more about the ability to stay and be with what’s happening.
Susan
That makes me want to revise my definition.It also makes me reflect on where I am in that process—becoming more comfortable with being, rather than doing.
Ryan Conklin
Yeah.I imagine a child who drops their ice cream and starts crying.
A wisdom keeper might still feel the urge to fix it or teach a lesson.
But an elder might simply say, “That must feel awful. Tell me about it.”
And that’s it.
They’re just with the experience.
Ryan Conklin (continued)
And then something shifts.The child feels seen. The grief moves. And suddenly they’re both chasing a caterpillar.
Because they were willing to be with the loss.
Susan
What just came up for me is… softness.And this connects to something else you mentioned earlier—your work with men.
I have three men close to me in my life—my husband and two sons.
And it feels like we’re in a shift in what it means to be a man.
I’m curious how you define “men’s work,” because for many people, that’s not something they’re familiar with.
Ryan Conklin
Every organization defines it differently.The organization I’m part of has a mission to end the suffering in men and the unnecessary suffering caused by men.
It invites men to be with their experience without numbing, without blaming others.
To show up as safe.
To connect with their head, their heart, and the part of the body that brings life.
Ryan Conklin (continued)
A lot of people live from the head up.The body becomes a vehicle for the mind.
So the work is a return to the body.
A return to presence.
And that can take years.
Ryan Conklin
At a networking event recently, someone and I were talking about “the work.”We paused and asked—what does that actually mean?
What we landed on was this: the work is giving yourself access to something you haven’t had access to before.
So the work becomes tending to what you don’t have access to.
That might be communication. It might be connection to your heart. It might be expressing anger, or joy, or play.
For some people, it’s softening into mystery.
Susan
As you’re talking, I’m thinking about how nature plays a role in that.Ryan Conklin
Yeah.Nature serves in so many ways.
It’s a mirror.
It’s a playmate.
It’s confrontation.
It’s a mentor.And it’s one of the most sacred containers for grief.
Susan
We haven’t touched on grief yet.Say more.
Ryan Conklin
It feels important to define it.For me, grief is an incredibly unpredictable and relentless dance between sorrow and gratitude.
So much of our gifts live close to our pain.
Our ability to be in relationship with our grief—the depth to which we can be with it—directly shapes the depth to which we can bring our gifts into the world.
Ryan Conklin (continued)
We live in a culture that is largely grief-illiterate.Just notice what happens when someone starts to cry.
Often, someone hands them a tissue.
But what’s underneath that is, “Clean that up.”
There’s this impulse to move past grief quickly—to fix it, to resolve it.
Even with major losses—relationships ending, someone passing away, losing a job—there’s an expectation that we move on.
There’s almost a prescribed timeline for how long it’s acceptable to feel sorrow.
Ryan Conklin (continued)
But in my experience, those are the most profound places to stand—inside the grief.Not to move past it, but to be with it.
Ryan Conklin
One of the vision fasts I went on was in Death Valley in 2024.During that time, I created a descanso.
If you’re not familiar with that term, it’s a way of marking loss—like the crosses you see on the side of the road.
It’s a way of acknowledging where something significant has happened.
Ryan Conklin (continued)
For me, that meant identifying all the losses I could remember in my life—big and small.There were about 30.
I brought that to the land.
For each loss, I chose a stone.
I placed each stone in a dry wash and told the story of that loss.
Sometimes that meant speaking.
Sometimes it meant yelling, drumming, crying.
Each one was witnessed by the land.
Ryan Conklin (continued)
Then, a couple days later, I returned.One by one, I carried each stone up the wash.
As I carried each one, I held the story again.
I placed it into a space I created—like a grave.
I acknowledged the loss. I said goodbye.
And for each one, I also acknowledged the gift.
Because in every loss, something is given—and something else goes into exile.
Ryan Conklin (continued)
That process took an entire day.And the relationship I now have with those losses is completely different.
They’re still there.
But I’m with them in a way I wasn’t before.
Susan
I’m… swimming a little bit right now.Ryan Conklin
Can I ask you a question?Susan
Yes. That might help.Ryan Conklin
What did that touch inside of you?Susan
I’ve been working through something recently—another layer.I met with a body worker who helped me understand what’s been happening in my body, and grief came up.
And over the last few days, I’ve been reflecting on that.
I’ve been asking myself, “I don’t know how to access this grief.”
And then I said—let the teacher appear when it’s meant to.
And here we are.
Susan (continued)
Listening to you, I can feel it.It’s this mix of joy and grief.
And also awe—just awe at how things unfold when we stay open.
Ryan Conklin
Yeah.May I offer something—for you and for the listeners?
Susan
Yes.Ryan Conklin
There are five conversations that can help us find completion.“I love you.”
“Thank you.”
“I forgive you.”
“Please forgive me.”
“Goodbye.”Ryan Conklin (continued)
You can take any experience—big or small—and move through those.Which one feels hardest? Which one feels most alive?
That’s usually where the work is.
Ryan Conklin (continued)
Even something simple—like a child dropping an ice cream cone.Can you forgive yourself?
Can you thank it for the experience?
Can you say goodbye?
Those conversations can be playful and full of sorrow at the same time.
Susan
Thank you.Take it for a walk.
Ryan Conklin
Exactly.Susan
As we talk about this, I’m thinking about how disconnected we’ve become from grief as a natural process.And we’re living in a time where so much is changing.
Your ritual—the descanso—feels like something that could really help people who don’t know how to navigate grief.
Ryan Conklin
Yeah.One of the most profound things you can do for someone who’s grieving is ask them to tell a story.
We can do that for ourselves.
You can take a glass of water, share your story with it, and then return it to the land.
Let that story—your sorrow and your gratitude—feed life.
Susan
I love that.Susan (continued)
I feel like we could talk for another hour, but I’m not a long-form podcaster.Ryan Conklin
Fair enough.May I land the plane?
Susan
Yes—land the plane. And then we’ll do a quick lightning round.Ryan Conklin
At the core of all of this—vision quests, rites of passage—there are three phases:Severance
Threshold
IncorporationInside every transition, something dies.
There’s a liminal space.
And then something is reborn.
Ryan Conklin (continued)
If we don’t acknowledge what’s dying, we don’t complete the transition.Grief is what allows that process to happen.
Ryan Conklin (continued)
There are so many transitions in life that go unmarked:Becoming a parent
Losing a job
Ending a relationship
Losing a loved one
Moving into a new phase of lifeWhen those aren’t honored, grief remains unprocessed.
And that grief waits.
Ryan Conklin (continued)
If we don’t meet it, it will be waiting for us at the end of our lives.And that’s why this work matters.
Susan
I’m in awe again. I’m in awe, and I can feel excitement bubbling up—which is interesting, that movement from grief into excitement.And I so appreciate you.
Let’s do a lightning round—speaking of sparking. This is just a fun way that I like to end, to get a little bit more of your personality out into the world, and maybe invite listeners to think a little differently about how they might answer.
So—five questions. No right or wrong answers. Think about it or answer right away, whatever works for you.
First question: your favorite natural sound.
Ryan Conklin
Birds. Birds.Susan
Mm-hmm. Ditto.Okay—favorite season, and why?
Ryan Conklin
Man… I have a couple answers. I’d say spring, but sometimes it’s the one that’s going away that I love most.Like this winter—we didn’t really get a winter here in Colorado. And I found myself thinking, “I was promised a break.”
Susan
So there’s a little grief there.Ryan Conklin
For sure. There’s grief there.But each season has its own kind of magic. I love spring.
Susan
Yeah. I love that.I was talking with someone recently who lives in Japan, where they have far more than four seasons—and there’s so much nuance in that.
Okay—next question.
What’s something you notice that many people walk right by?
Ryan Conklin
Tracks.Susan
Mmm. What’s the most fun track you’ve ever seen? Bigfoot?Ryan Conklin
I’ve seen bobcat tracks inside my own footprints.That’ll wake you up.
Susan
Oh boy. Yeah.Ryan Conklin
Yeah—being out in Canyonlands, moving through a canyon, knowing water is scarce… and then coming back down and seeing a cat track inside a footprint you made earlier that day.That gets the blood pumping.
Susan
Yes—wow.Okay—animal or creature you see as a teacher?
Ryan Conklin
Nighthawk.Susan
Mmm.Ryan Conklin
Nighthawk is a threshold walker.Susan
Do we have nighthawks all over the U.S.?Ryan Conklin
Yeah—they also go by the name “whip-poor-will.”They often look like dead pieces of wood or cactus. They’re really special animals.
Susan
I’m going to have to look that one up.Okay—the last question.
You have a dandelion that has gone to seed in your hand, and you get to make a wish for humans and nature. What is it?
Ryan Conklin
May we all slow down.Susan
Hear, hear. That one hit me right in the gut.Wow. Today was an absolute pleasure—full of unexpected surprises as we walked together. I really appreciate that.
I’ll share links to you in the show notes, but is there anything you want people to know—how to find you, or anything that’s important to you right now as this comes out?
Ryan Conklin
Yeah—I’m very findable. That’s one of my goals in the world—to be trackable.You can find me on Substack—I do a good amount of writing there. You can find me on LinkedIn.
And if this comes out with enough time before the May vision quest I’ll be leading, I invite people to join. If not, these happen regularly—with myself and others.
If you feel called to bring your story to the land, there’s a teaching that says the moment you receive the call to do a rite of passage is the moment it begins.
So allow that to come in. Allow yourself to receive the call and trust the process.
And if you’re listening and you’re curious, I truly invite you to reach out. I’d love to connect—whether it’s about coaching, vision quest, or just a conversation.
Susan
Thank you.Ryan Conklin
Yeah, thank you.
