Hard vs. Risky: A Week in Wyoming That Changed How I’m Thinking About Leadership and Life

Last week, I found myself back in Wyoming.

7,000 acres of wild, untouched land.
No cell service. No noise. No urgency.

Just vast landscapes, slot canyons tucked between them, and a river winding through the property, full of brown and rainbow trout. The air felt different. Clean and clear. The kind of air that reminds you how long it’s been since you actually breathed deeply.

It’s the kind of place where the sky feels bigger. And somehow your life feels smaller, in the best way possible.

This was my second time at Refuge.

I didn’t go back because I needed something specific. I went back because I knew what kind of place it is - a place where I’d find rest. Recovery, joy, brotherhood.

And space, real space, for God to move in my life. Scripture says He often talks to us in whispers...and I knew I would benefit from the quiet.

Refuge is a place built around a simple but powerful mission: keeping world changers in the game.

What Makes This Place Different

It’s easy to assume a place like this is special because of the land. And it is. But that’s not what makes it unforgettable.

It’s the people.

The staff, mostly young adults ages 18 to 25, are some of the most impressive humans I’ve been around in a long time.

They cook gourmet meals.
They make drinks.
They guide you on the river.
They anticipate needs before you even realize you have them.

They don’t let you lift a finger. And they don’t just do a job. They care.

They’re up before you. They’re awake until the last guy goes to bed, which can get pretty late when a group of men decides they’re not quite done talking around a fire.

They listen.
They observe.
They engage when appropriate.

And they serve with a level of intentionality and humility that’s hard to describe until you experience it.

Their hearts are incredibly tender. Kind. Grounded. Curious. Others-focused.

This, if you know anything about life and the world right now, is totally rare.

I spent a lot of time on the river with Cole, a Texas native who guided our days fly fishing. Great guide, even better human. It was great to get to know him.

There were only three of us out there. Cole parked the truck in the middle of a cattle field, led the way, and at one point found himself between us and a steer that got more aggressive than expected.

He was calm. In control. Ready to handle it.

We…took off running. At the time, it felt like the right move. I’ll share more about the moment in just a bit...

The Same… But Different

A lot was familiar about being back out at Refuge a year later from my very first trip.

Some of the same faces on the staff (greeted them with big hugs, and they remembered my name, despite hosting groups every single week of the year.)
Fly fishing. Horseback riding. Hiking.
Late nights around a fire pit with a drink in hand and no agenda.

At one point, a few of us fell into a rhythm while fishing.

We’d switch spots, cast, catch a fish, take a picture, high five, and toast with a little bourbon.
Then do it again.

Over two days, my fishing partner and I caught 34 fish – beautiful brown and rainbow trout.

It was simple. Repetitive. Almost meditative. And honestly perfect.

But what was different for me this time was more internal.

The first time I went, I probably showed up needing something. Answers. Clarity. Direction. Hope.

This time, I showed up open. Not trying to force anything. Not trying to “get something out of it.”

Just committed to being present. And that posture changed everything.

The Power of a Few Good Questions

Each night, we gathered around what they call "The Table." This is the ONLY expectation of Refuge – that you’re at dinner and the Table every night. No other “rules.”

It was led by our staff leader for the week, “Stokes,” and it was one of the most meaningful parts of the experience. It’s intentional time after dinner. No distractions, no phones. Just a group of men willing to be honest.

Over three nights, there were only a handful of questions:

  • What do you need most during your time here?

  • Where are you feeling challenged or burdened right now?

  • What’s bringing you fulfillment?

  • What’s something you want to take home with you from this week?

That’s it.

No frameworks. No slide decks. No teaching. Just questions.

And the space to actually answer them. What followed was real.

Raw honesty.
Tears.
Laughter.
Spontaneous prayers.
Support and encouragement.

It’s amazing what comes out of a person when they’re not rushed, not distracted, and not performing.

Doing What is Hard vs. What is Risky

One conversation has stayed with me.

I told my friend Luke that I felt like I hadn’t been doing the hard things lately. Like maybe I’d been taking the easy way out. He listened and then reframed it.

"Is it really about doing hard things, or is it about taking more risk?"

That question stuck. Because if I’m honest, to my credit, the last two years haven’t been easy. I’ve been engaged in hard thing after hard thing, and refusing to be backed down by challenge.

Navigating life after divorce.
- Learning how to co-parent well.
- Starting a new relationship.
- Walking through illness in my family and the decisions that go with that.
- Running and growing a business full time.
- And doing intensive, consistent counseling for myself.

That’s a lot, period. So maybe the issue isn’t that I’ve been avoiding hard things. Maybe it’s that I’ve been avoiding risk.

Risk looks different.

It’s stepping into something not fully formed.
Something uncertain.
Something where you don’t have the answers yet.

And I can feel that tension right now.

There are things in my life and business that I feel called to step into.
New offerings. New communities. New ways of serving. Killing off some of the work I’ve been doing that produces reliable revenue.

Not just aligned with my gifting, but with my calling.

And those things do not feel hard. They feel risky, for many (good) reasons.

Funny and Painful

Remember that moment in the cattle field?

The steer. The running. The gate. Here’s the rest of it: We got to the fence, climbed up, and as I was crossing over, waders and boots on, my boot caught the top rung.

I went straight down. Flat on my back. It knocked the wind out of me. I was in too much pain to be embarrassed.

It was also hilarious.

After we got back to the lodge and told the guys (my version of) the story, Cole just smiled and verified:

"Yeah, that thing was being aggressive. You guys were right to move." I’ll take the validation.

But the moment stuck with me for a different reason.

It was both funny and painful at the exact same time. And honestly, it felt like a perfect metaphor for life.

Hard and fulfilling.
Undesirable and meaningful.
A slog and deeply important work.
Life giving and life draining.

On the way to do something exciting and fun, and running into an unexpected obstacle.

We want it to be one or the other.

But most of the time, it’s both. This is what my therapist calls a “dialectic.” Two things can be true at the same time (and they often are).

It also underscored the very tension of “hard vs risky” for me. How illustrative that, when risk (by way of the steer) presented itself, I ran as fast as my feet would carry me away from the challenge. Hmm…this literally a learning I’m having out loud while typing these words.

As a Dad and Christ-Follower

Coming home, I was genuinely excited to see my kids. That part is always true. But this time, there was a deeper level of appreciation.

Not because something dramatic changed, but because I had the space to actually feel it.

At the same time, if I’m being real, I’m still tired. Still recovering, which tells me something important.

Even when you step away, your heart, your mind, your spirit are still doing work beneath the surface.

Sometimes what we need isn’t a quick reset. It’s deeper recovery.

I don’t have a perfectly packaged takeaway here. What I do have is a sense that God is moving things in my life that I’m not fully aware of yet. And for once, I’m at peace with that – we’ll see how long this lasts – there’s less pressure to figure it all out, less urgency to force clarity.

Just a quiet confidence that He’s working, even when I can’t see it.

Why Intentionality Like This Is So Rare

There’s something about being around a group of men in that environment that’s almost impossible to replicate in normal life. Not because it’s magical. But because it’s intentional.

No phones. No competing priorities. No constant pull back into work, notifications, or the next thing. Just presence. Heck, in everyday life, we struggle to stay focused in a one hour coffee meeting.

At Refuge, you get days of uninterrupted conversation. Curiosity about each other’s lives. Space to listen, not just respond or to solve someone else’s problems. And, again, I realize how rare that actually is.

What I’m Doing Differently

This week, I’m moving slower. Not less intentional. Not less committed. Just slower.

Taking breaks when I need them. Not forcing productivity for the sake of it. Paying attention to what my body and mind are telling me…or aren’t telling me (that’s data, too!).

If I’m being real,I want more of what Refuge offers in my day to day life.

More community. More recreation. More honest, spiritual conversations. More moments where I’m not just producing, but actually present. I tell my clients that we are “Human Beings,” not “Human Doings” – I want to take my own advice.

A Thought for You

If you’re a leader reading this, especially in the corporate world, consider this:

When was the last time you gave yourself real space?

Not a vacation filled with activity. Not a weekend where you’re still half working.

Space to think. To reflect. To be challenged. To be known.

Because leadership has a way of quietly isolating you.

And if you’re not careful, you’ll carry everything on your own longer than you should. And over time, that doesn’t just affect your work.

It affects your presence, your clarity, your relationships, your ability to lead the people who matter most (at work and at home).

Sometimes the most strategic thing you can do is step away long enough to see clearly again. Not to escape your life. But to re-enter it with intention.

So my question to you is this: What do you need most right now to reconnect to who you were made to be? I dare you to do the “risky” thing.

 

PS: Refuge is a place where you’re reminded of who you are and who you’re becoming. A place that truly lives out its mission of keeping world changers in the game. And now that I’ve been twice, I get to be part of bringing others into that experience. If something in this resonates and you’re curious about joining me for a future trip, reach out.

I’d love to have that conversation. Seriously, email me at jason@anchoredleadership.com to hear more. This is a part of my purpose in the world – to bring together groups of people to share the burden, fight against loneliness and to show up better equipped and more self-aware for the journey ahead.