Outdoor Education
Are we brave enough to let our students struggle?
Most of us joined the Outdoor Education industry for one of two reasons: a profound connection to the healing power of nature, or a specific, slightly reckless adventure we had as teenagers.
If you are here because of the latter, you know exactly what I mean. We are here because we struggled. We got lost, cold, or scared, and we came out the other side.
But let's be honest: if a student did today what we did back then, we would send them home.
We have sanitized the experience so much that we might be killing the very thing that made us who we are.
I was reminded of this paradox recently when looking back at my first "expedition" at 17. I convinced seven friends to join me for a 3D2N trip. We were fueled by that specific kind of invincibility that only teenagers possess—the belief that physics is just a suggestion, not a law.
We were a disaster waiting to happen.
Imagine a group of kids rocking up to a mountain looking like they are going to the mall. We hiked in denim jeans and school backpacks. Because we didn’t have proper hiking packs, someone carried a six-pack of 1.5-liter water bottles by hand while somebody else hand-carried the team tent.
If you are here because of the latter, you know exactly what I mean. We are here because we struggled. We got lost, cold, or scared, and we came out the other side.
But let's be honest: if a student did today what we did back then, we would send them home.
We have sanitized the experience so much that we might be killing the very thing that made us who we are.
I was reminded of this paradox recently when looking back at my first "expedition" at 17. I convinced seven friends to join me for a 3D2N trip. We were fueled by that specific kind of invincibility that only teenagers possess—the belief that physics is just a suggestion, not a law.
We were a disaster waiting to happen.
Imagine a group of kids rocking up to a mountain looking like they are going to the mall. We hiked in denim jeans and school backpacks. Because we didn’t have proper hiking packs, someone carried a six-pack of 1.5-liter water bottles by hand while somebody else hand-carried the team tent.
Our team of 8 with our denim jeans, hand-held team tents and water bottle
To make matters worse, the rangers stopped us at the trailhead and told us camping was banned in the park. Unphased, I improvised a "backup plan": we would camp at the summit of the highest peak instead. I promised them a superb view.
As the sun set, the mood shifted. I pulled the classic leader’s lie: "It’s just over that next ridge." I must have said "five more minutes" twenty times.
The Reality Check
By the time we reached the summit, we weren't greeted by a view. We were greeted by a massive metal lightning rod, humming in the wind, with a thunderstorm rolling in. I realized, with terrifying clarity, that I had led my friends into a giant electrical trap.
We couldn't rest. We had to slog another three hours in the dark to find safety.
The group went quiet—that specific, seething silence where you know your friends are secretly plotting your murder. By the time we set up camp, we were exhausted, angry, and dangerously thirsty.
As the sun set, the mood shifted. I pulled the classic leader’s lie: "It’s just over that next ridge." I must have said "five more minutes" twenty times.
The Reality Check
By the time we reached the summit, we weren't greeted by a view. We were greeted by a massive metal lightning rod, humming in the wind, with a thunderstorm rolling in. I realized, with terrifying clarity, that I had led my friends into a giant electrical trap.
We couldn't rest. We had to slog another three hours in the dark to find safety.
The group went quiet—that specific, seething silence where you know your friends are secretly plotting your murder. By the time we set up camp, we were exhausted, angry, and dangerously thirsty.
We finally managed to pitch a tent in the wee hours
Then came the breaking point.
We thought we were out of water. But then we discovered that two of the group had been hiding the last two water bottles in their pack. While the rest of us were parched, they had been secretly drinking.
The sense of betrayal was visceral. We didn't scream or cry—we just stared at them. It was a cold, ugly look at survival instinct right there in our circle of friends.
We thought we were out of water. But then we discovered that two of the group had been hiding the last two water bottles in their pack. While the rest of us were parched, they had been secretly drinking.
The sense of betrayal was visceral. We didn't scream or cry—we just stared at them. It was a cold, ugly look at survival instinct right there in our circle of friends.
Our body language the following morning says it all
The Safety Paradox
I share this story not because I think it was "good" education—it was reckless. But the learning from that night has stuck with me for two decades.
We learned on two levels that night.
First, the Logistical: We learned that denim kills, that maps matter, and that planning is critical. Second, the Ethical: We learned how quickly human decency evaporates when you are thirsty and scared.
If that were a school trip, a guide would have checked our packs (Logistical Safety). A guide would have rationed the water (Ethical Safety).
We would have been safer. We would have been comfortable. But by removing the logistical failure, the guide would have inadvertently removed the moral test.
We often treat these as separate buckets: Safe Logistics vs. Character Building. But they are deeply entangled. When we sanitize the logistics, we inadvertently sterilize the ethics.
If we remove the possibility of doing the wrong thing, do we ever truly learn to do the right thing?
Educational philosopher Gert Biesta calls this "The Beautiful Risk." If you remove the risk of failure, you haven't just made education safer—you've made it impossible.
We learned on two levels that night.
First, the Logistical: We learned that denim kills, that maps matter, and that planning is critical. Second, the Ethical: We learned how quickly human decency evaporates when you are thirsty and scared.
If that were a school trip, a guide would have checked our packs (Logistical Safety). A guide would have rationed the water (Ethical Safety).
We would have been safer. We would have been comfortable. But by removing the logistical failure, the guide would have inadvertently removed the moral test.
We often treat these as separate buckets: Safe Logistics vs. Character Building. But they are deeply entangled. When we sanitize the logistics, we inadvertently sterilize the ethics.
If we remove the possibility of doing the wrong thing, do we ever truly learn to do the right thing?
Educational philosopher Gert Biesta calls this "The Beautiful Risk." If you remove the risk of failure, you haven't just made education safer—you've made it impossible.
The Case for "Consequential Agency"
It’s not that I want students to be in danger. I want them to have Agency.
In my story, our incompetence created a crisis. And because there was no adult to "fix" that crisis, we were forced to inhabit a Moral Growth Zone.
My friends faced a real choice: Do I share, or do I survive?
You cannot "architect" a betrayal like that—and you shouldn't try. But you can architect the space for it to happen.
If we script every minute, check every bag, and solve every problem, we prevent the very stress that tests character.
If we remove the possibility of failing at the small things (planning), we deny them the chance to grow in the big things (character).
But how do we decide which failures are acceptable? Where is the line between "Agency" and "Negligence"?
I find it helpful to borrow a mental model from the tech industry (Jeff Bezos): The One-Way vs. Two-Way Door.
In my story, the Lightning was a One-Way Door (Negligence). The Water was a Two-Way Door (Agency).
We need Architects who can secure the One-Way Doors (Safety) while flinging open the Two-Way Doors (Growth).
In my story, our incompetence created a crisis. And because there was no adult to "fix" that crisis, we were forced to inhabit a Moral Growth Zone.
My friends faced a real choice: Do I share, or do I survive?
You cannot "architect" a betrayal like that—and you shouldn't try. But you can architect the space for it to happen.
If we script every minute, check every bag, and solve every problem, we prevent the very stress that tests character.
If we remove the possibility of failing at the small things (planning), we deny them the chance to grow in the big things (character).
But how do we decide which failures are acceptable? Where is the line between "Agency" and "Negligence"?
I find it helpful to borrow a mental model from the tech industry (Jeff Bezos): The One-Way vs. Two-Way Door.
- One-Way Doors are decisions with irreversible consequences (e.g., a lightning strike, a severe fall, deep psychological trauma). Once you walk through, you can't go back. This is the domain of the Guide. We never delegate safety here.
- Two-Way Doors are decisions with reversible consequences (e.g., getting lost for an hour, mild dehydration, a heated argument). If you get it wrong, you can fix it. This is the domain of the Student.
In my story, the Lightning was a One-Way Door (Negligence). The Water was a Two-Way Door (Agency).
We need Architects who can secure the One-Way Doors (Safety) while flinging open the Two-Way Doors (Growth).
The Elephant in the Room
I know what you are thinking.
"This theory is great, but have you met the parents? If I let a student run out of water, I’ll be fired by Monday."
You are right. We operate in a system that demands certainty. Parents are anxious, and schools are risk-averse. Navigating that fear is a massive challenge—one that deserves its own entire article.
But before we can convince the parents that struggle is safe, we have to believe it ourselves.
If we don't have the clarity to distinguish between a "Two-Way Door" (Growth) and a "One-Way Door" (Danger), we will never be able to defend our pedagogy to a worried parent.
"This theory is great, but have you met the parents? If I let a student run out of water, I’ll be fired by Monday."
You are right. We operate in a system that demands certainty. Parents are anxious, and schools are risk-averse. Navigating that fear is a massive challenge—one that deserves its own entire article.
But before we can convince the parents that struggle is safe, we have to believe it ourselves.
If we don't have the clarity to distinguish between a "Two-Way Door" (Growth) and a "One-Way Door" (Danger), we will never be able to defend our pedagogy to a worried parent.
Becoming Architects of Struggle
So, let's start with us.
We need to be honest with ourselves: We can't go back to the reckless days of our youth. But we also can't continue down the path of total sterilization.
We need to find a way to design for Agency.
We need to become Architects who build a safety net, but leave enough holes in it for the students to fall through—just a little bit. Enough to feel the gravity. Enough to realize that their choices have consequences.
Because if we don't let them struggle in the woods today, we aren't protecting them. We are just delaying the lesson until they are in a boardroom, or a marriage, or a crisis where the stakes are much higher than a bottle of water.
The pressure to patch every hole is immense. It always feels safer to step in. It always feels easier to fix it.
The real question is both whether we know which holes to leave open, and whether we have the discipline to keep them open when the world is screaming at us to close them.
We need to be honest with ourselves: We can't go back to the reckless days of our youth. But we also can't continue down the path of total sterilization.
We need to find a way to design for Agency.
We need to become Architects who build a safety net, but leave enough holes in it for the students to fall through—just a little bit. Enough to feel the gravity. Enough to realize that their choices have consequences.
Because if we don't let them struggle in the woods today, we aren't protecting them. We are just delaying the lesson until they are in a boardroom, or a marriage, or a crisis where the stakes are much higher than a bottle of water.
The pressure to patch every hole is immense. It always feels safer to step in. It always feels easier to fix it.
The real question is both whether we know which holes to leave open, and whether we have the discipline to keep them open when the world is screaming at us to close them.
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