Field Note 014 — Don’t Be Afraid to Look Stupid

October 7, 2026

I own an ushanka. Actually, I own two.

The first one came from a military surplus store and cost me something like four bucks. I bought it mostly because I thought it would be funny to wear camping. It was. Most people look at least a little stupid in an ushanka, and I certainly do.

Then I wore it outside when it was actually cold and discovered something important: the stupid hat works really, really well.

Eventually I bought a better one. The original surplus hat became the backup, and it still rides around with me for anybody who happens to need it. That probably says more about how I approach the outdoors than a lot of the expensive gear I’ve owned over the years.

I have an old shell jacket that I bought from some Facebook ad for maybe forty bucks. It was basically a knockoff of a much more expensive Condor jacket. The cords are stretched and faded. It has rips. It has paint stains. It looks like it has actually been somewhere. A year or two ago my lady bought me the real thing.

I still wear the cheap one.

I’ve probably burned through ten pairs of Mechanix gloves over the years. Red ones. Blue ones. Green. Gray. White. Whatever color happened to catch my eye. I actually like when they stand out.

Somewhere along the way, outdoor gear started becoming part equipment and part costume. Everything has to match. Everything has to look intentional. Everything has to signal that you know exactly what you’re doing.

I never cared much about that. If the stupid hat keeps my head warm, I’m wearing the stupid hat. If the cheap jacket works, I’m wearing the cheap jacket. If bright blue gloves make it easier to find my hands in a pile of shit around camp, even better.

I don’t need to look cool. I need the stuff to work.

That’s a very easy place to start.

Wear the dumb hat.

Looking Stupid Is Cheap

A hat is easy. There is almost nothing at stake. Maybe somebody laughs at you. Maybe somebody thinks your gear is ugly. Maybe some guy with six thousand dollars worth of coordinated earth-tone equipment thinks your jacket came from the wrong catalog.

Okay. You’ll survive.

But that little decision matters because the same fear gets much more expensive as the stakes get bigger. How many things have you not tried because you were worried you would be bad at them? How many places have you not gone because you thought everybody else would know more than you? How many opportunities have you taken away from yourself before anybody else ever got the chance?

There is a strange pressure to already be good at something before you’re willing to do it. That doesn’t make any sense.

Nobody is born knowing how to set up camp. Nobody starts out knowing how to drive off-road, climb a mountain, process firewood, repair a vehicle in the dirt, cook over a fire, pack for weather, read terrain, or figure out which piece of gear is actually worth carrying.

At some point, everybody is the idiot standing there asking how the door opens.

I know because I have literally been that idiot.

“You Brian’s Friend?”

My first trip to King of the Hammers was one of those situations where I probably could have talked myself out of going if I had known enough to understand how little I knew.

I didn’t own a 4x4. I had a little single-cab two-wheel-drive truck, a tent, and a minibike. That was about it. I also had almost no idea what I was getting myself into.

When I got out there, I had no cell service and no real directions to where everybody was camped. I eventually found the site because I recognized the back quarter of Brian’s trailer from a picture.

That was my navigation system.

I pulled in and nobody was there. Around me were serious rigs, trailers, side-by-sides, race equipment, and people who clearly had significantly more money invested in the whole thing than I did.

So I set up a chair, opened a beer, and waited.

Maybe five minutes later, a very expensive RZR rolled into camp. The driver looked at me through his helmet.

“You Brian’s friend?”

“Yeah.”

He threw me a helmet.

“Get in.”

His name was Tuan.

I didn’t even know how to open the damn door.

For a couple seconds, I felt like an idiot. Then I got in, and that was pretty much the end of it.

I got whisked away into a world I knew almost nothing about. Before long I was chopping it up with the rest of the group—people with serious machines, serious experience, and serious money wrapped up in the sport.

Nobody cared that I showed up in a two-wheel-drive with a minibike. Nobody made me prove that I belonged there.

I just went.

Since then I’ve been back many times. I’ve fixed vehicles, been to races, ridden in more machines than I can remember, made friends, learned things, and had a ridiculous amount of fun. Somehow I became everybody’s favorite co-pilot, and now at the beginning of the year I start getting messages asking if I’m coming back.

That entire branch of my life could have disappeared before it ever started if I had looked around that first day and decided I didn’t belong.

The funny thing is, by then I was already pretty comfortable being the experienced guy in other situations. I had already been taking people camping. I already carried extra gear. I already knew how to make somebody else comfortable in an unfamiliar environment.

But that didn’t mean I couldn’t walk into a different environment and suddenly become the new guy again.

Everybody is new somewhere.

Sometimes you’re the guy with the extra gloves. Sometimes you’re the guy who needs somebody to throw you a helmet.

Failure Is a Better Teacher

Part of being willing to look stupid is accepting that sometimes you actually will screw something up.

Good. That’s useful.

Success feels great, but I don’t think we learn nearly as much from it as we tell ourselves we do. When something works, we usually say, “Great,” and move on.

When something fails, we have a choice. We can walk away, or we can ask why. What went wrong? What did I miss? What could I change? What do I need to learn before I try it again?

That was always how I tried to teach guys when I was working in the trades. Somebody makes a mistake? Getting pissed doesn’t magically make them better at the job. Use it. Show them what went wrong. Figure out why it happened. Correct it. Then move forward better than before.

Failure is a teachable moment. The trick is not wasting it.

Of course, there’s a difference between being willing to fail and being a complete idiot.

I’ve learned that one too.

Maybe Listen to the Ranger

Years ago I was backpacking with a former Army Ranger and another guy who was getting ready to head to BUD/S. They wanted to climb a mountain.

Sure. Why not?

I didn’t have much experience with that kind of thing, but I was there, so I went. The climb itself went fine. It was the way back down where I decided to contribute something educational to the trip.

At some point I dropped one of my knives. They told me to leave it. They were taking a safer route down.

My dumbass decided I needed the knife.

So I went after it.

I got the knife.

Then I lost my footing.

I started sliding downhill, maybe fifteen feet from the edge of a cliff a few hundred feet up. As I was going, I grabbed a yucca. In my head, apparently, that little plant was going to stop a full-grown man sliding down a mountain.

It ripped straight out of the ground.

Excellent plan.

I kept going. A few feet from the edge was another yucca, this one in the stage of its life where it had apparently decided every surface needed to be covered in barbs from hell.

I wrapped my left arm around it.

It held.

My legs were hanging off the cliff.

I managed to pull myself up, crawl back onto solid ground, and eventually get back to the proper route. I also spent about two weeks pulling pieces of yucca out of my arm and side.

But I saved the knife.

Was the knife worth it? No. Probably not. That was probably the closest I’ve come to dying in my adult life, and yes, maybe I should have listened to the Ranger.

There’s a difference between being afraid to look stupid and refusing to listen to people who know what the hell they’re talking about. Confidence doesn’t mean ignoring good advice. Taking chances doesn’t mean turning your brain off.

But I’m still glad I did it. Not glad that I almost launched myself off a cliff. Glad that I survived it, glad that I learned something from it, and glad that I have the story.

Failure is useful. So is embarrassment. So is occasionally being able to admit:

Yeah. That was freaking stupid.

Don’t Be the Douche-Canoe

Experience can do one of two things to a person. It can make them useful, or it can make them insufferable.

I once brought a buddy out on a desert trip with a decent-sized crew. He knew his stuff. Instructor type. Very particular.

The rest of the group was there to have a good time. I’ll admit, they got a little rowdy, but nobody was trying to run a military operation. They were camping, hanging out, shooting, driving around, and being idiots with their friends.

The whole time, this guy was unhappy because people weren’t doing things exactly the way he thought they should be done. Correcting people. Complaining. Policing the experience.

He wasn’t a bad guy. Still isn’t.

But he has never been back, and I don’t think anybody has cared.

Knowing more than somebody does not give you the right to make their experience smaller.

That shit drives me crazy. The snooty climber. The off-roader who spent enough money to believe his checking account is a skill. The faux survivalist with perfect camouflage and not a rip, tear, stain, or story anywhere on it.

Anybody who looks at somebody else and says, in one form or another, “You don’t have X, so you don’t belong here.”

Eff that.

The goal is to get out and stay out. Not to be a douche-canoe.

Bitch, I Got You

For years I had an unwritten rule: buy two.

Not literally every single item I owned, obviously, but the useful stuff? Yeah. There was a good chance I had another one. Another headlamp. Another pair of gloves. Another warm hat. Another knife. Another layer. Whatever made sense.

Because if I asked somebody to come do something with me, I didn’t want them hiding behind, “I don’t have the gear.”

Nope. I have the gear.

If you don’t want to go, that’s completely fine. Say that. But if you want to go and the problem is that you don’t have the equipment or the knowledge?

Bitch, I got you.

That old surplus ushanka became the backup ushanka. I’ve handed out gloves, balaclavas, shemaghs, lights, and whatever else somebody needed.

“Oh shit, you didn’t bring gloves?”

Here.

“Getting cold?”

Take this.

“No headlamp?”

Got another one.

The goal was never to demonstrate how prepared I was. The goal was to make sure the person I brought with me had a good time, especially if they were new.

Because if somebody has never done this before, I want them leaving the trip thinking, “I want to do that again.”

Not, “Apparently I bought the wrong shit and everybody knows it.”

Experience should make you more generous, not more exclusive.

Make Them Want to Come Back

AJ is probably one of my favorite examples of this.

The first time I took him off-road was a little trip up around Big Bear. He had never been camping. Never been off-roading. Nothing. He grew up pretty sheltered, and on top of that he had legitimate reasons to be cautious about jumping into unfamiliar situations.

At the beginning of the day he was timid, unsure, and a little scared. He had no idea what was going to happen.

By the end of the day?

Cock of the walk.

Having the time of his life. Completely obsessed.

There’s a picture of him from the end of that first outing, standing there looking like he had been doing this forever.

That one little trip turned into another, and another, and another. He shows up in pictures from years of my camping life now. He has been part of multiple trips, multiple stories, and more than one Field Note.

If he had decided that morning that he didn’t know enough to go, none of that happens. If I had spent the day making him feel stupid because he didn’t know what he was doing, maybe none of it happens either.

He took the chance. I did my best to make sure he enjoyed himself.

And I got a camping buddy out of the deal.

That seems worth a little extra gear.

Pavement Ends

There was a sign on the way into the desert property.

PAVEMENT ENDS.

Fifteen miles per hour.

It was the last sign before the pavement actually turned into dirt, and especially when somebody was coming out for the first time, I liked stopping there and taking a picture.

Different people. Different trips. Different years. Same stupid sign.

It became a little ritual.

Looking back through those pictures now, I like what they represent more than I probably understood at the time. That was the line.

Before that sign, normal life.

After that sign: dirt roads, campfires, weird hats, broken shit, bad decisions, good food, new experiences, and stories that somehow keep hanging around years later.

Nobody in those pictures had to prove they belonged there.

They just had to come along.

Standing Still Is Pretty Safe

There is a very easy way to avoid looking stupid.

Do nothing.

Don’t try the new thing. Don’t go somewhere unfamiliar. Don’t ask the question. Don’t approach the person who knows more than you. Don’t buy the weird hat. Don’t show up with the little truck. Don’t climb the mountain. Don’t take the first trip.

Stay where you already know how everything works.

You’ll probably avoid a lot of embarrassment.

You’ll also avoid a lot of growth.

We all make mistakes. That’s human. We can stand still and be safe, but we’ll never go anywhere. If we take chances, make mistakes, examine them, learn from them, and keep moving, we grow.

And when you run into somebody who knows more than you, approach them. There are generally two possibilities.

They might be excited to share what they know. Those people can teach you a ton.

Or they might be a dickbag.

That’s useful information too. Now you know they don’t deserve your time. Move on.

The only person who wakes up with you every day is you. That’s the person you need to worry about.

Your camping trip is your leisure time. Your hike is your hike. Your stupid little minibike is your stupid little minibike. Your ugly jacket is your ugly jacket. Your hat can look ridiculous. Your setup can be weird.