September 16, 2026

What Could Go Wrong?

7 min read

Aspen Birthday Party Edition

There is a phrase I have used for years that, in retrospect, probably should have been interpreted as a warning rather than a question:

“What could go wrong?”

I say it all the time.

Going out Sunday night?

“What could go wrong?”

Monday night?

“What could go wrong?”

Tuesday and Wednesday night?

“What could possibly go wrong?”

I also use it whenever my friends and I are about to do something crazy and/or stupid.

Occasionally crazy-stupid.

Other times stupid-crazy.

There is a subtle distinction, although insurance companies apparently don’t recognize it.

Over the years, “What could go wrong?” has been followed by an impressive collection of answers.

Wrecked cars.

International police interventions.

Purchases of crazy-stupid crap that seemed absolutely essential at 1:17 in the morning.

Alligator chases.

Playing with rattlesnakes.

And numerous incidents that, for legal reasons, are probably best categorized simply as “travel.”

You would think that at some point a rational human being would examine the historical correlation between saying “What could go wrong?” and things subsequently going spectacularly wrong.

Apparently, I am not that human being.

Because as I sit on a plane heading to Aspen for a friend’s 50th birthday, I find myself saying it again.

Except this time:

WHAT COULD GO WRONG?!?!?!

Let’s examine the situation.

There are approximately a dozen guys going.

Some have hotel rooms.

Some do not.

I don’t completely understand this part of the planning.

Aspen is not Burning Man.

You can’t just wander into the woods at 2:00 a.m., construct a shelter from Patagonia jackets and Amex cards, and declare yourself a resident.

At least half the group has some sort of Special Forces background.

This is important.

Most groups of middle-aged men arrive in Aspen with chiropractors, CPAs and guys who sell commercial real estate.

We apparently have a small private army.

Three guys are flying in from overseas.

One from Australia.

One from India.

Others haven’t seen each other in years.

So we’re combining jet lag, altitude, nostalgia, testosterone and people who have previously been professionally trained to operate successfully when normal people are screaming.

This already seems promising.

Then there is Colorado.

Drugs are legal.

Technically, I understand that this statement requires some qualifications.

Nobody in this group is going to care about the qualifications.

We also have three nights to acclimate to the altitude before attempting what someone has described as a beautiful 12-to-14-mile hike from Aspen to Crested Butte.

Beautiful.

That’s always the word people use immediately before describing something horrible.

Apparently, we will climb to roughly 12,500 feet.

The weather forecast says rain.

So after three days of acclimating our bodies through what I assume will be a scientifically questionable combination of alcohol, steaks, very little sleep and whatever legal substances someone discovers in Colorado, we will attempt to walk 14 miles through the mountains at an altitude where oxygen has apparently become an optional amenity.

I have looked into traditional altitude acclimatization.

Hydration.

Sleep.

Gradual elevation gain.

Avoiding excessive alcohol.

Our plan appears to be:

Do the exact opposite of all four.

And remember: this isn’t twelve accountants.

From what I know, several of these guys have backgrounds that could reasonably be described as lethal.

I don’t think anyone is particularly afraid to throw a punch.

This creates another interesting Aspen possibility.

At some point, one of us will almost certainly encounter a 26-year-old wearing a $4,800 cowboy hat who says:

“Do you know who my father is?”

Statistically, this seems dangerous for everyone involved.

Then there is the Australian.

I don’t know exactly what role he’ll play yet, but history has taught me that adding an Australian to a questionable situation almost never makes it less questionable.

Australians seem to have a completely different risk-assessment system.

American:

“Is that safe?”

Australian:

“Probably.”

American:

“Has anyone done it before?”

Australian:

“Not successfully.”

American:

“Should we do it?”

Australian:

“Fuck yeah.”

And off we go.

There are also several predictable phases to a trip like this.

Night One:

Everyone is mature.

“We’re 50-plus years old now.”

“We’re just going to have a nice dinner.”

“Maybe one drink.”

“We have nothing to prove anymore.”

This phase should last approximately 43 minutes.

Night Two:

Someone discovers something.

Could be a bar.

Could be a person.

Could be a drug.

Could be a vehicle.

Could be an animal.

Historically, animals should concern me the most.

If there is an alpaca anywhere within 20 miles of Aspen, I would strongly recommend that its owner lock the gate.

Night Three:

Someone says:

“We should probably take it easy tonight. We have the hike tomorrow.”

This sentence will trigger the exact opposite behavior.

At 1:30 a.m., someone will order another bottle.

At 2:15, someone will disappear.

At 3:00, a person without a hotel room will suddenly become a logistical problem.

At 4:00, someone will announce that sleep is actually bad before strenuous exercise.

At 6:30, we will be eating eggs.

And at 7:00 a.m., twelve men who have spent three days actively dehydrating themselves will begin walking toward 12,500 feet.

In the rain.

What could go wrong?

We haven’t even discussed wildlife.

I have previous experience with alligators and rattlesnakes.

Colorado has bears.

This represents a natural progression in my career.

I assume at some point someone will explain what you’re supposed to do if you encounter a bear.

“Don’t run.”

“Make yourself big.”

“Back away slowly.”

Excellent advice.

Unfortunately, we have several former Special Forces guys, which means there’s at least a 40% chance someone looks at the bear and thinks:

“I have an idea.”

That is the sentence I fear most on this trip.

Not:

“There’s a bear.”

Not:

“We’re lost.”

Not:

“Where’s Steve?”

Not even:

“Is anyone else feeling chest pain?”

The most terrifying sentence in a group like this is:

“Guys… I have an idea.”

Because that’s how you end up at 11,800 feet in the rain watching an Australian hold someone’s belt while a former commando attempts something that was never contemplated by the National Park Service.

There are also certain items I expect will disappear during the weekend.

One wallet.

Two phones.

Someone’s pants.

At least one hotel key.

Possibly an entire person.

And dignity.

Dignity will be gone before dinner Friday.

There will also almost certainly be one inexplicable purchase.

Every trip has one.

Maybe someone buys a horse.

Maybe someone buys a sculpture.

Maybe three of us become minority partners in an Aspen restaurant.

Maybe someone wakes up Sunday morning and discovers that he owns a $170,000 vintage Land Rover that doesn’t start.

Nobody will remember negotiating the deal.

But apparently we got a great price.

The fascinating part is that every single person going on this trip is, individually, a reasonably successful adult.

Business owners.

Executives.

Fathers.

Husbands.

People entrusted with employees, families, money and important decisions.

Put us together, however, and our collective IQ will immediately drop by approximately 70%.

This is one of the great mysteries of male friendship.

Twelve intelligent men do not create twelve times the intelligence.

They create one 17-year-old boy with twelve credit cards.

And that’s what makes this weekend so concerning.

Because we’re not 17 anymore.

At 17, you can sleep on a floor, eat a cheeseburger and wake up ready to play basketball.

At our age, you can hurt yourself putting on a sock.

Yet somehow we are going to combine alcohol, altitude, legal drugs, rain, international travel, old friendships, missing hotel rooms, lethal skill sets and a 14-mile mountain hike.

What could go wrong?

Everything.

Absolutely everything could go wrong.

And based upon my historical record, several things probably will.

But I also know something else.

Twenty years from now, nobody is going to remember the conference call they took that weekend.

Nobody will remember the emails they didn’t answer.

Nobody will remember the responsible Saturday night they could have spent sitting at home watching Netflix.

We’ll remember the guy who disappeared.

We’ll remember whatever the Australian did.

We’ll remember the completely unnecessary thing somebody bought.

We’ll remember the rain.

We’ll remember the mountain.

We’ll remember laughing so hard somebody couldn’t breathe—which, at 12,500 feet, admittedly isn’t a great diagnostic indicator.

And hopefully, all twelve of us will eventually make it back home.

Alive.

Mostly intact.

Possibly with fewer possessions.

Possibly with more possessions.

Possibly with a horse.

So as I fly toward Aspen, knowing everything I know about my friends, myself and the historical consequences of this particular phrase, there is really only one appropriate way to begin the weekend:

WHAT COULD GO WRONG?!?!

I’ll let you know.

Assuming someone can find my phone.