August 27, 2026

My Life Philosophy May Be Terrible Advice

7 min read

Every once in a while, I come across a list of sayings that feels less like inspirational wisdom and more like somebody has been secretly following me around for the last several decades taking notes.

This was one of those lists.

It started with:

"Good behavior is overrated. A good story, however, is forever. Make your story count."

Well, that explains a lot.

I have apparently spent most of my life preparing material.

Some people collect watches.

Some collect wine.

I seem to collect situations that begin with:

"You are not going to believe what just happened."

And, unfortunately, people usually do believe me now.

That is probably not a good sign.

At some point, your friends stop saying, "No fucking way," and start saying, "Of course that happened to you."

Apparently that is when you have established a personal brand.

Then came:

"Say yes to the story. The itinerary can go fuck itself."

I could have had this tattooed on my forehead years ago and saved everyone a lot of confusion.

I have never been especially good at itineraries.

An itinerary assumes that Tuesday will go approximately the way Tuesday was supposed to go.

That has not been my experience.

My Tuesdays tend to involve going somewhere perfectly normal and discovering that the sushi restaurant has run out of all fish, my phone has independently decided to call people in the middle of the night, an airline passenger has apparently converted the Delta Sky Club buffet into an in-flight catering business, or my attempt to improve my intestinal health has somehow ended with Fleet's Enema becoming my pharmaceutical sponsor.

I don't need an itinerary.

I need a documentary crew.

Then:

"Wear something slightly inappropriate. People have become far too comfortable with ordinary."

Now we are getting somewhere.

I have never really understood the desire to blend in.

What is the goal?

To spend 80 years on Earth and have everybody describe you as:

"Very appropriate."

Fuck that.

I don't want my obituary to sound like a performance review.

"He was punctual. He dressed appropriately. He never made anyone uncomfortable."

That sounds less like a life and more like someone who successfully completed compliance training.

Ordinary has become a national obsession.

Ordinary houses.

Ordinary restaurants.

Ordinary meetings.

Ordinary businesses.

Ordinary ideas wrapped in PowerPoint presentations claiming to be disruptive.

I seem to have developed some sort of allergic reaction to all of it.

If I walk into a restaurant, club, community, company, racetrack, technology business, or random building and think, "This could be so much better," there is at least a 50% chance I am about to ruin the next two years of my life trying to fix it.

Which brings us nicely to:

"Go alone instead of waiting for someone to come with you. Life doesn't wait, and neither should you."

I believe this one.

Probably too much.

There is a particular type of person who waits until everyone agrees before doing something.

I am apparently the opposite.

Sometimes nobody agrees.

Sometimes nobody understands.

Sometimes people look at me like I just proposed opening a caviar-and-corndog cathedral with flowers, bread ovens, wine, restaurants, gardens, elevators that look like aquariums, and whatever else wandered through my head that morning.

And instead of hearing:

"That sounds insane,"

my brain hears:

"So you're saying there's a chance."

This has not always been financially prudent.

But it has rarely been boring.

Then I got to:

"Never overexplain a fabulous disappearance. Wet hair and no useful information will do."

This may be the greatest advice ever written.

We live in a world of catastrophic over-explanation.

Everyone needs a statement.

A follow-up statement.

A clarification of the statement.

An Instagram post explaining the clarification.

A podcast about the Instagram post.

And then an AI-generated apology for the podcast.

Maybe sometimes the correct answer really is just to reappear three days later with wet hair and say:

"Long story."

And then refuse to tell it.

Which connects beautifully to:

"Keep a part of your life completely unexplained. Mystery is good for the complexion."

Agreed.

Not everything needs a fucking FAQ.

There should be at least a few parts of your life where people ask:

"What exactly happened there?"

And the answer is:

"No one really knows."

That is how legends are made.

Or subpoenas.

Sometimes both.

Then came:

"Be soft when you feel soft. Wild when you feel wild. And impossible to domesticate."

This one sounds poetic.

In my case, "impossible to domesticate" mostly means I still cannot sit through a boring meeting without mentally redesigning the entire company.

I can be listening to someone explain a perfectly acceptable business and suddenly my brain starts screaming:

"What if we bought the whole thing, changed the model, added entertainment, rebuilt the customer experience, created a new category, and hired somebody completely unexpected to run it?"

That is not strategic discipline.

That is entrepreneurial Tourette's.

There should probably be medication for it.

I would refuse to take it.

Then:

"Quit auditioning for rooms you already outgrew. You are not begging for a chair. You're taking the whole damn table."

Now this one I really like.

Because at some point in life you realize something very liberating:

You do not need to be invited into every room.

Sometimes the room sucks.

Sometimes the people guarding the chairs have confused access with importance.

Sometimes the better move is to leave, build your own room, design a better table, invite more interesting people, serve better food, play better music, and wonder why you ever cared about getting inside the old one.

And if that sounds slightly grandiose, please refer back to the part about being impossible to domesticate.

Then:

"Laugh loud enough that the next table looks over. Give them something worth overhearing."

I fully support this.

Life is already serious enough.

People whisper too much.

Restaurants are filled with tables of four people quietly looking at their phones while sitting three feet from actual human beings.

If we are going out, somebody at the next table should eventually turn around.

Not because we are being obnoxious.

Because they are thinking:

"What the hell are those people talking about?"

That is a successful dinner.

If nobody laughs too loudly, says something wildly inappropriate, tells a story they probably should not tell, or causes at least one person to nearly spit out a drink, I am not sure why we bothered getting dressed.

Then came possibly the most useful advice of the entire list:

"Leave when you're bored. Stay when you're enchanted. Disappear when the energy starts smelling funny."

I wish I had learned this at 25.

Boredom is information.

Bad energy is information.

That slightly strange feeling where you think:

"I don't know exactly what is wrong here, but something smells weird."

That is information too.

And I am no longer talking only about restaurants.

Although, given my history, occasionally the smell really is the bathroom.

Life is short.

There are too many extraordinary people, places, ideas, meals, conversations, businesses, and moments to spend your time politely sitting somewhere thinking:

"When can I leave without being rude?"

Leave.

You are already gone emotionally.

Your body is just waiting for permission.

And finally:

"Stop making every decision look reasonable. Some choices are made because your soul said, 'Oh, fuck yes.'"

There it is.

My entire past, present, and possibly future in one sentence.

Reasonable has its place.

Reasonable is useful when selecting blood pressure medication.

Reasonable is probably good when landing airplanes.

Reasonable should definitely be involved when reading the instructions on psyllium fiber.

I have learned that one personally.

But I'm not convinced reasonable is how you are supposed to live an entire life.

Some of the best things begin with an idea that makes absolutely no sense on paper.

Some of the best people enter your life unexpectedly.

Some of the best trips happen after the itinerary has completely collapsed.

Some of the best businesses sound ridiculous the first time you explain them.

Some of the best nights are the ones that begin with:

"We'll just stay for one drink."

And some of the best decisions are the ones where your brain is still assembling a spreadsheet while something much deeper inside you has already decided:

Oh, fuck yes.

So maybe this list is not advice at all.

Maybe it is permission.

Permission to be slightly inappropriate.

To leave boring rooms.

To stay too long when the night is magical.

To laugh loudly.

To go alone.

To disappear occasionally.

To build the weird thing.

To stop begging for chairs.

To keep a few stories to yourself.

And to remain, even as the years accumulate, just a little bit impossible to domesticate.

Because good behavior may in fact be overrated.

But a great story?

That really might last forever.

And if I'm lucky, I'm nowhere near done creating mine.