My Brain Is Like a Luxury Hotel That Fails at Service

How executive dysfunction creates a minefield of constraints.

Feb 04, 2025

On a recent trip I stayed at an expensive hotel where lots of things went wrong.

The service was well-intentioned but poor in execution. More often than not, my water glass was left empty at mealtimes. I passed the time looking around at the many servers in the vicinity, trying and failing to catch their eye for a refill.

On the second morning, I requested a cup of coffee. Of course, I was told. But the coffee never arrived. Ten minutes later, I asked another server, who nodded and rushed off—presumably toward a coffee machine, but they never returned either.

The only time an employee was proactive was when they requested that I mention them by name in a TripAdvisor review—then hovered over my table with a QR code, not leaving until I pretended to scan it.

These are first world problems, of course. But the promise of the expensive hotel is that it’s worth the premium it charges its guests. If you want average service, stay at the three-star hotel, not the five-star one. Right?

Nice hotel, but can I get housekeeping service? 📷

If you’ve traveled a lot, you probably know that experiences like these are not uncommon. Many fancy hotels and nice restaurants struggle with service. If anything, it’s sometimes more surprising when everything goes the way it’s supposed to.

As a guest in these situations—an outsider to the internal process—you might feel frustrated. Surely this should not be hard to fix! But maybe it is hard to fix. If it was easy, it wouldn’t be common.

So what, I wondered, is the problem?

Ultimately, the answer comes down to something like “staffing and training,” but that’s like saying “rain is water from the sky.” The hotel business is based around staffing and training. So what is the problem more specifically?

Could it be:

Improper incentives, where staff don’t feel connected or fully invested in their work?
Some version of the bystander effect, where there are too many staff and everyone assumes someone else will do what’s needed?
Not enough life/work balance? (Get those employees some yoga mats!)
A cultural issue? It’s no secret that some parts of the world have much more of a hospitality culture than others.
Just the “wrong people in the wrong seats on the bus,” to use the management phrase?

The bottom line is it’s hard to know for sure. Sometimes every element seems to be in place to create a perfectly harmonious experience, but the sum of the parts fails to add up.

Like the cursed restaurant location, which seems like a great spot for a noodle place but instead hosts a succession of attempts that close after six months, these problems can be mysterious and hard to diagnose.

You’re In Charge: How Do You Fix This?

Now imagine you are the hotel manager trying to fix the problem. Your heart is in the right place—you want guests to be happy! You also know your employees will be better off if things run smoothly.

You try lots of different things:

You read a leadership book about creating operating procedures and checklists, and you dutifully implement its lessons
You try to collaborate with the employees, openly discussing the situation with them in an attempt to create buy-in and ownership
You do your best to model the service you want your employees to provide.

Something doesn’t get through, though. You make some small improvements but the big ones fail to stick. Before you know it, staff are missing things again. The hotel culture fosters the art of ignoring guests who need something, forgetting coffee orders, and failing at offering proactive solutions.

As the hotel manager, most likely you’ll eventually settle in and accept things as they are, at least somewhat. Turns out solving the problem was harder than you thought! Moving forward, you address major problems when they come up, but you abandon the quest to create the culture of excellence you aspired to.

Maybe it’s fine this way. After all, some guests don’t seem to notice or care. Still, you always wonder: couldn’t this be better? You never actually solved the problem, and the failure continues to nag at you.

My Brain Is Like the Luxury Hotel

As I pondered the tragedy of the fancy hotel with mediocre service, I realized an unsettling analogy: my brain is like this. This is exactly what happens to me on a regular basis.

I am generally smart and well-resourced. I have learned to be what is called “high-functioning,” and I have skills that I’ve developed over the years. I understand the power of hyperfocus. I have led large teams, given high-pressure talks, and generally gone through life as an achiever.

I list these experiences not as a compilation of bragging rights, but more to contrast them with the huge limitations that I also experience.

Because that’s the thing: I struggle with continual service failures. Over and over, I find myself unable to do what I direct myself to do.

I am seemingly incapable of doing many small things that other people find to be completely normal. I have written about some of these experiences in this newsletter, in particular in a post about failing to renew my driver’s license:

Writers often use the term “resistance.” Believe me, it would be easier for me to write a book than to deal with bureaucratic institutions. If someone said to me, how about you write 30,000 words or fly to Singapore to give a talk instead of spending half the day on something bureaucratic, I’d choose the book or talk.
But again, this isn’t necessarily the smartest move. It leads me to put off making healthcare appointments and many other things that would probably be good to do.

I have very low frustration tolerance for navigating simple challenges of daily life. Some of this is due to having ADHD—one of its core characteristics is being pretty good at some things and very bad at others.

The driver’s license post includes some other examples as well, but it is by no means a comprehensive list. A more complete list would include categories such as:

TASK COMPLETION. I find myself dreading certain tasks, but I do not complete them. Instead I just think about them over and over without doing anything. I write them down in dutiful productivity advice fashion. I schedule time for them and then I use the time for something else.

RELATIONSHIPS. My struggle has affected important relationships, including some that I’m sad to say did not end well. I have lost out on countless opportunities for growth, for friendship, and for general good things.

RELIABILITY. There are a lot of people who think I’m unreliable, even though reliability is something I try to pride myself on. (In the end, both things are true; I am highly reliable in some ways, and completely the opposite in others.)

I repeat the patterns associated with this behavior over and over.

My brain is like the luxury hotel that fails to meet basic standards. It has the marble staircase in the elegant lobby, with the understaffed desk at reception. It has the well-dressed doorman who stands at attention before looking the other way when a guest approaches in need of assistance. It has the room service menu with a dozen organic, plant-based entrees that fail to arrive in a reasonable time, or at all.

And this is all very frustrating!

The Two Responses I Receive When Describing This Problem

Whenever I talk about this problem in some form, inevitably I hear responses that fall into one of two categories. The first category is “But how hard could this be? Here’s an easy solution for you.”

Why is it hard for you to to call someone back? You just pick up the phone and dial.
You don’t have health insurance? All you need to do is go to this website or call this number and talk to someone to get the process started.
If avoiding a task causes so much distress, why not just tackle it and get it out of the way?
To focus better, make a list of high-priority items and work on them first thing every day.

And the thing about this kind of advice is: it’s not wrong. Most of it has value and truth, at least to a point. But will I follow it? Maybe—but probably not. Or more likely I’ll follow it sometimes, just not consistently. Before long, I’ll be back to my familiar patterns of angst and avoidance.

The other response category is also well-meaning, yet ultimately unhelpful. This category refers to my accomplishments, saying, in effect, “Well it doesn’t really matter that you have this problem, because you’ve been able to do x, y, and z. So your life is pretty great and people respect you for doing ‘so much.’”

As I said, this is well-meaning (and nice!) but ultimately doesn’t address the issue.

Yes, on balance I would not trade my life for anyone else’s. I do generally try to live purposefully and with gratitude. I want to realize life while it’s being lived.

But I am also doing myself no favors in living this way. I would much rather fix the problem! I would like to be the hotel manager overseeing a perfectly harmonious experience, directing the parts of myself to perform in an organized way, with the result being that I’m not constantly dropping plates or letting people down. (Including myself, of course.)

And I can’t! The struggle is real. The struggle is daily. The struggle is endless. If you don’t see it, it’s only because you don’t know me well enough.

I feel guilt and shame over this, usually on a very regular basis.

I also feel great aspiration—if I could only fix this problem, my life would be so much better. I could start and grow new businesses, I could be more responsive to people I care about, I could scale or leverage the successes I’ve had, and so on. I just know there’s an answer out there somewhere! Acceptance is one thing, but I don’t want to completely give up.

I've been thinking about that hotel manager a lot lately. The one who knows exactly what excellence looks like but can't quite make it happen. The one who tries new systems, reads the management books, holds the staff meetings—and still ends up with empty water glasses and forgotten coffee orders.

I don’t want to leave you hanging. I’ve been working on this over the past year, and I’ve found some answers. They aren’t secret answers, like those found in a Dan Brown novel. They’re all hidden in plain sight, but they can still be hard to unlock.

At the end of this post, I’ll link up a few others that offer some partial solutions—hopefully ones that offer real value, and aren’t just “Suck it up and do better.”

But I also want to acknowledge the problem without skipping ahead. If you relate to any of this—if you too feel like a luxury hotel with great intentions and spotty service—well, welcome to the club. We're all just doing our best with the brains we have.