Guarding the Gilded Cage: Why Money Doesn’t Buy Happiness (But It Does Buy Different Worries)

More Money, Same amount of Problems

My part time gig ebbs and flows. I may go two or three weeks without doing anything, then stuff will pop off and I’ll work four 12 hour days in a row. I like this pace; since I know when I’ll have long stretches of work coming well in advance, it really helps me appreciate my semi-retired state. Plus the infrequent spurts of heavy work help inject some variety in my life. 

I’ve mentioned some aspects of my work here before, but today I want to talk about something I’ve noticed, so you’ll need some context first. I’m intentionally leaving stuff vague because I like my privacy, and I especially want to respect the privacy of the people I work for. Please don’t dox me. 

I do Executive Protection (EP), which is a fancy term for bodyguard. It involves more than goonery though, hence the multisyllabic title. Your stereotypical bodyguard works for someone shady, following around their boss with the hopes that their size and intimidating nature prevents stupidity from happening. These guys are picked for their girth; not solely for intimidation, but so their boss can literally use them as a bullet sponge if shit goes haywire. Hence body and guard. 

The EP profession is much different. First off, I don’t work for anyone shady and I’m of average build; half the people I protect are taller and/or wider than me. I’m a part time W2 employee of a large legitimate company. I have a 401k and have to expense stuff through HR; totally normal corporate shenanigans. I’m sure there are some EP peeps working for less than reputable companies, but they are in the extreme minority as a big part of the gig is legal compliance.

That’s because those working in EP have some way of legally possessing a firearm as a condition of their employment. My employer requires all of us to be currently qualified under LEOSA. This is a federal law which allows cops and those that retired in good standing to pack heat nationwide as long as they pass an annual qualification test. 

This concentration on guns can be misleading though. Much of the “tactical” side of my job involves me conducting surveys and risk analysis of places the people I’m protecting will be visiting, figuring out ways to mitigate any potential threats, and creating multiple contingencies if a threat does arise. There’s some nuance and detail to it, but much of my plans can be generalized down to ‘Get the Fuck out most quickly and call the cops’. If things go south, the gun is the last option. If it goes to gunfighting, it means we screwed up and missed something along the way. 

The majority of the time, nothing happens. The few times threats do emerge, we can usually preemptively identify them (thanks to the RAS and Hypervigilance) before they engage in belligerence, and can talk them away from doing something idiotic. Since we work in teams, we split when this happens where some of us will go deal with the possible threat, while the rest of us will move our protectee somewhere safe. And this leads us to some third order consequences.

Much of my job is a lot less sunglasses and earpieces, and a lot more like being a chauffeur combined with a butler. Always within reach of our protectee, but a part of the background. If you were introduced to my protectee, you would see me but would feel zero social pull to introduce yourself to me. I’m like…the help.  

I open a lot of doors for my protectees (so I can ensure they go through the correct door which we’ve already checked for threats), and I drive them around a lot (road rage is one of the leading causes of violent assault , and if we run into this, my advanced driving training and experience will hopefully allow us to Get The Fuck Out more quicker). I spend a lot of time standing in the background while my protectee does their thing. It’s not glamorous, but I do enjoy the challenge of trying to ID and mitigate threats while also getting our protectee through their days as smoothly as possible. 

While my protectee is doing their thing, I’m doing mine. That involves me constantly scanning for threats, thinking through contingency plans, and mentally rehearsing what I’ll do. I’m watching everyone’s demeanor as well. Threats telegraph their intent through non-verbal language, and I’m looking for that. Maybe I missed a threat cue, but someone else may have seen it. Does anyone in the room seem scared or confused? I’m trying to read the room as best as I can, and paying attention to how everyone seems to be feeling. The presence of someone becoming aggressive can be almost palpable. It’s a basic hardwired human instinct that I try to keep attuned to. 

I’m also listening. I need to pay attention to what my protectee is saying, so I know if they’re getting ready to move. This way we can have their route out clear and their vehicle prepped for a seamless and fast exit, thus reducing their exposure to unknown threats. I also need to listen to what other people are saying, so I can hear if someone is becoming heated and may turn into a threat.

All this is to justify to you that I am eavesdropping the fuck out of a lot of conversations.

You probably already figured this out, but people like us don’t hire EP crews. One, because we can’t afford to. Two, because we don’t really need to-the people who pay for EP have enough money to get such a service exactly because they have that much money. Possessing crap tons of money absolutely puts a target on your back. So when I say I’m eavesdropping on some shit, I’m saying I’m constantly listening in on a bunch of super rich people talking. I believe the current term is “ultra high net worth”(UHNW) . Numbers wise, a UHNW individual has the combined net worth of everyone currently living in Longmont. 

Now obviously I’m not a complete asshole, nor am I a total idiot. We don’t talk about what we overhear, even among our team. This goes beyond being a professional. Unless someone is discussing how they will or have physically and/or illegally hurt someone, I think all people deserve some fucking privacy. This is one reason why this blog is anonymous.

That said, I would like to report back on some general feels.

The people I work for are people. They have their struggles. But for the most part, you know what? They’re actually pretty good people. They spend an amazing amount of time trying to figure out how to use their money to help others. Having spent lottttssss of time around them, I can tell you that the ones I protect do this because they genuinely give a shit, and they don’t have any ulterior motive. And despite what may be portrayed, they’re grounded in reality. No kidding, they’re actually down to earth.

From what I can tell, they seem to have gotten to where they are because of two things:

• They won the lottery when it comes to family and relationships. They have multiple people in their lives who are genuinely supportive, and a family raised them in a healthy, balanced manner.
• They worked hard as fuck for a real long time, in a field which highly compensates them for their efforts. And they got into this field because they love it. 

This has paid off well for them. We ride around in ridiculous luxury. Flying on jets that make first class look like coach, with concierge level security. Literally you park 100 feet from the plane, walk through quick screening, and then you’re in the air five minutes later. The hotels we stay in are off the hook; I can never find a normal coffee maker, it’s all espresso or some dude bringing me a custom latte or whatever. The cars I drive these people around in cost more than my first house. My comped daily meals cost more than my family’s monthly grocery budget.  

As you probably know given your familiarity with the concept of hedonic adaptation, none of this nice shit makes anyone’s lives any better. Most of it is used because it’s expedient; it allows our protectees and the team of people who support them to focus completely on their jobs and not worry about trying to find a healthy meal or how best to get from point A to point B.

For me, it was cool the first time I experienced all that stuff. And then I quickly stopped caring as I focused on doing my job, just like everyone else. For the people I protect, they long since stopped caring. This expensive stuff doesn’t solve the actual problems they’re constantly trying to solve; how to be the best at what they can do, how to be a good spouse and parent, how to make sure what they’re doing has the desired positive effect.

Sure, there’s some benefit from subtracting all the distractions so they can focus on what matters. But it seems to all balance out; while they have less mundane things to deal with, they have much more shit to keep up with. They work extremely long hours, with few days off, and their profession dictates their constantly changing location. They’re always dealing with the neverending logistical hiccups that occur when running an enterprise which involves thousands of people. 

Then there’s the fame. It does not seem attractive. While my protectees have accepted it as a part of their business, the luster has long since worn off. Everywhere they go, there are more people demanding their finite attention. Again, my protectees actually do give a shit, and try to help these people as much as they can. But these people outnumber the minutes in the day, so ultimately they must triage, which means someone is always going to be unhappy with them. Our EP team does our job, and makes sure unhappiness doesn’t go bad. But after we’ve gotten our people clear of some unsatisfied admirer, it still weighs on those we protect. While they try not to let it get to them, they’re human; it does. And it’s constant.

I was worried that my occasional interludes with extreme luxury would spoil me. If anything, it’s the exact opposite. Yeah, all the stuff I touch while working is new and shiny, but it works the same. The food is convenient and tastes good, but not any better than what I can make at home. When I do get a quick break, I read a book in the hotel. It feels exactly the same as reading a book in my house. 

What seems to happen when you have that much money is you get a lot more options, and you can have the very best of everything. Some guy wrote a book about how that doesn’t make anything better, and backed it up with research. More options, more cognitive load to make a decision.

But even then your options are limited by the constraints of your empire. Want to go to Paris for dinner tonight? Sure. But that means you’ll have to reschedule some of your meetings, and maybe miss out on a pre-planned event which may have a negative impact on your business. Thousands of people depend on you, so you don’t take that lightly. Looks like you have a window of some free time soon; how about we get you to Paris three thursdays from now? 

Not quite as fun, huh?

Overall it seems like it all evens out. From my firsthand experience, UHNW people have way more options, but a corresponding increase in constraints. They also have problems that only happen to people with that much scratch. So they spend a considerable amount of money hiring people like me, along with other types of staff that handle different problems unique to their position. When you subtract all the problems the help is taking care of, there’s still a good amount of crap your average UHNW has to worry about. In my observation, it’s like the exact same amount of shit you and I worry about on the daily. 

While some of that shit they worry about is the same as us, some of their problems only occur because of their net worth. Throwing money works on a lot of these, but not always. Which leads to another problem. When you run into a challenge, especially a persistent one that can’t be completely solved, it helps to get your head together with other people who have had the same issue. Maybe they can help, or at least lend a friendly ear and give some much needed empathy. But if you’re in the .01%, this means only .01% of the population can relate to some of your biggest problems. 

I see this, and it looks like it feels….lonely. You and me? Bet if we sat down at any bar in this country, we could find at least one person there that had similar shit we have going on now. Super rich guy? He’s got to fly across the country to meet up with a friend who understands. And good luck clearing both of their schedules on a whim. 

Getting to the point

What I’m telling you is this: I spend a decent chunk of time with super rich people, and their lives don’t seem any worse than ours. But they don’t seem any better. Why I’m telling you is this: I’m living in the same world you are. Despite my low intake of all forms of media, I’m bombarded by this cultural idea where increasing amounts of money leads to increasing happiness; that there must be this magical world which super rich and famous people inhabit where everything is fucking sparkly and perfect. 

Rationally we’ve all deduced that this is probably bullshit. Hence the persistence of platitudes like “money doesn’t buy happiness”, or what the wise Conan said about what is best in life. Like you, that’s what I thought, but I didn’t truly know. Therefore an annoying little sliver of me didn’t believe it. I gleaned this theory from what little media trickled through my filter, and other people’s lackluster reports on such a life. Then I started dancing in and out of the lives of the super rich. And I’ve come back to tell you all that shit was right. Money doesn’t solve all your problems. You can have astronomical amounts of money, and still struggle to find contentment. To become content, and occasionally happy, the super rich have to do the same amount of mushy self examination and work you and I do. Yes, they can pay for the very best to help them, but that path must still be walked alone, and the super rich have more distractions trying to pull them off it. 

This finally leads to my take away from all this. I am tempted to strive for some mega fat-FIRE level of wealth. I’ve been fortunate; through luck and perseverance, I was able to scratch my way to a point in life where I don’t need to work much (or at all, if I reverted to a little more frugality) to afford my lifestyle, and I’m still able to throw even more on the pile. I have wide swaths of time in which I could dedicate to getting more money; I could try my hand at real estate investing, I could upskill and get a higher paid job, shit-I could even go full time into EP and make more than my last job. But why? So I could have even more money? When I look at this temptation, I think it’s because of a subconscious belief that when I reach some ridiculous level of net worth I’ll finally be happy. 

I think I’m not the only one that does this. I also think that this pull never goes away. That’s why I’m reporting back from the land of the super rich, just to reiterate what you already know. Money doesn’t buy happiness. But there will always be the pull to get more because a part of you hopes it will. I love me some false dichotomies, so permit me to turn this into one:

Beyond covering a comfortable level of expenses, you can keep working to get more and more and you’ll still have the same amount of problems you currently have. Or you can instead work on yourself, and commit to the never ending cultivation of your contentment and happiness right now. 

I choose the latter. And I’ll keep trying to choose it, over and over. To focus on working on myself instead of my bank account. To try to be a better husband, father, and mountain biker instead of a better earner, investor, or saver. Like all posts, this one is primarily for me, to remind me to stay on this path.

Maybe my little report on the lifestyles of the rich and famous will help remind you too.