Entitlement is Bad
Jessie was a friend in my circle of friends who was in the middle of a contested divorce. At one point Jessie and I were very close. Then we weren’t. Even after we stopped hanging out I was able to maintain a window into Jesse’s life because she often overshared on social media. I was surprised at the divorce, mostly because Jesse had spent so many years in a dysfunctional relationship that I thought it reached an equilibrium. Therefore I didn’t think she would ever get divorced. Then she did. As I watched social media my feelings about the divorce crossed a range of emotions. I went from disinterest, to being entertained to settling on disgust at the whole affair. There were other feelings in the milieu. Knowing the couple, I felt the divorce shouldn’t have been contested. Maybe a little bit of arguing, but for the most part it should have been easy to figure out their separation. Unfortunately, Jesse made that impossible and I believe all the problems stemmed from one word: entitlement.
First a little bit about Jessie. She always thinks she’s the smartest person in the room. She’s an elementary school teacher by trade and more importantly, has a masters degree, albeit one from thirty years ago, but still it’s a masters. This plays into her entitlement but I’ll get to that in a bit.
On the topic of divorce, Jessie shared that she was spending tens of thousands of dollars on lawyers. I found that interesting. Jessie’s kids were grown and out of the house. If there were no kids, the only thing to argue about was money. Knowing Jessie and her husband, I knew they had clear delineations of their stuff. It wasn’t just things, it was the money too. They kept separate accounts. Also, neither had a great deal of cash or non-retirement assets. That meant all the divorce arguing had to be mostly about retirement. Jerry, Jessie’s husband, was the primary breadwinner and consequently all the retirement was in his name. Jessie, although she had a masters degree, mostly worked break-even side hustles the entire twenty years they were married. Jessie always said it was because it took long hours and hard work to raise great kids and she needed the flexibility of the side hustles.
All I could think to myself was “why the hell are you trying to steal his retirement?” Yes, I know. I’ll get many women arguing that they were a team, and a couple, and Jessie was doing her part and she was owed that money. I call BS on that. Remember Jessie was always the smartest person in the room. Smart people know that many relationships don’t make it. Smart people understand that in our world the closest thing we have to retirement comes from working a job that has a 401k program as a benefit. Smart people make a plan for when they have kids and for when they are empty nesters. Smart people know how to raise great kids and manage a career at the same time. I know hundreds of women who have done this.
Jessie could have done all of this easily. Her credential was in education and before she had a child, she was a teacher. After she gave birth she could have gone back to teaching and spent the years building a fantastic retirement and career. When I say fantastic, she could have had a state pension, healthcare for life, and a 401K! Unfortunately, she didn’t do this. Why? Because Jessie felt entitled to not have to get more education after earning her masters. The local school system wanted more classes to meet their own credentialing requirements. She balked at that request and talked Jerry into letting her be a stay at home mother who only went back to what was essentially a working hobby when her child reached school age. This is why my gut reaction was: If you had your own retirement then you wouldn’t feel entitled to another person’s retirement.
This was far from the first time I saw an entitlement out of Jessie. There were many examples over the years. She felt entitled to not care for the house when Jerry wasn’t available. Not only would she not do the easy job, she literally wouldn’t even call a company to come service what needed to be done.
She maintained her entitlement to not have to work at any job she didn’t want to even after her children left the nest and she closed her working hobby business. Doing what she needed to earn a livable wage or her own retirement and healthcare benefits was never on her radar. She filled her time with things like brand representatives at retail establishments and as a local model. These are very part time gigs that pay daily rates on the rare days each month when you get a call. Then when she split with Jerry and had to get a real job, she expressed intense frustration at ‘the system’ that didn’t recognize ‘her awesome skills’. She felt entitled to a job that paid a livable wage and benefits even though she hadn’t proven to the work world that she had skills. That’s something you have to prove by working from the ground up in virtually any industry.
Ultimately, it was also her sense of entitlement that destroyed our relationship. She felt entitled to demand things of me that I felt were very much inappropriate for a friend to request. It crossed a boundary and the relationship ended.
Jessie isn’t the only individual I was close to who had issues with entitlement that, from my perspective, destroyed their ability to lead a foundationally happy life. I had a neighbor named Carlo growing up, a neighbor that I’m still casually friends with today. Both being from big Italian families who were close, we had a great deal in common. Like most Italian families, Carlo was named after his father, grandfather, and many other family patriarchs up the line. I think he once told me it went back a dozen or more generations. Carlo was always entitled, even back then. I remember his father, Carlo Sr. lecturing him whenever the entitlement issue came up. His dad would say “The world doesn’t revolve around you” every time Carlo assumed he should be included in something or be given something he wanted. This happened very often. I don’t absolutely know if it was nature or nurture, but from my experience Carlo’s attitude came from everyone in the family except his Dad. Even if Carlo’s issues were innate, the family definitely made them worse. The problem was everyone else in Carlo’s big Italian family worshiped at Carlo’s feet. He was the first of his very large generation and he was the namesake in the long line of Carlos. Grandparents, uncles, aunts, and really everyone doted on him from the moment he was born. They promised him the world, and sadly, through their oft stated comments about what he will achieve, helped him create a level of unrealistic expectations for himself.
Carlo wanted to be a business owner. I watched over the years as Carlo struggled in the business world in the early part of his career. He exhibited the worst possible traits for an unproven entrepreneur. Arrogance, narcissism, and utter antipathy at virtually everyone he worked with and with virtually every customer he had. He was, and is, a racist and a misogynist. As you would expect his early business endeavors were very rocky. Later, he learned to hide his attitudes and be much more savvy about his business interactions. His various concerns started to grow. It wasn’t an innate or learned skill that got him there, at least not by themselves. Carlo’s ego and his ability to manipulate people in addition to some learned skills got him to the top of his local town’s economy. Carlo never stayed focused for long with any of his individual businesses, he didn’t have the skills to build the relationships needed for a long-term ongoing structure. For those relationships to exist over time Carlo had to have respect for others, something lacking in his world view. He’d start them, profit take, and then either sell or close when a negative reputation started to grow based upon the culture of the business. A culture that came directly from Carlo.
As a child, and as an entrepreneur, Carlo always exhibited rage at not getting what he felt entitled to. The worst I’ve ever seen happened later in life when Carlo’s business partners passed away. The partner had divorced and had remarried. Consequently, the partner left everything to his second wife. Unlike the first wife, the second wife had some very strong ideas on how the business should be run and started to assert her will through an army of lawyers as she lived across the country. Carlo, who saw women as nothing more than machines for baby making and for pleasuring men was enraged. Even though Carlo had had a falling out with his partner years before, the original conversation was that Carlo would always maintain full control of the business. The first wife was onboard with this arrangement. That entitlement built up into a rage that lasted for decades. The vitriol that came out of Carlo’s mouth towards the unexpected and unwanted active business partner and anyone related to her was truly terrifying. I was always afraid that if they ever met each other in person Carlo would see red, pull out a gun and shoot her.
As you would expect, there is much more to say about Carlo in the nearly four decades I’ve known him. The key takeaway is that the entitlement had a tremendously negative impact on every facet of his life. Yes, it drove his ability to build the businesses and money that came with them. Unfortunately the instability in how he was able to run them had huge impacts on his personal health. Ultimately, entitlement, and the resulting rage when reality didn’t allow his sense of entitlement to be fulfilled, affected his ability to have a traditional relationship with his family members. In the end, by holding on to his entitlement, it destroyed Carlo’s peace of mind.
In both of these examples, and really many others, I’ve seen the concept of entitlement destroy careers. relationships, and ultimately take good lives and turn them to utter shit. Entitlement does that, because if you feel entitled to something that you don’t get, anger and rage soon follow. Anger and rage almost never result in positive outcomes. Note that I’m not talking about government entitlement programs. Yes, we see very strong emotions around government welfare, but I would argue we tend not to see the level of rage and hatred that happens when it’s personal. What I’m talking about in this article is much more personal. It’s entitlement built upon societal norms and relationships. It’s the sense of entitlement that has a teenage boy stab his girlfriend sixteen times because she broke up with him. Sadly something that recently happened in the next town over.
Unfortunately entitlement is to a greater or lesser extent a part of all of us. Sadly, we don’t age out of it. I personally witnessed the siblings in my parent’s generation experience an irreconcilable schism, in part because of an entitlement mentality. They were all older and mostly emotionally mature individuals. You would think they would have known not to be unreasonable with their expectations about each other’s behavior. I know even I feel it occasionally.
The best way I’ve found to fight this is to simply remind yourself that you are not entitled to anything in life. No matter what your boss promised you, the world of business is finicky and often you never get close to what was promised in the interview. No matter what you believe to be right and true in a relationship, unless it’s against the law, people can do whatever they want. And of course, no matter what your parents or grandparents promised you will be passed down, unless it’s written in the will, it’s not rightfully yours and never was. This is a very very tough pill to swallow which is why it has such a caustic effect on people.
One last bit of advice. If you have a Jessie or a Carlo in your life, then my suggestion is to aggressively drive some healthy distance. Yes, sometimes you’ll miss a relationship, especially one that’s lasted years. Still, I can tell you that nobody benefits with that kind of influence from their friends, and your life will simply be better without it. Just be prepared, you’ll get some pushback and maybe even some anger for not hanging out anymore. Remember, these types of friends and family members will never understand your decision because they will always feel they can demand as much of your time and focus as they want. After all, in their mind they are entitled to it.
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