I once knew a guy; we’ll call him Jimmy.
Jimmy always had various business ventures going. On any given day, if you asked him what he was doing, he’d rattle off the name of some firm he was consulting with, or he’d describe a promising medical app he was looking for angel investors to fund, or he’d talk about some charity event he was supposed to be the keynote speaker for, or how he had an idea for a more efficient type of gas pump that was going to make him billions. The guy was always rolling, always on, and if you gave him an inch of conversational daylight, he’d pulverize you about how world-spinning his work was, how brilliant his latest ideas were, and he’d name-drop so much it felt like you were talking to a tabloid reporter.
Jimmy was all positivity all the time. Always pushing himself, always working an angle—a real go-getter, whatever the fuck that means.
The catch was that Jimmy was also a total deadbeat—all talk and no walk. Stoned a majority of the time, and spending as much money in bars and fine restaurants as he did on his “business ideas,” Jimmy was a professional leech, living off his family’s hard-won money by spinning them as well as everybody else in the city on false ideas of future tech glory. Sure, sometimes he’d put in some token effort, or pick up the phone and cold-call some bigwig and name-drop until he ran out of names, but nothing ever actually happened. None of these “ventures” ever blossomed into anything.
Yet the guy kept this up for years, living off girlfriends and more and more distant relatives well into his late twenties. And the most screwed-up part was that Jimmy felt good about it. He had a delusional level of self-confidence. People who laughed at him or hung up on him were, in his mind, “missing the opportunity of their lives.” People who called him out on his bogus business ideas were “too ignorant and inexperienced” to understand his genius. People who pointed out his deadbeat lifestyle were “jealous”; they were “haters” who envied his success.
Jimmy did make some money, although it was usually through the sketchiest of means, like selling another person’s business idea as his own, or finagling a loan from someone, or worse, talking someone into giving him equity in their start-up. He actually occasionally talked people into paying him to do some public speaking. (About what, I can’t even imagine.)
The worst part was that Jimmy believed his own bullshit. His delusion was so bulletproof, it was honestly hard to get mad at him, it was actually kind of amazing.
Sometime in the 1960s, developing “high self-esteem”—having positive thoughts and feelings about oneself—became all the rage in psychology. Research found that people who thought highly about themselves generally performed better and caused fewer problems. Many researchers and policymakers at the time came to believe that raising a population’s self-esteem could lead to some tangible social benefits: lower crime, better academic records, greater employment, lower budget deficits. As a result, beginning in the next decade, the 1970s, self-esteem practices began to be taught to parents, emphasized by therapists, politicians, and teachers, and instituted into educational policy. Grade inflation, for example, was implemented to make low-achieving kids feel better about their lack of achievement. Participation awards and bogus trophies were invented for any number of mundane and expected activities. Kids were given inane homework assignments, like writing down all the reasons why they thought they were special, or the five things they liked most about themselves. Pastors and ministers told their congregations that they were each uniquely special in God’s eyes, and were destined to excel and not be average. Business and motivational seminars cropped up chanting the same paradoxical mantra: every single one of us can be exceptional and massively successful.
But it’s a generation later and the data is in: we’re not all exceptional. It turns out that merely feeling good about yourself doesn’t really mean anything unless you have a good reason to feel good about yourself. It turns out that adversity and failure are actually useful and even necessary for developing strong-minded and successful adults. It turns out that teaching people to believe they’re exceptional and to feel good about themselves no matter what doesn’t lead to a population full of Bill Gateses and Martin Luther Kings. It leads to a population full of Jimmys.
Jimmy, the delusional start-up founder. Jimmy, who smoked pot every day and had no real marketable skills other than talking himself up and believing it. Jimmy, the type of guy who yelled at his business partner for being “immature,” and then maxed out the company credit card at Le Bernardin trying to impress some Russian model. Jimmy, who was quickly running out of aunts and uncles who could loan him more money.
Yes, that confident, high-self-esteem Jimmy. The Jimmy who spent so much time talking about how good he was that he forgot to, you know, actually do something.
The problem with the self-esteem movement is that it measured self-esteem by how positively people felt about themselves. But a true and accurate measurement of one’s self-worth is how people feel about the negative aspects of themselves. If a person like Jimmy feels absolutely fucking great 99.9 percent of the time, despite his life falling apart around him, then how can that be a valid metric for a successful and happy life?
Jimmy is entitled. That is, he feels as though he deserves good things without actually earning them. He believes he should be able to be rich without actually working for it. He believes he should be liked and well-connected without actually helping anyone. He believes he should have an amazing lifestyle without actually sacrificing anything.
People like Jimmy become so fixated on feeling good about themselves that they manage to delude themselves into believing that they are accomplishing great things even when they’re not. They believe they’re the brilliant presenter on stage when actually they’re making a fool of themselves. They believe they’re the successful start-up founder when, in fact, they’ve never had a successful venture. They call themselves life coaches and charge money to help others, even though they’re only twenty-five years old and haven’t actually accomplished anything substantial in their lives.
Entitled people exude a delusional degree of self-confidence. This confidence can be alluring to others, at least for a little while. In some instances, the entitled person’s delusional level of confidence can become contagious and help the people around the entitled person feel more confident in themselves too. Despite all of Jimmy’s shenanigans, I have to admit that it was fun hanging out with him sometimes. You felt indestructible around him.
But the problem with entitlement is that it makes people need to feel good about themselves all the time, even at the expense of those around them. And because entitled people always need to feel good about themselves, they end up spending most of their time thinking about themselves. After all, it takes a lot of energy and work to convince yourself that your shit doesn’t stink, especially when you’ve actually been living in a toilet.
Once people have developed the thought pattern to constantly construe what happens around them as self-aggrandizing, it’s extremely hard to break them out of it. Any attempt to reason with them is seen as simply another “threat” to their superiority by another person who “can’t handle” how smart/talented/good-looking/successful they are.
Entitlement closes in upon itself in a kind of narcissistic bubble, distorting anything and everything in such a way as to reinforce itself. People who feel entitled view every occurrence in their life as either an affirmation of, or a threat to, their own greatness. If something good happens to them, it’s because of some amazing feat they accomplished. If something bad happens to them, it’s because somebody is jealous and trying to bring them down a notch. Entitlement is impervious. People who are entitled delude themselves into whatever feeds their sense of superiority. They keep their mental facade standing at all costs, even if it sometimes requires being physically or emotionally abusive to those around them.
But entitlement is a failed strategy. It’s just another high. It’s not happiness.
The true measurement of self-worth is not how a person feels about her positive experiences, but rather how she feels about her negative experiences. A person like Jimmy hides from his problems by making up imagined successes for himself at every turn. And because he can’t face his problems, no matter how good he feels about himself, he is weak.
A person who actually has a high self-worth is able to look at the negative parts of his character frankly—“Yes, sometimes I’m irresponsible with money,” “Yes, sometimes I exaggerate my own successes,” “Yes, I rely too much on others to support me and should be more self-reliant”—and then acts to improve upon them. But entitled people, because they are incapable of acknowledging their own problems openly and honestly, are incapable of improving their lives in any lasting or meaningful way. They are left chasing high after high and accumulate greater and greater levels of denial.
But eventually reality must hit, and the underlying problems will once again make themselves clear. It’s just a question of when, and how painful it will be.