12/01/2025
Disclaimer: Not a Swiftie. Have not heard any songs from the last several albums, even in passing. Just an observer.
I’ve referenced this before, and I find myself thinking about it again. Taylor Swift is indeed a billionaire, but like, the billionaire that other billionaires don’t really like. There’s a lot of love for other billionaires, like their wealth is seen as a strength instead of a source of disconnection and misunderstanding. Taylor Swift doesn’t get the plight of the common man, but billionaires like Elon Musk, Donald Trump, or Peter Theil do. In general, the people who used this meme and hold these sentiments toward Taylor seem to have no problem with Trump and the majority of his administration being billionaires (or if not billionaires, far wealthier than most of us can comprehend).
It makes me wonder, why is that? Why does Taylor’s wealth make her unrelatable, but for others, particularly Trump and his ilk, it seems to give them an almost savior-like complex? It’s like they represent the best of us, and their wealth gives them a sense of status and deference to their greatness. When they speak, we need to listen. Not so with Taylor.
Consider the overarching value within our society, the one we hold above all else, in practice despite what we may say, is the belief that the creation of wealth is the source of all good and the singular means to solving all of society’s problems. The way to make the ideal society is to make it as wealthy as possible. From this perspective, it is like life is playing football, and most of us are playing around the middle school level. Some of us get to the high school, college, and pro level, fewer and fewer with each level. Billionaires then are the elite among the pros, the ones on everyone’s fantasy team every year, a class all their own even among the professionals. Billionaires have a level of wealth incomprehensible even among the wealthy. From this perspective, with the underlying value as the driving force, the adulation of billionaires makes sense.
While certainly not true for every single billionaire, I think it is fair to say that for many billionaires, the continuous generation of wealth is their coping skill. Workaholism is the drug of choice, where most time and energy is poured in a vain hope to feel good enough, as the default feeling is less than, or not good enough. With enough wealth, eventually there will come validation. We all know someone like this, so it's not an uncommon phenomenon, but it's a bit more pronounced with billionaires because, like their money, it's so much more. We all know someone who will work 80 hours a week to hit a high 6 or possibly 7 figures, but with many billionaires, you'll see the same behaviors but working with much bigger numbers, usually focused on investment instead of the direct exchange of labor for money. The underlying belief is the same either way: when the person has “enough” money, or power, or influence, everything will be okay. The emotional injuries being nursed through overworking cannot be helped in that way, so it never actually is or will be enough. Trapped in a continuous loop they go.
By contrast, Taylor Swift has built her wealth by doing what she loves. I'm sure she works hard and there are probably times when it is a grind, but she loves what she's doing and derives joy from it, independent of the wealth it brings. It's not limited to simply liking what she does to earn a living more than most other billionaires. She has achieved the “love what you do and you'll never work a day in your life” status, and has been very financially successful at it. Contrast this with most other billionaires, at least the ones idolized by people who tend to not like Taylor Swift, and most of them are pretty miserable in their desperate but vain attempts to ease their internal suffering through work and wealth.
For them, wealth generation is a coping skill. It does not bring joy, it temporarily eases pain, and poorly so. It’s not as scary as actually looking at and addressing the source of their pain and suffering, so they continue it day after day, chasing that next moment of less pain, of getting their head above water for a moment to take a breath. It is no wonder they would look upon someone else experiencing joy from their work with envy. As they are unable to take accountability for addressing the source of their suffering, instead opting to manage with constant temporary fixes, that envy devolves into contempt.
So too is it with the people who idolize them. Connecting on a subconscious level not by wealth (indeed, most people are much closer to a homeless person in terms of their net worth than a billionaire), but by the never ending cycle of inner pain and suffering temporarily soothed by something that fails to address the source of the suffering. The fear of going to the root of the pain is too overpowering, and so continues another trapped, endless loop. While not working to generate obscene wealth, the temporary fixes of the non-wealthy who idolize the wealthy that envy someone like Taylor Swift are still focused on the idea of doing “enough” to become “enough” - to prove one’s worth and place in society. The wealthy and the non-wealthy, connected of sorts through unresolved pain of which neither is consciously aware, united in disdain of someone who has what they strive for but, because of fear, never manage to achieve.
