We see every day how nobody can escape the society we live in, and even the top of the top aren't happy. Money makes your problems extreme without trying. A clear example of this is in Austerlitz (Season 1 Episode 7), how Kendall can keep on going and going with no limit because he will never run out of money for drugs. Personally, if I had more money right now I would spend it on drugs too. I spent $50 yesterday to get myself a weed pen when I could've saved that money and had $75 in my bank account instead of $25. Money stopped me, not myself. Kendall's wealth means he can order coke like Uber Eats and not even care how much it costs. Of course he's going to get into harder and harder shit because it's accessible to him, and he wants to escape. 

Kendall's life falls apart completely after the end of season 1. It does, but the world was built to support Kendall and doesn't let his life fall apart. He would've killed himself in Safe Room (Season 2 Episode 4) if he could've, but he physically can't. He's in a glass prison. His father enables his drug addiction too so it makes life bearable for a time. Logan and the world he created technically gives him a lot, but it traps him in an ever going cycle of abuse with very little freedom. ​

Money makes you lose yourself. Even Logan, who thinks of himself as the largest pile of economic units, isn't capable of seeing who he really is. Maybe I shouldn't say even, because it makes sense that the most rich are the most lost-- ones that are slightly lower in the pyramid maintain scraps of identity, the ones they had before joining Waystar. Tom has always been stressed and subservient (maybe once it was kindness and compassion) and Greg has been an awkward creature his whole life. We see glimmers of identity in Kendall with his love of performing arts. I think these are moments where we get to see Kendall before he became Kendall Logan Roy-- creative, idealistic, and a little bit fulfilled. But because of the society his father created, the pressures of white supremacy, capitalism, and sexism were imposed upon him. As a child you have very little control in your life. If you're taught to not question that control you never will, until that control has proven to you that it is illegitimate or wrong. And maybe you don't want it to be shaken because you don't know who you are without that outside control.

Kendall said he'd be broken when his father died, and we see that brokenness in Season 4. Watching his form of broken is like psychosis for the viewer because he becomes a totally different person. Kendall is gone, and he becomes KLR for a minute who replicates Logan's abuse and yells at his kids and leans hard into misogyny. This is a problem caused by money too, not just grief. 

Everything is a relationship but you can't solely define yourself in relation to other people. If you're only existing and acknowledging yourself as ______ of, you're not defining yourself in a healthy or true way. In All the Bells Say, we see that Roman's motivation for being a horrible person is because he's not letting Kendall be the worst person in the room. He's horrible on purpose because yes, it can be funny to be horrible. It can also be something for others to base themselves around. As long as Roman's around, other people know they're not the worst in the room anymore. But in the real world, you can't do that shit. You exist independent from your relationships. You need to define yourself as your own person, then you can identify yourself as a person who wants xyz relationships. Roman basing his whole life around being the punching bag is realistically tragic though, so maybe I shouldn't say "the real world". In the best world, you don't do this shit.​