First of all my statement should be taken with a huge grain of salt. I make no claims towards any sort of universal observation about human nature, but rather a set of general principles that I believe to be worth examining.
- Breaking rules can help you grow as a person. Anecdotally, the people from my youth who ended up being the happiest adults were those who tested the boundaries early on and fit the "lovable rogue" archetype. This experimentation gave them leeway to understand themselves better and their mischievous but life-affirming behavior made them paradoxically more appreciated and valued by others than youths who never rocked the boat. The latter are left unsure that they will still be loved in case they stop conforming to expectations.[0]
- Many valued traits and rules in the modern world aren't that valuable. To echo Taleb's green lumber story [1], you can spend your time gaining accolades and achievements such as medals on a debating team or knowledge of trivia and then wonder why someone you secretly judge to be inferior to you is doing much better. The reality is that your judgment was based on peripheral metrics that instilled a false sense of superiority, even if those actions may have helped you a bit in some indirect way. What matters are the core traits that help you provide value to others and secure your position in the world. Unfortunately for rule followers, there is an inundation of not-so-useful rules and contests that cloud your judgment. For instance, some people end up in graduate school with no clear interest or purpose because it gives them the illusion that they are being productive and moving forward according to commonly accepted metrics. Or more commonly, you have people taking cold showers or waking up at 4:00 am because they learned that's what the 30 under 30 fellow they just read about does.
- As a corollary to this, to be a healthy adult you need to exercise critical thinking and reason from first principles pretty damn often. The most captivating people do seem to have an intuitive understanding of what is essential to a good life and what isn't. They are prepared to examine rules and make bold choices as to whether to follow them or not. Paradoxically, understanding of when you should in fact coöperate with the system allows them to do so more smoothly when the need arises.[2]
In the modern world, rules aren't always to the individual's interest. Some people go on a box-ticking spree like godzillabrennus' sibling and end up feeling empty handed. But the entities that draw up those boxes always had their own interests in mind, whether or not the boxes' design was the result of direct action or organic development. The rules can change themselves in an instant, or be completely irrelevant if some other factor changes. In our world, you end up with VCs and billionaires telling underpaid employees to stop moaning, internalize hustle porn and work themselves to death for rewards that will in all likelihood never come. Some of these folks end up spending their hard earned salary on Veblen goods [3] that are simultaneously too expensive to their freedom and too cheap to even give them the status they seek.
- Directly linked to that is the notion of ressentiment. [4] To some limited extent, our moral rules can be interpreted as a tool to comfort the weak. If you are too keen to follow the rules, you end up with a ton of ressentiment because you often find yourself trapped in peripheral pursuits. You neglect to fulfill important needs out of a stronger need to conform. You die having never really lived.
If you look at people like Trump, they are essentially modern-day Diogenes whether they realize it or not. Their behavior strips away the abstract and peripheral metrics (being classy, having a certain demeanor etc.), leaving only the raw power balance. This creates extreme anger and frustration because a person might look at such an individual and judge him to be inferior according to some ressentiment-based rules but then be unable to reconcile that impression with their obvious relative lack of power and importance.
Rule breakers are more aware of the power balance and what society actually rewards and generally tend to pursue that without fear. That doesn't mean they end up being sociopaths (although obviously you have your fair share of those), in fact it can lead them to being better people because they take on traits that others genuinely value. They let go of resentment because they lead a life-affirming existence, whereas many instinctive rule followers find themselves building up a degree of resentment that poisons their character over time. Rule breakers can help others more easily because they are themselves in a stronger psychological position and have more of their needs met.
[0] https://www.youtube.com/watch?v=5DTIzzf6ncg
[1] https://fs.blog/2016/11/green-lumber-fallacy/
[2] https://www.cs.virginia.edu/~robins/YouAndYourResearch.html
[3] https://en.wikipedia.org/wiki/Veblen_good
[4] https://en.wikipedia.org/wiki/Ressentiment