TLDR;

A little bit of backstory

Lately I've been reading a lot about the problem with being too much of nice guy.

According to philosophical YouTubers and self help gurus out there, nice guys often finish last because they are actively putting others need in front of theirs, leaving them unable to muster any courage to be honest with others, much less confront them.

Having been a nice guy all my life, it should come as no surprise that I've been treated quite badly during school, and I was still a shy guy well into college. At work I came across as being a submissive, sheepish person who doesn't really want to ruffle any feathers.

Having raised in a morally strict Asian family, I never was taught about the value of standing for yourself, or to confront others. As our culture value politeness, obedience and honor above our emotional and spiritual needs, that leads me to believe subconsciously that confronting others is inherently a risky behavior, which will potentially humiliate me further and put myself in an even tougher spot.

The problem only got worse when my family sheltered me from having normal human experiences ( like going on roadtrips with friends, solo traveling to favorite destinations ).

The obsession of honoring your left me unable to speak the language properly, leading to more isolation and emotional suffering.

Therefore the fear of conflict is a problem that runs deep in my identity. And it takes copious amounts of deep thought to gain insights behind my behavior.

What Machiavellianism actually means

After studying the psychology behind tyrants, oligarchs and my former work bullies, I came to discover that they all share one common personality - Machiavellian.

The name "Machiavellian" comes from an Italian Renaissance diplomat called Niccolò Machiavelli, best known for his political philosophy from his tome - The Prince.

Politics, for him, was and has always been meddled with crime, treachery and deception. Therefore, morality is incontrovertibly not a solution to desired outcomes. Effectiveness could be guaranteed if we were to ignore popular judgment and do whatever it takes to reach your personal goals.

His way of thinking would justify the rise of countries, kingdoms and corporations. These large entities would go anywhere close to formations, if the forefathers were listening to their hearts all the time and never protect themselves against the malevolence of the murky world they live in.

Thus, he is the father of "the ends justify the means" credo. We abhor chasing money and power, but our undesirable behavior such as greed, lust, hatred and jealously still lies intact inside of us.

Therefore, any people or group with money and power would resort to crappy measures (at least once) in order to maximize their gains. Without Machiavellianism, multinational companies wouldn't be nearly as filthy rich and some countries wouldn't nearly be as influential.

And it appears to me, that Machiavellianism is a desirable trait for a young man like me. If I were to be a bit more cunning, inconsiderate and charismatic, then I'd be able to muster enough courage to move out my parents' home, earn some street cred, become an authority in my niche, and go on dates with women I like.

Man, had it not been for my strict parents....I would've been that person.

Is there a better alternative to being a Machiavellian ?

As much as I hate being beaten in an argument, or being subservient to my fear of conflict, I most likely have to go through intense periods of self-questioning before I take these Machiavellian leaps of faith.

My family seemed to be the antithesis of Machiavellian ideals - they want to live a principled life full of virtue and morals. But their adherence to selflessness and wholesomeness is also what makes them moral assholes. By failing to educate me about how the world really works, and distort my worldview in ways that makes me feel inferior.

Their overcommitment to creating a loving family removes them from considering my own needs, and allowing their inflated sense of entitlement to take over our conversations. Because they always think they are always doing the right things for me, so I have no place in arguing with them.

It is that single reason that I lost a good chunk of respect for them.

But on the other hand, being too much of a Machiavellian lands you in the same position that I hate.

Because once you've amassed enough enemies and harvested enough karma, the only solution to protect yourself is to keep going down the rabbit hole of evil.

You can no longer trust anyone in this world, and after so much deceit, control and manipulation there you have little option but to continue doing so, because the world is growing more desperate to outwit you, so chances are turning back means turning yourself in.

The only possible way, which I will not like, is to play with the system. Yes, be an asshole once in a while, but it has to be in the service of the greater good.

Learn to keep boundaries when things don't go your way. Always be more rational with people no matter how emotional the situation gets. Screw up other people if they take advantage of your forgiveness.

In other words, don't be too nice, but don't try to become the next mafia ever. Try to change the situation to favor you, but never at the great expense of others.

Hurting people is fine, so long as it doesn't jeopardize your dignity and your relationships. While you can get enormous rewards from exploiting your friends, family and other people, sadly, dignity and deep relationships aren't something you can actually buy.

Sure...this strategy doesn't help you to dominate the market, nor that it will equip you with the means to challenge the mafiosos, but one good thing is that you won't finish last. Because you don't have to abandon your morality and conscience to achieve your short term goals.

Being a total asshole is rewarding, but not mentally fulfilling.