And why are we still trying to solve this riddle?

‘Cause this is indeed a riddle…

Remember those metaphorical stories whose heroes end up having to find the answer to one in order to save themselves/the day?
Like Sophocles’ “What walks on four feet in the morning, two in the afternoon and three at night?”

A riddle, of course, being a question which cannot be answered until the individuals attempting to solve it stick their heads out of the box into which the riddle had been framed.

So. Individualism? Collectivism?

Having grown up under communist rule – supposedly the most collectivist social arrangement to date, I can testify that there is no such thing as collectivism without individualism nor individualism without collectivism.

Libertarians’ mantra is that socialism/communism – and even liberalism, as Americans understand it, is a form of collectivism. And, of course, that collectivism is bad for you.
Socialists, on the other hand, maintain that the current situation – which is seen as being bad, is the consequence of the growingly extreme individualism which plagues modern societies.

Interestingly enough, both sides are simultaneously right.
Communism is indeed bad for you and the bad aspects of today’s society are a consequence of callous selfishness.

On the other hand, all communist societies are composed of a huge mass of obedient subjects AND a small number of individual, and very individualistic, leaders.
Similarly, all developed capitalist societies – including those sporting huge discrepancies between the shrinking number of haves and the growing number of utterly destitutes, have reached the current level of sophistication because most of their members continue to share the belief that ‘all men have been created equal and that all of them have certain, nonnegotiable, rights: Life, Liberty and the Pursuit of Happiness’.

“Share the belief…”
But wasn’t this the very definition of collectivism?
A social arrangement where the most important possession belongs to THE public?
Was there anything more consequential for what is currently known as the ‘Euro-Atlantic’ civilization than this shared belief? Other peoples have been in possession of way more abundant natural resources. Had reached ‘astronomical’ levels of civilization way before we were even able to wipe our noses… And yet…

Haven’t we, individual thinkers, figured out yet that unless we agree on ‘the basics’, we’ll be easy prey for the callous ‘snake oil merchantmen’ who have no qualms to use collectivist slogans to pitch some of us against the others?

Haven’t we figured out, yet, that there is no ‘political collectivism’ without fear? All collectivist social arrangements, both socialist and fascist/nazist, have been built using fear/contempt (of the other) to cement ‘the people’ into believing the lies proffered by false prophets. Lenin, Mussolini, Stalin, Hitler, Mao… Lies proffered by callously individualistic political agents… bent on satisfying their own domineering instincts and making ‘good use’ of pre-existing conditions.

Haven’t we figured out yet that individualism, the tame version developed along with the good aspects of the Western Civilization, is, by nature, the very beneficial consequence of the mutual respect which (still) exists among the members of our societies?

So, to answer the riddle, we need to understand that there is no real conflict between bona fide individualism and bona fide collectivism.
Just as there is no conflict between two perpendicular lines.

Since, by trade, I’m a mechanical engineer, I’ll use a very practical metaphor to illustrate this idea.
Consider a pressurized Oxygen tank. The more pressure inside, the more Oxygen you can store in it. The more useful the tank. Only if you ramp up the pressure too much, you end up with an explosion.
In this situation, you might consider ‘pressure’ to be in conflict with the ‘walls of the tank’, right?
Wrong. The conflict is only in your mind. Pressure is simply perpendicular to those walls. The more pressure those walls can withstand, the more useful that tank is for you.

But it’s your responsibility to determine the thickness and resilience of those walls. It’s your responsibility to choose how much to ramp up the pressure.
For the very simple reason that that tank is yours.
It is you who will suffer the consequences.