Fierce individuality comes with the heavy price of being the sole person responsible for your being. The benefit is full freedom over yourself and your decisions.
Tribalism, on the other hand, has the opposite problem. You follow the decisions of the tribe and thus none of the decision making pressure falls on you. It might be true that this approach leads to worse outcomes, but we feel more content with them.
We know it’s true that people are happier when they have three menu items to choose from rather than twenty three. When there are so many options, it’s easy to walk away with regret. You fear you said no to a better option. As part of a tribe, or a clique, or whatever you want to call it, you only have one decision: follow the tribe or leave. Since you’re there in the first place, that decision is usually made for you, so you follow the tribe.
The more individual you become, the more options you have and the more choices you have. Reenter the problem with feeling like you’ve missed out on a better option. Since you have no tribe to follow, your menu of choices is large and thus regret comes naturally since you could have followed many different paths.
To wrap up, the tribal route and the individual route both have their positives. One comes with freedom and the other comes with contentment and belonging. Luckily, our lives are lived somewhere in between those two extremes. Finding the right place on that sliding scale is the real challenge.