This question is about as nebulous as "what should I do with my life?"

There is value in conforming, and there is value in not conforming. Both of these are really contextual. Often your choices will be between two competing parties offering different criticism. Often these parties will be influenced by their own prejudices and biases. Unless you have significant resources, your choice will likely depend entirely on material consequences, rather than any belief you hold or ideal you seek.

When someone says this, it's often code for "care less about what they think, and care more about what I think". I'm definitely guilty of that.

in response to kb's churchill quote:

"You have enemies? Good. That means you've stood up for something, sometime in your life." - Winston Churchill

There is not really any value in conflict alone. It matters what the conflict is for. I had enemies the moment I was born. I have enemies that hate me, really hate me, for involuntary elements of my existence. I have enemies that hate me for survival decisions made in situations they deliberately forced upon me.

I don't use the word "enemy" lightly. They would kill me if they could, and I them.

Do I get credit for being naturally despicable in their eyes? No. Do they get credit for irrational malevolence? Certainly the opposite.

The quote has been used by literal nazis to justify their bullshit. Churchill was an imperialist that deserved to die anyway.