Life is movement, as we know. But in what direction is it moving? And here, perhaps, you should think about where you are moving.
Why is "going with the flow", which is the same movement, considered a weakness? Has someone special and authoritative given me a vector and unquestionable argumentation? If in your life a series of events is formed in such a way that does not change your mood and attitude to life, is it necessary to change something? Why turn down a path that makes you feel happy? Ah, yes... Some may answer: to make it even better. But there is a saying: better is the enemy of good.
Moving against the current is a difficult and sometimes long work, which does not always lead to the desired result. At the same time, the significance of the achieved result can be artificially inflated... well, how could it be, you had to work hard, while "going against the stream" without putting in any effort gets a similar result to the first one. And where is justice? ))))
The justice of choosing this or that movement lies in sincerity and honesty before oneself. But none of the choices is the source and end in itself for achieving happiness. If you have less, you can be happy, while if you have a lot, every morning you wake up with resentment towards life.
Getting out of your comfort zone is first and foremost personal growth! This path "against the current" is akin to the formation of new neural connections when exploring/learning new things. It is a path worth taking for a while to gain not only experience, but also a "spare part" that can be used further in the work of building your happy future.