I usually equate it with passivity and conformity, but I guess it could also mean embracing chaos. There would be no need to 'go with the flow' if you're 100% sure of the outcome of a situation. For me, it's usually when I approach a situation blindly because there's some uncertainty as to the outcome. Ironically, as much mental calculation as I do it doesn't seem to jibe with reality quite enough and I end up inadvertently 'feeling things out' (opt instead for organic emotions and intuition) or thinking on my feet as opposed to tightly calculated actions. The results are varied. Some of the more positive moments could very well be blissful ignorance; I wouldn't know.

I'd venture to say that you already 'go with the flow' since none of us can achieve complete control without chaotic elements coming into play. And you've adjusted accordingly.

But what does it feel like specifically? Assuming our concepts of 'going with the flow' are the same, I can only speak for myself: it's as anxiety-inducing as it is contentment-inducing because I view it as pure feeling. That will mostly lead to irrational decisions if you're not adept at reading your intuition. Many people who had children just went with the flow, after all. It net them the outcome of unnecessary, added responsibility.