Most people are good at one or the other. Some of us are good at planning our interactions. These "planners" set up everything just right, but often do not get out of their head so they can let go (of control) and surrender to the experience. Life is not very fulfilling or fun for planners.
Others of us are good at letting go and flowing with experiences, but do so without much forethought. These "free spirits" often surrender to experiences that are not conducive to what they are after and impulsively act without considering the effects of their actions. Free spirits often do not create the life they really want.
Why not do both? We could point our boat in the right direction and then let go. We could briefly consider if the experience in front of us is good place for us to be, what our parameters and intentions are, and what the possibilities and likely effects are. Then we could make our choice and surrender to the experience. We trust ourselves and our "survivability" enough to let go and surrender to the unknown. We might even lose ourselves in the experience (that could be fun). If the experience starts to go south, we could step back, repoint our boat, and then jump back into the experience again- or leave. We have the rest of our lives to analyze it, but just that moment to experience it.
So how does that float your boat?