Dear TB,
I think not knowing is one indication that the path you're walking is your own because if you had followed someone else's footsteps, you would foreseen the (probable) outcome of the journey. Another thing is that how much personal satisfaction you're getting from the choices you have made is also important. Regardless of the outcome (success or failure), if you feel satisfied with the choices that you have made, then it is the right thing that you have done. It is a risky venture for sure but we all have to take such risks... Remember "His First Flight" by Liam O' Flaherty...