The ability to dentify the challenges is an important skill for the career musician. In order to this, you'll need to use your imagination. First, I'd like to invite you to accept everything as possible. anything otherwise would just be making excuses.
a fork in the road
Imagine a single path before you. The road ahead branches and each one of those branches represents your decisions. Imagine at the end of these paths, your goals. It's not about wandering aimlessly down a path that's already laid out for you. Nope, we're making our own path, our own way. So what's it gonna take to blaze a trail, a road, a highway. what does the landscape look like? are we going to need bridges and tunnels?
So in anticipation of challenges as a part of goal-setting. I'd recommend putting pen to paper. list everything you've got, from things you're already doing, to ideas that might seem like a pipe dream, unreachable, impossible.
As you begin to understand more about what your options are, you can start to understand what's attainable, and what it might take to make it happen. This Link, gives an animated breakdown that goes into more detail.
Basically, this part is going back through what you thought about during this mental excersise. say x ammount of time later and asking questions like: