Tactical, strategic, or existential problem
You have a tactical problem when you don't know how to do something.
You have a strategic problem when you don't know what general approach to take to achieve something.
You have an existential problem when you don't know why you want to do something at all.
If you're thinking about going 1099, a tactical problem may be not knowing how to calculate what your 1099 rate should be or how exactly to phrase an e-mail to a program manager.
A strategic problem would be choosing how you're going to get your first 1099 gig. Are you going to be a technical hot shot and then convert your job? Are you going to leverage a previous client relationship to land a gig?
An existential probem would be not knowing why you should go 1099 in the first place. Is it for the money and flexibility? Are you just bored and want to shake things up?
It's important to know what type of problem you have so you can address it effectively, and they're easy to confuse.
You may think you have a tactical problem like not knowing how to write an e-mail, but what you really have is a strategic problem because you don't know who to write it to and how to do it systematically.
You may confuse a strategic problem with an existential one. You may be deciding between networking your way to a 1099 gig or "applying" for one, but you haven't reflected on the real reason why you want to go 1099 at all. If it's just money and flexibility, maybe you can get a new W2 job. If you're bored, maybe a new side project or hobby is what you need.
If you're stuck, think about what level of problem you're really dealing with. This will open up more solutions and help you get unstuck.