It's supposed to be (a little) hard
If someone walked up to you on the street and offered you $50,000, you'd think the person was crazy and move on with your day.
That's because the $50,000 came too easy. No one just gives you $50,000 without a catch.
Similarly, you wouln't trust anyone that told you "oh you can make $50,000 more/year if you go 1099 and you can do that tomorrow."
It doesn't work like that.
But when it gets hard it's tempting to throw up our hands and say, "Why is so hard for me?! It should be easier..."
I was feeling that the other day when another remote opportunity fell through. I thought "why can't someone just give me a flexible, remote gig where I work for myself and that pays $250,000 per year?"
Of course it should be hard! Those opportunities don't just fall into your lap.
Going 1099 is like that. But it's not hard because of it's intensity. It's hard because it requires some persistence in the face of ambiguity.
If you're feeling a bit frustrated by the whole process, just understand that it's normal and that it should feel that way.