Don't force it
I started a project and blog called The Ancient Wisdom Project when I was still working as a W2 employee. I would choose an ancient wisdom tradition and take one practice from the tradition and implement it for 30 days with the hopes of cultivating a particular virtue.
During that time I actually made the transition to becoming a 1099. It was during my Taoism month and I wrote a blog post about it.
I Quit My Job and Started My Own Business, Taoist Style
My main point in the post is that sometimes you shouldn't force things to happen. Going 1099 in the government consulting space was a far easier path to starting a business than my previous attempts.
"But I also think there is room for a Taoist approach, one in which you make entrepreneurial moves based on concrete opportunities that present themselves to you. Perhaps we should call this the “passive opportunism” approach to entrepreneurship. We don’t to try brazenly force success to happen, but rather, take small actions and keep our eyes open to favorable situations."
I still think "don't force it" is a good outlook to have. However, I now think you can be a bit more deliberate about going down the solo 1099 path which I why I wrote the book.
But, if it feels like you're beating your head against a wall with your 1099 efforts, take a step back and do nothing for a bit. Pay attention to your current circumstances and see what opportunities lay in front of you.
Then, when it's time to act, act.
Want the full playbook? Check out Going 1099.