Don't forget the big picture (or why I might get a W2 job)
It may suprise you to learn that I'm considering getting a W2 job.
My wife and I are planning a move to the Pacific Northwest to be closer to her family. There is not a ton of government contracting out there, which means I'd have to either find a remote 1099 project (which I'm pursuing) or find a regular W2 job outside of the government contracting industry.
If I do go back down that route, it will be tough because I have been working for myself for a long time now.
Is this a 1099 career failure?
No. The goal was never to become a 1099 for its own sake. The goal when I started was to make more money, have more free time, and get closer to my ideal lifestyle.
1099 was a means to that end.
1099 might not be the best way to help me achieve my new lifestyle goals, which is to live in a different part of the country closer to family.
So, my tactics need to change. Getting a W2 job or building out a different business may be more effective.
I'm sharing this because going 1099 is just one option to getting what you want (autonomy, money, entrepreneurial skills, etc.)
However, there are potentially many options that can help you get to the same place, ones that don't involve dealing with bureacratic program managers.
Don't forget the big picture of why you want to go 1099. It may turn out 1099 is not the best path after all.