"Cheating" to go 1099
When I was a kid I liked to play a video game called Mario Kart 64 with my friends. It's a racing game with characters from the Mario universe.
I wasn't particularly good and would lose to my friends most of the time.
However, there was one course in the game that I would almost always win: Rainbow Road.
It's a long course, and whenever I tried to race the normal way, I'd lose.
However, there is a way to cheat that allowed me to win. It basically involved going backwards and "jumping" a section of the course.
This allowed me to complete the course in a fraction of the time and win.
It would drive my friends nuts but I got great joy out of pulling it off. My friends could have practiced the trick and used the "cheat" too but they didn't, so I would win.
I got the same feeling when I first went 1099. It felt like cheating because by taking a little risk, I could "win" the game that mattered to me: more money and more free time.
I knew I couldn't win if I just tried to play the "get a promotion" game or "find a better job at a new company game." I knew my personality was such that I would always be at a disadvantage as an employee.
So I "cheated." I got leverage with my company and clumsily negotiated my way to my first 1099 project.
Cheating is a negative way of describing how I went 1099; I didn't actually do anything wrong.
But, it's always helpful to assess your strengths and weaknesses and see how you can best achieve your goals in the most efficient way possible.
Your strength may be a good client relationship, a security clearance, strong technical skills, or even some personality trait like an appetite for risk or a lack of embarrassment.
Find ways to leverage whatever your strength is to get what you want and put yourself in situations where your weaknesses don't matter.
If you have to play the game differently than your peers, so be it.
It's better than losing on Rainbow Road every time.