Be slightly pushy
The threshold to annoy someone in a professional context is pretty high.
You're not going to offend anyone or lose a deal because you send polite follow up e-mails every week.
You're not going to be fired if you push back on a bureaucrat saying no.
You're not going to be considered an idiot if you ask "dumb" questions.
Being slightly pushy or persistent or curious will actually help you get those 1099 gigs.
So be slightly pushy.
Want the full playbook? Check out Going 1099.