Normal 1099 sticking points

There are lots of potential sticking points that pop up when you're pursuing a 1099 gig that may frustrate or discourage you. I want to list a few here just so you know that it's totally normal if you run into these:

  • Not knowing how to manage your security clearance as a 1099
  • Not understanding legalese contract language
  • Not knowing how to invoice
  • Not knowing how to calculate a profitable bill rate
  • Not knowing who to talk to about going 1099
  • Getting pushback or ignored by your boss when you bring up switching to 1099 status
  • Not knowing if you're good enough to go 1099
  • Thinking you don't have a network
  • Not getting enough inbound interest when you apply for jobs
  • Not knowing if your non-compete applies
  • Not knowing how to negotiate a 1099 arrangement
  • Not knowing where to buy business insurance, or how much
  • Not knowing what to do about taxes or how to pay them
  • Feeling scared about the potential risks

There are lots of "not knowing" items on here. The key is to learn how to proceed when things are ambiguous. You should do your research (or just read my book), take some risk mitigation steps, and then start taking small and systematic actions. Don't get paralyzed.

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