Best way to go about asking for a rate raise at a permalancing gig?

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Tell your boss (now if you’ve been there over six months, or before end of Q2 if not) that you have a policy of raising your rate every year by 2.5% (or 3% or 5% or whatever is appropriate)... and ask if that will be a problem. It’s pretty much just as if you were full-time: you decide how strongly you ask, and if you’re willing to leave if they say no.

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