What’s the best way to ask for higher pay when renewing contract with an employer?

I work freelance for a startup, doing three month contracts at a time. My current contract is about to end and I’d like to ask for higher pay if they ask me to continue (im assuming they will). I’m fairly new to working this way and have never asked for higher pay before.

What would be the best way to ask this? Should I bring it up beforehand or should I wait for them to set up a call with me about a new contract? Should I ask for a specific amount or should I just tell them I’m hoping to make more this contract?

**Some other info:**

The company is small, everyone’s close with each other so I don’t want to come off the wrong way or play “hard ball”, but the money I’m making now only covers bills which is getting difficult, I dont do much besides work. Most of it goes to my college loans, which I have a LOT of unfortunately (not sure if I should bring that up). I’m not sure how much the company pulls in so I’m afraid of asking for too much or too little (compared to what the company makes). The company seems to be doing well though.

The work I’m doing is pretty important to what they’re doing so I feel like its fair for me to ask for more, I just want to make sure I do it the right way. Also, they sort of threw me a bone when I started working with them, I didn’t have a ton of professional experience at the time so it was likely a gamble from their perspective (that’s why initially I just asked for enough to cover my bills) but I have definitely proved myself and my work I think, there’s a lot more work to be done too.

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