Can a freelancer ask for more money when freelancing at an agency for a while? If so, when is the best time to do it?

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Yes. It helps if you have another freelance opportunity for leverage. Or you can just pick a time and ask for more. But be prepared for them to say no, or worse yet, end your gig. The freelance pool is deep and they can easily replace you.

I have when the workload ended up being more intense than promised. I’ve also done it when an initial contract wraps and I have other jobs available at higher rates. Freelance rates go up and down throughout the year depending on how busy things are so I think recruiters are used to it.

It depends. Some places are offended by it.

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