head in my hands, as someone who does extensive freelance TTRPG work - an industry in which the vast majority of those involved are doing it as a passion project/side hustle, and in which many people are friends with those they work for and with:
if you are doing any creative project with someone else in which money will be involved, make a contract. Doesn't need to be super formal. Get something laid out in writing that very clearly indicates what the person you are asking to do something is responsible for, the timeline in which they're expected to complete it, and the compensation they'll get for doing so.
"oh but we've been best friends since eighth grade" make a fucking contract.
"oh but this probably won't make much money anyway" make a fucking contract.
"oh but I don't know all that legalese" there are tons of pretty accessible templates available online if you research, just make sure it's one that suits your needs and you understand what's in it (it can be written in normal language without legalese, as long as it's clear), and make a fucking contract.
I've heard horror stories about this shit destroying projects, friendships, livelihoods, and in most cases the fallout could have been avoided (or at least mitigated) by having a clear legally binding document about everyone's responsibilities and compensation from the get-go. Do not assign someone work without a contract or some form of written agreement; do not work without a contract or some form of written agreement. please for the love of god.
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