For my ex, running out of money was barely a blip on his radar. He stole from me, emptied my account several times. He stole my possessions and pawned them. He stole from my family, his family, his job. He shoplifted, pickpocketed, sold drugs, stole from the big dealers.. Etc etc. Eventually it's not up to you whether he's working or not, that's his decision and IMO you shouldn't be influencing him one way or another. BUT I will say that I'm in the UK so the benefits system here is very different- will you be paying for his living expenses while he's not working? And if you're telling him not to work, is the motivation for that 'if he's got no money he can't buy drugs'? Because that sounds a bit like an attempt at control, to me at least. I understand you have the best of intentions but sometimes what seems best isn't always.