Freelancer here, went through something similar in Chicago a couple of times. This line in particular stood out: > Others make tenants pay the whole year’s ren

Freelancer here, went through something similar in Chicago a couple of times. This line in particular stood out: > Others make tenants pay the whole year’s rent up front I had resistance from a landlord who didn’t want to take a freelancer as a tenant, so I asked, “How many months up front would you want me to pay for you to feel comfortable, and then how can you make me feel comfortable that you’d take care of complaints and not just give me the finger because you already had all my money? I’m fine with whatever compromise you think is fair as long as we’re both protected.” Just that conversation alone was enough. She said, “if you’re this fair with me, you’re probably this fair with your customers, and we’ll be fine.” The end, no deposit required. I’m not saying that’ll always work - but just remember that negotiation isn’t binary. Find out what the person on the other side wants, and let them offer you a compromise they think both sides would accept. And if you’re a freelancer, pick up the book Getting To Yes.