Not many people buy The Big Issue.
This is an issue when you’d be bettering someone’s life by doing so.
How do you manage to get over the stigma associated with homelessness?
Address it.
Look it square it in the eye and call it out.
It’s not necessarily always right to call your customers out for something that they do, but if you can prove that their assumptions are incorrect and then provide the solution then they are more likely to let you off.
Sure, let them know what they are doing is wrong (don’t do it in a patronising manner, just say it how it is).
But make sure they know exactly how to make it right.