Painting shop/bar windows for Christmas and other holidays. By which I mean painting Santa or the like with whatever holiday message the proprietor wanted to convey. So far so great idea. Except I didn’t have [poster] paint, brushes, markers or anything.

So I used to pick a large, commercial street and with a pad of blank paper (some times loose-leaf) I’d cold call every business on the road and on the spot sketch them a targeted cartoon of how their windows could look. I also offered a cast iron “don’t like, don’t pay” refund guarantee. In other words if they didn’t like the finished job I’d wash it completely off, no payment required. In this light, worst case scenario they’d get a free window clean.

If they were amenable I’d then hit them for a cash advance enough to get the paints and what not. If it was a bar I’d usually hit them up for a drink or two while I was working also (thirsty work!), to be taken off the overall price.

On the ‘big’ holidays you could make serious, serious coin at this gig, I mean more than twice the industrial wage for the 3,4 weeks you could exploit it for. I spent October (Halloween, Thanksgiving for American owned or orientated businesses) to the end of December (post-Christmas but then you have the New Years’ promotions) raking it in. One year I earned enough to live like a king for a few months afterwards - rent paid and enough disposable income to do pretty much what I liked - at least as much as my modest desires stretch to. Another year I paid our equivalent of community college fees for the whole year by the same method.