C'mon, what's the dumbest thing you've done which seemed a good idea at the time?
The first one that springs to mind - and there will be many more I'm sure - was to think it would be a good idea to chip a golf ball over our conservatory roof. Fortunately the shot was bad enough to hit the huge glass pane (roughly 6 feet by 4 feet) right in the middle so it didn't break. Nearer the frame and the vibration would've caused it to shatter and cost a fortune to replace.