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I used to take a lot of stupid risks. Mostly climbing-relate risks.
When I was around 12 I made a harness with one of those yellow nylon ropes (basically tied a figure-8 on the bottom to put my legs through and sit on it), and i would throw the other end of the rope over a branch (usually I would climb a tree as high as I could and then throw it over an even higher branch). Then I would use the branch as a pulley and hoist myself up with the other end of the rope, tie it off, and swing around the top of the tree like 50ft off the ground like a retard. When I got more and more brave I would push off the trunk as hard as I could and swing way out and then come crashing back to the trunk like a wrecking ball. That was like 1/4" nylon rope. Never broke, never died.
Also one time I was building a tower in the woods, which was maybe 25ft high, and I was at the top and the support I was standing on popped loose and I fell down the center of the tower all the way to the ground. Nearly got impaled on all the sapling stumps I'd left sticking out of the ground as I cut then down to make the support beams. Puked, was so massively bruised I had to drag myself out of the woods on the ground,