Standing on the parapet of a skyscraper to photograph another skyscraper.
In my defense, it was not windy and the parapet was rather wide, but security sure looked uneasy.
Another, standing at the edge of a sloped roof that had no parapet to photography another skyscraper. This building was only 4 stories with a couple ledges underneath, so I am pretty sure I would have survived if I fell.
I also had my first insurance company cancel on me since they prefer not to insure professionals who knowingly put their equipment in precarious situations. When I told my current company that for what, they just laughed and said they have photographers who put themselves in much worse situations.
Not so precarious, but awkward and embarrassing at the same. I have to access a lot of roofs for what I do and one time I needed to get on the roof of a hospital just outside of DC. It was a rather hot day in the summer and the head of construction for the hospital was a fit attractive woman in her mid-30s who decided to wear a short skirt to work that day. To be honest, I did not think about what she was wearing until she climbed up the 15 foot ladder to unlock the roof hatch. I followed behind her and naturally looked up, and then proceeded to climb a ladder looking straight ahead. I had no plans on mentioning anything, but I guess she noticed how I was climbing, decided to bring it up and, in so many words, apologized for wearing a skirt.