Yup, I was in one of those situations. Working for a building renovation contractor who I liked and respected, we'd done several jobs on roofs, but low flat porch roofs, maybe 10' up. No problem. This one project was on a barn where the low edge of the roof was probably 30' up (vertically) and the peak 50', and it was pretty steep. I felt this was not a good place to free-solo and try to work at the same time. I asked about getting some way to rope in, and he had nothing. I told him I regretfully had to quit at the morning break.

Despite having been in all kinds of alpine rock climbing and international downhill ski racing competition experience, or perhaps because of it, that was just a hard NOPE. I think it was just the intense awareness that, once a slip starts, there was no recovering or stopping before the ground. The weird thing is just how totally casual he was about it, even seeming to think my question about protection was a bit odd.

I'm just damn fortunate to have the option, especially considering the statistics for roofing work.