I will dare to say that I am not alone among golf course architects who have woken up in the middle of the night (sometimes in cold sweat) dreaming of the problems of meeting payroll, finding the next job, being sued, etc. at some point in their careers, probably multiple points.
As to actual design dreams, the also trend towards nightmares. When I did the Legend Course at Giant's Ridge, on boulder fields, I spent many nights tossing and turning that first winter obsessing whether in spring, I would find all the topsoil earth works had seeped between the boulders leaving pot holes. This was especially true on holes like 7 where you could (and still can) hear subsurface water running below you when standing in the fairway. The good news was, the contractor, experienced in such conditions, had done a wonderful job of mixing boulder, stone and cobble size and packing it together to eliminate voids and there were no problems.
On the Quarry, I was worried about them taking the old quarry slope back to something stable (on the 18th) No problem for them and I was amazed at where their track hoes could go and set up.
And of course, the night before any bid is due from contractors, I find myself dreaming that low bid is about 50% over my estimated budget, which can be a mess. (Happy to say I never missed one by quite that much, however. Still doesn't stop the nightmares.)