I'm talking about both work tasks, and personal. Surprisingly I can get through assigned work tasks typically without issue. It is the tasks that I set out for myself that I have a problem with. Which fits in with why I'm primarily in a systems administration / engineering role -- I can pull on my decades of experience to solve tasks readily, however whenever I have to do a programming / design related task (which I can be fairly good at), I can't pull that off consistently. I can only do that if it is an area I'm not familiar enough with, where I can trick myself into thinking that it isn't that big of a project. But if I end up going down the wrong path and have to start over, then I fall apart and can't even think about working on it anymore. Or if I get a basic system developed (MVP), I find it difficult to work on improvements because the list of things I can do is never ending.
For my non-work related projects (open source software, home system builds, woodworking, 3D modeling) I wish I could hire a project manager to oversee my work on them. (would that be a variation of hiring a life coach?)