[karaterobot]

I don't think the value of inverse reasoning is that it lets you think of new ideas. If you're trying to list all the ways something could go wrong, you're pretty much just listing the ways they could go right, and flipping them. What I mean is, I think your list of bullet points for "how to have a great career" would be able as long as your list of bullet points for "how to have a terrible career". Both lists would usually contain the same essential information, just framed differently.

Where I think such a practice can be useful is in forcing you to confront unpleasant possibilities you would otherwise try to ignore, and thus at least briefly plan for them.