How to handle unconscious learned helplessness

I have dealt with depression/gambling issues for the last near decade and although I have worked well to deal with those specific problems, part of what remains is a crippling learned helplessness. For years I was very lazy and avoidant of problems and everything was an exuberant effort. However now when I do somethings I feel incapable of doing those things in an unconscious manner. I will have what I refer to as "half-thoughts" in which I realize there's a problem but I don't have the conscious and therefore ability to diagnose/address it enough to deviate from my original path.

Example: I was attempting to grow out a beard. Last time I shaved, something went wrong because it was uneven and I had to end up shaving it all off. I don't believe I did the proper problem solving to make sure it wouldn't happen again, I think I just believed I was doing something wrong and couldn't fix it. The next time I was planning to shave, which was a while later, I remembered that I had this issue in a vague way, but just preceded to do the same thing again.

Eventually with enough failure, the unconscious or semi-conscious will become conscious, in this case two times. However, how can I ensure the issues become conscious from the get-go.