This is interesting to me, Ryan, I just wrote a story around a similar theme. I included a book review of a book called "The Big Leap" by Gay Hendricks, that has really helped me with all of the same things you have listed. If you are in the market for a new book you might want to give it a peek. (I don't have any type of affiliate marketing thing going, I just really found this book helpful). I will hopefully post my story tomorrow, if you come across it, please let me know if it strikes a chord. Yours definitely did for me.
It would be great if you read that book to write a piece on if it helped or not I'd be interested to know.
I guess the only bit of comfort I can give you is to let you know that you aren't the only one mucking things up for yourself. It seems to be a very common problem.
All the best and keep on keeping on! I'm rooting for you:)