Lots of self-doubt along the way. Lots of disappointment in other people. I was over-extended and taking chances in life that made little sense.
In my experience-
Few of the people in the world have the skills and abilities to even begin to manage a business and to be successful at it for a while.
You have those skills and abilities.
Few of the people in the world have the insight to see what they did wrong, and lack the integrity to admit, to themselves or others, that they made a mistake.
You have insight and integrity.
Few of the people in the world can examine their lives and develop a plan to make a change, and fewer still can express their plans, doubts and fears in a coherent and compelling fashion.
You can do these things.
Most folks let their lives happen to them, and proceed into time governed by simple momentum. You have taken control of your life, developed a plan, discarded the things that don't fit the plan, and gone to work to make things better. The plan may be successful or unsuccessful. Whatever way it turns out, you will learn from it, and be stronger and wiser in developing the next plan.
Bad things and good things happen to us, and those things don't matter. Our response to them matters. You seem to be responding just about as well as it can be done.
Feeling uncertain and tentative in pursuing the new plan is a lot healthier than feeling arrogantly self-confident.
You are a powerful and intelligent guy. It shows in your observations and in the way you express them. The things you will be doing will be difficult and dangerous, frustrating and frightening-but I can guarantee that it will not be boring.