I battle daily with self loathing and regret.
It take effort to be happy with what I have achieved. Character flaw I guess. But I do try to overcome it and be my best self.
I too have the sleep demons. My mind races 100 mph and robs me of that much needed sleep...
The good thing is you know those things plague you which means it's possible to work towards mitigating them...the hard part is making that happen. I guess (self) forgiveness is a good place to start, and momentum will build from there.