I know what you mean about shame and disappointment. I don't think I went through the shame part, but definitely very disappointed in the beginning stages - I looked at my MR as the 'lost decade'. But it looks like that because you're seeing it through the lens of pain.
I am sure someone looking from the outside would give a well balanced perspective of our lives, but we only have ourselves so that makes it difficult. The world was full of possibilities, but I also realize that I didn't have the perspective and tools that I have now to go after them, but also have the wisdom and insight to pursue them.
You're younger than me and there is still so much life ahead of you. Heck, I know I have it too.
When you get past the melancholic stage - i know that place very well and it was super comforting to be there - one thing you'll realize is that the insight and learnings you have now will allow you to accelerate moving towards your goals. You can't circumvent the process, but you can speed it up. So, take solace in that.
I can tell you after so much soul searching, I came back to what is true to my core and it circles back to when I was a child. Life, through various mechanisms, made that dormant and now when I realize what I want to do with my life, I can see that it was always who I was but other people's expectations, life struggles, and society got in the way. If I had just listened to my inner voice and paid it good attention, I would've been in a different place right now.
So, yes, the past can be full of disappointment and shame, but if you don't take the wisdom from it and apply it, then it will continue to do that.
I know intuitively you know all this, but I am just vocalizing it. It really helped when other people confirmed these things for me initially when I needed external validation to keep going and learning how to trust myself again.
And trust me, it will get noticed by other people when you start radiating your true self. I just had two female colleagues compliment me on my dress sense and how I carry myself. They told me how so many men don't do that, including the ones in their lives and it was refreshing to see a man take care of himself. The external and internal confidence will always show and when it's genuine, it's unbelivably attractive.
About reaching out to W for what you learned, don't do it. There will always be some reason to reach out. I am sure she will find out on her own in some way. Just let that urge subside and just be with yourself.