Disclaimer: I am not a professional in the field of medicine, psychology, psychiatry or similar. I am just a guy, an older guy, who was socially awkward/shy for decades on end and I have things somewhat under control now.

Being shy, being socially awkward, having low-self esteeem and similar are all manifestations and symptoms of a root cause: Anxiety.

And while one might be able to alleviates the symptoms and manifestations here and there, the one and only cure is to address the root cause: the Anxiety.

And that's easier said than done.

To top it all, I also carried with me, for decades, undiagnosed severe clinical depression. So many times in my life I have reached bottom only to "settle" there fore a while and - later on in life -r each new bottom(s), over and over again, And then over.

Things that I have tried:

- hitting the gym till I was ripped. It helped with the ladies, which then helped overall, but... not really

- meditation: I have meditated thousand of hours, it actually didn't do anything for me

- I have read hundreds of books on depression, anxiety, happiness, confidence, relationships.. you name it, I have read them. The classic, the famous and the not so famous.

- I tried to get married, twice. And twice got divorced. I also tried heterosexual relationships of any type: affairs, FWB, just friends, just hooking up.... Nothing worked (now I say: of course, but that's for another day)

- talk therapy. 18 months of that and got me to a professional diagnosis of being "Depression free'. The anxiety and associated crap was still there.

- I even walked on coals!

What I did not try: meds, drugs (legal or illegal)

What has helped:

- time, yeah, age brings interesting perspective

- reading as much as possible science-based books and articles (and not new age crap. Honorable mentions are "Feeling Good", all the Rational Emotive Behavioral Therapy (REBT) books on Amazon, "The Subtle Art of Not Giving a Fuck", "12 Rules for Life", "Not Nice: Stop People Pleasing, Staying Silent, & Feeling Guilty... And Start Speaking Up, Saying No, Asking Boldly, And Unapologetically Being Yourself ", "No More Mr Nice Guy" and "The War of Art"

- my therapist helped too. I had a GREAT therapist. Bu she helped up to a point.

- writing helped. Writing almost every day, writing the dark crap that came to mind, anonymous writing on my own blog(s) and on Reddit too.

- REBT (mentioned above) helped me immensely

- I left the best for last: looking at my misadventures in life from the point of view that I am both accountable and WRONG for how I react/respond to life, and how I act in it, and writing about it daily has helped me the most. It has helped me unpack that a lot of my worldviews, presuppositions, what I though was "normal", my cause->effect expectations were, and to some degree still are, utterly wrong. And there's a LOT that I can do to chance things around, to tweak my behavior, to become a better person because, unbeknown to me for decades, my Anxiety had me angry inside and often I was a complete self righteous A-hole

I wrote about being wrong on HN a while back, here: https://news.ycombinator.com/item?id=30656873

Every day I realize how wrong I have been in certain aspects of my life, and I struggle to remedy and rectify things.

I look back and I an see the same wrong patterns of behavior in my parents, their parents, my sister, her kids.... And in quite a few people around me.

OP: that is how I improved, from a shy awkward kid I am now living a good life, and still improving. It never ends, keep on searching and improving and trying trying trying. Find a way.