I am your age and I turned my life around in the last few years and now have much of the things you wish for. I can attribute much of it to therapy. It's ok to ask for help, you have shown you can do it here. Best of luck, know that it is possible.
I could reply to this for hours and wish you the best.
I will say, I am in my 40s and so what I will share now is different than I would have 20 years ago and would probably share 20 from now but.
- Self-improvement is a good thing to aspire to, improve the things that prevent you from having what you want. But realize there is a tax to this.
- Own it. It's ok to be socially awkward and shy. There are jobs, lifestyles, communities and passions that suit those of us with these traits.
No-one is happy being someone who they are not. So, even if you change the characteristics you currently have to get to a different place, know that it could ultimately make you less happy when you get there if you are not true to yourself.
I think something to keep in mind (really for any job search scenario) is that there will be companies, people and company cultures that just won't get what you're doing and what you stand for. Some hiring managers who know great teams are made up of players from very differing backgrounds will get it. Hiring managers who have been there themselves (gone the entrepreneurial route) will also get it. You may have to pace your audience here and select companies that seem to embrace bringing on people like yourself. You can do this kind of research on the company itself, on the hiring manager (check their LinkedIn) or see if you can set up a call with someone on the team. It's easier said than done, but if you can honestly believe (by yourself) that what you did for those years is an asset then it will just come through in telling your story. For context, I've come from a mixed experience background with some gaps where I started things and experimented. Although it did slow my formal career path, it's made me much more valuable than someone else with the same traditional years experience. Good luck!
