"you just have to put yourself out there" is lazy thinking, you are ignoring all the underlying psychological and physilogical factors preventing people from doing it.
Making the society more welcoming works. It worked wonders for me. I moved from a country where things like meetup events are not common and groups are less welcoming to strangers. Having moved to UK, meetup events allowed me to go out and socialise because I could sign up without speaking to anyone, and go there and participate in the activity, without the pressure to socialise, it was an optional benefit. These settings allowed me to socialise with strangers that I could never do before.
And that's extremely harmful. In theory we have democracies. In practice, if you have the capital, you get to decide for what products and services the world's resources are used for.
Why would it be impossible to start a business? You would still be able to list your business in mediums where potential buyers willingly go and search for products and services. If anything, it would level the playing field, paying more for ads would not mean you getting your poorer services more visible buy paying more for ads.
I actually think so, yes, the world would be better off with everything you listed happening.
When we used to pay for newspapers, the informational value of the news was a lot higher, news and news-like social media posts were not the primary tool to spread stupidity.
Free speech does not mean you get to yell at me. In the same way, banning ads where they are shown to users without their consent would not mean violation of free speech.
You generally do not go to the gym and fail, exercising works more or less the same for almost everyone, you get good hormones, you feel good.
Socialising, on the other hand, is entirely different. Some people thrive in it, some people feel much more dread afterwards.
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