I don't care about the outcome, i care if guys here have the balls like you have, to act in the moment.
It's just the way I am - I've become generally very sociable as I've got older, with everyone, not just women.
I have no problem speaking to people I don't know, women included.
And you've mentioned there, what I think is the key.
For me,
the trick is not to be anxious about the outcome - If things go well..... great! - If not, then I just go about my day.... no harm done.
When speaking to women, I've become good at picking up on whether or not she's interested - and if I think she is, I'll try to steer the conversation so I can get an idea of her availability.
When all goes well - She seems interested AND probably available - then I'll ask for some form of contact method (phone no./social media/etc.) - or even straight out ask for a low-commitment date such as coffee/drinks/etc.
I've mentioned this a few times already on SS - but the woman I'm currently seeing semi-regularly... Our paths crossed while parking our cars in town - some positive-looking eye contact so I spoke to her, just small-talk (you don't have to be dazzlingly witty or clever) - she seemed interested so I just straight-up asked her to meet up for a coffee.... A week later we had dinner, followed by a beach walk, and ended up back at my place.