The 1 way you need to attack shyness
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I think the best solution for some folks is to simply force yourself into the situation over and over, like going to a meetup and making yourself talk to everyone. Eventually, your brain will get the idea: okay, I can deal with meeting and talking to new people.
Here's my tip: learn how to ask great questions when you meet people. It takes the spotlight off of you and let's them "do the work". I can have entire conversations where I say very little if I'm feeling anxious at the moment.
i put my pants into a device which holds them open, then i stand on a platform and jump into them.
BTW I'm thinking of starting a company to sell this device. Anyone interested in being a co-founder?
That said, I think you're right on about habituation combating the anxiety of meeting and talking to new people. I'm a rather ambivalent about the value of all these web 2.0 meetups (yes, even drankkit) but I envisioned this kind of scenario:
Startup founder is waiting in line at SFO, looks up to see Ron Conway (or the like) standing in front of him and looking equally as bored. It's probably not the time to go into the pitch, but it shouldn't be how many startups he's funded/sold/acquired that stops you from talking to him (or anyone).
Maybe you'll even score his phone number.
EDIT: That being said I can give one piece of advice to guys who are shy. Work out. Work out. Work out. You will be amazed how much NATURALLY produced testosterones can affect your behavior.
I believe we are shy because we make too many assumptions and judgments about our surroundings. And most of the time those are totally wrong.
Extrovert bluster can be so cute!
Maybe one day I'll be able to vote again =x
That's what makes it a joke. If it didn't cause pain (at some level), no one would care enough to laugh.