Really great post full of insights you tend to get when you mature a little. The great change for me in overcoming shyness and connecting was someone told me shyness is a form of cowardliness. Without becoming an annoying asshole overcome your inner coward and dare to express yourself in the world, many benefits will follow.

Brene Brown talks about vulnerability and leadership in her TED talk: https://www.ted.com/talks/brene_brown_on_vulnerability

Her book describes research on leaders who discuss their vulnerabilities with their teams. The outcomes included more motivated staff, more self-directed managemement, and better normalization of risk-taking, e.g. the famous startup mantra "move fast and break things".

Quick summary here: https://www.scottsmarketplace.com/blog/business/brene-brown/