The positives of ‘putting yourself out there’ are worth it. Having a great conversation with a stranger will be worth the awkwardness of starting that exact conversation. Joining a small community of people you will see regularly is worth having to get through a scary first day. Getting your dream job is worth the scariness of chasing it. Don’t pick and choose experiences based on the level of ease now, but choose them based on how you want to come out of them.
