do you lack confidence Jason ? If so just imagine yourself at 95 looking back on your life . Remembering the opportunities you passed up because of some useless apologetic complex , what would be the advice to you from the 95 yr old you ? It's very cliche, but it's true that if you believe in yourself then the rest of the world buys it too. Doesn't matter what you look like , how much money you have , because being unashamedly yourself is the most attractive weapon you have .
What would I know , you might be the most confident person in the room . If so , apologies for my presumption .
. When I met my wife 30 years ago the standing joke has always been from her " she wasn't actually even sure that she liked me , she just wanted to stay around to see what crazy thing was going to happen next "
Perhaps living every day as your last day is a bit over the top , but living every day without fear is def not .
Find your own way.