Do you feel unconfident?
The issue that proliferates a lack of confidence is absence of validation. If we knew that we would be validated in everything that we pursued, our confidence would be substantially higher. High enough to try anything once; high enough to let go of overthinking everything.
The best way to free yourself from a lack of confidence is to free those around you. You can do this by choosing to validate everything and everyone who you interact with. Nobody gets this right 100% of the time. However, if you can increase the amount of validation that you express, you will find that confidence within yourself and everyone who you love substantially improves.
Focus on cultivating the confidence of those around you first, then notice as your confidence and willingness to connect shifts to a new level.