Fear keeps most people from reaching out at all, so simply doing it puts you ahead. Their fear is your competitive advantage.
The idea
When Americans were surveyed about their fears, the only thing that beat spiders, snakes, drowning and clowns was public speaking. We're social creatures, and social rejection feels like a survival threat. So before you contact an old friend, a past client, a prospect or someone you admire, your mind catastrophizes. Everyone gets that same knot in the stomach before hitting Send, and most people let it win. Which puts the bar on the floor. If you're one of the few who presses Send, you're already way ahead of the pack. Their fear is your competitive advantage.
How to do it
Notice the hesitation before a message. It's normal and universal.
Remember that everyone has the same psychological barriers, and most of them won't act.
Say the mantra: "Most people won't."
Send it.
Example
In my coaching, "Most people won't" was the mantra for the last week of our six-week program, the final thing we handed members, with a reminder that everyone has the same caveperson wiring. And in years of making coaching clients send the message they've been dreading, right then and there, I have yet to hear of a negative or awkward response.
Rejection Math: A yes is worth maybe 100 times the small ego hit of a no, so the math almost never justifies staying silent.
Time and Fear, the Two Universal Blockers: Almost every reason people don't stay in touch comes down to two things: not having time, or fear of how the outreach will land.
Caveperson Wiring: Our brains evolved to treat outreach as danger and to forget people, so go easy on yourself, then build systems that compensate.