Create your own reasons to reach out: a holiday nobody else uses, an article that made you think of them, or simply that they came to mind.
The idea
You don't have to wait for something to happen to them. You can supply the occasion yourself. Everyone sends a card the last two weeks of December. Boring. Pick a different day. September 26 is National Pancake Day (also Shamu the Whale Day). There's a company in DC that skips the holiday party and throws a giant Cinco de Mayo bash for staff and the community instead. Or skip the holiday entirely and reach out because something reminded you of them.
How to do it
Pick an odd holiday, ideally one in midwinter or late summer.
Share what you read. When an article grabs you, ask who else would care, then send it right away.
Act on the stray thought. When someone pops into your head, take that as the trigger and message them.
On shared holidays, get personal. Skip the generic greeting and share something about your own day.
Example
Eating waffles, you think about how much better Belgian waffles are, which reminds you of your trip to Belgium, which reminds you that Bob Smith grew up there. Bob Smith! How's he doing? That's a complete reason to reach out.
Script
Something like this beats "Wishing you a Happy 4th!" (which is what your optometrist from five years ago sends):
"Hey! Just want to wish you a happy 4th! I'm dropping off our eldest at summer camp (!!!!) then the usual BBQ. Hope you have a fantastic day!"
Event-Driven Outreach: Use moments in their life, from new jobs and kids' milestones to illness and loss, as reasons to reach out between your regular check-ins.
The Smooch: The smallest possible touchpoint, and the one I've seen work best: 'Hey! You came to mind this morning. Hope you're doing well!'
Stand Out: Identical annual gestures become wallpaper. Change the occasion, the timing, the channel or the format, within reasonable bounds, so you get noticed.
CAPITAL: Timely Engagement: The T in CAPITAL. Give each group of people a fallback rhythm, then react to events, so prioritized relationships never quietly fade.