the power of recurrings

the magic of showing up, consistently

I never fully appreciated the value of recurring 1:1s - until I saw firsthand the magic of consistent conversations in both work and life.

What might seem like a corporate routine actually creates space for serendipity: opportunities that wouldn’t have surfaced otherwise, staying top of mind, and allowing relationships to deepen over time through shared memories and growing trust.

serendipity by showing up

I set up a recurring meeting with another teammate, who I don’t work directly with, but is in a similar career stage as I was, to catch up every three weeks.

It became one of my favourite rituals to look forward to - talking shop, teaching each other about the projects we were working on, and sharing advice on how we’re navigating work. These conversations often helped connect the dots. At one point, I realized she was working on something similar to what my mentor had built before, and I was able to connect them to share knowledge and context.

When she started preparing for her leave, I was the first person she thought of to take over her project, not because I explicitly asked, but because we had built trust through our recurring chats. In one of our earlier conversations, I had shared that I wanted to broaden the scope of my work, as up until then I’ve mostly been working on mobile prototypes. So when the opportunity had come up, she immediately thought of me! Her project was a TV prototype, and she knew it would be a valuable learning experience given the goals I shared.

Since getting to work on her TV project, I’ve now been considered for both mobile and TV prototyping opportunities when new projects come up! I realized how important it is to have touchpoints with people outside your direct manager on your team because they can advocate and surface opportunities for you in ways you wouldn’t really expect.

recurrings help things scale

As time goes on, it’s become harder to fit in 1:1 coffee chats and meetings throughout the week. I still think they’re one of the best ways to connect with someone for the first time and have deeper conversations, but they’re hard to sustain at scale.

That’s why I’ve come to appreciate the value of hosting recurring events. Although I’m not super consistent with this, having one event I’m hosting a month is a lightweight way to stay connected with people since I can just invite people to that instead.

And if there’s someone I’ve been meaning to connect with and might be interested in what I’m hosting, having an event gives me a good reason to reach out.

creating surface areas for connection

Recurrings are also an easy follow-up after a first meet. Sometimes you’ll have an amazing conversation when you meet someone for the first time but struggle on follow-up and keeping in touch especially as there’s no clear action item. Having something you’re hosting is an easy crux to get them in your orbit again without overthinking things too much.

It’s probably why I see a lot of great friendships come out of communities like Socratica. The formula of the weekly co-working session gets people building friendships over shared memories, values, and inside jokes that compound from seeing each other in the same room consistently over a period of time.

I’ve also found that most of the magic of rabbitholeathon often reveals itself after the retreat. Of course, the weekend itself is incredibly special, but with the number of attendees and it taking place within a short weekend, I only get to talk deeply with a small fraction of them. Getting to hang out with more rabbitholeathon alum in SF post-retreat has been really amazing! The retreat itself plants the seeds, but it’s the touchpoints after a great event that help things grow.

being consistent

I’ve come to realize that recurrings don’t always have to look like scheduled calls or planned meetups - they can show up in more ambient ways in the background like a quick text or random FaceTime call just because.

I have two close friends who, on paper, wouldn’t be people I thought I’d be in touch with for this long, especially since we don’t live in the same cities. One I only overlapped with for a year in an after-school program in high school. And yet, over five years later, they’re two people I highly trust and frequently stay in touch with.

They both had a subtle consistency of reaching out, almost like it was built into their DNA. It was never anything that was formal or scheduled, but they’d check in from time to time, randomly FaceTime or ask to call if it’s been a while. I admire both of these friends for how they show up without really needing a reason, which makes it even more meaningful. Long-term friendships, like relationships, are a choice you make each day to show up for your people.

becoming top of mind

Being in the venture world, I’ve noticed that some of the best investors, especially those focused on scouting early talent, are incredibly good at maintaining recurring touch points.

One of the most important goals of a VC is to become top of mind, so when a founder is raising, they’ll be the first they reach out to. The reality is, recency bias plays a large role - so even if an investor had a great meeting with them years ago or was helpful early on, they can be easily forgotten if there hasn’t been any follow-up since. That’s why many investors have coffee chats, host events, or create content to find lightweight ways to check in and be top of mind.

It’s also why I try to share some writing a few times a year - not just to stay visible, but to stay present. It’s another surface area for someone to reach out for the first time, or reach back out if something you wrote resonated.

putting recurrings in practice

Okay now I’ve rambled on why recurrings are important, some ideas to get you started ✨

At work

• Peer touch points - occasional chats every 3 weeks with someone at a similar career level to you to share learnings

• Mentorship chats: a more casual version of a manager 1:1 - either weekly or bi-weekly to talk about growth, day-to-day technical learnings and career navigation with someone more senior to you

• Skips/leads: once a quarter - to share visibility of what you’ve worked on, learned, and provide feedback to the broader team

Community/fun/with friends

• Reading groups - ex. book clubs or thematic article discussions every 2 weeks.

• Workout-events: It’s a win-win: you get a workout in and you get to see your people often! Run-clubs (lol!), monthly hikes, weekend workout classes. My example is organizing women who lift in sf every month or so!

• Creative sessions: Co-working sessions, demo/presentation nights, crits. Sometimes on Fridays I like to work from my friend’s offices.

• Retreats: Yearly trip with long-distance friends to bring everyone together for a weekend

• Dinners - I’ve seen friends host/cook monthly dinners and make someone bring a +1 they haven’t met!

• Game nights

• Weekly writing clubs

• Pre-work morning walks - I’ve made it a habit to do morning coffee walks to catch up with friends on Fridays when I WFH

some parting thoughts

Repetition makes you remembered! Relationships take time and investment, and recurrings are a great way to build it within your routine.

Hope you’ve enjoyed this read :) would love to hear about any traditions/recurrings you incorporate into your routines.

~ mathu