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Events bring us into the same room, but not into each other’s lives. After years of hosting meetups, I’ve learned that when you take care of the room’s layout and how people interact, you can multiply the odds of meaningful connection.
Marcus is halfway through explaining why this is Bitcoin’s breakthrough year when you notice it. Three seats down, laughter bursts from a group sharing their weekend hiking disasters. You’d love to join them, but between you and them is the vintage board-game collector, already shuffling through the rules of something called Wingspan. You’re trapped.
At a networking event, you cling to the first friendly face. Like shipwreck survivors, the two of you circle the room, eyeing clusters of laughter you can’t reach without crossing an awkward gap and intruding mid-sentence. So you don’t. You retreat to the snack table, make another loop with your safety partner, and leave early.
At a presentation, you sit with sixty other people in silence. When the last important question is asked, everyone’s stiff, tired, and ready to leave. A few brave souls attempt post-talk mingling, but no one wants to force polite chatter.
Most events bring people together physically, but not socially.
I once went to a meetup called Overcome Loneliness where dozens of lonely digital nomads sat quietly side by side, watching someone speak from Singapore – through a screen!
Compare this to a party at a friend’s house, a dynamic event with different areas. Within minutes of arriving, you’re talking to a couple of people. You know someone who knows someone, and it’s natural to join the conversation. By the end of the night, you’ve made new friends.
Experiences like this are rare. Even when people manage to talk, they rarely get past the surface. Two people with the same obscure passion exchange the usual script about where they’re from and what they do, then walk away, never knowing they’re both hooked on retro arcade games, obsessed with brewing the perfect stout, or devoted to late-night poetry debates. They were one question away from a fun conversation and didn’t know it.1
After six years hosting meetups, I’ve learned that you can recreate the house party atmosphere by designing the interaction around three elements:
You want people flowing through the room like atoms, bumping into each other to form brief connections before breaking apart to mix again.
Picture a cocktail party: Someone gets a drink, joins a conversation by the window, then drifts to another group by the door. That’s the movement you want. But certain setups make it impossible.
Meet the long table. You can only join where there’s an empty chair, and once you sit you’re stuck talking to your immediate neighbors. Group topics stay superficial to include everyone. Escaping isn’t easy. “Hey, Frank, great talking, but I should catch Phil before he disappears.”
In a space where people can mix and mingle, you can talk to almost anyone. Walk up to a group, and they naturally open to let you in. Joining the right conversation becomes effortless.
Instead of long tables, create condensation points, spots where people naturally gather. Like the kitchen at a house party, the smokers’ corner, or the bar line.
Use cocktail tables with bar stools so people can rest for a moment without settling in. Provide only a few stools, so most guests remain standing and moving.
Keep circulating even if others are sitting. Make it clear this isn’t the kind of night where people stay put.
But movement alone isn’t enough. The layout sets the tone for everything that follows. You can tell within minutes if it’ll be a night of easy mixing or small circles of people sticking to their friends.
If groups are too far apart, they’ll form little bubbles, each with its own gravity but no exchange. People stick to the first conversation they stumble into and never drift to another, as no one wants to cross a yawning void to step into a group that’s watching them approach.
In a good space, you overhear others discussing something interesting and casually turn around to join in. Who would have thought that Frank, you tried to escape from earlier, is a hidden gem – once you get him talking about his sourdough experiments.
To encourage these natural encounters, arrange tables2 with enough space for two or three people to stand between them. Closer than that and they blend into one big table, with no easy way to get around. Too far apart and conversations become isolated islands.
At the start of the event, when attendance is light, keep early arrivals close so the first conversations happen within earshot of each other. As more people arrive, the group naturally expands and divides but maintains that connected feeling.
A good layout will help people mix and mingle. But if you want to take it to the next level, you don’t just let the room do the work, you actively connect the people in it.
There’s nothing more awkward than being sent into a room full of strangers, not knowing who to approach. But no one should have to figure this out alone.
When someone arrives, introduce them to a couple of people. You don’t have to know them. Ask their names and connect them. “Josh, Rob. Rob, Josh.” If someone is standing alone, do it again.
Add context when you can, using whatever you just learned: “Sophie is a Korean philosopher who started a travel YouTube channel.”
Magic happens when you spot a link and walk someone across the room: Josh wants to visit Seoul; Sophie just moved from there. You’re not just connecting two people, you’re teaching them the social map of the event. Now Rob knows where the creative travelers hang out and can introduce Sophie to the product management group.
Within an hour, you’ve created a web where everyone knows someone who knows someone else. The shy person who walked in alone now has three groups they can rejoin, and they’re confident enough to bring someone with them.
Peter Finger, who used to run my university’s alumni events, showed me how this is done. At his events, he’d remember your story3 and know exactly who to connect you with. He’s not doing it for himself. He’s doing it for you. He knows how to give everyone a good time.4
We never know who will connect or why. Chemistry is mysterious. But we can create more opportunities for it.
Here’s what happens: The accountant passionate about urban beekeeping gets stuck talking to three people about crunching numbers and goes home feeling disconnected. If she’d had ten conversations instead of three, if she’d overheard someone mention sustainability, if she’d been introduced as “the one with the rooftop hives” she might have found her people.
More shots, better aim. Every conversation is a chance to discover connection. Every overheard comment is a potential hook. Every context-rich introduction is a shortcut past small talk.
Movement, proximity, and introductions multiply the odds of a genuine connection, one that lasts beyond the event. When all three come together, you get the kind of night you come home from smiling, not quite knowing why.
Your next event could connect the banker with his new head of IT, the introvert with her badminton partner, or the immigrant with the love of his life. It could spark a friendship, a romance, a future. And you might never know.
Design for connection, then watch what happens.
Let me know how it goes.
Consider adding conversation triggers. A Polaroid camera, a book, or a map of attendee countries can create natural talking points at these spots. ↩︎
Peter even taught me a trick: If you forgot someone’s name, take a guess. When they correct you, you’re far more likely to remember it next time. He isn’t afraid to get it wrong today – because he cares about getting it right in the long run. ↩︎
This is what networking is about. It’s not about getting “connections” to “leverage”. It’s meeting interesting people and making new friends. And then you might help each other because you genuinely like each other. ↩︎
Bill Maher visited Donald Trump at the White House, where he not only got Trump to sign sixty of the insults he’d hurled at Maher but also encountered a president who was surprisingly self-aware and willing to listen.
Maher concludes:
The most surreal part of the whole night was when I got home. I flew back right after the dinner and I’m in bed watching 60 Minutes from the night before, and there’s Trump in one of their stories, standing at a podium in a room that looked to me like one of the rooms and podium places we’d just been in. And he’s ranting: “Disgusting.” “You’re a terrible person.” And I’m like: Who’s that guy? What happened to Glenda the Good Witch, and why can’t we get the guy I met to be the public guy? And I’m not saying it’s our responsibility to do that. It’s not.
I’m just reporting exactly what I saw over two and a half hours. I went into the mine, and that’s what’s down there. A crazy person doesn’t live in the White House. A person who plays a crazy person on TV a lot lives there — which I know is fucked up. It’s just not as fucked up as I thought it was.
I really enjoyed listening to Tim Cook on Table Manners. What a personal and friendly conversation.
Herman Martinus wants his products to be like a garden:
That’s what I want from my products. I want to putter about, feel connected to the process, and have fun doing so. I want to make things that don’t scale. To see people tuck into them and enjoy them as people, not as stats. I’ve done this fairly successfully with JustSketchMe. We have a small, diverse, and amazing community of artists and illustrators making awesome things. I’m trying to build a similar product with Bear Blog. Something niche but valuable. Something I can spend time on because I want to.
Being able to talk to, and interact with the people using my tools is fulfilling. Spending time meticulously improving subtle aspects of the product is enjoyable.
The authors of The Pragmatic Programmer about users not knowing what they need:
Dave Thomas: Tying in to what Andy said earlier about software having a Heisenberg effect, where delivering the software changes the user’s perception of the requirements, almost by definition, your target is moving. The sheer act of delivering the first release is going to make the user realize, “Oh, that’s not quite what I wanted.”
Andy Hunt: Or even worse yet, “Oh, that’s exactly what I wanted. But now having seen that, I’ve changed my mind. I’ve learned. I’d now like to do this instead, or this in addition.” Just by introducing the software, you’ve changed the rules of the game. Now the user can see more possibilities that they weren’t aware of before. The user will say, “Oh, if you can do that. What I’d really like is if you could do this.” And there is no way to predict that up front.
Cal Newport:
Between this newsletter, my podcast, my books, and my New Yorker journalism, I offer a lot of advice and propose a lot of ideas about how the modern digital environment impacts our lives, both professionally and personally, and how we should respond.
This techno-pontification covers everything from the nitty gritty details of producing good work in an office saturated with emails and Zoom, to heady decisions about shaping a meaningful life amid the nihilistic abstraction of an increasingly networked existence.
With the end of year rapidly approaching, and people finding themselves with some spare thinking time as work winds down for the holidays, I thought it might be fun to try to summarize essentially every major idea I discuss in one short primer.
He then shares his thoughts about knowledge work, personal technology use, deep life, and the internet and future technology.
Masks by Shel Silverstein:
She had blue skin,
And so did he.
He kept it hid
And so did she.
They searched for blue
Their whole life through,
Then passed right by—
And never knew.
The first time it happened, I was writing a paper. The paragraphs I had just typed vanished into thin air, faster than Time Machine or Backblaze could save them. Gone. The next occurrence was during app development; Xcode suddenly flagged numerous errors in previously error-free code. My recent changes to several files were erased.
Months later, the mystery is solved: iCloud Drive detected a file conflict. It assumed different versions of the same file existed on my Mac and iPhone and couldn’t merge them automatically. This was impossible; the affected files were never opened on the iPhone. But they were in iCloud, as I had moved my Mac’s Documents folder there.
Dropbox manages version conflicts by storing all conflicting files side by side, labeled as “(John Doe’s conflicted copy)“. iCloud Drive, however, doesn’t show these conflicts in the file system. If you open the file in an editor that supports conflict handling, a popup appears asking which version to keep. Editors like Textifier, Xcode, or Obsidian, lacking conflict handling, leave iCloud to decide which version to store on your disk and in your backup.
Over time, newer backups overwrite older ones containing the correct version; your content is gone for good. The only way to get it back is to open the file with an editor that supports conflict resolution.1 Once moved out of iCloud Drive, even that won’t help. The content is lost.2
Masking version conflicts might appear user-friendly, but it has catastrophic consequences. You might not discover the data loss until years later, when reopening significant but infrequently used documents.
Until iCloud Drive exposes version conflicts in the file system or a central, easily accessible location, my strong recommendation is to move all crucial data out of it. Meanwhile, set up a Git repository to monitor your critical files; you might uncover surprising changes.
Update: For files that need to stay in iCloud Drive I’m building Cloud Cub, a simple way to detect and resolve hidden sync conflicts before they cause data loss.
Within a few days of prototyping a game mechanic, Valve’s designers start watching users play. And they conduct playtests once a week until their games are fun and it is “no longer excruciatingly painful” to watch.
On a side note: At least in 2012, when its Handbook for New Employees was published, Valve was completely self-organized.
Morgan Eua does a great job introducing Niklas Luhmann’s Zettelkasten method for personal knowledge management.
In follow-up videos with easy to understand examples she details how she implements a Zettelkasten in Obsidian.
For a more comprehensive overview, check Sönke Ahrens’ book How to Take Smart Notes.
Haruki Murakami’s What I Talk About When I Talk About Running inspired Cal Newport’s theory of deep work. Newport explains:
Against the advice of nearly everybody, he sold his bar, and moved to Narashino, a small town in the largely rural Chiba Prefecture. He began going to bed when it got dark and waking up with the first light. His only job was to sit at a desk each morning and write. His books became longer, more complex, more story driven. He discovered what became his signature style.
You might have heard of Parkinson’s Law. It states, that a project will always fill the available time. If you have two weeks, it will take you two weeks. If you have two years, it will take two years.
Cal Newport dug up the original article in which C. Northcote Parkinson describes how the naval bureaucracy grew after World War I was won.
Tyler Wetherall writes in the New York Times about how she helped her ex-boyfriend recover from memory loss:
To break up with someone is to lose the imagined future you would create together, but you would always share the landscape of your collective past. If Sam could not remember, I would be alone in that landscape.
YouTubers MrWhoseTheBoss and MKBHD explain the techniques tech companies use to get a more positive coverage of their products.