Last week, walking my dog Biba back from the mailbox, I found an actual letter. Handwriting on the envelope. It stopped me mid-step: that old warmth of being thought of by someone who wasn't in the room. Strange, because a letter is about as far from "being in the room" as communication gets. You write, you wait days, they read it alone... and it still did exactly what CEOs insist only an office can do.
A letter takes real effort to produce. Someone sat down, found the words, addressed an envelope, and waited days without knowing whether any of it landed. Effort and intention created that warmth; the paper just carried it. A shared office worked the same way. It happened to be the medium effort and intention usually traveled through.
That's what leaders get backwards when they talk about missing the office. The office was never the source of connection. It was one medium among many that forced effort and intention to happen as a side effect: the hallway run-in, the shared lunch. We've built a whole mythology around that accident, as if a building were doing something a building can't do. The feeling of loss is real. But the fix keeps getting aimed at the wrong target, a building, because a building is what you can see and budget for.
Companies that have been remote for years already found the right target: batch your in-person time and spend it on purpose.
MailerLite has been fully remote for over a decade and leaves nothing to accident. Every team gets its own annual trip to its own destination: eleven "Work-together" events across ten countries in one recent year, Budapest to Malta to Rio de Janeiro. They live together for the week, cook together, and go home already knowing each other better. The budget line is the easy part. The deliberate effort behind each trip is what does the work.
Doist didn't get it right on the first try, which makes them the better example. Since 2018 they've sent individual teams on their own mini-retreats, separate from their company-wide alignment retreat. It worked, until teams kept hitting points where their work depended on another team that wasn't in the room. So this year Chase Warrington, Doist's Head of Operations, tried one location: 95 people, 60-plus workshops, 10 teams, five days, so any team could get focused time and still pull in whoever the work needed. His own framing, posted the day it started: "Great idea or fixing something that isn't broken?" They never stop rethinking the employee experience and what valuable connection means.
So here's the actual ask. Everyone wants connection at work; that instinct was always right. Go after the thing you're actually missing. Build culture on purpose, and hire people who make it worth building. Then do the smallest deliberate version of what MailerLite and Doist do: pick one team, give it a real budget and a week together, and see what comes back. That single line item buys more genuine connection than a year of hoping the hallway does it for you.
I don't get a letter every day. If I did, I'd stop reading the envelope before I opened it. A retreat runs on the same math: rare, deliberately built. The effort and intention is what earns the moment.
