☕️ (R)emote Expresso #60

☕️ (R)emote Expresso is your weekly dose of creator insights on remote collaboration designed to fuel your day, delivered once a week in your inbox 💌

Hey Remote Rebels and Digital Daydreamers,

I have a confession: Last Monday, I was on a call with community leads and we spent 15 minutes discussing which Muppet each of us would be.

Zero deliverables. No action items. Completely useless.

And it was the most productive thing we did all week.

Not because it generated output. Because it generated something we'd been running on fumes without: actual connection.

Here's the reality about remote work: The meetings that produce nothing often produce everything.

The play isn't a break from the work. It's the structure that makes the work possible.

So this week, we're making the case for the most radical act in remote work culture: protecting time that looks completely pointless.

What We Lost When Productivity Became the Point

Remote work promised flexibility. Instead, we turned every interaction into a transaction.

Every meeting needs an agenda. Every conversation needs a purpose. Every five minutes needs a deliverable.

We optimized connection right out of existence.

Here's what actually disappeared:

The wandering conversation. The kind that starts with "how was your weekend" and ends up solving the problem you've been stuck on for three weeks. You can't schedule serendipity.

The permission to be human. When every interaction is measurable, being playful feels unprofessional. Being silly feels like wasting time. Being yourself feels like a performance review risk.

The trust that makes everything else work. You can't collaborate with people you don't actually know. And you can't know people through status updates and Jira tickets.

The ideas that come from nowhere. Breakthrough thinking doesn't happen in structured brainstorms. It happens in the margins - the moments when nobody's performing competence and everyone's just... present.

We didn't mean to kill play. We just made everything else feel more urgent. And now we're wondering why our teams feel brittle, burned out, and barely holding on.

What if the "waste of time" is the only thing holding your team together?

Why It Matters

This isn't about being more fun or building culture or any other HR buzzword.

This is about survival.

When teams skip play, here's what breaks:

Psychological safety disappears. You can't build trust through task management. Trust comes from moments when someone shows up as themselves and nothing bad happens. Play creates those moments. Productivity meetings don't.

Innovation dies. Your best ideas don't come from structured brainstorms where everyone's performing competence. They come from the conversation that wandered off-topic, got weird, and stumbled into something brilliant.

Burnout accelerates. When every interaction is transactional, work becomes exhausting. There's no release valve. No moment where you can just be human without it needing to produce something.

People quit quietly. Not always by leaving. Sometimes by staying but checking out. When work is all output and no connection, people stop caring. They show up. They deliver. They're gone.

Remote work stripped away the accidental moments - the coffee break chat, the hallway conversation, the lunch where nothing work-related happens but everything work-related gets easier afterward.

If you don't protect time for play, you're not saving time. You're spending the trust you need to actually function.

And here's the truth nobody wants to hear: The teams that waste time together stay together. The teams that optimize every minute? They're already looking for the exit.

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How Each Generation Plays (Or Forgot How To)

Gen Z: You were told to "bring your whole self to work" and then got written up for being too casual in Slack. Play feels risky because the rules keep changing. You learned early: professionalism means performing serious. So you edit every message three times and wonder why work feels exhausting when you're just... existing.

Millennials: You remember when work had ping pong tables and "culture" as a selling point. But play was always branded, always sanctioned, always with a purpose. Now you're managing teams and you want to create space for fun - but you're not sure if it counts unless there's an icebreaker agenda and a Miro template.

Gen X: You grew up when work and life were separate. Play happened after 5pm. Now remote work blurred everything and you're not sure where play fits anymore. The idea of "wasting time" on a call feels indulgent when you've got three hours of email to catch up on. But you miss the days when people just... hung out.

Boomers: Play at work wasn't a thing you talked about - it just happened. The conversation in the hallway. The joke before the meeting started. The lunch that wasn't about work but somehow made work easier. Remote work took those moments away and nobody bothered to rebuild them. You're wondering if anyone else notices what's missing.

Different generations. Same loss: We all forgot that play isn't a perk. It's the foundation.

Fixes: Reclaim the Pointless Meeting

You can't wait for permission. Start small. Start weird. Start this week.

Block "Pointless Meeting" time on your calendar. 15 minutes. Once a week. No agenda. No deliverables. Just show up and see what happens. Call it "Creative Caffeine" or "Chaos Hour" if "pointless" feels too rebellious for your company culture.

Start meetings with 2 minutes of completely unrelated conversation. Ask: What's the weirdest thing you've seen this week? What fictional character would solve this project better than us? If this meeting was a snack, what snack would it be? Sounds stupid. That's the point.

Institute "No Business Fridays" for 15 minutes. Last 15 minutes of the last meeting every Friday - no work talk allowed. Memes only. Pet appearances mandatory. Complaints about the week encouraged.

Create a "Weird Wins" channel. Celebrate the moments that didn't produce output but created connection. Someone's kid crashed a client call and made it better? Document it. Team went off on a tangent about cheese? Screenshot it.

Use AI to generate play prompts. When your team is stuck or exhausted, ask AI: "Give me 5 completely ridiculous icebreaker questions that would make a burned-out remote team laugh." Then actually use them.

Rotate "Chief Fun Officer" weekly. One person each week is responsible for starting one meeting with something completely pointless. No pressure to be clever. Low effort is encouraged. The weirder, the better.

Protect the wandering conversation. If someone goes off-topic in a meeting and it's actually interesting - let it wander. Not every deviation is a distraction. Some are the whole point.

Schedule "Creative Collisions." Random 15-minute 1:1s between people who don't normally work together. No agenda. No purpose. Just "hey, we're humans who work in the same place - let's talk."

AI Prompt of the Week

Role: You are a workplace culture consultant specializing in psychological safety, play theory, and remote team dynamics.

Objective: Help me design low-stakes, high-connection rituals that make play feel safe and normal on my remote team - without turning it into forced fun or corporate cringe.

Context: I work on a [insert: fully remote / hybrid / distributed] team of [insert: size and roles]. Right now, every meeting feels transactional. People are efficient but disconnected. I want to protect time for play, but I need it to feel organic, not mandated. I'm looking for things that work for [insert: introverts / different time zones / people who hate icebreakers / burned-out teams / etc.].

Output: Give me 5 specific, actionable rituals to normalize play on my team. Make them:

1. Grounded in research on psychological safety, play theory, or team cohesion

2. Low-effort and energizing (not performative or exhausting)

3. Realistic to implement in the next two weeks

4. Include at least one ritual that feels delightfully weird but still possible

For each ritual, include: what it is, why it works, and one concrete example of how to launch it without making it feel forced.

Role: You are a workplace culture consultant specializing in psychological safety, play theory, and remote team dynamics.

Objective: Help me design low-stakes, high-connection rituals that make play feel safe and normal on my remote team - without turning it into forced fun or corporate cringe.

Context: I work on a [insert: fully remote / hybrid / distributed] team of [insert: size and roles]. Right now, every meeting feels transactional. People are efficient but disconnected. I want to protect time for play, but I need it to feel organic, not mandated. I'm looking for things that work for [insert: introverts / different time zones / people who hate icebreakers / burned-out teams / etc.].

Output: Give me 5 specific, actionable rituals to normalize play on my team. Make them:

- Grounded in research on psychological safety, play theory, or team cohesion
- Low-effort and energizing (not performative or exhausting)
- Realistic to implement in the next two weeks
- Include at least one ritual that feels delightfully weird but still possible

For each ritual, include: what it is, why it works, and one concrete example of how to launch it without making it feel forced.

Your Turn

What's the most pointless thing your team has done together that actually mattered? Or confess: when's the last time you had a work conversation that didn't need to produce something?

Reply to this email or share in the Community. The best ones might show up in a future Expresso.

Closing Transmission

Productivity will tell you every minute matters.

Connection will tell you some minutes matter more.

The meetings that look pointless? Those are the ones holding everything else together.

So this week, waste some time. Go off-topic. Let the conversation wander. Spend 15 minutes on something that produces absolutely nothing but the feeling that you're not alone in this.

Your team doesn't need another deliverable. They need a reason to stay.

Play isn't the break from the work. It's the thing that makes the work survivable.

— The (R) Generation Team 🧡 🫶🏻

PS: The Muppet conversation? I'm a cross between Miss Piggy & Animal. Unapologetically extra, occasionally feral, and absolutely committed to mischief. What's yours?

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