☕️ (R)emote Expresso #27

Hi (R)emotes,

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

Hey Remote Rebels and Digital Daydreamers,

Let’s call it.

Not all teamwork is collaboration.

And some of what we’re labeling “remote collab” is just a chaos spiral dressed in Notion links and good intentions.

You know the flavor:

• 5 meetings a week, no decisions.

• 10 people in a doc, no clarity.

• “Quick syncs” that eat your whole afternoon.

It looks collaborative.

But it feels like burnout - slow, frustrating, disconnected.

This week, we’re unmasking the illusion. Because collaboration isn’t about checking a box. It’s about building something real… together.

🔥 CHAOS IN COSTUME: RED FLAGS TO WATCH FOR

📆 You’re in meetings constantly - and still unclear on the goal.

• Alignment should reduce chaos, not multiply it.

👩🏻‍💻 Everyone adds comments - no one makes decisions.

• When feedback becomes the end instead of the means, you’re in loop limbo.

🗣️ One loud voice dominates. The rest nod like it’s hostage footage.

• This isn’t co-creation - it’s control with better lighting.

🎨 The deck is gorgeous. The outcomes? Confused.

• Collab theater looks productive. But it doesn’t move anything forward.

💥 THE ILLUSION OF COLLABORATION

Remote work gave us a thousand tools to look like a team.

And zero space to ask: Are we actually acting like one?

We confuse activity with alignment.

We measure collaboration by how full our calendars are - not by what we’re actually building.

And so we:

• React instead of create

• Edit instead of decide

• Watch the “collab doc” turn into a slow-motion pile-on of polite ideas no one believes in

Collab ≠ chaos with a timestamp.

🤝 WHAT REAL COLLABORATION LOOKS LIKE

Real collaboration feels different.

It’s not smoother - it’s sharper. Clearer. Braver.

It asks more of us - and gives us back something better:

🔧 Structure with space - Clear roles, with room to contribute.

💬 Psychological safety - Where disagreement doesn’t derail momentum.

🎯 Collective ownership - It’s ours, not mine vs. yours.

You’ll know it’s real when:

• You leave energized, not exhausted.

• Quiet voices are invited - not sidelined.

• The messy middle doesn’t scare the team.

• Progress is tangible, even if it’s not perfect.

✅ COLLAB THAT ACTUALLY WORKS: 4 QUICK FIXES

1. Stop inviting everyone.

Invite contributors, not spectators. Fewer voices = more clarity.

2. Name the decider.

Collaboration dies in limbo. Assign a “decision driver” from day one.

3. Build async muscles.

Not everything needs a call. Use Loom, voice notes, comments - but set a clear purpose + deadline.

4. Choose shared ownership, not shared docs.

True collaboration isn’t “we all touched it.” It’s “we all believed in it.”

🗓️ TWO EVENTS THIS WEEK THAT GET IT

🤖 Build Bots That Connect

Tuesday, May 28 | 60 min | No-Code Friendly

With Marion Zoé Puertas

Tired of bots that sound like elevator hold music? Marion will walk you through building an AI bot with personality, clarity, and purpose — even if you’ve never done it before.

🎤 Human connection + AI = actual collaboration

🫶 COWORK is in the (R)

Thursday, May 30 | 90 min | For Remote Creatives

With Tatiana Rodriguez

Focus sprints. Gentle accountability. A quiet room full of big ideas. Bring your mess, your magic, and that thing you’ve been “totally getting to” since Tuesday.

💻 Come create with other humans (not just your inbox)

🫶 ONE LAST SIP

Collaboration shouldn’t feel like a group project where one person does all the work.

It should feel like progress. Alignment. Shared joy - even when it’s hard.

So the next time your collab starts looking like chaos in costume?

Rip off the mask.

Name what’s broken.

Rebuild what matters.

Together.

With clarity and caffeine,

— The (R) Generation Team 💜

👨‍💻 Big Desk Energy : Our biggest startup insights & stories

🦾 EverydAI : AI news for Founders & C-Suite Executives

🌎 Thrive Remotely : Lifestyle and Wellness for Remote Workers

👩‍🎤 Customer Success Jobs : Our remote high-paying jobs for you

🤖 Responsible : Responsible business practices in AI & cybersecurity

🔴 Creator Spotlight : Our favorite inspiration for world class creators journeys

R GENERATION is a dynamic global community where remote professionals, creators, and digital nomads come together to reimagine the future of work. We bridge cultures, time zones, and creative frontiers, uniting around a shared passion for innovation and meaningful connection.

Through engaging events, hands-on workshops, and exclusive access to cutting-edge AI tools, we’re transforming remote work into a space for bold experimentation, open knowledge-sharing, and limitless growth.

Join us in a collaborative and empowering environment where your ideas spark innovation, your curiosity fuels lifelong learning, and your ambition shapes the future of remote collaboration.

Go forth and disrupt the chaos. Loudly. Lovingly. With receipts. 💥