☕️ (R)emote Expresso #42

Hi (R)emotes,

☕️ (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,

Remote work promised pajama pants, no commute, and blessed freedom from microwave fish in the break room.

What it didn’t warn us about? The quiet ache of loneliness.

Gallup says 1 in 5 employees worldwide felt lonely just yesterday.

Buffer ranks loneliness as the #2 pain point for fully remote workers (collaboration still wins #1).

And the U.S. Surgeon General? He says loneliness hits your health like smoking 15 cigarettes a day.

So this isn’t a “just get out more” situation. It’s a crisis.

🎭 How Each Generation Feels It

• Gen Z: Launched their careers on Zoom. Still waiting for their first “real” water-cooler moment.

• Millennials: Juggling Slack, childcare, and caregiving. Busy ≠ connected.

• Gen X: Grew up on cubicles and side-eye across the conference table. The silence cuts.

• Boomers: Know the rhythm of the office. Remote feels like semi-retirement… without the golf.

Different flavors, same ache.

🌐 Why This Belongs in (R) Generation

Because no matter what year your driver’s license says, we’re wired for connection.

Because fixing loneliness isn’t a perk - it’s survival.

Because bridging generations is how remote work avoids becoming exile.

Remote work isn’t about productivity hacks or saving commute time. It’s about reimagining how humans find belonging when we’re scattered across time zones, cultures, and kitchen tables. Loneliness is the tax we pay when connection is an afterthought. But here, in (R) Generation, we treat connection as the main event.

We experiment with new rituals. We test playful structures. We design for trust, not just tasks. And when we succeed, we don’t just survive remote work - we create teams that feel alive, creative, and capable of more than the sum of their Zoom squares.

Loneliness isn’t “your problem” or “my problem.” It’s our problem. Which means we get to reimagine remote work, together.

✨ This Week’s Workshop: From Chaos to CLICK

If you’ve ever felt like your “team” is really just a bunch of parallel solo acts - you’re not alone. Most remote groups confuse collaboration with coordination. The result? Leaders buried in firefighting, teammates stuck in silos, and endless noise instead of clarity.

That’s why I’m thrilled for this week’s We Are The (R)emotes session:

From Chaos to CLICK with Daria Rudnik — Team Architect, Strategic Clarity coach, and creator of the C.L.I.C.K. framework.

In this interactive workshop, Daria will show you how to:

• Spot the difference between a true team and a “group project in disguise.”

• Assess where your team lands on the maturity scale.

• Restructure communication so collaboration becomes smoother, smarter, and way less exhausting.

This isn’t theory - you’ll leave with a hands-on Miro template and practical tools to cut through the noise and actually lead without the constant fire drill.

📅 Thursday, Sept 11 | 7:00 AM CDT

💛 Free, in partnership with Miro + Butter

Remote work doesn’t have to feel like chaos. Let’s build teams that click.

🧩 Science-Backed Fixes (Now With Sass)

1. Change your scenery. Coffee shop, library, co-working space - your brain needs background humans.

2. Use video for connection. A quick Loom or call beats a 27-message Slack spiral.

3. Find your micro-communities. Pet photo channels, random hobby Slacks, virtual lunches. Small ties matter.

4. Protect your boundaries. Your bed is not your office. Rituals help your brain clock out.

5. Push for equity. Ask for stipends, retreats, or perks that include remote workers. Culture changes because we squeak.

These aren’t magic tricks - they’re small, doable shifts that stack up over time. But your best fix might not even be on this list. Let’s get creative.

🪄 AI prompt to try:

“I work remotely and sometimes struggle with loneliness or disconnection. Suggest 10 unconventional strategies (beyond the usual co-working spaces, video calls, or Slack channels) to help me feel more connected. Make them: 1) grounded in research on well-being or social connection, 2) playful and energizing, and 3) realistic for someone who is [insert: introvert / extrovert / parent / single / night owl / etc.]. Include at least one strategy that feels delightfully weird but still possible.”

🪄 Your Turn

Remote work can feel less lonely when we borrow rituals from each other - even the silly ones. I want to hear yours:

• What’s one ritual (big or tiny) that helps you feel connected during the day?

• Or confess: what’s the weirdest thing you’ve said out loud to yourself (or your pets) on a very long remote day?

Still narrating my cats’ inner monologues,

— The (R) Generation Team 🧡

👨‍💻 Big Desk Energy: our biggest startup insights, & stories

✈️ Nomad Cloud: get the latest on remote work and location independence.

🌎 Thrive Remotely: lifestyle and wellness for remote workers

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

🤖 Americans Abroad: insights about visas, residency, & cost of living

🔴 Creator Spotlight: inspiration for world class creators journeys

BE A PART OF
THE R GENERATION COMMUNITY

R GENERATION brings together remote professionals from 50+ countries to explore the future of work through events, workshops, and AI-powered collaboration. Join a community where curiosity meets innovation and connections transcend borders.

Make mischief, not busywork 😼