☕️ (R)emote Expresso #55

☕️ (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,

Your Slack channel spans 50+ countries.

Which means right now, someone on your team is:

• Celebrating a holiday you've never heard of

• Working through a day you have off

• Resting while you're in full hustle mode

• Lighting candles, fasting, feasting, or just... existing through December like it's any other month

And that's not a problem. That's the whole point.

Last week, we talked about protecting your humanity from December's productivity demands. This week? We're celebrating how humanity shows up differently everywhere.

Because remote work gave us something most people never get: the ability to witness 50+ ways of being human, all at once, all equally valid.

Your December doesn't have to look like mine. Your traditions don't have to match the person three time zones over. Your way of marking the year's end doesn't need to be anyone else's way.

Different isn't divisive. It's beautiful.

This week, we're not trying to find common ground. We're celebrating that there isn't one.

The Holiday Slack Paradox: When Nobody Knows What to Celebrate

Let's be honest about what December looks like in a global remote team:

Awkward Slack messages. Someone posts "Happy Holidays!" and three people love-react it while five others ignore it because they're not celebrating anything. Someone else posts a Christmas tree emoji and immediately wonders if they should've been more inclusive. Another person stays completely silent because they don't want to explain (again) that they don't do December holidays at all.

The performance of cheer. Half the team is genuinely excited about time off. The other half is working straight through because their country doesn't recognize these holidays. Everyone's pretending the disconnect doesn't feel weird.

The guilt spiral. You're either guilty for celebrating when others aren't, guilty for working when others are resting, or guilty for not feeling festive when the channel is full of holiday GIFs.

The invisible default. Most companies try to be inclusive by saying "Happy Holidays" instead of "Merry Christmas" - but the whole framework still centers Western Christian traditions. The days off. The year-end timing. The expectation that December is somehow special.

And remote workers feel it most - because you can see it all happening at once. The Pakistani teammate working through Christmas. The American teammate off for two weeks. The Brazilian teammate celebrating something entirely different. The Japanese teammate wondering why everyone's acting like the calendar is ending when their New Year happens later.

How do you honor December without centering one story? How do you acknowledge rest without religious framing? How do you celebrate people without assuming everyone's celebrating the same things?

You start by admitting: there is no one "right" December.

There's just 50+ versions of it, happening simultaneously, all equally valid.

Why It Matters (R Generation Context)

50 Countries, Infinite Ways to Be Human

Here's what makes R Generation different from every other remote work community:

We don't pretend there's a template.

We're not selling you "the remote work playbook" or "the one true way to build culture." We're 50+ countries figuring it out together - messily, beautifully, with all our differences on full display.

And December proves why that matters.

When you work in an office, everyone defaults to the dominant culture. The holidays on the calendar. The traditions in the break room. The way "everyone" does year-end celebrations. You assimilate or you opt out quietly.

But remote work broke that default.

Now you're on a Zoom with someone in Mumbai, someone in São Paulo, someone in Lagos, someone in Melbourne. And December looks completely different to all of them. There's no dominant culture to default to. There's just... all of us, showing up human in different ways.

That's not a bug. That's the feature.

Remote work - especially global remote work - means you get to witness humanity in all its forms. Not the sanitized, corporate-approved version. The real version. The messy, contradictory, infinitely varied version.

You learn that "presence" doesn't always mean showing up on camera. That "connection" happens in a thousand different ways. That "hope" takes different shapes depending on where you're standing.

This is what we're building: a community where different doesn't need to be reconciled. Where your way of being human and my way of being human can coexist without one being "right" and the other being "other."

December is our annual reminder that we're doing something most workplaces can't: celebrating difference instead of erasing it.

The Global Human Collection

Your December Looks Different Than Mine (And That's Perfect)

Let me show you what 50+ countries of humanity actually looks like:

In the Philippines, December starts in September. Simbang Gabi masses begin before dawn. Christmas isn't one day - it's a season, loud and joyful and impossibly long by anyone else's standards.

In Japan, December 25th means KFC and Christmas cake, but it's not a holiday. New Year's is what matters - visiting shrines, sending cards, eating toshikoshi soba for longevity. The year turns over quietly, deliberately.

In Sweden, December 13th is St. Lucia Day - children wear candles in their hair (somehow safely), singing in the dark. It's about light returning, not about any particular religion anymore.

In India, December might mean nothing special, or it might overlap with Diwali's afterglow, or it might just be wedding season. The Western calendar's ending doesn't dictate the year's rhythm.

In Mexico, Las Posadas reenact Mary and Joseph's journey for nine nights. Piñatas. Tamales. Community showing up for each other in ways that have nothing to do with gifts under trees.

In South Africa, December is summer. Braais on the beach. Swimming on Christmas Day. The whole "winter holiday" framing makes zero sense when you're sweating through it.

And for some people? December is just... December. Another month. Another set of deadlines. Another rotation of the earth that doesn't require special meaning or celebration or acknowledgment at all.

All of these are correct.

Not "all of these are valid despite their differences." Not "we should respect each other's traditions even though they're not ours."

All of these are just... how humans do December. Period.

This is what you get when you work remotely with people from everywhere: proof that there's no default human experience. There's just your experience and mine and theirs, all happening at once, all mattering equally.

The Practical Challenge

How to Honor December Without Centering One Story

Okay, so how do you actually DO this? How do you acknowledge that December exists without making it weird for half your team?

Here's what NOT to do:

❌ "Happy Holidays to those who celebrate!" (Translation: Christmas is the default, but we're being polite about it)
❌ Decorating the virtual background with Christmas trees and calling it "festive" (Whose festive?)
❌ Scheduling the "holiday party" on December 20th (Whose holiday?)
❌ Giving everyone December 25th off and calling it "inclusive time off" (Still centering one tradition)

Here's what actually works:

✅ Acknowledge rest without religious framing. "We're slowing down in late December" beats "Happy Holidays." It's honest. It's neutral. It doesn't pretend everyone's celebrating the same thing.

✅ Let people name their own. "What does December look like for you?" Instead of assuming, ask. Let people share if they want. Don't make it mandatory cultural show-and-tell.

✅ Distribute the visibility. If you're posting about Christmas, also post about Hanukkah, Kwanzaa, Winter Solstice, Omisoka, Pancha Ganapati, HumanLight - or better yet, create space for people to share what matters to them without you curating it.

✅ Separate "year-end" from "holidays." Reflecting on the year doesn't require a religious framework. Resting doesn't require a holiday. Planning for 2026 doesn't need to be tied to any particular tradition.

✅ Make time off actually flexible. If your company shuts down for Christmas week, you've just told everyone which holiday matters most. Give people choice about when they take December time off - or don't take it at all.

✅ Stop performing cheer. Not everyone feels festive. Not everyone wants to. A simple "December vibes to all who need them, and regular Tuesday vibes to everyone else" goes further than forced jolliness.

The goal isn't to celebrate everything equally. That's exhausting and performative.

The goal is to stop defaulting to one thing and calling it universal.

The Invitation

Show Us Your Human

Here's what I want from you:

Share one way December shows up for you that's uniquely yours.

Not to educate the rest of us. Not to justify your tradition or explain its history. Just to be witnessed by this community.

Maybe it's:

• A food your family makes that nobody else has heard of

• A way you mark the year's end that has nothing to do with holidays

• A ritual you've invented that's just yours

• A belief you hold about this time of year that doesn't fit anyone else's framework

• The fact that December is just another month and that's perfectly fine

This isn't cultural exchange. This is human witnessing.

We're not trying to learn about each other's traditions so we can be "good global citizens." We're just... seeing each other. Acknowledging that your way of being human exists. That it matters. That it doesn't need to be translated or explained or made palatable.

You exist. Your December exists. That's enough.

Drop it in the comments, send it in a reply, share it in the R Generation Circle - however you want. The point isn't to collect stories. The point is to remind all of us that there are 50+ ways to be human in December, and every single one of them is valid.

Your weird is our beautiful.

AI Prompt of the Week

Craft Inclusive December Messages.

Ready to communicate with your global team without accidentally centering one culture? Try this:

Let AI help you navigate December with actual inclusion - not just corporate buzzwords.

Your Turn

💬 Show Us Your December

What's one way December shows up for you that might surprise the rest of us?

Maybe it's a tradition nobody outside your family/culture knows about.
Maybe it's that December means absolutely nothing to you and that's valid.
Maybe it's a ritual you invented that's just yours.
Maybe it's how your December looks wildly different from the "standard" narrative.

Or flip it: What's one thing you learned about someone else's December that changed how you see this month?

Hit reply and tell us. The most beautiful shares might just make it into a future Expresso - but mostly, we just want to witness your human. ☕️🌍

Taking Your Human Into 2026 + Message from Deb

Here's what I want you to take into 2026: Pick one. One way someone else in this global community stays human that resonated with you. One ritual. One belief. One small act of presence or creativity or hope. Borrow it. Adapt it. Make it yours.

Not as a resolution. As protection. Because 2026 will try to make you efficient again. Productive. Optimized. And you'll need reminders that you're human first.

This community - these 50+ countries, these thousands of different ways of showing up - this is your proof that there's no one right way to be human. There's just your way. And it's enough.

From Me to You 💜

This is my last newsletter of 2025, and I’m saying: thank you for letting me be weird here.

When I started writing ☕️ (R)emote Expresso in March, I had no idea what I was doing. I'd never written a newsletter that wasn't corporate communications. I didn't know if anyone would read it. I definitely didn't know if my voice - the sass, the rebellion, the questionable metaphors - would land.

But you showed up. You read. You replied. You told me when something resonated and when I missed the mark. You made weird feel like home.

This year, I learned that my strength isn't in having all the answers - it's in asking better questions and creating space for all of us to figure it out together. That's what this community does. That's what you do.

So as we close out 2025: You don't owe anyone a strong finish. You don't need a perfect plan for 2026. You don't have to optimize your way into the new year.

You just have to stay human. And from what I've seen in this community - across 50+ countries, infinite time zones, and more Slack channels than any of us can keep up with - you're already doing that beautifully.

See you in 2026. Stay weird. Stay human.

— The (R) Generation Team 🧡 🫶🏻

PS: Your way of being human doesn't need to match anyone else's. It just needs to be yours. Protect it. ✨

👨‍💻 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.

Join us where bold ideas meet global community, and where 50+ ways of being human make all of us stronger.