☕️ (R)emote Expresso #61

☕️ (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,

Boris is out. I'm covering the January roundup.

Full transparency: I have no idea what I'm doing.

What's supposed to go in a roundup? Month highlights? Event recaps? Inspirational leadership thoughts about crushing Q1?

I'm a Gen Xer. I don't crush quarters. I show up, wing it, and hope nobody notices I'm making this up as I go.

So here's what I saw happen in January in the R Generation community - the messy, unpolished version from someone who definitely wasn't supposed to be writing this.

The truth? Nobody's coming to tell you it's your turn. Sometimes you just... take it.

I grew up learning to respect authority - but only when it earned respect. When the person in charge is busy, somebody's gotta step in. Today, that's me. The clueless intern with newsletter access.

Welcome to the unauthorized January edition. We're all figuring this out together.

What Actually Happened in January (The Messy Real Version)

Okay, so Boris usually does this with polish and structure. I'm doing it with screenshots from Circle and a prayer.

January kicked off with a retrospective. Marion, Clotilde, Silvia, Tobias, Steve, Rodrigo, Quinn, Maeva (our AI crew), and a bunch of us gathered to look back at 2025 and forward to 2026. Boris said it best: "We're not predicting 2026, we're surfing it." That retrospective was emotional, energizing, and the reminder we all needed that community isn't about rigid goals - it's about riding the waves together.

We launched Premium Membership. Not with fanfare - just with "hey, some of you asked for more structure, here it is." Founding pricing locked in. People showed up. The ones who were ready to go from consuming to creating together.

The Miro Engage launch happened. Jakob Knutzen and Christopher Holm-Hansen walked through the real thing - V1 limitations and all. The kind of transparency that builds trust instead of hype. Because remote workshops still suck in 2026, and they're done with it.

Boris had a birthday. Jakob Knutzen showed up on his teleprompter to record an entrepreneurial journey conversation. Boris's caption: "The real value of life: sharing time and experience with the people you like." That's (R) Generation in one sentence.

Shruti Agarwal dropped an episode on soft skills. Turns out they're not optional - they're transformational. "Even reaching out to someone senior can open doors you didn't know existed."

Adrien Heury launched Suitable Timezone. Because managing multiple time zones is a constant source of friction, and he just... built the solution. No permission. Just did it.

Remote job opportunities got shared by community members. Two AI/ML engineering positions. Open to all followers. Because that's what we do here - we share the opportunities.

Three Expressos dropped. Curiosity recession. Performing fine. Play beats productivity. The metrics were mixed. Some landed. Some didn't. We're learning what resonates when the world won't stop breaking.

And somewhere in there, people just kept showing up. In Circle. On calls. In DMs. Asking questions. Offering help. Starting things without permission. Being human in a space that protects that.

January wasn't perfect. It was real. And honestly? That feels more valuable.

What I've Learned This Week

I'm covering for Boris. And honestly, I'm winging it.

Here's what became visible when I stepped into a role I wasn't trained for:

Most of us are waiting for someone to tell us it's okay. To start the thing. To try the experiment. To admit we don't know. To just... do it.

I grew up Gen X - which meant a lot of "figure it out yourself" parenting. I learned to respect authority when it showed up real. But when it didn't? You just handled it.

Remote work stripped away the visible hierarchy. There's no boss watching. No one standing over your shoulder saying "good job, carry on."

Which means: If you're waiting for permission, you might be waiting forever.

This week, I didn't ask if I could write the roundup. I just wrote it. And nothing broke. Nobody fired me. The world kept spinning.

That's not about being Gen X. That's about what happens when you realize the person who's supposed to authorize you... might just be you.

What Happens When You Stop Waiting

Last year, I was working on a global program building a taxonomy for HR capabilities and skills. We were tracking everything in Google Sheets. It was a mess. Hard to follow. Definitely not working.

I thought: a Miro board would fix this.

So I built it. Nobody asked me to. I just did it because the problem was there and I had an idea.

Nine months later - this week, actually - the organization sent me a leadership certification.

Not because I lobbied for recognition. Not because I pitched my value. Because I built something that solved a problem, and eventually someone noticed.

Here's the thing about unauthorized action: the payoff isn't immediate.

You build the thing. You solve the problem. You move on. And maybe - months later, or never - someone says "oh hey, that mattered."

But the taxonomy got built either way. The work moved forward. That was the point.

Remote work trains us to wait for approval before we start. Business owners just start. They see what's missing and they build it. The recognition - if it comes - shows up later. Sometimes way later.

This is February. Q1 plans are probably sideways. Your team is still figuring it out.

You can wait for someone to fix it. Or you can just build the thing and see what happens nine months from now.

(I just realized that 9 months can be a very loaded timeframe for some… I could rewrite it but nah - Boris won’t read this. 🤞🏻)

The Permission Problem: By Generation

Gen Z: You launched careers on Zoom into a world that kept changing the rules. Every move feels documented. Every mistake feels permanent. So you ask first - for feedback, for approval, for confirmation you're doing it right. Not because you're incapable. Because the cost of getting it wrong feels too high.

Millennials: You were told to follow your passion, disrupt industries, be authentic. Then you got into the workforce and learned that actually meant "ask permission politely and have a deck ready." Now you're managing teams and stuck between wanting to empower people and needing to cover your own ass. So you create processes. Safe spaces. Clear guidelines. All the structure you wish someone had given you.

Gen X: You figured it out alone because nobody was watching. That made you resourceful. It also made you suspicious of anyone who claims they have all the answers. You don't wait for permission because you learned early: nobody's coming. But you also don't always tell others it's okay to just try things - because you assume they already know.

Boomers: You built careers in systems with clear hierarchies. Permission wasn't a question - it was the structure. Now everything's flat, distributed, and nobody's asking anymore - they're just doing. It feels like the guardrails disappeared. Some of you adapted. Some of you are still waiting for someone to draw the org chart that makes sense.

Different generations. Same trap: We're all waiting for something - clarity, approval, proof we won't fail. Meanwhile, the work that matters is happening when someone just decides to start.

Hang out & Tinker: The Unauthorized Experiment

Speaking of not waiting for permission...

I'm starting something new. Nobody asked me to. Nobody approved it. I just decided it needed to exist.

Hangout & Tinker with Deb - a bi-weekly, low-pressure coworking hang for curious remote humans who want to experiment with tools, ideas, and things you haven't tried yet because there's no "official" reason to learn them.

No agenda. No deliverables. No performance required.

Just: show up, try the thing, see what happens.

Maybe you want to mess around with AI prompts. Maybe you're curious about Miro templates. Maybe you just want to be in a room with other people who are figuring things out in real time without pretending they have it all together.

This isn't a workshop. It's not a masterclass. It's the remote work equivalent of staying after school to mess around in the art room.

Why I'm doing this: Because waiting for the "right" training or the "official" learning path means you never actually learn. You just collect bookmarks and good intentions.

Who it's for: Anyone who's tired of waiting for permission to try things.

When: Starting Wednesday, March 11, 10:00 AM - 12:00 PM CST

Bi-weekly from there.

I have no idea if this will work. But I'm done waiting to find out.

Fixes: Stop Waiting

You don't need permission. You just need to start.

Identify one thing you've been waiting to try. Not the big thing. The small thing. The 15-minute experiment. The tool you bookmarked six months ago. The question you've been afraid to ask. Write it down.

Do it this week. Without asking. Don't announce it. Don't create a plan. Don't wait for the perfect time. Just try it. Messy counts. Half-done counts. "I have no idea what I'm doing" absolutely counts.

Tell one person you're trying it. Not for permission. For accountability. "I'm experimenting with X this week" is enough. You're not asking if you should. You're saying you are.

When someone asks "who approved this?" - own it. "Nobody. I'm just trying it." That's the whole answer. You don't owe justification for learning.

Start something nobody asked for. A Slack channel. A weekly experiment. A 15-minute coffee chat. If it doesn't work, you'll know. If it does, you just solved a problem without waiting for someone else to notice it existed.

Stop saying "I'll look into that." Either do it now (5 minutes) or admit you're not going to. There's no shame in "not interested." There's waste in pretending you'll get to it "later."

Model unauthorized action for your team. "I tried this thing. It didn't work. Here's what I learned." Permission to fail is permission to try. Show them what that looks like.

AI Prompt of the Week

Role: You are a workplace culture consultant specializing in self-directed work, psychological safety, and remote team dynamics.

Objective: Help me identify where I'm waiting for permission and design my own authorization to move forward.

Context: I work in a [insert: fully remote / hybrid / distributed] environment as a [insert: role]. There's something I want to try/start/build, but I keep waiting for [insert: approval / clarity / the right time / someone else to do it first]. The thing I want to do is: [insert your specific idea or experiment]. I'm held back by [insert: fear of looking stupid / not being "qualified" / unclear who to ask / worried about stepping on toes / etc.].

Output: Give me 5 specific strategies to authorize myself to move forward. Make them:

1. Grounded in research on self-directed work or psychological safety

2. Practical and low-risk (I need to start small, not blow everything up)

3. Include concrete first steps I can take this week

4. Address my specific barrier without requiring me to become someone I'm not

5. Include at least one strategy that feels surprisingly simple but still effective

For each strategy, include: what it is, why it works, and exactly how to start.

Role: You are a workplace culture consultant specializing in self-directed work, psychological safety, and remote team dynamics.

Objective: Help me identify where I'm waiting for permission and design my own authorization to move forward.

Context: I work in a [insert: fully remote / hybrid / distributed] environment as a [insert: role]. There's something I want to try/start/build, but I keep waiting for [insert: approval / clarity / the right time / someone else to do it first]. The thing I want to do is: [insert your specific idea or experiment]. I'm held back by [insert: fear of looking stupid / not being "qualified" / unclear who to ask / worried about stepping on toes / etc.].

Output: Give me 5 specific strategies to authorize myself to move forward. Make them:

1. Grounded in research on self-directed work or psychological safety
2. Practical and low-risk (I need to start small, not blow everything up)
3. Include concrete first steps I can take this week
4. Address my specific barrier without requiring me to become someone I'm not
5. Include at least one strategy that feels surprisingly simple but still effective

For each strategy, include: what it is, why it works, and exactly how to start.

Your Turn

What's one thing you built, started, or tried without waiting for permission? Or confess: what are you still waiting for authorization to do?

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

Closing Transmission

Boris will be back.

Until then, I'm here - writing roundups nobody asked me to write, launching experiments nobody approved, and showing you what happens when you stop waiting for authorization.

January taught us something: communities don't fall apart when the leader steps away.

February is messy. Q1 is sideways. The world is still breaking.

But the work that matters? It's in the margins. The unauthorized experiments. The moments when someone sees a problem and builds the solution instead of waiting for permission.

You don't need perfect conditions. You don't need a clear plan. You don't need someone to tell you it's your turn.

You just need to start.

The recognition - if it comes - shows up later. The work shows up now.

— The (R) Generation Team 🧡 🫶🏻

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