60 min read

The Anywhere Operating System

A free book on how to run your business from anywhere.

By Luke Thomas | Published April 2022

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Table of Contents

Preface: Why I wrote this book

In 2013, I was living in Boston, working in a traditional office like millions of other people. I had a laptop. I had an internet connection. And one day, a question hit me that I couldn’t shake: if I do all of my work from a laptop, why do I need to live in Boston?

It wasn’t a philosophical question. It was a practical one. I was paying exorbitant rent to live near an office where I spent most of my time staring at a screen, typing on a keyboard, and hopping between video calls and Slack conversations. The work wasn’t tied to the building. It was tied to me and my colleagues, wherever we happened to be.

That realization set me on a path. Over the following years, I worked remotely across multiple companies in a variety of roles. I experienced firsthand what it means to collaborate with people you rarely see in person, to build relationships through screens, and to try to do meaningful work without the ambient structure that an office provides. Along the way, I kept running into the same challenges, over and over again.

I struggled to understand what my colleagues were actually working on. I found it difficult to connect my daily tasks to the company’s bigger goals. Building genuine relationships with teammates I’d never met in person felt unnatural. And the meetings — the endless meetings — were almost universally unproductive, filling calendars while emptying the hours available for real work.

These frustrations eventually led me to launch Friday, a software company designed to help distributed teams work better together. We built tools for async check-ins, goal tracking, and team alignment. And through that work, I got a front-row seat to how hundreds of companies were navigating the same challenges I’d experienced.

Then COVID hit. Overnight, the number of people working remotely increased roughly tenfold. Companies that had never considered remote work were suddenly thrust into it with no playbook, no infrastructure, and no cultural norms to fall back on. The results were predictable: Zoom fatigue, disengaged employees, managers who didn’t know how to lead without walking around the office, and workers who felt more connected to their Slack notification sounds than to their actual teammates.

I looked for a practical, no-nonsense guide to help these companies. A book that would say: here’s how you actually make this work, day by day, meeting by meeting, hire by hire. I couldn’t find one. Most of what existed was either too academic, too high-level, or too focused on the why of remote work without addressing the how.

So I wrote one. This book is co-written with Aisha Samake, and it’s designed to be the practical how-to guide I wish I’d had when I started working remotely almost a decade ago. It covers everything from asynchronous communication to hiring to leadership to burnout. It’s opinionated, because I believe the worst thing you can do is hedge when people need clear guidance. And it’s grounded in real experience, not theory.

Whether you’re a founder figuring out your company’s operating model, a manager leading a distributed team for the first time, or an individual contributor trying to do your best work from your kitchen table, this book is for you.

Chapter 1: What if the office is the new invention?

We tend to think of remote work as the disruption and the office as the default. But if you zoom out far enough, the opposite is true. The modern office is a remarkably recent invention, and for most of human history, work happened wherever people happened to be.

The word “office” itself traces back to the Latin officium, which didn’t describe a place at all. It described a duty, a service, a sense of obligation. For the Romans, your officium was what you did, not where you did it. The concept of a dedicated room for administrative work didn’t emerge until centuries later, when monks in medieval scriptoriums began organizing themselves around specific locations for reading, writing, and record-keeping. Even then, the “office” was less about the room and more about the ritual — a designated time and space for focused intellectual labor.

The office as we know it — a building full of desks where employees gather to work for a set number of hours — is largely a product of the Industrial Revolution and the rise of large-scale organizations. The British East India Company, one of the first truly massive corporations, needed centralized administration to coordinate its global operations. Clerks, accountants, and managers were brought together under one roof not because co-location made the work itself better, but because it made coordination possible. When your communication technology is a handwritten letter that takes weeks to arrive, physical proximity is a hard requirement.

The invention of the light bulb extended the workday beyond daylight hours, further cementing the office as the locus of productivity. Frank Lloyd Wright introduced the concept of the open-plan office in the early twentieth century, imagining vast, flowing workspaces that would inspire creativity and collaboration. Decades later, Robert Propst at Herman Miller designed the “Action Office” — a modular system of movable walls and surfaces intended to give workers autonomy and privacy. Corporate America looked at Propst’s beautiful, flexible design and turned it into the cubicle: a cost-cutting tool that packed the maximum number of workers into the minimum amount of space. Propst himself called the result “monolithic insanity.”

The point is this: the office was designed to solve a coordination problem that existed in a world of manual work, paper documents, and slow communication. Every major design decision — from open plans to cubicles to corner offices — was a response to the constraints of its era, not a timeless truth about how humans work best.

Now look at the tools we have today. High-speed internet. Real-time messaging. Video conferencing that works (most of the time). Cloud-based documents that multiple people can edit simultaneously. Project management software that makes work visible without requiring anyone to walk over to someone’s desk. The coordination problem that created the office has been largely solved by technology.

Maybe work-from-anywhere is the model that’s grounded in history, and the office is the new invention.

This isn’t an argument that offices are bad or that everyone should work remotely. It’s a reframing. When we stop treating the office as the natural state of work and start seeing it as one option among many, we can make better decisions about how, where, and when work should happen. The goal isn’t to eliminate choice. It’s to offer each employee the choice that lets them do their best work.

Chapter 2: Is working from anywhere a fad?

Every time a major shift happens in how we work, skeptics ask the same question: is this just a fad? They asked it about email in the 1990s. They asked it about smartphones in the 2000s. They asked it about Slack replacing email in the 2010s. And now they’re asking it about remote work.

The answer is no, and it’s not a close call. At least seven structural forces are converging to make work-from-anywhere not just viable but inevitable for a large and growing share of the workforce.

1. The talent problem is geographical

The best person for your open role probably doesn’t live within commuting distance of your office. This has always been true, but companies used to accept the tradeoff because remote collaboration was too difficult. That constraint has evaporated. Companies that restrict hiring to a single metro area are now competing for talent with companies that hire from everywhere. The math doesn’t favor the restrictive approach.

2. The cost of living is unsustainable

The average rent in San Francisco is $3,546 per month. In New York City, it’s $3,073. In Boston, $2,595. These numbers represent a significant portion of even well-paid knowledge workers’ take-home income. Remote work gives people the option to live where their money goes further, which effectively functions as a raise without costing the employer a dime. For many workers, this isn’t a perk — it’s a financial necessity.

3. The commute is a daily tax on your life

The average American commute is 27 minutes each way. That’s nearly an hour a day, five hours a week, and over 200 hours a year spent sitting in traffic or on a train, producing nothing. For many people in major metro areas, the commute is significantly worse. Remote work gives people that time back — time they can spend exercising, being with their families, or simply starting work without the cognitive drain of a morning commute.

4. Millennials are growing up and moving out

The generation that spent their twenties in urban apartments is now in their thirties and forties, starting families, and moving to suburbs and smaller cities. They want yards, good schools, and affordable housing. They also want to keep their careers. Remote work makes both possible. This isn’t a temporary preference — it’s a demographic wave.

5. The technology has finally caught up

Zoom launched in 2011. Slack launched in 2013. Microsoft Teams launched in 2017. Each of these tools made remote collaboration meaningfully easier, and the pace of improvement continues to accelerate. The technology gap between in-office and remote work has shrunk to the point where, for most knowledge work, it’s negligible.

6. Pioneers have proven the model

Companies like Basecamp, Zapier, GitLab, and Automattic have operated as distributed organizations for years, in some cases more than a decade. They’ve proven that you can build great products, create strong cultures, and scale to hundreds or thousands of employees without a central office. These aren’t experiments anymore. They’re established, successful companies that serve as proof points for the entire movement.

7. The office was never designed for deep work

Open-plan offices are collaboration theaters. They’re optimized for spontaneous interaction and visibility, not for the kind of deep, focused thinking that most knowledge work actually requires. Studies consistently show that open offices increase noise, reduce privacy, and fragment attention. For many workers, going to the office means spending the day trying to work despite the environment, not because of it.

Here’s the data point that seals it: 97% of remote workers say they want to continue working remotely, at least some of the time, for the rest of their careers. Once people experience the flexibility, autonomy, and reclaimed time that remote work provides, they don’t want to go back. That’s not a fad. That’s a preference so strong it reshapes labor markets.

The network effects are real. As more companies adopt remote-friendly policies, more workers come to expect them. As more workers expect them, more companies adopt them. This isn’t a cycle that reverses easily. The structural shift toward working from anywhere is real, it’s accelerating, and companies that ignore it will find themselves at a permanent disadvantage in the competition for talent.

Chapter 3: The office vs. remote work

Let’s be honest about both sides of this equation, because the debate around office vs. remote work is plagued by people romanticizing whichever model they prefer while ignoring its flaws.

A typical day at the office

You arrive after a 35-minute commute, grab coffee, and settle into your desk. Within minutes, a colleague stops by to chat about last night’s game. Nice moment. Then your manager swings by with a “quick question” that turns into a 20-minute conversation. You haven’t opened your laptop yet.

At 9:30, there’s a standup meeting. At 10, a cross-functional sync. At 11, a “brainstorm” that three people dominate while everyone else checks email under the table. You get back to your desk at 11:45 with fifteen minutes before lunch. You start working on the thing you actually need to do today, but someone taps you on the shoulder because they’re stuck on something and you’re the person who knows the answer.

After lunch, you have two more meetings. At 3:30, you finally get an uninterrupted block, but your energy is gone. You push through, produce something mediocre, and leave at 5:30 with the nagging feeling that your most important work is still undone. You’ll think about it during your commute home.

A typical day working remotely

You roll out of bed and sit down at your makeshift workspace — maybe a dedicated home office, maybe a kitchen table with a laptop stand. You open Slack, and there are 47 unread messages across 12 channels. You start triaging, responding to the urgent ones, flagging the rest. An hour passes. You haven’t started your actual work.

At 10, you join a video call. Your internet stutters. Someone’s kid walks in. The meeting runs 15 minutes over because there’s no natural endpoint the way there is when a conference room is booked by another team. At 11, you finally start working, but notifications keep pulling you back — a DM here, an @mention there, a “hey, got a sec?” that turns into a 30-minute call.

By afternoon, you’ve been “working” for seven hours but feel like you’ve accomplished very little. You’re also vaguely lonely. You haven’t talked to another human being face-to-face all day. Your work and home life have blurred into an indistinguishable gray zone. You close your laptop at 6:30, or maybe 7, because when there’s no commute, there’s no clear signal that the workday is over.

The honest truth

There is no perfect solution.

Both models have real strengths and real problems. The office gives you informal encounters, ambient awareness of what’s happening, and clear physical boundaries between work and life. Remote work gives you flexibility, quiet, and freedom from the commute. Both can be productive. Both can be miserable.

The real issue isn’t office vs. remote. It’s the gap — the loss of contextual awareness that happens when you move from a co-located environment to a distributed one. In an office, you absorb a surprising amount of information just by being there: who’s stressed, what projects are on fire, which teams are collaborating, who just got promoted. That information flows through the air like oxygen. You don’t notice it until it’s gone.

When you go remote, that ambient information disappears. And the traditional tools we use to replace it — more meetings, more Slack messages, more status updates — don’t actually fill the gap. They just create noise. The challenge of remote work isn’t distance. It’s finding new, intentional ways to create the shared context that offices provided accidentally.

That’s what the rest of this book is about.

Chapter 4: The not-so-secret to remote work

There’s a persistent misconception about people who work remotely: that they’re introverts who want to be left alone. That they chose remote work because they don’t like people. That working from home is fundamentally about isolation.

This gets it exactly backwards.

When you ask remote workers why they prefer working outside an office, the answer is almost never “because I don’t want to interact with people.” It’s almost always about two things: flexibility and autonomy. The ability to structure their day around when they’re most productive. The freedom to handle a personal errand at 2pm and make up the time at 8pm. The capacity to integrate work and life in a way that an office schedule makes impossible.

I like remote work because it helps me better integrate work and life.

Think about it through an analogy. In high school, you’re told exactly when to be in each class, when you can eat lunch, when you can use the bathroom. Your schedule is controlled because you’re a teenager, and the assumption is that you need structure imposed from outside. In college, you choose your classes, manage your own time, and take responsibility for your output. The assumption is that you’re an adult.

Most office culture operates like high school. Be at your desk by 9. Take lunch between 12 and 1. Look busy between 2 and 5. The implicit message is that you can’t be trusted to manage your own time — that without visible supervision, you’ll slack off. Remote work operates like college. Here are your responsibilities. Here are the expectations. Figure out when and how to get it done.

This matters because knowledge work is fundamentally different from physical work. When you’re assembling widgets on a factory floor, your output is directly proportional to the hours you spend at the workstation. When you’re writing code, designing a marketing strategy, or solving a complex problem, your output depends on the quality of your thinking, not the number of hours your body occupies a chair. Some people do their best thinking at 6am. Others hit their stride at 10pm. Some need a long walk in the middle of the day to work through a problem. The idea that everyone should be productive during the same eight-hour window is an artifact of industrial work, not knowledge work.

Here’s the not-so-secret secret: when people say they love working from home, what they really mean is that they love working during their most productive hours. They love not pretending to be productive when they’re not. They love the honesty of a work arrangement that says: we care about what you produce, not when you produce it.

This is the foundation everything else in this book builds on. If you understand that remote work is about flexibility and autonomy — not isolation — then the operating system you build around it will look very different from the one you’d build if you thought remote workers just wanted to be left alone.

Chapter 5: The #1 ingredient to working from anywhere

If there is a single concept that separates companies that thrive remotely from companies that merely survive, it’s this: asynchronous communication.

Async communication means interacting with your colleagues without requiring everyone to be present at the same time. Instead of tapping someone on the shoulder and expecting an immediate answer, you write down your question or update, and they respond when they’re ready. Instead of pulling six people into a meeting to share a status update, you post a written summary that everyone can read on their own schedule.

This sounds simple. It’s not. Because what’s actually hindering work-from-anywhere isn’t distance or technology — it’s habit. Most organizations have deeply ingrained expectations about communication that are rooted in the office model, and those expectations don’t translate to distributed work.

The meeting problem

The average employee attends 61 meetings per month. Workers report that roughly half of these meetings are a waste of their time. That’s 30 wasted meetings per month, per person. Multiply that across your organization and the cost is staggering — not just in hours, but in focus, energy, and morale.

The chat problem

Workplace chat tools like Slack and Teams were supposed to reduce meetings. Instead, they’ve created a new problem: the expectation of constant availability. Studies show that 40% of knowledge workers can’t go 30 minutes without being interrupted by a notification. Slack’s real-time nature means that if you don’t respond quickly, people assume you’re not working. So you stay tethered to the chat window, responding to messages all day, and your actual work happens in the margins — if it happens at all.

The core insight

When work requires your constant presence — whether in meetings or in chat — your colleagues’ availability becomes a mandatory dependency. You can’t make progress until someone responds to your message. You can’t make a decision until everyone is in the same room. You can’t move forward until you’ve checked with three people who are currently in other meetings.

Asynchronous communication breaks this dependency. When you default to async, you liberate people to work on their own schedule, in their own time zone, during their most productive hours. You reduce interruptions. You create a written record of decisions and context that anyone can reference later. And you force clarity, because writing something down requires more thought than saying it out loud in a meeting.

The longer a company works from anywhere, the more they want to communicate asynchronously by default.

This isn’t to say that synchronous communication is bad. Real-time conversations have their place, and we’ll get into when and how to use them in the next chapter. But the default — the starting assumption for any communication — should be async. If something can be written instead of spoken, write it. If a meeting can be replaced by a document, replace it. If a Slack message doesn’t require an immediate response, don’t expect one.

Getting this right is the single most important thing you can do to make distributed work succeed.

Chapter 6: That meeting should have been an email

We’ve all heard the joke. But beneath it is a real framework that can transform how your team communicates. To use it, you need to understand the two fundamental types of communication.

Conveyance vs. convergence

Conveyance is one-directional information transfer. You’re sharing facts, updates, context, or data with someone. The information flows in one direction: from the person who has it to the person who needs it. Status updates, project recaps, announcements, FYIs — these are all conveyance.

Convergence is a two-way process of negotiating shared understanding. You’re not just transferring information — you’re working together to interpret it, discuss it, and reach agreement. Brainstorming, problem-solving, conflict resolution, strategic planning — these require convergence.

The mistake most organizations make is using synchronous communication (meetings, calls) for both types. When you pull eight people into a meeting to hear a status update, you’re using a convergence tool for a conveyance task. It’s the wrong tool for the job, and it wastes everyone’s time.

The async superpowers

Asynchronous communication is the right tool for conveyance, and it has several advantages that meetings can’t match:

The sync superpowers

Synchronous communication has its own irreplaceable strengths:

The decision matrix

When deciding whether a conversation should be async or sync, consider two factors: how strong is your relationship with the other person, and how clear is the topic you need to discuss?

If the relationship is strong and the topic is clear, go async. You already have shared context and trust — a written message will be efficient and well-received.

If the relationship is strong but the topic is ambiguous, go sync. You have the trust to have a productive conversation, and the ambiguity means you need real-time back-and-forth to reach understanding.

If the relationship is weak and the topic is clear, lean async but be extra careful with tone. You don’t have much trust built up, and written communication can be easily misread without it.

If the relationship is weak and the topic is ambiguous, definitely go sync. You need the richness of real-time interaction to navigate both the interpersonal and substantive complexity.

This matrix won’t answer every question, but it will prevent the most common mistakes: using meetings to share information that should be written, and using Slack to navigate sensitive conversations that should be face-to-face.

Chapter 7: How to go async-first

Understanding the value of async communication is one thing. Actually implementing it is another. Here are six concrete strategies that we’ve seen work in distributed teams of all sizes. Together, they represent what we believe is the most important organizational change you can make.

1. Require written updates before recurring meetings

Take every recurring meeting on your calendar and add one rule: before the meeting starts, every participant submits a short written update. What are you working on? What’s blocked? What do you need from others? When everyone reads these updates before the meeting, something remarkable happens: the meeting gets shorter, or it disappears entirely. The conveyance is handled asynchronously, and the meeting can focus exclusively on convergence — the things that actually require real-time discussion.

2. Use the Amazon memo format for proposals

Amazon famously banned PowerPoint in favor of six-page memos. Before a meeting, the proposer writes a detailed narrative document that lays out the problem, the proposed solution, and the reasoning behind it. The meeting begins with everyone reading the memo in silence. Then they discuss. This approach forces clarity from the proposer and ensures that everyone enters the conversation with the same information. It also creates a permanent record of the decision and the thinking behind it. You don’t need to go full Amazon — even a one-page brief is better than a slide deck that someone talks over for 30 minutes.

3. Record and recap every meeting

If a meeting does happen, make sure its output is accessible to people who weren’t there. Record the call (with consent). Write a brief summary of decisions made and action items assigned. Post both in a shared channel. This accomplishes two things: it makes the meeting’s output available asynchronously, and it forces whoever is running the meeting to ensure that it produces clear, documentable outcomes.

4. Create a written log for company announcements

Don’t announce important news verbally in an all-hands meeting and then wonder why half the company didn’t hear about it. Create a dedicated channel or document where all company announcements are posted in writing. This gives everyone, regardless of time zone or meeting attendance, equal access to important information. It also creates a searchable archive that new employees can reference during onboarding.

5. Publish weekly CEO or leadership notes

Every week, someone in leadership should write a short note to the company. What are the top priorities this week? What key metrics should everyone be aware of? What decisions were made and why? This takes 30 minutes to write and saves hours of meetings, Slack conversations, and water-cooler speculation. It also models the async behavior you want the rest of the company to adopt. When the CEO communicates in writing, it signals that writing is valued.

6. Use async questionnaires for new hire introductions

When someone new joins the team, don’t rely on an awkward “introduce yourself” moment at the start of a meeting. Instead, send them a questionnaire with questions like: What’s your superpower? What’s a misconception people have about your role? What do you do outside of work? What’s the best way to communicate with you? Post their answers (with a photo) in a shared channel where the whole company can read them. This gives the new hire a low-pressure way to share their personality, and it gives the team a reference document they can revisit. It’s more thoughtful and more effective than a 30-second introduction that nobody remembers.

Chapter 8: How to create a company handbook

If async communication is the operating principle of distributed work, the company handbook is the infrastructure. It’s your single source of truth — the place where anyone in the company can go to find out how things work, why they work that way, and who to talk to when they don’t.

Most companies either don’t have a handbook or have one that’s so outdated it’s worse than having nothing at all. A stale handbook is an active source of confusion, because people trust it, act on its information, and then discover too late that the information was wrong.

Here’s how to build one that actually works.

Section 1: Building blocks

This section covers the foundational elements of your company. The founding story — not a polished PR narrative, but the honest, messy story of why this company exists. The mission — what you’re trying to accomplish in the world, in one or two sentences. Your values — the beliefs that drive how you operate, described in concrete behavioral terms (not platitudes like “integrity” and “excellence”). And your goals — the specific, measurable objectives the company is pursuing right now.

Section 2: People and teams

This section makes your organization visible and navigable. Include an org structure that shows who reports to whom and how teams are organized. Add individual profiles for every employee — not just their title and department, but their working hours, communication preferences, personality type, and a few personal details. When someone new joins, this section should answer the question: “Who are all these people and how do they fit together?”

Section 3: Day-to-day operations

This is where the practical stuff lives. Policies on time off, expenses, equipment, and anything else employees regularly have questions about. Communication methods — when to use email vs. Slack vs. a video call, expected response times, and meeting norms. Tools — a list of every tool the company uses, what it’s for, and where to get help with it. And standard operating procedures (SOPs) for recurring tasks and workflows.

Common roadblocks

Building a handbook is straightforward. Keeping it useful is hard. Four problems tend to emerge:

A living, well-maintained handbook is one of the highest-leverage investments a distributed company can make. It answers questions before they’re asked, onboards new hires faster, and ensures that critical knowledge doesn’t live exclusively in someone’s head.

Chapter 9: How to cut internal meetings in half

This is the chapter that will save your company more time than any other. The core principle is simple: share written updates before meetings, not during them. When you do this consistently, meetings become shorter, more focused, and in many cases, unnecessary.

Meetings are for collaboration, relationship building, and removing blockers — not sharing facts.

The problem with most meetings is that they spend 80% of their time on information sharing — people taking turns reporting what they’ve been working on — and 20% on actual discussion. Flip that ratio by moving the information sharing to an async channel, and you’ll find that most meetings can be cut in half, condensed to 15 minutes, or eliminated entirely.

Automate the process

Don’t rely on people remembering to send updates. Use tools like Slack, Teams, or dedicated check-in software to automate the prompt. Set up recurring questions that go out at specific times, and let people respond on their own schedule. The automation removes friction, ensures consistency, and creates a searchable archive of team activity.

Four routines that replace most meetings

Monday kickoff. Each team member answers two questions in writing: What did you do over the weekend? (Yes, this matters — it’s how you build connection.) What are your priorities for this week? This replaces the Monday planning meeting.

Daily standup at 9am. Written, not spoken. What are you working on today? Is anything blocking you? This takes two minutes to write and two minutes to read. It replaces the 15-30 minute daily standup meeting that most teams dread.

Friday check-in. This one is private, between each employee and their manager. Three prompts: pick an emoji that represents how your week went, rate your productivity on a scale of 1-10, and share any wins or challenges. This is the async equivalent of a quick end-of-week 1:1, and it surfaces issues before they become crises.

Monthly review. Once a month, step back and look at the bigger picture. What went well? What didn’t? What should change? This can be done in writing and then discussed synchronously if needed. The key is that the reflection happens asynchronously, so the meeting (if there is one) focuses on action, not recap.

If you disconnect information sharing from meetings, you will spend less time in meetings.

This isn’t theoretical. Teams that adopt these routines consistently report cutting their meeting load by 40-60%. That’s not just saved time — it’s saved energy, saved focus, and saved sanity.

Chapter 10: How to build company culture from anywhere

The biggest fear that leaders express about remote work isn’t about productivity. It’s about culture. “How do we maintain our culture if people aren’t in the office?” It’s a legitimate concern, but it’s based on a misunderstanding of what culture actually is.

Edgar Schein, the organizational psychologist who literally wrote the textbook on corporate culture, describes culture as operating on three layers, like an iceberg.

Layer 1: Artifacts

These are the observable, surface-level expressions of culture. How people dress. How the office (or workspace) looks. What the meeting rituals are. How people communicate. In a traditional office, artifacts include things like ping pong tables, free snacks, and open floor plans. In a remote company, artifacts look different: they might include written communication norms, emoji reactions in Slack, async check-in routines, or the way people sign off at the end of the day.

Layer 2: Espoused values

These are the shared beliefs that the organization says it holds. Things like “we value transparency” or “we trust our employees” or “we prioritize work-life balance.” Most companies can articulate their espoused values. The question is whether those values are actually lived or just posted on a wall.

Layer 3: Basic assumptions

These are the deeply held, often unspoken principles that truly drive behavior. They’re so embedded in the organization that people don’t even think about them — they just act on them. An organization that genuinely believes in autonomy will make decisions differently than one that believes in hierarchy, even if both claim to value “empowerment.”

Culture in practice

At Friday, our cultural artifacts included minimal meetings, personal sharing in async check-ins, fun and playful product design, and a bias toward written communication. But these artifacts weren’t random. They were expressions of a deeper value: autonomy. We believed that adults should be trusted to manage their own time and work, and everything we built — our tools, our processes, our rituals — reflected that belief.

Building culture from anywhere means being intentional about reinforcing your values at every touchpoint. In hiring: screen for values alignment, not just skills. In onboarding: teach new hires not just what to do, but why you do things the way you do. In your handbook: make your values concrete and specific, with examples of what they look like in practice. In performance reviews: evaluate people against your values, not just their output. In recognition: celebrate behaviors that embody your values, publicly and consistently.

Culture isn’t something that happens in an office. It’s something that happens in every interaction, every decision, and every system your company builds. When you’re remote, you just have to be more deliberate about it.

Chapter 11: How to feel connected to your team

Loneliness and disconnection are the most commonly cited downsides of remote work. Not because remote work is inherently isolating, but because most remote teams haven’t built intentional systems for connection. In an office, connection happens accidentally — you bump into someone in the hallway, chat over coffee, overhear a conversation that makes you laugh. Remotely, connection has to be designed.

Async strategies for connection

People profiles and personal user manuals. Have every team member create a profile that includes not just their role and responsibilities, but their personality type (DISC, Enneagram, or similar), their communication preferences, their working hours, and a few personal details. What are their hobbies? What do they care about outside of work? What should you know about them to work with them effectively? Make these profiles easily accessible, and update them regularly. They serve as a foundation for understanding your colleagues as full human beings, not just Slack avatars.

Icebreakers in daily standups. Add a fun question to your daily async check-in. “What’s the best meal you’ve had recently?” “What’s a skill you’d love to learn?” “What’s your unpopular opinion?” These questions take 30 seconds to answer and create small moments of personality and connection that accumulate over time. They’re the async equivalent of water-cooler conversations.

Embedded kudos prompts. Build recognition into your regular workflows. In your Friday check-in, include a prompt: “Who did great work this week?” Make it easy and natural to call out colleagues’ contributions. Public recognition in a shared channel is one of the most powerful culture-building tools available, and it works just as well asynchronously as it does in person.

Sync strategies for connection

Flip meetings. Instead of the standard meeting format (95% work, 5% personal), flip the ratio. Schedule regular calls where the explicit purpose is connection, not productivity. Spend 95% of the time on personal conversation and 5% on work. Talk about your weekends, your families, your lives. This feels unproductive, and that’s the point. Relationships are built in the margins, not in the agenda items.

Coffee shop co-working. Open a video call and just work together in silence, the way you might sit in a coffee shop near a friend. No agenda. No pressure to talk. Just the ambient presence of another person. It sounds strange, but many remote workers find it surprisingly comforting and effective at reducing the feeling of isolation.

Games and shared experiences. Play online games together. Skribbl, Gartic Phone, and Quiplash are all great for distributed teams. Book an Airbnb experience that you can do together virtually — a cooking class, a wine tasting, a magic show. These aren’t just “fun” — they create shared memories and inside jokes that form the connective tissue of team culture.

Virtual office tours and happy hours. Have people show their workspaces on camera. Tour the home office, introduce the pets, show off the view. Schedule regular happy hours where the only rule is no work talk. These rituals are small individually, but cumulatively they bridge the gap between colleagues and friends.

Chapter 12: How to create accountability from afar

Accountability is one of the trickiest aspects of distributed work, and it’s where many remote teams quietly fall apart. Not because people are lazy — most remote workers are more productive than their office counterparts — but because the mechanisms that create accountability in an office don’t exist in a remote environment.

Three obstacles to remote accountability

Limited observational data. In an office, managers can see who’s at their desk, who’s in meetings, who looks focused, and who looks disengaged. This data is crude and often misleading (presence doesn’t equal productivity), but it exists. Remotely, managers have almost no observational data about how people are spending their time. This creates anxiety for managers and ambiguity for employees.

Reduced nudging. In an office, a manager can walk by and casually ask, “Hey, how’s that project going?” This gentle, informal nudge keeps things on track without feeling like micromanagement. Remotely, every check-in has to be intentional — a Slack message, a scheduled call, a formal request for an update. These feel heavier and more intrusive, so managers either do them too much (micromanagement) or too little (things fall through the cracks).

Vague commitments. When commitments are made verbally in a meeting, they’re easy to forget, reinterpret, or deny. “I think I said I’d try to get to it this week” is a different thing from “I committed to delivering X by Friday.” Without clear, written commitments, accountability becomes a matter of memory and interpretation.

The accountability framework

Effective remote accountability follows a four-step cycle:

Step 1: Written commitments. Every commitment should follow the format: “I will do [specific deliverable] by [specific date].” Write it down. Post it publicly. Make it visible to the team. Vagueness is the enemy of accountability.

Step 2: Progress sharing. Between the commitment and the deadline, share updates on your progress. Not constant updates — just enough to signal that the work is moving forward and to surface blockers before they become crises.

Step 3: Delivery and reflection. When the deadline arrives, report on the outcome. Did you deliver what you committed to? If not, why not? What will you do differently next time? This isn’t about blame — it’s about learning and calibration.

Step 4: Peer pressure. When commitments and outcomes are visible to the team, a healthy form of peer accountability emerges. People don’t want to be the person who consistently misses their commitments. This social pressure is more effective and less toxic than top-down monitoring.

Three practices that make it work

Monday priorities. Start each week by writing down your top priorities and sharing them with the team. This creates a public commitment that frames the rest of the week.

Daily standups (async). Each day, share what you’re working on and what’s blocking you. This creates a rhythm of visibility and progress-sharing that keeps everyone aligned.

Friday recaps (private). End each week with a private check-in with your manager. Pick an emoji that represents your week. Rate your productivity from 1 to 10. Share your wins and challenges. This gives managers the signal data they need to support their team without resorting to surveillance or micromanagement.

Chapter 13: How to build trusted work relationships

Trust is the invisible infrastructure of every high-performing team. When trust is present, communication is efficient, conflict is productive, and people take risks because they believe their colleagues have their back. When trust is absent, everything slows down. People hedge, CYA, avoid difficult conversations, and spend more energy protecting themselves than doing good work.

Building trust remotely requires understanding what trust actually is and how it works.

The trust equation

Trust is the belief that someone is reliable, able, and strong — that they’ll do what they say, they’re competent at their job, and they can handle challenges. We can break this down into four factors:

Ability. Does this person have the skills to do what they’re responsible for? Ability-based trust is built by demonstrating competence over time. It’s earned through the quality of your work, not by talking about how good you are.

Reliability. Does this person consistently deliver on their commitments? Reliability is the most important factor in trust, and it’s built through repetition. Every time you say you’ll do something and then do it, you make a deposit in your trust account. Every time you miss a commitment, you make a withdrawal. The math is unforgiving: one big miss can erase dozens of successful deliveries.

Rapport. Does this person understand and care about me as a person? Rapport is the empathetic dimension of trust. It’s built through personal connection — learning about someone’s life, showing genuine interest in their wellbeing, being vulnerable about your own experiences. In a remote environment, rapport requires the most intentional investment because it’s the hardest to build without face-to-face interaction.

Time. Trust compounds over time, but time is a multiplier, not a builder. Two people who interact deeply and frequently for three months will build more trust than two people who interact superficially for three years. Relationship depth matters more than elapsed time.

In a distributed team, your job is to create the conditions for each of these factors to develop. Demonstrate your abilities by doing excellent work. Build reliability by making clear commitments and keeping them. Invest in rapport through personal conversation and genuine curiosity about your colleagues. And create enough interaction density that time works as a multiplier, not a barrier.

Trust isn’t built in team-building exercises or trust falls. It’s built in the daily rhythm of working together — in every kept promise, every honest conversation, and every moment where someone shows up for their team.

Chapter 14: How to stay aligned

Alignment is one of those words that every company talks about but few achieve. The statistic is staggering: 95% of employees don’t understand their company’s strategy. In an office, misalignment is partially masked by physical proximity — you can always walk over and ask someone what you should be working on. In a remote environment, misalignment is exposed and amplified. If people don’t know what they’re supposed to do or why it matters, distributed work will feel chaotic and directionless.

Alignment rests on two pillars: roles and goals.

Role clarity

Every person in the organization needs to know exactly what they own and what they don’t. Role ambiguity creates duplication, dropped balls, and interpersonal conflict. In a remote environment, it also creates a more insidious problem: people default to inaction because they’re not sure if a task is their responsibility.

To create role clarity, assign clear ownership for every area of the business. Write down each person’s responsibilities in a format that’s accessible to the whole company — not in a job description that was written when they were hired and never updated, but in a living document that reflects their current work. Make responsibilities visible so that anyone in the company can look up who owns what. When ownership is visible, handoffs are smoother, decisions are faster, and accountability is unambiguous.

Goal alignment

Goals are the mechanism that connects individual work to company strategy. Without them, people are busy but not productive — they’re doing things, but those things may not be the right things.

The most common failure mode for goals isn’t that companies don’t set them. It’s that they set them, put them in a spreadsheet, and never look at them again. Goals need to be stored centrally, not scattered across Google Sheets, Notion pages, and someone’s notebook. They need directly responsible individuals (DRIs) — one person who owns each goal and is accountable for its progress. And they need to be integrated into the daily workflow, not treated as a quarterly exercise that lives outside the real work.

Integrate goals into your async check-ins. When someone shares their weekly priorities, those priorities should map to a goal. When someone delivers a project, they should be able to point to the goal it serves. When the company reviews its progress, the review should center on goals, not activities.

Alignment isn’t a state you achieve and maintain. It’s a practice you perform continuously. It requires constant communication, visible documentation, and a willingness to adjust when things drift. But the payoff is immense: a team where everyone knows what they’re doing, why they’re doing it, and how it connects to the bigger picture.

Chapter 15: How to hold company meetups

For all the power of async communication, written updates, and video calls, there is no digital replacement for being in the same room with your colleagues. Screen-mediated interaction is remarkably effective for getting work done, but it’s not as good at the things that make work meaningful: building deep relationships, reading subtle social cues, having the kind of free-ranging conversations that generate unexpected ideas.

That’s why in-person meetups are essential for distributed teams. Not as a replacement for the daily async rhythm, but as a supplement — a periodic injection of the kind of connection that only happens face-to-face.

The trust battery

Think of each relationship on your team as having a “trust battery.” Every positive interaction — a kept commitment, a kind gesture, a moment of vulnerability — charges the battery. Every negative interaction drains it. In-person meetups are the most powerful way to charge the trust battery, because they provide the density of interaction and richness of experience that digital tools can’t match. The effects of a single well-run meetup can sustain a team’s trust and connection for months.

Frequency

How often you meet depends on your company’s size and stage. For early-stage companies with small teams, one to two meetups per year is ideal. The team is still forming its identity, and frequent face-to-face time accelerates trust-building. For larger organizations, once a year is typically sufficient, supplemented by smaller team-level meetups as needed. The key is consistency: make meetups a regular, predictable part of your operating rhythm, not an ad-hoc event that happens when someone remembers to plan it.

What to do (and not do)

The biggest mistake companies make with meetups is trying to pack them with work. You fly everyone to the same city, and then you spend three days in a conference room doing the same kind of work you could have done on Zoom. This is a waste of the rarest resource you have: physical co-presence.

Focus meetups on relationship building. Shared meals are more valuable than shared slide decks. Outdoor activities, group cooking, city exploration, and unstructured social time do more for team cohesion than a three-hour strategy session. Have some work sessions, but make them the minority of the schedule, and make them the kind of work that genuinely benefits from being in the same room — brainstorming, whiteboarding, resolving complex disagreements.

Set financial guardrails before the event, not after. Meetups can get expensive quickly when you factor in flights, hotels, meals, activities, and venue costs. Decide your budget upfront, communicate it clearly, and plan within it. Don’t let the excitement of getting everyone together lead to spending decisions you’ll regret.

Finally, gather post-meetup feedback. Ask people what worked, what didn’t, and what they’d change. Use that feedback to improve the next meetup. Like everything else in distributed work, meetups get better when you treat them as a process to iterate on, not a one-time event.

Chapter 16: How to hire from anywhere

Hiring is the highest-leverage activity in any company, and it’s even more consequential in a distributed organization. When everyone works from an office, a mediocre hire is somewhat contained — they’re surrounded by the ambient structure and social pressure of the office. In a remote environment, every person needs to be self-directed, communicative, and capable of working without constant supervision. The bar for hiring goes up, not down.

Where to find candidates

Start with remote-specific job boards like WeWorkRemotely, which attract candidates who are already experienced with and enthusiastic about distributed work. This self-selection is valuable — you’re more likely to find people who understand the rhythms and challenges of remote work.

Prioritize writing ability

In a distributed company, writing is the primary medium of communication. A person’s ability to express themselves clearly, concisely, and persuasively in writing is not a nice-to-have — it’s a core competency. Evaluate writing ability throughout the hiring process. Look for clarity of thought, logical structure, and the ability to convey complex ideas simply. A great writer in a remote company is worth more than a great speaker in an office.

Ask open-ended application questions

Replace the standard cover letter with specific questions that reveal how a candidate thinks. “Describe a time you worked asynchronously to solve a complex problem.” “How do you structure your workday when no one is watching?” “What’s the most effective piece of written communication you’ve ever created?” These questions give you signal that a resume can’t provide.

Lead with email, not video

Start the process with written communication before moving to video calls. This mirrors how the actual job works and gives you early signal on a candidate’s writing skills, responsiveness, and communication style. If someone struggles to communicate clearly over email, they’ll struggle in a remote role.

Use paid test projects

Before making a final decision, give candidates a paid test project that takes 3-6 hours to complete. This should be real work, or as close to real work as possible. Pay them fairly for their time. This approach gives you far better signal than any interview — you get to see the quality of their work, how they manage their time, how they communicate during the project, and how they handle feedback.

If you want to know what it’s like to work with someone, actually work with them.

Infrastructure for international hiring

If you’re hiring within the US, Professional Employer Organizations (PEOs) can handle payroll, benefits, and compliance across states. For international hiring, platforms like Deel and Remote simplify the complexities of global employment law, tax compliance, and local benefits. These tools have made it dramatically easier to hire the best person for the role regardless of where they live.

Chapter 17: How to onboard a new hire from anywhere

The first weeks at a new job are disorienting in any environment. In a remote company, they can be isolating, confusing, and overwhelming. Everything that an office provides automatically — proximity to colleagues, casual conversations that provide context, the ability to observe how things work by just being there — has to be provided deliberately in a distributed setting.

Context is king. The single most important thing you can do for a new hire is make your organization’s accumulated knowledge accessible. This is where your company handbook pays for itself a hundred times over. A new hire who can answer their own questions by reading the handbook is a new hire who can ramp up faster, with less burden on their teammates.

Day one essentials

Handbook review. Walk the new hire through the handbook, or assign them a structured reading plan. Don’t just hand them a link and say “read this” — guide them through the most important sections and invite questions.

Job scorecard. Give them a clear document that defines what success looks like in their role. Not a generic job description, but a specific scorecard: here are the outcomes you’re expected to produce, here’s how they’ll be measured, and here’s the timeline for getting up to speed.

Team introductions. Schedule 1:1 calls with their direct teammates. Not a single group call where twelve people say “hi” and the new hire immediately forgets everyone’s name, but individual conversations that allow for real connection.

The onboarding buddy

Assign every new hire a buddy from an adjacent team — not their manager, not a direct teammate, but someone from a different part of the organization who can provide perspective, answer “dumb” questions without judgment, and help the new hire build their internal network. The buddy relationship is informal by design. It’s meant to replicate the “person you sit next to at lunch on your first day” experience that offices provide naturally.

Check-in rhythm

Establish a regular check-in cadence that combines sync and async touchpoints. During the first week, daily sync check-ins with their manager. During weeks two through four, every-other-day syncs supplemented by async standups. After the first month, transition to the normal team rhythm with additional support as needed.

Task-relevant maturity

Andy Grove, the legendary CEO of Intel, introduced the concept of “task-relevant maturity” in his book High Output Management. The idea is simple: your management style should be calibrated to the employee’s experience level with their specific tasks, not their general seniority. A senior engineer who’s never worked with your tech stack needs more structure and guidance than a junior engineer who’s been on the team for six months and knows the codebase inside out.

Apply this framework to onboarding. New hires, regardless of their experience level, have low task-relevant maturity in your specific organization. They need more structure, more context, and more support than they’ll need once they’ve ramped up. As they gain experience and confidence, gradually reduce the scaffolding and give them more autonomy. The goal is to move them from dependence to independence as quickly as possible, without leaving them unsupported during the transition.

Chapter 18: How to lead from anywhere

Leadership is harder in a distributed environment. Not because the principles of good leadership change, but because many of the tools that leaders rely on in an office — physical presence, informal observation, spontaneous conversation — simply aren’t available. Remote leadership requires a different toolkit.

Five challenges of remote leadership

You can’t manage by walking around. The MBWA approach that defined a generation of management — strolling through the office, observing, chatting, getting a feel for how things are going — doesn’t translate to a Slack workspace. You lose the ambient awareness that comes from physical proximity.

Writing is less persuasive than speaking. Leaders are often effective because of their personal presence — their charisma, their body language, their ability to read a room and adjust in real time. In writing, much of this is lost. Your words have to do all the work, without the support of your physical presence.

It’s harder to gauge sentiment. In an office, you can sense when morale is low. People move differently, talk less, avoid eye contact. Remotely, the signals are much weaker. By the time a disengaged employee’s behavior becomes visible in a distributed environment, the problem is usually much further along than it would have been in an office.

Output vs. activity confusion. Without the ability to see people working, there’s a temptation to equate activity with productivity. Leaders start paying attention to Slack activity, login times, and meeting attendance as proxies for work. This is corrosive. It shifts the culture from outcomes to performance theater.

Meeting fatigue. Remote leaders often compensate for the loss of informal interaction by scheduling more meetings. This creates the opposite of the problem they’re trying to solve: instead of more connection, people get more exhaustion.

Seven tactics for remote leaders

1. Use async routine check-ins for pulse-taking. Instead of scheduling meetings to find out how people are doing, use a simple weekly prompt: pick an emoji that represents how your week is going, and rate your energy or productivity on a scale of 1 to 10. This takes 30 seconds for each employee and gives you a real-time dashboard of team sentiment. When someone’s numbers drop or their emoji turns dark, that’s your signal to reach out.

2. Make 1:1s sacred. Based on the data from your async check-ins, dedicate your synchronous time to the people who need it most. A standing 1:1 meeting should be the most important meeting on your calendar. Use it for coaching, relationship-building, and addressing the issues that surfaced in check-ins. Don’t use it for status updates — those should happen asynchronously.

3. Write clear roles and expectations. Document what each person on your team is responsible for, how they’ll be evaluated, and what success looks like. Make this visible to the whole team. When expectations are written and shared, there’s no room for “I didn’t know that was my job” conversations.

4. Schedule collective hangout time. Block regular time on the calendar for non-work interaction. Team lunches, game sessions, or just open video calls where people can drop in and chat. This is how you maintain the social fabric of the team without relying on accidental hallway encounters.

5. Avoid information gatekeeping. In a remote environment, information hoarding is devastating. Share context proactively. Over-communicate. When in doubt, share more, not less. If you learned something relevant in a leadership meeting, write it up and share it with your team within 24 hours. Information asymmetry erodes trust faster than almost anything else.

6. Establish communication norms. Be explicit about expectations. What channels are used for what purposes? What’s the expected response time for Slack messages vs. emails? When is it appropriate to call someone vs. message them? Document these norms and enforce them consistently. Ambiguity about communication creates anxiety and conflict.

7. Deliver feedback synchronously. This is a hard rule: never deliver negative feedback asynchronously. Written feedback lacks the tone, nuance, and opportunity for real-time clarification that difficult conversations require. Negative feedback delivered via Slack or email is almost always received worse than it was intended. Have the conversation live, on video if possible, and follow up with a written summary.

Chapter 19: What about hybrid work?

Hybrid work — splitting time between home and an office — has emerged as the dominant model for many organizations. On paper, it seems like the best of both worlds: the flexibility of remote work combined with the social benefits of the office. In practice, it’s the hardest model to execute well, because it inherits the challenges of both without the full benefits of either.

The information sharing problem

When some people are in the office and others are at home, information naturally flows faster among the people who are physically together. The in-office group has conversations in the hallway, makes decisions over lunch, and shares context casually throughout the day. The remote group misses all of it. Unless you’re extremely intentional about documenting and sharing everything, the remote workers become second-class citizens with less information and less influence.

In-group dynamics

Related to information flow: the people who are in the office together tend to form closer relationships, which creates an in-group/out-group dynamic. This isn’t intentional or malicious — it’s just what happens when humans spend more time with certain people. But the effects are real: promotions, high-profile projects, and informal influence tend to flow toward the people who are physically present. This is called the mere exposure effect, and it’s one of the strongest biases in human psychology.

Meetings become procrastination tools

When people are in the office, there’s a natural tendency to schedule in-person meetings for things that should be handled asynchronously. “Let’s just grab a conference room and figure it out” replaces “let me write up a proposal and share it.” The office becomes an excuse to defer decision-making to synchronous interaction, which undermines the async-first habits you’re trying to build.

Leadership behavior sets the tone

If the CEO and executive team are primarily in the office, the rest of the organization will interpret that as a signal about what’s valued. Leaders who are always in the office, intentionally or not, create an incentive for others to be in the office too. The mere exposure effect applies to leadership attention as well: leaders will naturally form stronger relationships with the people they see most often.

Meeting equity

Hybrid meetings — where some participants are in a conference room and others are on video — are notoriously bad. The in-room participants dominate the conversation, the remote participants can’t read the room, and the technology rarely works well enough to create an equitable experience. The fix is simple but requires discipline: even if some people are in the office, require everyone to join meetings from their own individual video connection. No conference rooms. No shared screens. Everyone on their own laptop, on their own camera. This levels the playing field and ensures that remote participants have the same experience as in-office ones.

How to make it work

Survey your teams regularly about what’s working and what isn’t. Don’t assume you know — ask. Make clear decisions about your hybrid model and communicate them explicitly. “We’re hybrid” is not a policy — it’s an abdication of a policy. Which days are office days? What’s expected? What’s optional? Be specific.

Most importantly, experiment and adapt. Hybrid work is new territory for most organizations, and the right model will be different for every company. Treat your hybrid policy as a living document that evolves based on feedback and results, not a decree carved in stone.

Chapter 20: How to stay productive and avoid burnout

Burnout is the dark side of remote work’s greatest advantage. The same flexibility that lets you work from anywhere, at any time, also makes it possible to work everywhere, all the time. Without the physical boundary of leaving the office, work bleeds into every corner of your life. Without colleagues going home at 5:30, there’s no social cue that the day is over. Without the commute, there’s no transition between “work mode” and “home mode.” The result, for many remote workers, is a slow, quiet deterioration of wellbeing that they don’t notice until it’s severe.

Parkinson’s Law states that work expands to fill the time available for its completion. In a remote environment, the time available is potentially infinite. If you don’t create artificial constraints, your work will consume everything.

Create structure where none exists

Set firm start and end times for your workday, and honor them. Not “I usually try to stop around 6ish” — a real boundary. “I close my laptop at 5:30. If it’s not done, it’ll be there tomorrow.” This feels risky at first, because remote workers often fear that setting boundaries will be interpreted as not being committed. In reality, boundaries are what make sustained commitment possible.

Exercise daily

This isn’t optional productivity advice. It’s a requirement for long-term remote work. When you work from home, your body doesn’t move unless you make it move. No commute, no walking to the conference room, no trip to the coffee shop across the street. The physical stagnation compounds into mental stagnation. A daily walk, workout, or run serves as a physical reset that separates work blocks and restores cognitive energy.

Manage your time and attention, not just your tasks

Techniques like the Pomodoro method (25 minutes of focused work followed by a 5-minute break) and calendar blocking (scheduling specific times for specific types of work) are especially valuable in a remote environment where distractions are abundant and self-discipline is essential. The key insight is that managing your attention is different from managing your time. You might have eight hours available, but if your attention is fragmented across Slack, email, and meetings, you might get two hours of actual work done. Protect your attention as fiercely as you protect your time.

Change your environment

One of the most underrated productivity tools for remote workers is simply changing where you work. Go to a coffee shop. Work from a library. Sit on your porch. The change in scenery provides a cognitive refresh that working from the same desk every day cannot. It also helps re-establish the separation between home and work: when you leave the house to work, you create a physical transition that your brain uses to shift into a different mode.

Plan your day intentionally

Before diving into your inbox or your task list, spend five minutes answering three questions:

  1. How are you feeling? Check in with your energy and emotional state. If you’re running on empty, plan accordingly — don’t schedule your hardest work for a day when you’re already depleted.
  2. What are today’s must-wins? Identify the one to three things that, if accomplished, would make the day a success. Everything else is secondary. If you try to do everything, you’ll finish nothing.
  3. What’s occupying your mind? Surface the worries, distractions, or unresolved issues that are taking up mental bandwidth. Sometimes just acknowledging them is enough to release their hold on your attention. Other times, you’ll realize that the thing occupying your mind is the thing you should actually be working on.

Burnout isn’t caused by hard work. It’s caused by hard work without recovery, boundaries, or meaning. The strategies in this chapter aren’t about doing less — they’re about doing the right things, at the right times, in a way that’s sustainable for years, not just weeks.

Chapter 21: 12 principles for working from anywhere

If you distill everything in this book down to its essence, you get twelve principles. These aren’t rules — they’re operating principles that should guide your decisions as you build a distributed company or team.

1. Flexibility applies to when, not just where

Working from anywhere is only half the equation. The real power of distributed work is the ability to work during your most productive hours, not just from your preferred location. If you offer location flexibility but require everyone to be online from 9 to 5, you’re capturing a fraction of the benefit. Let people design their schedules around their energy, their obligations, and their lives.

2. Documentation is essential, not optional

If it’s not written down, it doesn’t exist. This is the fundamental truth of distributed work. Decisions made verbally evaporate. Context shared in passing is lost. Knowledge stored in someone’s head is unavailable to the rest of the team. Write things down. Not because you love documentation, but because writing is the medium through which distributed teams think, decide, and remember.

3. Information flow needs structure

In an office, information flows organically. In a distributed environment, it doesn’t flow at all unless you build channels for it. Create regular rhythms for sharing information — weekly updates, daily standups, monthly reviews. Define what information goes where. Build systems that ensure the right people have the right context at the right time.

4. Choose appropriate channels

Not every conversation belongs in Slack. Not every update needs a meeting. Not every decision requires a video call. Match the communication channel to the type of communication. Use async for conveyance, sync for convergence. Use writing for facts, video for feelings. Be intentional about where and how you communicate.

5. Visibility prevents blind spots

When work is invisible, problems are invisible. Make work visible through shared dashboards, public commitments, and transparent progress tracking. Make people visible through profiles, async updates, and regular social interaction. The more visible everything is, the fewer surprises you’ll encounter.

6. Preserve humanity

Behind every Slack message is a human being with a life, feelings, and a bad day now and then. Don’t let the efficiency of async communication strip the warmth from your workplace. Share personal details. Ask about people’s weekends. Celebrate birthdays. The social fabric of your team is as important as its operational infrastructure.

7. Measure outcomes, not activity

Hours logged, messages sent, and meetings attended are vanity metrics. They measure effort, not impact. Focus on outcomes: What was delivered? What problems were solved? What goals were advanced? When you measure outcomes, you give people the freedom to work in whatever way produces the best results.

8. Document processes, not just decisions

It’s not enough to write down what you decided. Write down how you do things. Standard operating procedures, workflows, and playbooks ensure that work can be done consistently, regardless of who’s doing it or where they’re located. When a process lives in someone’s head, the company is one resignation away from losing it.

9. Time zones are immutable

You can’t negotiate with time zones. If your team spans twelve hours, you need to design your operating system around that constraint, not pretend it doesn’t exist. Default to async. Minimize the number of meetings that require everyone to be present simultaneously. When sync meetings are necessary, rotate the time zone burden so the same people aren’t always attending calls at inconvenient hours.

10. Minimize unnecessary meetings

Every meeting is a decision to interrupt multiple people’s focus at the same time. That decision should be made carefully and sparingly. Before scheduling a meeting, ask: Can this be a document? Can this be a Slack thread? Can this be an async update? If the answer to any of those is yes, don’t schedule the meeting.

11. Cultivate individual accountability

Accountability in a distributed team starts with individuals, not managers. Make clear commitments. Share your progress openly. Reflect on your results honestly. When every person on the team takes ownership of their work without waiting for a manager to check on them, the entire organization operates at a higher level.

12. Maintain community engagement

A distributed company is still a community. It needs rituals, shared experiences, and spaces for non-work interaction. Invest in the social infrastructure of your team — not as an afterthought, but as a core operating responsibility. A connected team is a resilient team.

Chapter 22: Our favorite software for working from anywhere

Tools don’t solve organizational problems on their own, but the right tools reduce friction and make good habits easier to sustain. Here are the tools we’ve used and recommend, organized by who they serve.

For individuals

Brain.fm — AI-generated music designed to improve focus. Unlike regular music, which can distract as often as it helps, Brain.fm creates ambient soundscapes that are specifically engineered to support sustained concentration. It’s one of those tools that sounds gimmicky until you try it, and then you can’t work without it.

Krisp.ai — Noise cancellation for calls. Krisp removes background noise from your audio in real-time, which is a lifesaver if you’re working from a coffee shop, a shared apartment, or any environment where you can’t control the ambient sound. It works with any video conferencing tool and makes you sound like you’re in a professional studio regardless of where you actually are.

CleanShot — Screenshot and screen recording tool for Mac. In a remote environment, visual communication is essential. When you’re trying to explain a bug, show a design, or walk someone through a process, a screenshot or quick screen recording is worth a thousand words. CleanShot makes it fast and frictionless to capture, annotate, and share what’s on your screen.

For teams

Slack — The de facto communication hub for most distributed teams. Used well, it’s the central nervous system of your company. Used poorly, it’s a firehose of noise that destroys focus. The key is discipline: clear channel structures, explicit norms about response times, and a culture that doesn’t expect instant replies to every message.

Zoom — Video conferencing that works reliably at scale. Despite the “Zoom fatigue” discourse, video calls remain the best tool for synchronous remote communication. The video quality is excellent, the reliability is strong, and the feature set covers everything from small 1:1s to large all-hands meetings.

Trello — Visual project management using a kanban board approach. Trello’s strength is its simplicity: cards move from left to right across columns, making work progress visible at a glance. For teams that need straightforward task tracking without the complexity of enterprise project management tools, Trello hits a sweet spot.

Loom — Asynchronous video messaging. Instead of scheduling a meeting to explain something, record a Loom. Walk through a document, demo a feature, or share feedback in a short video that the recipient can watch on their own time. Loom bridges the gap between the richness of video and the flexibility of async communication.

Grain — AI-powered meeting recording and highlights. Grain records your video calls, transcribes them, and lets you clip key moments to share with people who weren’t there. It solves the “I wasn’t in that meeting” problem without requiring anyone to write comprehensive meeting notes.

Butter — Collaborative meeting facilitation tool. If you do need to have synchronous meetings, Butter makes them more interactive and structured with built-in timers, polls, breakout rooms, and agenda management. It’s designed to make meetings productive, not just present.

Almanac — Collaborative document platform designed for remote teams. Almanac combines document creation with workflows, approvals, and version history, making it easier to create the kind of written artifacts that distributed teams depend on.

For company operations

Post Scan Mail — Virtual mailbox service. Your company’s physical mail gets scanned and uploaded digitally, so you can manage it from anywhere. This solves a surprisingly persistent problem for distributed companies that still receive paper correspondence, checks, and legal documents.

OpenPhone — Business phone system that works on any device. Gives you a dedicated business number for calls and texts, with shared inboxes so multiple team members can handle customer communication. No desk phones required.

Deel — Global payroll and compliance platform. Deel handles the complexity of paying and managing employees and contractors in different countries, including local tax compliance, benefits, and employment contracts. If you’re hiring internationally, Deel dramatically reduces the legal and administrative burden.

Rippling — Unified HR, IT, and finance platform. Rippling combines payroll, benefits, device management, and app provisioning in a single system. When you hire someone, Rippling can set up their payroll, ship them a laptop, provision their software accounts, and enroll them in benefits — all from one place.

1Password — Team password management. Shared passwords are an unavoidable reality of team work, and managing them through Slack messages or shared documents is a security nightmare. 1Password gives you secure, organized, role-based access to shared credentials without anyone needing to type or remember passwords.

Tools evolve quickly, and the specific products you choose matter less than the categories they serve. The point is to build a toolstack that supports your operating system — async communication, documentation, visibility, and connection — rather than one that creates noise, friction, and fragmentation.

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