CHAPTER ONE

Remote State of Mind

LET’S START BY playing a game. Take a look at the two photos in figure 1.1. What differences do you see?

Telecommuting entered the public interest in the 1990s after Microsoft launched Microsoft Office (remember Clippy?). The advent of the personal computer inspired a wave of digital enthusiasts, dreamers, and dot-com entrepreneurs (at least until the bust), who imagined a different future.

As Woody Leonhard, a 1990s blogger and author of those bright yellow Windows for Dummies books, once said, “Work is something you do, not something you travel to.”¹ This is truer than ever today.

Since then, this utopian dream of being able to work from anywhere, at any time, without the grating aspects of office life—commuting, micromanagement, bleak office parks, smelly lunches, loud talkers—has moved in fits and starts. Behavior is notoriously hard to change—hence, all the gym memberships purchased in January that grow dormant by March. Our habitual nature is partially why remote work has stayed on the fringes despite the technical capabilities being in place.

FIGURE 1.1 Comparison of Work, Then and Now

Sure, there had been hype around digital nomadism and beach-front coworking hubs on Instagram (no complaints here—we would be lying if we said there was no photo evidence of us working at a beachfront café). But the real mass movement to remote working happened in 2020 when COVID-19 turned the world upside down. Knowledge workers and their organizations were slingshot into the future with little preparation and lots of panic. There were Band-Aid solutions and emergency transition plans. And then back-to-office plans, later reneged as the pandemic carried on. We’ll remember the early 2020s as the years we survived by adapting to remote work.

But before we potentially send you down the memory lane of rough patches with remote work, we want to remind you that you likely practiced some form of remote working even before the pandemic.

It was a common theme as we interviewed remote work experts across the globe, and upon reflection, it applied to us as well!

Let’s take a look at their stories for inspiration. You may find you’ve already been flexing your remote muscles too.

REMOTE ORIGIN STORIES

The Frequent Flier

Tam Sanderson (yes, one of the two names on the cover) decided there must be a better way after spending her first year as a management consultant flying to and from Dallas in 2006. She ended her lease on her uptown apartment in 2007, where she rarely was, and started living in hotels near her consulting projects (and with friends and family when back in the United States). Her “homes” were the Sheraton hotel in El Salvador and the Four Points in Zurich; she bopped between London and Dublin (cue the movie Up in the Air, except there was no George Clooney), exploring bits of Europe and North Africa in between.

She didn’t realize she was working remotely, even though she was flying back to her home office only once a quarter. All she needed were her BlackBerry and laptop computer. While she had yet to learn the art of traveling lightly (she kept two rolling suitcases in the luggage check at her hotel), she had opened her eyes to a fundamental truth: in many cases, you can untether your work from your location.

The Freelancer

While freelancer is often associated with the digital nomad, we found in our conversations that many freelancers started working remotely out of necessity.

For example, Staszek Kolarzowski, cofounder of Pilot, a payroll and benefits platform, was hired by a local marketing agency in Poland to make digital animations. But there was one problem. Staszek was still in high school. “I had to go to lessons. I couldn’t go to the office. So, we had an agreement. I was the only person on the team who could work flexible hours and from home. I met them in person every few months because we were in the same city, but besides that, I worked from home. It was great! Super-flexible. They only cared about deadlines, so I could organize myself and work from my hub.”

Likewise, Andrew Gobran of Doist found himself freelancing in college. “I designed Prezis for people all over the world. At the time, I never thought, ‘Oh, this is a remote role.’ But I developed many skills, like communication across cultures and time zones, managing individual autonomy, and having responsibilities and owning them.”

The Colocated

On the other hand, some found themselves technically remote working . . . in an office. For example, Ali Greene (Hi! Yes, the other coauthor) started her career at the fast-growing start-up LivingSocial, at the height of the group-coupon craze. When she first started, the company easily fit into a small office in Chinatown in Washington, DC. But they quickly grew out of that office and expanded to a second office across the street. Soon, they had offices in different neighborhoods of DC and had local salespeople based on the ground in the United States and Canada.

Ali soon found that meetings previously conducted around a conference table were now being scheduled as conference calls; likewise, information was being shared via systems like Salesforce and not by shouting across the cramped shared desks, as in her early days.

Sara Robertson, of Edinburgh Futures Institute, noticed something similar while working at a software company early in her career. “They were using Jira and GitLab. They were all in the same room, but they hardly ever spoke to each other, which was a completely new experience in an office for me. Sometimes they would decide to work from home for the day. And it didn’t affect anything.”

The same was true for Daniel Davis, formerly of DuckDuckGo, when he was working at Opera in Japan. He found that although colocated, they were all working on different things. “Nobody knew what I was working on. It was similar to being in a shared office where you don’t talk about your work because you don’t know what everyone’s work is. Instead, you talk about movies and games.”

Whether you’ve been a remote worker since high school or first prototyped a new way of working during the COVID-19 pandemic, we can sense that something is different. It can sometimes feel intangible, and we know that it’s more than just videoconferences. It’s truly a state of mind.

THE PATH TO THE FUTURE

Before you embark on your remote working journey, you need a remote state of mind. What’s that? It differs for everyone, but it ultimately comes down to a few things.

First and foremost, it’s the ability to conduct your job remotely. Today, this means harnessing the power of the internet so that your workflows, information, and processes are saved on the cloud and accessible anywhere. Though we’d argue you can still be a remote worker with just a phone.

Once you’ve covered the work, it is time for a mindset shift. You begin asking questions (like where and when you do your best work), challenging the status quo (that commuting is normal), and imagining your ideal work life (if you had more variables in your control).

Does that sound like a tall order? We’re here to help. This chapter will explore how to get you into a remote state of mind using the journalistic framework—5Ws and 1H (Who, What, When, Where, Why, How).

The Who

You are no longer limited to teammates in the same room or even the same country. You have the opportunity to hire the best team from all over the globe and leverage time zone differences to create an around-the-clock workforce if needed.

You’ve probably heard the phrases “The future is here; it is just not evenly distributed” or “the lottery of birth.” Remote work can level the playing field and give more people access to opportunities, regardless of their zip code or passport.

Even if your team stays the same, the way you get to know them and collaborate with them has changed. You can no longer rely on hallway conversations or elevator rides for small talk. You may recognize coworkers’ avatars now more than their body language. As a manager or a teammate, you need to shift your relationship-building methods and find new ways to learn about each other—perhaps using the backgrounds on their video screen as a head start.

You’ll also need to rethink your daily socialization. Gallup polls used to say that having a friend at work increased job satisfaction.² While it is important to have strong relationships and trust in your team, we believe that in a remote world, sometimes you just need a friend to work with and not necessarily at your same company, whether at a café, in your backyard, or at the office. You can also intermix socialization breaks, either virtually or in real life, between focus time or meetings. Ali often coworks with her partner from their kitchen table and with family members, joking that her sister’s house turned into the “Family HQ” for work during her last visit home. Tam also recommends getting involved with your local community if you are new in town, like volunteering, playing sports, taking continuing education classes, and joining Meetup groups.

Remote State of Mind

On staying in your local community . . .

“Not requiring folks to move and enabling them to stay deeply embedded in their life/community allows for less stress and greater satisfaction.” —ANNE McCARTHY

On opening up your hiring pool . . .

“If you are looking to recruit in one kind of location or a handful of locations, you have significantly closed up your diversity pool to people who live within commutable distance to that office. Many socioeconomic factors have determined your talent pool.” —HILARY CALLAGHAN

On expanding opportunity . . .

“Why does the accident of birth have to determine their life path? Remote work is completely deconstructing this.” —LORRAINE CHARLES

The What

Remember all those ways we used to fill time during the nine-to-five? Meetings to plan meetings. Surfing the internet in a cubicle. Filling out reports that should be automated. Joining meetings that shouldn’t be on your calendar (but you were added out of courtesy). Asking, yet again, for a status update.

These things no longer need to exist in a perfect remote world (though they are still happening or you wouldn’t be reading this book!). If anything, all the optics of traditional office work can feel more draining when you see the alternatives in front of you, whether it’s your child who’s just finished school, an offer to meet friends for lunch, or the sun begging you to take a quick stroll.

In traditional office culture, we often conflate things that look like work—how many meetings you attend, how long you were at your desk, face time with your manager at the coffee machine—with real work. When remote work is effective, it focuses less on visual cues and inputs and relies more on measuring the outputs. As mentioned, you were probably doing some remote working already, even if from your office desk. Sending emails, setting up conference calls, working from home on a sick day. Those are all, technically, activities of remote work.

Remote State of Mind

On monitoring results . . .

“At the end of the day, you need to make sure that results are delivered: x is shipped, tickets are closed, or articles are written. Results are more important than whether or not people are sitting at their desks.” —STEPH YIU

On the false god of proximity . . .

“So a lot of management has been by proximity rather than performance. Most of the work is organized around physicality. It’s even in our tech systems. We have files. We have a desktop. We have a trash bin. It mimics a physical desk. So much of our paradigms around tech are rooted in a physical sense.” —BEN BROOKS

The When

Imagine the following scene. It’s 26 degrees Celsius outside (79 degrees Fahrenheit for our American friends), not too hot and not too cold. Goldilocks perfect. The sun is shining, the sky is a crayon-box shade of blue, and it’s the first day of a local art exhibition you’ve been dying to see.

But there’s one problem—it’s a Thursday. In a traditional workplace, you’d witness those perfect clouds from the window of your office building. You might not even have a view because your windows face a parking lot. Or worse, you may work in an office or a cubicle with no window at all! In between meetings, you might try to reserve a weekend ticket online—but you hate crowds, and you’re sure that’s when everyone else will be trying to see it too. Ali swears by this trick and often reverses her week. She loves to work on weekends and go hiking or out to restaurants on weekdays for this exact reason.

Now, let’s cut to the remote world. The “when” matters less if you’ve coordinated with your team and can finish your work independently. This means you could enjoy that sunny day and the art exhibition for a few hours in the afternoon and complete your tasks that evening. Or you could run an errand for an elderly parent nearby, pick up a sick kid at school, or have that cavity worked on pronto without making a massive production out of it.

By taking advantage of time zones and asynchronous communication, teams can design work schedules around the moments that matter to them, giving them the flexibility they crave.

If you’ve ever had someone break your trust at work, you might be rolling your eyes now (“Sure, that sounds great, if you live in a utopia”). You don’t have to take our word for it. Remote work isn’t successful if it’s the spitting image of a traditional office on a 13-inch screen. It works when it frees up your time and energy to do your best work while managing your home life with care and creativity.

Remote State of Mind

On making your dream life a reality . . .

“I think the one thing I would say is I would have the leaders of those companies ask themselves, what does their dream life look like? I would ask them to look at their [work] practices and say, ‘How could we create a work environment in which many different individuals’ dreams can be achieved?’” —DARCY BOLES

On breaking out of the nine-to-five routine . . .

“You’d be surprised how many people still do the nine-to-five even when working remotely. I don’t understand it. I prefer variety in my day as opposed to routine. As a father of a 20-month-old, I prefer maximizing daylight hours for exercising and being outdoors with my family. Some of my biggest breakthroughs have come to me while trail running (never sitting in an office). My schedule looks different every day, depending on my life/work circumstances.” —CARLOS SILVA

On the many variations of “perfect” . . .

“What perfect conditions are for 20 people in a team is going to lead to 20 different definitions. By design, you’ll always fail. But instead, ask how we empower each individual. Change the organization by activating the individuals, rather than changing the culture or cascading something down. None of those paradigms have worked.” —BEN BROOKS

On surprising choices . . .

“We let people back to the office on a strictly voluntary basis. And guess what? The day with the highest footfall in the company’s headquarters in Mumbai was Friday. Exactly the opposite of what I’d expect in the US. Commuting is so bad, they want to work from home or a nearby coworking center during the week. But they come in on Fridays to socialize and then go out together after work.” —JASON MORWICK

The Where

The “where” is the most apparent change. You no longer have to commute to the office in rush hour to stay in the same place for eight hours. (Did you know the average worker pre-pandemic spent 4.5 hours per week commuting?)³

At a minimum, this means you can design a space customized to you—maybe that’s creating a dream home office, picking out a few cafés to add to your rotation, or finding a fun coworking space or public library (like Tam!). On a larger scale, if you’re moving to remote full-time, you may relocate closer to family or somewhere less expensive. Or, simply, somewhere you like better.

While hybrid is not something we’ll specifically cover in this book, we believe our advice still stands, regardless of location. Ali often says, “If one employee is remote, then the whole company is working remotely.” That is to say: the culture, collaboration, documentation, and business operations are remote-first (or should be!). Hybrid, therefore, describes a real estate strategy, like deciding whether a company should own or lease private office space in which employees will work. In the future, we believe the lines we draw today—in person, remote, or hybrid—will blur, and all knowledge work will be digital-first.

Remote State of Mind

On headquarters bias . . .

“When I joined the international start-up, they had three primary offices and one headquarters. And the headquarters was where their leadership was. If you were a product manager, you felt like you needed to be there to be in the mix for the decision-making, to be aware of what was happening. Essentially all of their senior leaders relocated to the headquarters . . . hallway conversations were happening all the time. And sometimes those hallway conversations were decision-making conversations on strategy.” —ALI BRANDT

On location independence . . .

“I left [that job] and sought out somewhere that would give me location independence. So again, I took a big step back financially and in terms of hierarchy within an organization. I joined Doist with one criterion: give me location independence and let me live where I want. . . . I’ve been now with the company for six years.” —CHASE WARRINGTON

On keeping remote “a secret” . . .

“I went to India in 2009, for about two to three months, and kept doing my consulting projects. They did not know where I was. It felt back then like a secret I needed to keep. If there was a call they needed to have at 3 EST, I had to wake up in the middle of the night to make that call. That rarely happened, but I did have to do that a couple of times. The idea to keep it secret was probably my insecurity.” —AKSHAY KAPUR

On having a room of one’s own . . .

“Neurodiversity and disabilities take a lot of energy to manage. Getting ready in uncomfortable clothes, leaving the house, driving/taking transportation, and having unnecessary social interactions would be too much. Instead, I can wear comfortable clothes. I can control things like temperature, pets, music, and lights in my workspace, which eliminates a sensory overload.” —CAT CONTILLO

The Why

Transitions are a natural point for reflection. It’s so easy to get tied to the day-to-day routine and forget to ask the simple question: Why?

Why does your team exist?

Why does a manager exist in your organization?

Why do you want to make “remote” work—for yourself and your team?

• • • • • •

Those questions sound deceptively simple. Of course, we should all know why we were hired and what we’ve been doing five days a week. But in reality, why can be very hard to answer. Luckily, there’s no correct answer, and sometimes it even leads to more questions. Like a little kid testing a parent’s patience, “Why?” and “Why?” again.

We believe it’s through questions, not always answers, that you uncover the root of an issue and find creative solutions to achieve your goals. After all, it is a lesson in intentionality that we see leading the charge of remote work.

Remote State of Mind

On finding your North Star . . .

“Stop for a second and think: What am I really monitoring to ensure that my team is high performing? What is the North Star for this team? How do I make sure that that’s highly visible to me, my team, and my boss? That’s very powerful. Most managers can’t tell you: Why does my team exist? Why does the company pay me? What are the metrics I need to track? How are we performing? You’d be surprised at how many managers don’t.” —STEPH YIU

On finding your superpower. . .

“Honestly, none of my ideas are like ‘my ideas.’ My first title was chief curator because I was the CEO of $1. I chose chief curator because I’m really listening to great ideas and trying to curate them in a useful way that’s practical. My skill is taking amazing ideas and distilling them into actionable ways that you can apply them.” —SALLY THORNTON

On creating your best life with your family . . .

“I’ve spent the last eight years living nomadically and traveling the globe with my wife and two kids. Not only is Hotjar the best job I’ve ever had, but it’s allowed me to also pursue my passion for travel along the way.” —KEN WEARY

The How

We’re sure you’ve already picked up at least a few tricks on how to make remote work more attractive—whether it’s adding a fun background to Zoom or buying an ergonomic chair for your home office. Search online or check out your LinkedIn feed. We’re positive you’ll find dozens of listicles.⁴ We’ve read a lot of them, and yeah, we wrote a few ourselves.

While those are important, true expertise in remote work requires going deeper to the roots of work to reimagine it. We’ll examine the mental models you and your team already have on how work should work. We hope to distill the myth from the truth (what actually needs to happen) and help you better communicate ideas, preserve organizational intellectual capital, and structure workloads.

As Matt Mullenweg, the CEO of Automattic (WordPress.com) and an avid remote work advocate, once blogged, there are essentially “Five Levels of Autonomy” for distributed work.⁵ Level zero starts with jobs that cannot be done unless you’re physically there—for example, nannying an infant, building a house, or working in an end-of-life nursing facility.

As levels of autonomy increase, the efficacy of remote work also increases. By the time an organization reaches level five, work is primarily asynchronous, and the organization is outperforming its doppelgänger in an office. Whether you are on level zero or at moments flying high in remote work Nirvana, we’re excited to come along on this journey to help you design remote working experiences for you and your team.

Remote State of Mind

On building trust . . .

“What matters are the outcomes you achieve. So as long as you’re achieving the outcomes and delivering your work, it doesn’t matter. It is the cornerstone of remote work, isn’t it? You’ve got to have people who you can trust. And you’ve got self-driven people who understand that they just need to focus on results.” —SIOBHAN MCKEOWN

On being intentional . . .

“It’s not that you cannot do cultural work remotely. Doing it remotely requires you to be more intentional about it. But if you don’t intentionally address culture, you’re going to have a bad culture in most cases. It’s no longer just the atmosphere or an unconscious feeling. It’s really about values, processes, and rules on how we interact.” —MARIO GIULIO BERTORELLI

While the 5Ws and 1H framework is one way to summarize the shifts, we’ve included a “10 Ways ‘Remote’ Changed Work” info-graphic for safekeeping (table 1.1). We recommend that you set aside 30 minutes to review the questions in the infographic. You can answer the question prompts alone or with your team.

TABLE 1.1 Infographie—10 Ways “Remote” Changed Work

ALI’S ADVICE

The joy of remote work is that you are reinventing work.

You can learn all the best practices and read all the listicles, but it will mean nothing unless you truly believe in and want your team to thrive in this new iteration of work. It’s not about remote versus hybrid versus a return to office. Or about artificial intelligence and robots. It is about integrating best practices into your day-to-day work.

Remote simply adds a magnifying glass to any broken processes, cultural gaps, or miscommunications that already existed in your team. Now you have an opportunity not just to fix it but to make it even better!

TAM’S TIPS

I’m a design thinker with some Buddhist leanings, so my advice would be twofold. First, approach change with curiosity. Ask questions. Be willing to learn and change your mind. Find ways to test new ways of working as a mini-prototype across your organization and then iterate.

Second, let go. Remember, there’s only so much in your control. It’s great to think and organize and plan, but at some point you have to let nature take its course. Your company will not be the same today as it will be in five years, and it’s not the same today as it was five years ago. That’s OK.