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Updated March 23, 2023You’re reading an excerpt of The Holloway Guide to Remote Work, a book by Katie Wilde, Juan Pablo Buriticá, and over 50 other contributors. It is the most comprehensive resource on building, managing, and adapting to working with distributed teams. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, 800 links and references, a library of tools for remote-friendly work, commentary and future updates, and a high-quality PDF download.
The nature of work is shifting significantly in the early 21st century—from traditional, corporate structures where every employee commutes to a nearby office for eight hours a day, to gig economy models and a deconstruction of what the “workplace” means. While checking into a physical office every day is still the norm, remote work—working outside the office (primarily from home)—has been steadily on the rise in the U.S., with over 50% of U.S. companies supporting some form of remote work,* and at least 5% of the population working from home consistently.*
Source: U.S. Census Bureau (2017)
A variety of factors have contributed to this shift, including:
Broadband access. Decreased costs of—and increased access to—broadband internet have led to the widespread prevalence of high-speed internet.
Technological advances. Easier, cheaper access to technology and tools that facilitate digital communication—like computers, smart phones, video meetings, and an explosion of widely available, largely inexpensive cloud-based services—have made being together in an office less necessary for getting work done, even for more team-based, collaborative work.
A rise in knowledge worker jobs. These are largely “thinking-based” jobs focused on solving problems and typically coming up with new products and services. Management consultant and writer Peter Drucker characterizes knowledge work as “ever-changing, dynamic, and autonomous,”* and predicted as early as the 1950s that it would be increasingly intertwined with computers and technology.*
Increased costs of living. Housing prices are becoming increasingly out of reach up through the middle class in dense, urban areas, and are often paired with lengthy, expensive commutes. People are either looking to live in less expensive, smaller locations, or to at least avoid commuting hours per day.
Environmental concerns. Working from home poses a number of environmental benefits, from reducing or eliminating commuting to minimizing waste and greenhouse gas emissions associated with centralized offices.* (It’s worth noting, however, that remote work incurs different environmental impacts related to company retreats and potentially increased airline travel for some of the workforce, notably managers and executives. No data that we’re aware of factors these aspects into the overall environmental impact analysis of remote work.)
Changing individual values. Evolving attitudes regarding work, personal time, and life/work balance are pushing employers to shift strategies to continue to retain talented workers who wish for more flexibility and better quality of life.
Source: Brookings Institute
Remote work is just work.Hiten Shah, co-founder and CEO, FYI*
Depending on whom you ask, remote or distributed work is The Future of Work—the biggest shift in the workplace since the industrial revolution; a trend that’s not going to last; or a phenomenon that’s been growing for decades. We embrace the latter view, noting that remote work as we know it now began back in the U.S. in the 1970s (when it was initially referred to as “telecommuting”), and has been on the rise in terms of popularity and reach slowly ever since.*
In 1973, NASA engineer Jack Nilles wrote The Telecommunications-Transportation Tradeoff,* in which he posited that telecommuting was a way to reduce gridlock, sprawl, and reliance on fossil fuels (this was the era of OPEC oil embargoes). He saw a not-so-distant future in which “either the jobs of the employees must be redesigned so that they can still be self-contained at each individual location, or a sufficiently sophisticated telecommunications and information storage system must be developed to allow the information transfer to occur as effectively as if the employees were centrally collocated.”*
A big part of the rise of remote work is tied to technological advancements over the past decade or so. When Hiten Shah notes that remote work is “just work,” he also adds that it’s because “software is everywhere.” But while technology has greatly aided the expansion of remote work, it’s not why remote work will succeed (or fail) at any given organization. Nilles saw this truth early as well: “organizational—and management—cultural changes [are] far more important in the rate of acceptance of telecommuting.”
importantNot every job can be done remotely. Outside of physical jobs like healthcare work, construction, and service industries, every company may have a range of what’s feasible and some specific constraints. A hardware startup might have a mix of roles that can be done remotely, but the core product has to be built and tested in a physical space. Some industries (financial services, healthcare tech) have such significant security and compliance constraints that a remote workforce might be too much effort or risk to maintain.
Laurel Farrer, CEO of Distribute Consulting, assesses whether a job can be done remotely based on the following set of criteria:*
Even within knowledge work, some roles may have heavier in-person needs at various times, such as sales, where closing a deal (especially a big one) likely means getting on a plane and meeting face-to-face. More junior roles that require much higher levels of mentoring and hands-on learning can also be challenging in a remote environment.
Finally, remote work can prove challenging for anyone who thrives on the built-in social and collaborative aspects of working in an office with other people. While many of the necessary skills for remote workers—increased autonomy, adjusted communication practices, managing potential feelings of isolation and loneliness—can be acquired and improved by individuals, and enabled by companies and managers, remote work is not for everyone.
Successful remote work requires intentionally examining how and why people communicate, make decisions, collaborate, and learn to trust each other. Being together in the same space makes up for a lot of messy, inefficient human tendencies, all of which are critical to examine and account for when you won’t be together. It has little to do with which new whiteboarding SaaS app your company tries out or how many channels you have in Slack.
Even in fervently titled posts like “Why Naval Ravikant Thinks Remote Work Is The Future,” Naval Ravikant acknowledges that remote work isn’t a magic solution. “It’s going to be done through lengthy trials. It’s going to be done through new forms of evaluating whether someone can work remotely effectively,” Ravikant says.
This Guide covers knowledge work at startups and high-growth companies where everyone does not work from the same physical office location. While this applies to companies with offices in multiple geographic locations (aka “satellite offices”), we intend the Guide more for companies (and their employees) that intentionally have at least some percentage of their workforce working entirely remotely, rather than coming into a physical office location.
Remote work (or distributed work) is an organizational approach where employees of a company do not conduct their daily work from the same physical location on an ongoing basis. In-person communication and coordination are typically replaced by a combination of telephone calls, email, internet video calls, online chat, and written documentation. In the past, remote work was referred to as “telecommuting,” but this term has fallen out of favor with the advent of ubiquitous internet access that supports online forms of communication.
We do not cover large, multinational companies looking to dramatically cut costs via offshoring or other related methodologies; nor do we cover remote work for digital nomads or freelancers/contractors as a broad category (though we will discuss how contractors play a role in international remote teams, and the legal and other complexities associated with such approaches). For the time being, we are also not addressing remote work at non-profits or government agencies, though many of the ideas and practices in the guide will be relevant to both. We also don’t cover how to find remote jobs for prospective employees.