The crashing surf from the ocean. The cry of seagulls. A gentle salt breeze. A laptop balanced upon a pair of nicely tanned legs. 

We’ve all seen this scenario described in countless articles, sticking out in our minds like a bad stock photo. But here’s the deal: these articles are always either for or against remote work. No middle ground. Like many subjects, it’s difficult to find a balanced and informed discussion about working remotely. You’ll either find an enraptured freelancer claiming they’ll never set foot in an office again, or you’ll find a concerned middle manager discussing how inefficient a distributed workforce is.

It’s hard to get a realistic grasp on the possibilities of remote work. As employers, we want the best for both our employees and our company. When we’re making a decision for our business, we don’t want to fall prey to emotional decisions – we want data to back it up. We want informed anecdotes from folks who have experienced this directly. We want to know about the failures and the successes. It’s great to learn from history. But I think we’d all rather learn from someone else’s mistakes than 

learn from our own.

When you’re researching remote work, there’s little balance. I have a few ideas why this is so. Re- mote work in the modern world is fairly new, and it’s a hot-button topic. It’s emotional. It’s cultural. It’s somewhat revolutionary. And it’s right in the middle of two playing fields: the traditional corporate world of enterprise business, and the roguish new future of solo tech junkies. 

So, when we go out there to take a look at the empirical data around remote work, we’re instead assaulted on both sides by opinions and biased – and, unfortunately, research studies on either side backed by folks with just a little bit too much in- vested in their own correctness. 

I see more and more content out there, harping on the benefits of remote work. I think this is a great thing, but you’ve got to remember that the sample is very biased. Content marketers, writers, and journalists are one of the most likely of anyone to already work from home. Of course they’ll be primarily on one side of the equation: remote work has been working for them for years. 

On the remote side, you’ve got a lot of writers, marketers, and tech junkies claiming that the office is dead. Long live the laptop! 

On the office side, you’ve got a lot of managers, owners, HR departments, and investors claiming that remote workers aren’t productive and increase liabilities. Long live the nine-to-five! 

The reality? Both are right, and both are wrong. 

There may not be a single silver bullet that works for everyone, but there definitely is a best solution for your own unique problem, and that’s what I’d like to explore in this book. 

I want to talk about the pros and cons of both models. In doing this, we’ll talk to remote workers, managers, and business owners who have been involved in some form with operating within a distributed team. We’ll discuss productivity, challenge some basic assumptions about work, talk about what “work” is anyway, and explore some of the down- sides of remote work in the context of personal fulfillment, business investment, career progress, and look at trends to see where we might end up with remote work after a few more years. 

We started Discosloth in early 2017. From the beginning, we knew we’d be a remote company. Started as a side gig by Anya and I while we still worked our day jobs, it was a slow first few months in the search marketing industry, managing and creating Google Ads and Bing Ads campaigns and SEO projects. We worked incessantly every evening to onboard clients and find projects. 

Things took off, and within a few months we were making more from Discosloth than we were from our normal jobs. We went full time, and since then we’ve never looked back. We hired remote col- leagues, first contractors and then full-time employees. Our client list grew, slowly but steadily, and we began the long project of diversifying and pivoting away from a mere services company into a tech-focused company with multiple streams of revenue. Throughout the years, we’ve built processes and established best practices for working remotely, and those practices continue to evolve and perfect. 

I have personally been working remotely since 2011. Like many who started working remotely be- fore it was a super popular trend, it started out of necessity rather than desire. My first internship right out of college lasted for just under a year, and after that, I found myself diving directly into the deep waters of freelancing. Those first few months of free- lancing was supported by a side gig as a barista, but after I quit the coffeeshop I never went to work at a physical location again.

Since then, I worked for almost five years as a freelancer and consultant, almost two years as a remote full-time employee (a creative director for an airfare company) and almost three years as the co-founder of a fully remote marketing company. 

I’ve done almost everything entirely remotely. As a freelancer, I both bid for projects and found sub- contractor to hire out, all remotely. As an employee, I was both interviewed and hired remotely, and then interviewed dozens of new hires myself. And as the cofounder of a company, I’ve read hundreds of applications, interviewed, and ultimately hired both full-time employees and part-time contractors of our own. 

With that level of remote pedigree, you’d think I’d be a diehard no holds-barred proponent of remote work. Well, I am, and am not, at the same time. We’ll get into the complexities later on in the book – it’s a very convoluted subject, and not one you can just make a declarative decision on within a few minutes. There are potentially massive upsides and potentially cataclysmic downsides when you’re dealing with a distributed work force, and I’d like to approach these factors in as balanced a way as possible. 

Something to remember is that what we call “remote work” is actually the historical norm. Over the long course of humanity, the vast majority of people have worked from home. Going into an office that was anywhere further than the shop down- stairs was a luxury reserved only for the most elite. It wasn’t until a couple hundred years ago – a fleeting instant of time in the grand scheme of things – that people starting going to a factory or office. With the advent of the Industrial Revolution in the late 18th century, mass production became an employer of thousands, and the trend only grew well into the 20th century. The advent of fast communication – the facsimile and the telegraph and the steam engine – brought with it the ability to do work outside the traditional limitations of slow travel and slow communication. 

Throughout the twentieth century, this trend continued to grow, but then the internet happened. Since we were already going into the office to type on a computer and talk on the phone, we found we could do the same things from the comfort of home. 

For the first few years of the new “remote work”, this work-from-home status was reserved for a very select few – people like regional managers who traveled to district offices, nerdy webmasters who started making good money from running forums and blogs, freelance writers who could email in their work instead of handing it in on a floppy disk. 

As the internet got faster and laptops got cheap- er, remote work kept growing. Why pay for office space when you can just work from your home office? 

And then, the younger generation who had entirely grown up surrounded with computers started to get into the work force. By this time, it was hardly a question of “how” – today, for the average worker, it’s more a question of “why not?” 

There are many reasons why a company might decide to distribute their workforce: added financial savings, increased timezone coverage, territorial market expansion, gaining access to a wider pool of skillsets and workers, improved diversity of ideas, better job perks, and an almost endless amount of other equally valid factors. 

Financial savings is perhaps the most common of reasons that a company goes remote. By doing this, a company can effectively provide a better level of income to those in the company who live in lower cost of living areas, from the C-suite to customer service. 

Why do millions of New York workers commute hours daily from Connecticut or New Jersey? They’re making big-city wages and living in a much cheaper area, and often their standard of living ex- ceeds anything but the most fortunate of New York City’s natives can afford. This is an example of re- mote work on a micro scale, if slightly inefficient and onerous. You see this pattern in every large metro area: Oakland to San Francisco, Rockford to Chicago, Round Rock to Austin. With remote work, you can work for a Silicon Valley company while living in the middle of Nebraska, or on the beach in Thailand. This income arbitrage, as it’s known, is the single most influential reason why remote work has swept the digital world by storm. If you can work from anywhere, why would you pay $4000 for rent? 

Unfortunately, there’s a dark side to this reason. I’ve seen more than one company use going fully remote as a last-ditch effort to save a dying business. Cutting overhead like offices can be a massive bene- fit for a company in a cash flow crunch. But this doesn’t make it ideal, any more than amputating a gangrened leg to save the rest of the body is ideal. I’ve seen it happen too often as a last-ditch effort to induce profitability in a dying industry, and when this is the case it’s hardly the best long-term strategy from a business perspective. 

If you go a little bit further, there’s an even dark- er side. You don’t see it super often, mostly because it’s unsustainable, but an increasing amount of companies use remote work as a form of in-sourcing – bringing cheap offshore labor into the company as full-time workers. This strategy operates on the assumption that you can run a first-world company on workers that cost four hundred bucks a month. We’ll go into this in far more detail later on, but there’s some simple reasons why it doesn’t work in the long term. Good workers are worth their wages no matter where they’re from, and companies that try to cheap out on payroll quickly learn that their good remote employees will move on to somewhere they’re paid a competitive wage. 

That’s not to say that it doesn’t make financial sense to go fully remote: in many cases, it’s absolutely the best decision a company can make. But in order for it to work, the remote ethos needs to be baked into your company from the start, not as a last-ditch effort to cut costs and turn a company around. 

Timezone coverage – the ability to have hands on deck at every moment throughout the day – is an- other benefit that is especially unique to certain industries. Having remote employees spread out throughout the globe is invaluable to companies, allowing you to keep an eight-hour workday but have constant uptime. This can be a huge benefit to businesses dependent upon heavy customer service, high-touch service businesses, or IT businesses in sensitive industries like healthcare, security, or fi- nance. Adding just three or four positions can ensure that the entire globe is covered. It’s a rare need, but one that is perfectly suited for a distributed team. 

Territorial market expansion is another reason. A rapidly growing global company can’t always afford the immense expense of establishing physical offices in every new market, and remote employees can be the perfect antidote to this problem. Instead of spending tens or even hundreds of thousands on new office space, HR, company registration, and banking, you can simply hire regional employees able to travel within the specified area during launch. 

Gaining access to a wider pool of skillsets is a massive benefit, and perhaps my favorite. If you’re operating in an uncommon niche, finding the perfect candidate for a role who both matches your company’s culture, possesses the specific skillsets, and also lives in your immediate area can be a literally impossible task. Our first full-time hire was re- mote, simply because there was no one within commuting distance who had the requisite skillsets (managing ad campaigns on the Google and Microsoft advertising platforms). Not only were we able to get hundreds of applicants for the position, but we found an employee who matched our culture perfectly – and was actually an ex-Googler, on top of that. 

Going remote can also vastly improve your diversity of ideas and operation. We’ll go into far more detail about the upsides and downsides of bringing in more cultures into your company, but for tech-centric businesses I can’t think of something more valuable than bringing in people who can shatter the status quo. I’ve worked in hyper-local businesses be- fore. Don’t get me wrong: it can work extremely well, especially in a small-town scenario, because everyone works together like clockwork. But any expansion outside of that small town comfort zone becomes impossible, because an entirely homogenous company isn’t terribly flexible or adaptive. Bringing in additional cultures can be the spark that takes you from mediocre to amazing. 

Offering a remote workplace is also an incredible job perk. More and more, as remote work becomes somewhat normalized within the tech-forward world, excellent developers and marketers and project managers want to work from home or from a beach somewhere. The freedom and independence that you’re afforded with a remote job can be priceless. Giving someone the option to work remotely can be the difference in hiring the perfect candidate, or getting passed over for some other company.