Introduction

“The supreme accomplishment is to blur the line between work and play.”

– Arnold J. Toynbee

It was November 13, 1980. One year after the Iran hostage crisis, and a few days after Ronald Reagan defeated Jimmy Carter to become the 40th president of the United States. Lesser known to the rest of history, but very important to me, my father officially started his first company on this date, when I was just a little over four years old. He would run Metalworking Specialty Sales, his (at its peak) two-person operation out of our house until he retired.

As such, self-employment was more than just a romantic notion to me. It was normal. In fact, in elementary school, I didn’t quite understand why other people chose to have “normal” jobs when my dad got to travel (and in the summers take my mother and sister and me with him so those trips could double as summer vacations), and had the flexibility to work from home.

Soon enough, I learned about the “normal” workplace. For high school, I attended a boarding school where work was required half of each day. While there were a variety of types of jobs available (anything from cafeteria work, the furniture shop, grounds maintenance, teachers’ assistants, dormitory work, and much more), I was fortunate enough to get an office job, which allowed me to both observe how organizations work, and also required me to use their computer systems. Previously, my computing experience included playing Summer Games on my dad’s Commodore 64, and a few cheat codes for Legend of Zelda on my NES.

As a freshman in high school, I was put in charge—with some supervision, of course—of tracking class attendance (which counted as a grade that was part of our GPA score), as well as grades. My first foray into computer programming, outside of a BASIC course on our cutting-edge cadre of Commodore 64 computers, was to assist in reprogramming the school’s classes to switch from a five-day week to an alternating A-B “two-day” system where there were two unique schedules for classes that took place every other day. “A days” and “B days,” they called them. This would be the first of many times in my life where I took on a task with little preparation and qualification to do it, but I’m proud to say the results were a success. The main things I learned, however, were a determination to believe that there is always a way to solve problems, and a refusal to be “intimidated” by computers and technology. I never gave them enough credit, but the Vice Principal Steve Davis, and my boss Betty Crandall, for some reason believed I was capable of helping, and sure enough, we figured it out. You could say I first learned the concept of agile in those years through our numerous trials and errors.

Years later, but still early in my career, in the late 1990s, I was working at a startup called Multicity, where I eventually became head of product design for their SaaS-before-they-called-it-SaaS suite of web apps. I started out as their Webmaster, having taught myself HTML in the early ‘90s, on my university’s system, writing code in the UNIX app Pico and previewing it using the very latest version of Netscape Navigator (which would have been 2.01). Despite this, I didn’t have any “formal” training, as my degree was in Photography (still old-school film at that point), and the handful of interactive courses available for me to take focused on CD-ROM creation using programs like Macromedia Director (Flash was in 1.0 the year I graduated).

I’m proud to say that, through the team at Multicity’s combined efforts of product design, sales initiatives, and some forward-thinking marketing techniques (remember, this is several years before the advent of social media; digital marketing and advertising was the Wild West) we grew our platform to well over 1 million users, and many of my colleagues have gone on to found companies and be part of other successful ventures.

Multicity lasted longer than many other startups of that time, but eventually it ran out of money and wasn’t able to find its footing. After pivoting (before “pivot” was the preferred term) one time too many, myself and most of my colleagues (about 50 of us in all) were laid off one day in late summer of 2002.

That unfortunate event ended up having a profound effect on me and my future trajectory. I decided to get into the world of freelancing and self-employment. For the next almost two years, I built a freelance business from nothing, and learned that I was more resourceful, stress-tolerant, and resilient than I ever imagined, though it is certainly thanks to countless people who helped me along the way.

When I found myself with too many clients for one person to effectively serve, I partnered with a few others and started Carousel30, the digital experience agency which I’d end up running for a little over a decade until selling it in late 2017.

The value of what I learned was immeasurable, however. Being able to do repeatable tasks quickly, finding ways to think of big, time-consuming tasks as problems worth investing a little time to solve, and always thinking about how to make unsavory tasks easily repeatable helped me as a freelancer, a business owner, and an entrepreneur.

The other takeaway is the undeniable benefits of being agile. In my last book in this series, The Agile Consumer, I described how I see myself as an agile person. This means I can define myself by the following:

I know I’m not alone, either. There are many people who share these common traits of agility. I don’t think I was simply born agile. Instead, the same factors that are shaping our mindsets, our economy, and our workforce today, shaped those things in me and my agile compatriots.

We are now at a point in history where many tasks and repeatable processes can be done better by machines than humans. While this has been true in some industries for decades (think car manufacturing), it will soon be true across the board in every industry imaginable.

While many see this as a doomsday prophecy, I see it as an opportunity for humanity to transcend the grunt work and tasks that many have found themselves doing to make ends meet, and to instead gain an agency and freedom over how they earn their living.

Yet this more utopian vision is not without its challenges. As I pointed out several times in my last book in the Agile series, The Agile Consumer, there isn’t so much a gap as there is a huge chasm between those who are privileged enough to envision their place in a world where machines help humans with daily tasks, and those whose very livelihoods will get replaced by them. Despite this challenge, I believe there is a path forward for everyone, but it will take solving many challenges, and we must all be willing to do so. We’ll discuss these later in the book.

Living in this agile world, one of the things that affects us most is our ability to make a living, and to provide for ourselves and our families. Work is how we in the white-collar, salaried-position world define this in the abstract, but that word simply doesn’t do the topic justice. For better or worse, and for too many, work isn’t something we can just leave behind at the end of our shift. We’ve woken up at 2 a.m. and checked our phones, only to see a work email that caused enough of a startle to get us out of bed. We’ve missed our friend’s important moments because things were “rough at the office.” We’ve put off making important personal decisions because “it’s just not a good time at work right now.”

In short, we’ve sacrificed much in order to get a raise, a promotion, or a bonus; to get ahead, or in far too many cases, to just stay employed in the first place.

In return, what have we traded for this? Stability of work every day of the week, assurance that our bills will be paid (in full or at least in part) steadily each month. The ability to take time off, or see a doctor or specialist, and potentially many other perks.

While this is true for many, how true is it for even the majority of knowledge workers or others with office jobs? And this says nothing of those who don’t have the privilege of a salaried job that supports their lifestyle. Hourly workers, temporary workers, independent or self-employed workers, and others don’t have those luxuries to begin with.

With the COVID-19 pandemic, we’ve seen what a thin line there is between the ability for companies to support a steady payroll and furloughing or laying off mass amounts of employees. We saw this a decade earlier in 2009, and the same in 2001. Each time, we seem surprised as a collective, yet the numbers tell a different story. Those who work independently are part of a growing population. We’ll explore how this came to be, and what this means for our future in the pages that follow.

What is certain, is that the world continues to iterate and evolve, and its workforce...