The Great Contemplation

author: @paul-millerd

If Tim Ferriss’s 4-Hour Workweek kickstarted the “first wave” of the post-industrial reimagination of work in 2007, 2022 was the year that a newer, and weirder, second wave began. 

Unlike the first wave, which largely played out at the individual level, this one is happening at the societal level. While it is still early, this “great contemplation,” as I’ve been calling it, will likely shape the work stories that people use to orient their lives over the coming decade. 

Ferriss offered a powerful alternative script that inspired millions around the world to escape the default path, travel the world, take mini-retirements, start businesses, and take breaks from work. However, these people embraced their new paths in direct opposition to the 20th-century industrial economy “organization man” paradigm that still had a strangle-hold over the popular imagination, well into the 2010s. Even if you followed Ferriss’s playbook and found a path you enjoyed, it was likely that many people in your life still thought you were a bit crazy (raises hand). This is what drew people to leave cities organized around big companies and full-time work to escape to nomadic communities around the world, like Bali; Chiang Mai, Thailand; Medellin, Colombia; and Las Palmas, Spain.

As the worst blows of the pandemic have receded, people who seemed committed to traditional employment and working for big companies have started to soften their attachment to traditional work scripts. This has encouraged many digital nomads, the early adopters of work norms, including myself, to return “home,” noticing that the vibe really has shifted. It was telling that in a visit to Lisbon earlier this year, most of the scrappy digital nomads had been replaced with well-paid full-time workers who were flexing their increased freedom and driving up the cost of rent. 

As someone who quit my job and walked away from a promising and well-paid strategy consulting path more than five years ago, and has been making a living while self-employed, it is jolting to experience people shifting from mocking my lifestyle to asking how they might, too, claim a little more freedom. I’ve had a unique front-row seat to this shift, having been obsessed with our collective relationship to work soon after leaving my full-time job in 2017. I was fascinated by how different being self-employed felt compared to the first 32 years of my life, which had been oriented around school, employment, and a steady stream of goals and achievements. 

I was so hungry to talk to anyone about what I was experiencing that I decided to put an open booking link on my website for “curiosity conversations” every Wednesday. Over the next couple of years, I talked to hundreds of people from dozens of countries, and they told me how they felt about work with raw honesty. I was surprised at how consistent issues were across countries, industries, and even socioeconomic status. People told me that they felt trapped, uninspired, stuck, and hopeless, and that they desired a better relationship to work but didn’t know what to do. The most shocking thing was how many people told me they hadn’t even told this to a single person in their life, not even their spouses. Just me—a stranger on the internet.

This “secret knowledge” fueled my writing, and in 2020, the world seemed to catch up. In April 2020, my calendar was full each week with seven or eight calls. Suddenly, everyone wanted to talk about work. Some of my friends made dramatic changes in their lives that I never would have predicted. Family members inquired about how I was working and living. The media tried to cover this shift but kept missing the mark by getting distracted by terms like “anti-work” and the “great resignation” rather than going deeper.

If they did go deeper, they would have seen what I was seeing: a more gradual, and harder to define, change bubbling under the surface. While some people made dramatic shifts in 2020, most of those were moves that were accelerated by a couple of years. The bigger impact of the pandemic was planting seeds of possibility in many more people that have yet to even sprout.

I believe that Ferriss—whose book laid the groundwork for this shift—has had a bigger impact on our collective relationship to work than people think. In 2018, I followed many others before me in living abroad and trying to make it work running a business on the internet. I was surprised at how many people I met in places like Indonesia, Taiwan, Korea, Spain, and Mexico, who all treated The 4-Hour Workweek like a sacred text. While some were embracing the automation and outsourcing hacks that sometimes get unfairly pinned to Ferriss, most were inspired by his philosophical stance against the default path of work.

Yet while Ferriss’s book did have impressive success, staying on the New York Times bestseller list for years, its underlying message to “question work” did not break through to our broader understanding of work. It resonated most with tech-adjacent rebels who had the skills to find opportunities in a growing digital economy and many people who would have done anything to escape the tedium of many full-time jobs. Whenever I mentioned the book to people outside of this bubble, they would mockingly dismiss it: “Only four hours a week—good luck, buddy!”  

They had never read it. If they did, they would have found that it is a philosophical wake-up call disguised as a bunch of life hacks. The whole book is basically him channeling the energy of poet Mary Oliver and yelling, “Don’t waste your wild and precious life!” 

Unfortunately, The 4-Hour Workweek and the first wave of reimagining our relationship with work has become paired with the archetype of the software engineer whose stance toward life is one of optimization and efficiency. Other movements that were aligned with Ferriss’s philosophical vision from the 2010s, like FIRE (Financially Independent, Retire Early), also attracted a different type of person, from the early creative weirdos who wanted to get more joy out of life to people who were trying to earn a specific amount by age 30 so that they would never have to work again.

Escaping work is enticing when you’ve never really known what it is to find work that matters to you, and I unwittingly got sucked into a slightly different trap. When I moved abroad to Taiwan and then Bali, and figured out I could be happy living on $1,000 a month, I calculated that I could go five years without earning an income. For a few months, I experienced a blissful state of leisure that was valuable for my own growth, but I realized that playing accountant is useful for paying the bills but wouldn’t make for a great personality as I aged.

In the 1990s, the sociologist Andre Gorz argued that most people live in what he called “wage-based societies.” What determined membership in such a society was participation in formal work. Put more simply, to be a good person, thou shall be employed. This was undoubtedly a hidden force that held the ideas in Ferriss’s book from reaching mass adoption. But for the first time, the conventional thinking that it is taboo to question these 20th-century scripts is starting to evaporate.

Once I realized I was trying to escape work, I leaned in a different direction. I embraced a principle I now call “design for liking work.” The reality is that most people want to be useful, and that means some form of work in people’s lives. With patience and a willingness to feel lost and take it slow, over the last few years, I started to find a better relationship with work. Inspired by ideas from internet writers, poets, books on spirituality and religion, my own writing, self-experiments, and those conversations with internet friends from around the world, I’ve been able to build a life I am excited to keep living. While it took me more than five years to come close to matching my previous income—a reality that holds many people back from leaving their jobs—I can say without a doubt, it might be harder on this current path, but it’s worth it.  

To share what I have learned and inspire others to dream bigger about the possibilities of their lives, I published a book, The Pathless Path, in 2021. I wrote it after many of those people in conversations during 2020 told me I had to do it. If you listen and pay attention, I bet you can find a deeper journey you are meant to be on, too.  

What comes next? I have no idea. But I’ve spent enough time on this uncertain journey to know that when it comes to finding work you love and building a life around it, there are no hacks, roadmaps, or instructions. The best we can do is share our stories. The 4-Hour Workweek was one that inspired many, including me. I hope that in 10 years, my book is merely one of many that helps people figure out the “real work” of their lives: finding things to work on that matter. 

We are going to need them because at a societal level, we are indeed on a pathless path.