Revisiting The 4-Hour Workweek

on an alluring vision of adventure and entrepreneurship

Fall 2007. South Lake Tahoe, California.

After running away to South America, getting inspired to write my first book, and returning to serve back-to-back sessions of Deer Crossing Camp and Not Back to School Camp, I once again find myself in Lake Tahoe. My friend Aly is running the marketing research department at Heavenly Ski Resort, and she hires me to snowboard around the mountain and interview guests all day. It’s a dream job—but it’s also just another job. I’m feeling hungry to stop working for others, start taking ownership, and blaze my own trail through life. I’m just not quite sure how.

Enter: The 4-Hour Workweek. 

The author is Tim Ferriss, a Princeton-educated tech bro, five years my senior. After launching his book at South by Southwest in Spring 2007, the book promptly lands on the NY Times Bestseller list—where it will remains for years. I snag a copy. I’ve read quite a few small-business books already, but this is a different beast.

Sharp, witty, and a powerfully effective self-educator and self-promoter, Ferriss sells a vision of life in which the intelligent application of technology and entrepreneurship leads to an automated income stream (requiring just 4 weekly hours of maintenance), freeing the owner to pursue a life of global adventure, learning, and hedonism. The 4-Hour Workweek is a vision of maximal personal freedom, of liberation from bosses, schedules, meetings, and emails, and of “geoarbitrage” (earning money in wealthier countries and spending it in poorer ones). Despite Ferriss’ many exhortations that “anyone can do this,” the book is clearly written for those with a Silicon Valley skillset and mindset, skewing toward the young, male, highly-educated, and tech-savvy. (In other words: me.) More than anything, it is an well-written business book in the American tradition of promising vast riches with minimal effort—and a well-timed book, arriving just before a global recession that leaves many unemployed, questioning retirement, and contemplating entrepreneurship.¹

For 24-year-old Blake, already pursuing self-employment and actively working toward his first book, The 4-Hour Workweek lands like an asteroid.

First, it gives me a writing style to emulate. In South America I took extensive notes on the topics of unschooling, self-directed learning, and college—but I’m not sure how to put them together in an engaging, non-academic fashion. Ferriss’ voice and the structure of the 4HWW feel so compelling that I immediately adopt it as the model for the manuscript which will become College Without High School.

Second, I connect many dotes between Ferriss’ critique of work and my critique of school. Ferriss argues that the modern corporate office is a farcical, soul-destroying institution; I argue the same for school. Ferriss argues that a radically unconventional and independent path is the solution; I argue the same. He argues for meticulous self-examination, goal-setting, the flouting of conventional success, and “excitement” as a metric for decision-making—yes, yes, yes, yes. I shamelessly borrow many of Ferriss’ key concepts, including the 80/20 rule, Parkinson’s Law, goal-mapping, and task-batching, for my own book. (I even title one of my chapters The Six-Hour School Week.) Ferriss’ philosophy aligns neatly with that of another adventure-seeking Silicon Valley acolyte—Jim Wiltens—whose philosophy guides me at the moment.

More than anything, The 4HWW speaks to my quarter-life existential confusion. Ferriss’ entrepreneurial suggestions—building a fully automated and outsourced business—don’t actually convince me. They seem both difficult to implement and a poor personal fit, as I clearly desire to work in a face-to-face, service role. Yet like a pick-up artist for tech bros, Tim Ferriss finds his way into my heart, kindling a long-gestating desire to live an unconstrained, free-wheeling life of adventure. Ferriss’ philosophy of “lifestyle design” and “mini-retirements” are ultimately what draw me in, shape me, and stick.

It’s hard to admit how much this book influenced me at age 24. Many aspects of the book made me cringe then, and more do now. But with 15 years of distance, I’m ready to revisit, reassess, and give credit where credit is due.

Age 24 Blake, getting paid to snowboard — but wanting so much more

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Allow me to introduce you to Tim Ferriss, in his own words:

Assuming you can find me (hard to do), and depending on when you ask me (I’d prefer you didn’t), I could be racing motorcycles in Europe, scuba diving off a private island in Panama, resting under a palm tree between kickboxing sessions in Thailand, or dancing tango in Buenos Aires. The beauty is, I’m not a multimillionaire, nor do I particularly care to be. […]

Gold is getting old. The New Rich (NR) are those who abandon the deferred-life plan and create luxury lifestyles in the present using the currency of the New Rich: time and mobility. This is an art and a science we will refer to as Lifestyle Design (LD). 

I’ve spent the last three years traveling among those who live in worlds currently beyond your imagination. Rather than hating reality, I’ll show you how to bend it to your will. It’s easier than it sounds. My journey from grossly overworked and severely underpaid office worker to member of the NR is at once stranger than fiction and—now that I’ve deciphered the code—simple to duplicate. There is a recipe. 

UGH! The blatant salesmanship! The grandiose promises! The luxury lifestyles and private islands and bending reality and deciphering the code. There’s so much to dislike, so quickly.²

Yet he is onto… something.

Life doesn’t have to be so damn hard. It really doesn’t. Most people, my past self included, have spent too much time convincing themselves that life has to be hard, a resignation to 9-to-5 drudgery in exchange for (sometimes) relaxing weekends and the occasional keep-it-short-or-get-fired vacation.

Thus far, a standard anti-rat-race argument. Where Ferriss stands apart is in his framing of freedom and his critique of retirement. 

People don’t want to be millionaires—they want to experience what they believe only millions can buy. . . . $1,000,000 in the bank isn’t the fantasy. The fantasy is the lifestyle of complete freedom it supposedly allows. The question is then, How can one achieve the millionaire lifestyle of complete freedom without first having $1,000,000? 

The “Deferrers”—those who buy into the traditional notion of retirement, deferring real life until retirement age, or even early retirement—are the real chumps in Ferriss’ eyes.

The Deferrer’s dream is to one-day work for yourself. The dream of the “New Rich” is to be an owner—to have others work for you.

A Deferrer works when she wants, but still full-time. The New Rich works only when she wants and as little as possible.

A Deferrer wants “more” in life, whereas the NR wants:

To have more quality and less clutter. To have huge financial reserves but recognize that most material wants are justifications for spending time on the things that don’t really matter, including buying things and preparing to buy things. You spent two weeks negotiating your new Infiniti with the dealership and got $10,000 off? That’s great. Does your life have a purpose? Are you contributing anything useful to this world, or just shuffling papers, banging on a keyboard, and coming home to a drunken existence on the weekends? 

The New Rich have clearly defined passions, dreams, and hobbies which they are pursuing now. Not next year, nor some mythical future. They’re do not wait to lead a life of adventure. They toil for a few months, and then take a few months of mini-retirement. Like Eric Cartman, they do what they want.

The New Rich—which, let’s be honest, really means Tim Ferriss and his handful of case studies, which include many fellow Princetonians—are entrepreneurially enlightened beings. They have arrived. They combine the physical with the spiritual, the books with the gym, old-world luxury with new-world mobility. And they do it all from their laptop in a posh Buenos Aires Airbnb or Tokyo coworking center.

It was a sexy, alluring vision in 2007—and one that remains sexy and alluring 15 years later. Pay no attention to the massive time and effort required to get a fully-automated-and-outsourced business off the ground. Pay no attention to the small army of low-paid remote workers in developing countries required to sustain such a business. Pay no attention to the fact that Ferriss’ own business sold performance-enhancing drugs (“Are you contributing anything useful to this world,” Tim?). Ferriss sold a roller-coaster version of globalized entrepreneurship that spoke to the dreams counter-cultural warriors and office dwellers alike. “I’ve seen the promised land, and there is good news. You can have it all.” You can be both free and rich.

Yet for all his contradictions and blind spots, I have to hand it to the guy—he had his finger on the pulse of something big and real: an early version of digital nomadism combined with a cultural critique not far removed from Occupy Wall Street.

Here, for example, are a few statements with which I totally agree:

[Retirement] is predicated on the assumption that you dislike what you
are doing during the most physically capable years of your life. This is a nonstarter . . . Most people will never be able to retire and maintain even a hotdogs-for-dinner standard of living. Even one million is chump change in a world where traditional retirement could span 30 years and inflation lowers your purchasing power 2–4% per year. The math doesn’t work. The golden years become lower-middle-class life revisited. . . . [And if] the math does work, it means that you are one ambitious, hardworking machine. If that’s the case, guess what? One week into retirement, you’ll be so damn bored that you’ll want to stick bicycle spokes in your eyes. 

Doing less meaningless work, so that you can focus on things of greater personal importance, is NOT laziness. This is hard for most to accept, because our culture tends to reward personal sacrifice instead of personal productivity.

[The] 80-hour-per-week, $500,000-per-year investment banker is less “powerful” than the employed NR who works 1/4 the hours for $40,000, but has complete freedom of when, where, and how to live. 

Options—the ability to choose—is real power.

Ferriss drives home the idea that the timing is never right for big life moves, busy-work is a perennial enemy, time wealth is harder to accumulate than monetary wealth, and figuring out what to do with our freedom—even when time and money are plentiful—is really, really hard.

These are true and timeless insights, well-presented. And they connect to education! I could write a whole piece on how Ferriss’ vision of entrepreneurship parallels (and partially informed) my vision of unschooling. For example: the success stories we champion are typically those of individuals who could find or already did find success in the conventional system. “You're a successful tech worker but you’re still unhappy,” Ferriss says in so many words. “Here is a way to live better with less effort.” That’s what I say to disgruntled teens (and their parents), in so many words. Yet for the employees and students who don’t find it so easy to play the game, the pill is harder to swallow, and the tactics are harder to pull off. Ferriss employs precious few examples of workers who were struggling to fit into any job but then succeeded with his non-traditional approach. Most alternative paths through life do require a certain amount of privilege, luck, and supportive networks/communities. Nevertheless, for those of us managing large amounts of freedom—especially unschoolers—Ferris’ guidance rang true.³

Be a rule-breaker, a disruptor. Beg for forgiveness instead of asking for permission. Learn the rules, find the loopholes, and exploit them ruthlessly. Trick your boss into believing you’re working from home when you’re really traveling. Employ email autoresponders to avoid expectations of a quick reply. Join a Chinese kickboxing competition, dehydrate yourself to drop three weight classes, rapidly rehydrate, and then take gold by pushing your lesser-sized competitors off the platform instead of fighting them (an actual loophole that Ferriss exploited). Both tinkerer and troublemaker, Ferriss nudges his readers toward unconventional (and borderline ethical) tactics in all realms of life. But just as he starts feeling too huckster, he becomes the good-kid again, promoting the healthy travel ethics of Vagabonding or encouraging his Princeton lecture student to boldly reach out to strangers online.

Constant self-challenge and self-improvement are as much Ferriss’ message as anything else, and this I appreciate. For example:

Role models who push us to exceed our limits, physical training that removes our spare tires, and risks that expand our sphere of comfortable action are all examples of eustress—stress that is healthful and the stimulus for growth.

I’ll repeat something you might consider tattooing on your forehead: What we fear doing most is usually what we most need to do. As I have heard said, a person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have. Resolve to do one thing every day that you fear.

There is a direct correlation between an increased sphere of comfort and getting what you want.

And his productivity advice is on-point. One prompt that particularly struck me as I re-read the book: “What are the top-three activities that I use to fill time to feel as though I’ve been productive?” Oof—well.. checking email, checking Facebook, browsing blogs, reading news, looking at bank accounts. The list goes on. Guilty as charged. Just because I’ve used my self-employment to liberate large chunks of time does not mean I use those chunks well (i.e., effectively instead of efficiently).

That’s The 4-Hour Workweek: a grab-bag of bold promises, detailed business advice, helpful productivity tips, questionable life hacks, and timeless philosophy. It’s a book that’s easy to hate and hard to ignore. It reads like a thriller novel. And it clearly benefited from Ferriss’ (surely) thousands of hours of self-promotion.⁴ The guy could easily could have been a corporate consultant or financial analyst, but he wrote this instead.

At a crossroads moment, Tim Ferriss’ book landed in my life. It shaped my assumptions about freedom and retirement. It reinforced my biases toward goal-setting and self-challenge. I did not follow Ferriss’ advice to create an automated, product-based business, instead staying true to my vision of working face-to-face with teenagers. His writing helped me hold fast to my dreams of frequent nature immersion, long-term travel, and outdoor adventure. And he helped my first book come to life. For these reasons, I’m indebted to the book and its author, no matter how cringy and tech-bro it can feel at times.

So thanks, bro.

1. This podcast episode offers a helpful context for understanding why Ferriss wrote the book and the cultural moment surrounding it.

2. For the record, I don’t think Tim Ferriss is a bad guy. I know many people who adore his works, and he seems genuinely well-intentioned (if a tad smarmy). The Tim Ferriss of 2007 just exemplifies a certain attitude toward life that generates very mixed emotions for me.

3. Upon finishing the book, I felt so strongly about the overlap between his vision of entrepreneurship and my vision of education that I emailed him and invited him to join me for a free weekend of snowboarding in Tahoe (with guest passes provided by Heavenly Ski Resort). One of his remote assistants wrote me back, thanked me for the offer, and said he doesn’t have time.

4. Read this for a humorous and highly critical take on Ferriss’ self-promotion tactics.