Beyond the Four Hour Workweek: The “portfolio lives” of Jeff Goins and Chris Guillebeau

“Everywhere you look, people are giving excuses for not pursuing what they were born to do.” — page xxiii, introduction, The Art of Work, by Jeff Goins
“It’s easy to come up with ideas. Making ideas come to life is where the real value is.” — page 93, Born For This, by Chris Guillebeau

Back in April 2007, Tim Ferriss published the Four Hour Work Week and forever challenged everyone to think differently about money, career, and even geographic location. Almost a decade later many continue to build on his lessons and stories on the back of quantum growth in technology and serious disrupters that have created an entire marketplace that is popularly known as the “gig economy.”

Putting aside the ongoing legal issues that vary from country to country (in the United States, for example, there is a war on about whether people are to be classified as “contractors” or “employees” whereas the Canadians and Germans have quite sensibly simply created new legislation to deal with what they call “dependent contractors” instead of trying to pretend that labor laws written in the time of railroads are relevant in the day of the internet) the reality of the gig economy is what its participants are doing now. The legal issues will resolve themselves in time. But entrepreneurs, who live in an accelerated present, bend and create a reality that contributes to the lives of their staff and clients. And so, for those interested in being part of this new economy, which offers more possibilities for joy and mobility than the work models of the past three hundred years, two good starting points are The Art of Work by Jeff Goins and Born for This by Chris Guillebeau. They both advocate for the idea of a portfolio life: one in which your income streams are diversified — not just to hedge risk, but to maximize your enjoyment. If Jeff’s book is the “why-to,” Chris’ is the “how-to.”

More goodness available from Chris here:

Both Jeff and Chris make the point that very few people can point to some “aha” moment when they realized what their life’s work was going to be, but rather, worked at something they were good at and were often surprised by what came next.

Perhaps you are already in the “Winning the Career Lottery” zone that Chris illustrates above. If so, great! But for those who are not, consider a “side-hustle” that will allow you to move towards that special place.

As you do this you’ll discover something fascinating. That “side-hustle” (or something similar) will start to become part of your portfolio. As you start to find your feet in this new and unconventional world, you’ll have to collaborate with others and this may lead to other projects.

On p. 135–136 of his book Jeff walks us through an average day in his life, in which his work is as varied as writing, preparing for an upcoming speaking gig, consulting with a designer who is helping him build software, and running an e-commerce website. In his book, Chris tells us that in addition to Cards for Travel, a business he owns that makes money referring others to credit cards that give great travel benefits, he started the path to authorship by writing useful digital travel guides that people really enjoyed. In fact, before before even picking up a pen, Chris was picking up and loading boxes for FedEx during the night shift, and selling stuff on eBay by day. Both of these authors aren’t writing about theories. They are writing about their lives and the true stories from the lives of others.

In Charles Handy’s The Age of Unreason, we observe five sorts of work in your portfolio: fee work, salary work, homework, study work, and gift work. This holistic approach to work, in which some is paid but most is not, reminds us that “work” isn’t a dirty word at all, but something we are in charge of and can determine everyday.

Both of our authors do a remarkable job of integrating real-life stories into their narratives. This is partly a rah rah you-can-do-it-too strategy, but more importantly it’s a “look at the universe of possibilities” strategy. You won’t necessarily be interested in the passions of the subjects they observed, but you’ll be able to say “message received” when you’ve read about all of them: there’s definitely one…or two…or more things I can do to build a portfolio life.

Both men are clearly balanced and reflective and aren’t trying to sell you on “get rich quick” or even “get rich,” honestly. They are both advocates of “flow,” that intellectual analogue to the well-known “runner’s high,” and that opposite of a simple “job” (Chris Rock famously parses this in his Job v. Career bit but we could easily substitute: “Flow vs. Job” and capture a more humorous look at this). For those who prefer a definition to the visual Venn diagram above, Jeff defines flow simply as, “the intersection of what you are good at and what challenges you — where difficulty and complacency meet.”

But perhaps most overlooked in this age of the “motivational business book” is that both Jeff and Chris refuse to offer you pointless platitudes. They both tell you that in order to find the work you love you’re going to have to work. It’s not going to come to you in a dream or be delivered in a package. Read, reflect, and ask help of those closest to you. What matters is that you begin, and you can do so by reading these short but powerful books — which have so many other great ideas you can discover on your own.

PS If you’d like to hear Chris talk about his book, tune in to this Art of Charm podcast.

Stephen Heiner is a writer and entrepreneur living in Paris, France. If you like what he wrote here and want to see more, click on his Patreon page, and if you feel like it, drop some coins in his tip jar. Also, since this is Medium, please click “recommend” if this post contributed to your intellectual life or feel free to respond with major disagreements. He’s looking forward to engaging with you.