"You Don't Have to" Series, Alternative Living, Happiness

You Don’t Have to: Escape the 9 to 5

Tim Ferriss is a popular self-help author who is well-known for his book ‘The Four Hour Work Week: Escape the 9-5, Live Anywhere and Join the New Rich.’ The basic idea is that by running a business or enterprise that can be operated via the internet, you can earn in dollars and live in a place where you spend pesos.

This conjures such an alluring lifestyle, sipping margaritas by your laptop overlooking a serene seascape. It must be especially enticing to the 70% of Americans who are reportedly unhappy with their jobs.

More often than not, dinner conversations conjure up venting about annoying bosses, and the restrictive lifestyle of the standard office job. But is it really better? Is the grass really greener outside the cubicle farm? Would most of of us be happier flipping our manager the bird and going at it alone?

As someone who’s attempted the one-man-show, work-from-home, supposedly-way-better-job route, I can tell you…it ain’t all white sand and Coronas.



David Cain, the author of Raptitude.com wrote about his experience leaving the 9-5 grind and writing full time. Shortly into his self-employment, he realized that it was an strange and unfamiliar feeling being your own boss. The majority of our lives are guided by a higher figure (whether it be a teacher, parent or boss), and though we probably will never admit it, it’s a comfort we take for granted.

As he puts it: “Thirty years of conditioning is extraordinarily difficult to overcome. Most people, when they emerge from the conventional child-school-workforce tunnel, are almost entirely untrained to manage entire weeks and months in which the bulk of one’s time isn’t committed to serving an institution of some kind.”

It’s not to say we can’t learn to be our own boss, but the problem I see is that it creates an unwarranted discontent among those in an office role, believing the job they have is unquestionably inferior to that guy with his laptop on the beach (on that note, how enjoyable is a beach, really, if you’re just working on your laptop?).

Personally I operate well with a routine, and I’m the most productive when I go to a place of work rather than at my home computer which is incredibly prone to procrastination and a high frequency of naps. In an office I also get to see friends and colleagues and interact and collaborate with other people on a daily basis. I get to feel like I’m in a team and I’m part of something bigger. 

On top of that, working for a company means paid holidays, benefits and designated time off. If you run your own business, every hour of every day is potentially work time. You don’t necessarily get to hang your hat at 5pm and enjoy the evening uninterrupted.

In David’s article, he quotes a friend who remains in his corporate job despite considerable success as an author, because “he’s aware that without the structure imposed by a job, he’s liable to devolve into an unwashed caveman, eating cold cereal three times a day and gradually forgetting how to talk.”

Instead of chasing the highly sought-after ‘escape’ from the cubicle, regardless of what the actual nature of the work is, my advice would be to do what you enjoy doing, or what you feel you’re good at. It doesn’t have to be your ‘passion,’ (in a previous post I express my beef with this whole passion thing), but simply something that takes you in a direction and involves people that you like to be around.

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