Americans both love and hate pioneers and cowboys at the same time.

Our cultural icons are those hard-working men and women who do their own thing and become really successful. Yet, on a day in and day out level, we teach people to get in line and follow the route laid down before them.

We see people work their entire lives and peacefully retire, all the while never rocking the boat. We see those hardworking but line-toeing people get replaced by younger people with fresh ideas. We don’t want to be those people quietly ushered out the door, but the majority of us show up and toe the line.

Part of the problem is that we have conceptually tied together financial security and happiness. We see artists and creatives struggle and assume that they’re desperate and unhappy because of their financial situation. We don’t see that they’re happy doing what they love – we just see their broken-down vans.

One of the most significant advancements of Tim Ferriss’ 4-Hour Workweek is his very forceful presentation of those who would rather show up to a job they hate every day but be comfortable with their misery rather than creating their own freedom while being insecure about the prospects. “Better the hell we know,” indeed.

Another contributing factor to our schizophrenia is how we value people. On the one hand, we think that human lives are priceless and equal. But in the trenches, we very quickly evaluate people by how much income or exchange they command. Those who command more income get more respect, and those who generate ideas and identities that sell get a larger share of our attention.

We learn this from a very early age, as well. We learn that art, creativity, and free expressiveness are the wrong path because, obviously, the path that leads to financial insecurity is the wrong path. Rather than asking ourselves what we enjoy, we ask ourselves first how we’ll make money.



Those who have quit walking “the right path” are liberated up until the point in which they have to explain what they’re doing to someone who believes in “the right path” nonsense. It’s at those points in which they have to deal with the condescending attitude of those people who think they’re just naive and will soon grow up.

(Go ahead, try to get people on “the right path” to talk about happiness without referring to economic position and material stuff. It’s a strange combination of funny and tragic that they can’t.)

We know that family, friends, creative pursuits, and quality leisure are the stuff that human life is made of, yet we march to the beat of the dollar everyday.

Untangle measures of happiness from money and security. Money is a means to an end, not the end itself. If you know this, you probably live from the outside-in. If you truly understand it, you’re on the path to living from the inside-out.

Just a warning, though. People will love and hate your individuality. You will rock boats, and you will unsettle people’s reality as your path challenges theirs. You may become alienated from those you were once close to.

You’ll no longer be schizophrenic, but people will think you’re crazy. And that’s the true irony.