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the end goal. Living more—and becoming more—is.
In the beginning, the external fantasies will be enough, and there is nothing wrong with this. I cannot
overemphasize the importance of this period. Go nuts and live your dreams. This is not superficial or
selfish. It is critical to stop repressing yourself and get out of the postponement habit.
Let’s suppose you decide to dip your toe in dreams like relocating to the Caribbean for island-hopping
or taking a safari in the Serengeti. It will be wonderful and unforgettable, and you should do it. There
will come a time, however—be it three weeks or three years later—when you won’t be able to drink
another pifia colada or photograph another damn red-assed baboon. Self-criticism and existential panic
attacks start around this time.
But This Is What I Always Wanted! How Can I Be Bored?!
Don’t freak out and fuel the fire. This is normal among all high-performers who downshift after working
hard for a long time. The smarter and more goal-oriented you are, the tougher these growing pains will
be. Learning to replace the perception of time famine with appreciation of time abundance is like going
from triple espressos to decaf.
But there’s more! Retirees get depressed for a second reason, and you will too: social isolation.
Offices are good for some things: free bad coffee and complaining thereof, gossip and commiserating,
stupid video clips via e-mail with even stupider comments, and meetings that accomplish nothing but kill
a few hours with a few laughs. The job itself might be a dead end, but it’s the web of human interactions
—the social environment—that keeps us there. Once liberated, this automatic tribal unit disappears,
which makes the voices in your head louder.
Don’t be afraid of the existential or social challenges. Freedom is like a new sport. In the beginning,
the sheer newness of it is exciting enough to keep things interesting at all times. Once you have learned
the basics, though, it becomes clear that to be even a half-decent player requires some serious practice.
Don’t fret. The greatest rewards are to come, and you’re 10 feet from the finish line.
Frustrations and Doubts: You’re Not Alone
People say that what we are seeking is a meaning for life. I don’t think this is what we’re really
seeking. I think what we’re seeking is an experience of being alive.
—JOSEPH CAMPBELL, The Power of Myth
O.. you eliminate the 9-5 and the rubber hits the road, it’s not all roses and white-sand bliss,
though much of it can be. Without the distraction of deadlines and co-workers, the big questions (such as
“What does it all mean?’”) become harder to fend off for a later time. In a sea of infinite options,
decisions also become harder— What the hell should I do with my life? It’s like senior year in college all
over again.
Like all innovators ahead of the curve, you will have frightening moments of doubt. Once past the kid-
in-a-candy-store phase, the comparative impulse will creep in. The rest of the world will continue with
its 9-5 grind, and you’ll begin to question your decision to step off the treadmill. Common doubts and
self-flagellation include the following:
1. AmTreally doing this to be more free and lead a better life, or am I just lazy?
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