Booknotes: The Four-Hour Work Week pp.46-47

At the end of chapter 3 is an exercise in directed pessimism. I’m not
going to go through all the details, but basically he asks you to
imagine the worst possible outcome of taking whatever bold step you
are afraid to take, then the more likely outcome, and finally the
result of not taking the step.

I had a hard time with this one. For two reasons. First, I’m not
contemplating any bold steps at the moment. The only leap of faith
that is prominent in my mind right now is the decision to go freelance
– and that’s one I’ve already taken. Out of necessity, as most of my
major life changes seem to be. So I tried going through the exercise
retroactively using “going freelance” as the Big Change.

But that’s where I ran into the second issue. I feel like Tim has
someone other than me in mind with this. Someone with fewer kids and
fewer responsibilities. He’s trying to make the point that the worst
case scenario probably isn’t the end of the world, and you could
bounce back from it pretty quickly.

Which is true if you are a young, healthy bachelor in America. Drop
your law career and become a wandering minstrel? Why not? Worst thing
that can happen is you spend some time broke and crashing on people’s
couches for a while. If you get sick of that you can always clean up
and go back to the law office. Nothing lost except some time.

It’s not the same when you have a family. Losing your livelihood has
grave, longterm implications in that scenario. Couch surfing isn’t a
big deal when you’re single, but when you have to find a place for a
wife and multiple kids to stay, it starts to get seriously difficult.
The debt you incur while down and out may take years or decades to
climb out of. Serious health issues might go untreated while you are
lacking health insurance. And there may be long-term repercussions for
your family’s mental health and solidarity.

In short, the worst case scenario is pretty fucking bad. Perhaps not
irretrievably so, but still, it’s not a thought to embolden one into
taking action. If anything, it will inspire the opposite. If I were
considering, say, dropping my contract work to work on a product idea
full-time, doing this exercise would make me seriously question my

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