In The $100 Startup, you wrote
about dropping out of traditional
employment. Did your work on
that book influence the new one,
which is about finding meaningful work anywhere, whether on
your own or in an established
I did a lot of traveling and touring
[for the book] and met a lot of people who crafted a dream job within
a company or organization. I’m fortunate to be connected with a great group of readers, entrepreneurs, and people working regular jobs all over the world. I
researched for a couple of years before I started writing [Born
What did you learn about how people land their dream
Some people felt very lucky, but it’s not just luck. Fortune and
privilege certainly play a role. And then at the same time,
most people make decisions and choices to get to where they
are. I wanted to decode that process of making decisions.
When you come to that fork in the road, how do you know
which path to proceed on, and what do you do when you
make a choice that isn’t the best for you?
Making bad choices is something most of us can relate
to—and probably would prefer not to do.
The lesson is not just that it’s okay to make mistakes, but that
they actually can benefit you. One way around having to risk
it all is the side hustle [having a part-time business venture].
That aspect seems to be resonating with a lot of people. It
helps people to think entrepreneurially even if they don’t
want to be an entrepreneur.
Many people dream about being famous athletes, actors,
or pop stars—but then there’s reality. How can we bal-
ance fantasy and the real world?
It’s a case of looking at all of our passions and interests and saying, “What here relates to things that other people also want
that can bring value to some company or other people, and
that’s how I’ll monetize it?” I interviewed the first female firefighter in Ontario, Canada. She’s been a firefighter for more
than 20 years. That’s something that’s very meaningful—she’s
saving lives—but obviously if you want to be a firefighter,
there needs to be a real commitment. You can be passionate
about all sorts of things, but it doesn’t mean that you can
make a living from it. Some people are passionate about something that would make a better hobby than a career. —J.V.
University of Toronto Press
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In Born for This (Crown, out now), Guillebeau
coaches readers on bagging the ultimate white
whale: a dream career.