Best-Selling Author Chris Guillebeau Talks Side Gigs and Financial Freedom

Chris Guillebeau remembers clearly the sense of freedom he felt
the first time he earned money on his own terms, not his

It was circa 1998, Guillebeau was in college and was working the
graveyard shift at FedEx. He didn’t know what he was doing with
his life. But he knew he was fed up.

Then, by chance, he stumbled onto eBay, joined the gig economy
and everything changed. That was 21 years ago.

Since then, Guillebeau has traveled all over the world, keeping
himself afloat through side gigs while he studied the side gigs of
other cultures. Then he authored several best-sellers and started
the successful podcast “Side Hustle School.”

He sat down with us to chat about the gig economy, things to
consider before taking on a side gig and his latest book, “100
Side Hustles: Unexpected Ideas for Making Extra Money Without
Quitting Your Day Job.”

A Q&A Interview With Chris Guillebeau

This interview has been edited for length and

Adam Hardy: The terms “side gig” or “side hustle”
mean different things to different people. Before we jump in, can
you first explain how you define these terms?

Chris Guillebeau: I define it as an income-generating project
that you start aside from your day job. Ideally, it’s not a
part-time job. It’s something that has the potential to be an
asset for you.

That’s why just about every story in “100 Side Hustles”
portrays a gig that generates money for that person in a way
that’s not dependent on some other platform, like freelance
websites or some other structure.

Side hustles should be sustainable, not just another job you go to
after an eight- or 10-hour day. They should help you have more
options in the future.

AH: “Follow your passion” is common career advice. What
are your thoughts about this phrase? How does it relate to your
definition of a side hustle?

CG: The problem with that phrase is that there are all kinds of
things you can be passionate about that aren’t going to make you
money. And there are a lot of things you should be passionate about
that shouldn’t make you money.

When it comes to having a money-making project, it’s more
important to follow your skills. Ask yourself: What am I good at?
What skills do I have that could be applied in a different way than
my day job? When you follow your skills, it can also lead you to
things that you are passionate about because we tend to get excited
about the things we’re good at.

So it’s not like you’re pursuing the most dispassionate thing,
but it’s more about asking yourself what are you good at that
other people value, and that can set you up for financial

AH: A lot of people may think that they don’t have a
marketable skill to start a side hustle. What’s your advice to

pages from the author's book.

CG: This comes up a lot when I meet with my readers at book
events. I’ve never, after about a 10 minute conversation, come
across a person that doesn’t have a marketable skill.

So I think it’s a perception issue. Usually people who ask
that are thinking, “Well, I don’t have a marketable skill
because I didn’t get a degree in X field, therefore I’m not

A big part of what I do with my podcast is show a different
story every day ― 850 days and counting — of different ways
people are making money. Most of those people probably said at one
point. “I don’t have a marketable skill.”

But they found a way: They bred rabbits to pay for
their college
, or they designed literature
books and started a Kickstarter campaign that raised

I really, really do believe that everyone has a marketable
skill. Now I’m not a get-rich-quick person — I know that not
everyone out there is going to have a huge business. But I do think
it’s about uncovering that skill, adapting it and applying it to
this new economy.

Pro Tip

If you’re not sure what skills you have, take a little
inventory and write down a list of topics that you have knowledge
of. Ask your friends to see if they can spot something that you

AH: You traveled to every country on earth. What are some of
the most interesting side hustles you came across in your

CG: Through traveling and being an aide worker in Western
Africa, that kind of started everything for me. The greatest
realization is that we have such a Western perspective on what a
side hustle is and what entrepreneurship is. This kind of thing
really isn’t new. Some of the technology is new, but the concept

All over the world, and in parts of the world that don’t have
a more formal economy, this is how everyone has been making a
living for generations and centuries. All those people are
entrepreneurs, whether they call themselves that or not.

While I was traveling in India, I knew I had made it as an
author when I came across a merchant who was selling a pirated copy
of my book. My team was like “Whoa, we gotta shut this down,”
but I was really excited about it. I was like “No, I want
pictures of this!” The book was actually photo-copied. Like how
long did that take, first of all?

AH: Wow, that’s some dedication right there. In terms of
our economy, though, do you view side hustles as a necessary evil
because there aren’t enough fulfilling and high-paying jobs, or
do you see side hustles as a way for people to escape the current
restraints of the economy?

Author Chris Guillebeau gestures while in front of an audience during an appearance in Mumbai.

CG: Yes and yes, and a little more on top of that. I don’t
think side gigs are evil, but a lot of people are gravitating
toward them for two reasons.

One, there’s a realization that we can’t depend on
corporations, organizations or government for our well-being. That
doesn’t mean they are all inherently bad. It’s just that we are
starting to understand that no one is going to better look out for
our well-being than we are.

The other thing is that I hear over and over again is about the
confidence people gain and the self-worth people feel when they are
able to make income on their own.

I do think people are recognizing the necessity of this, but it
can be something that brings you joy not something you dread or
have to check off a list.

Side hustles should be sustainable, not just another job you go
to after an eight- or 10-hour day. They should help you have more
options in the future.

AH: Before your books and podcast ― when you were living
off side hustles — what was the highest amount of gigs you held
at once?

CG: I guess I’ve never really counted them up, but I’ve
always had more than one side gig at a time. I’ve never been the
kind of person to do just one thing.

But I would guess somewhere around five to eight projects at
once. I try to focus on maybe three main things and the rest are
either passive things I have set up, or they come up in the

Some people thrive on that, and other people get really
overwhelmed. It depends on your goals. It can be really empowering
to make your first $100. If you’ve never made money outside of a
paycheck from your employer, it can feel really good. But I
wouldn’t recommend doing 10 things at once. To start, pick one
thing and see what you can do with it.

If it doesn’t work, stop after 30 days and do something

AH: What was your first $100 working for yourself?

CG: I can tell you exactly what that was. This goes back 21
years. I was going to school and I worked the night shift at FedEx,
like 10 p.m. to 2 a.m., loading boxes on a truck.

Then I learned about online auctions for the first time, and I
looked up how to do it. I knew nothing about copywriting or taking
photos, but I sold some random stuff from my apartment (on eBay and
other sites) and made a couple hundred dollars from it.

I looked at the hourly rate and thought, wow, this is more than
twice what I’m making at FedEx, breaking my back during a night
shift. It wasn’t just the financial aspect, it was the

Everything I do stems from that.

AH: How important is creating a game plan or some kind of
larger goal when starting a side hustle?

Author Chris Guillebeau's book sits on a desk.

CG: I think people tend to get hung up on this and think they
have to have a life plan. Goals are good, of course. Are you trying
to pay off debt? Do you need extra money? Are you trying to replace
the income from your day job? All good things to think about.

But I also see and hear from a lot of people that get hung up on
this. They get kind of stuck in analysis paralysis. So if you’re
not sure what you want to do, just do something. And if you don’t
like it after about 30 days, do something else.

Not everything has to connect to your larger life purpose. If
you’re 20 years old, you don’t first have to figure out what
your life purpose is to start a side gig.

AH: You’ve mentioned that number a couple times: 30 days.
Is this a good amount of time to give yourself to try out a new
gig? Is that the best way?

CG: I would say after 30 days, cut your losses and start over.
Don’t be afraid to say “I thought this was a good idea but it
wasn’t.” Maybe you can learn something from that process that
motivates you to try something different.

I feel that most successful people in this world have false
starts, and that’s normal. Whereas those who struggle, they might
think they have to persist because they hear, “persistence is the
key.” Well, not necessarily. I think adaptation is the key.

Take the experience of your failure and ask: With what I’ve
learned here, what’s a better way of going about this?

That’s when you’re going to be more successful. Don’t be
afraid of letting go of something.

AH: To wrap up, I want to ask a question about something
you’ve hinted at in a couple of your answers: Are side hustles
for everyone?

CG: The simple answer is yes. I don’t see any downsides to it
when we’re talking about starting something that doesn’t
require a lot of risk and you’re not investing a lot of

You know, what could go wrong?

Adam Hardy is a staff writer at The Penny Hoarder. He
specializes in ways to make money that don’t involve stuffy
corporate offices. Read his ​
articles here
, or say hi on Twitter @hardyjournalism.

This was originally published on
The Penny Hoarder
, which helps millions of readers worldwide
earn and save money by sharing unique job opportunities, personal
stories, freebies and more. The Inc. 5000 ranked The Penny Hoarder
as the fastest-growing private media company in the U.S. in

Source: FS – All-News2-Economy
Best-Selling Author Chris Guillebeau Talks Side Gigs and Financial Freedom