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Chris Guillebeau

Create Your Side Hustle and Take Control of Your Money

Having one job is good, but having two is better.

It’s no secret that many of us have lost our jobs due to the COVID-19 pandemic. Things are financially unstable right now, and many of us need to put our goals on hold. We all have countless questions about how long this will go on. Unfortunately, the answer is: we don’t know.

But here’s what we do know: Finding new sources of income is more important than ever. Everyone should have a side hustle — one that can act as an emergency fund, a vacation fund, or just another way to make extra cash.

Luckily, my guest on The School of Greatness today knows all about side-hustling and how it can allow you to take control of your money. In this episode, we go into how you can develop side-hustles that you actually enjoy and find meaningful. We dig into questions like: What can you do to learn how to earn? And what does it take to stand out as an individual or brand to break through? Lastly, we also discuss the greatest skill for every side hustler to master today.

So, without further ado, let’s dive into this with the one and only Chris Guillebeau!

Who Is Chris Guillebeau?

Chris Guillebeau is a New York Times bestselling author, entrepreneur, podcaster, and modern-day explorer. During a lifetime of self-employment that included a four-year commitment as a volunteer executive in West Africa, he visited every country in the world (193 in total) before his 35th birthday. Since then, he has modeled the proven definition of an entrepreneur: “Someone who will work 24 hours a day for themselves to avoid working one hour a day for someone else.”

Every summer in Portland, Oregon, Chris hosts the World Domination Summit, a gathering of creative, remarkable people with thousands in attendance. Chris is also the founder of Pioneer Nation, Unconventional Guides, the Travel Hacking Cartel, and numerous other projects.

His newest book, The Money Tree: Finding the Fortune In Your Backyard, comes out in April 2020. It is his first full-length fiction book, and it tells the story of a man who learns to take control of his finances and live a better, healthier life. His daily podcast, Side Hustle School, is downloaded more than two million times a month.

Do you find yourself living paycheck to paycheck? Do you want to start making extra money to spend on the things you want? This episode is designed to help you create a new source of income without quitting your job.

Learning How To Earn 

Learning how to earn can be tricky and confusing. I know that because I was once there, too! When the economy crashed in 2008, I was desperate, broke, and living in student debt. I was also sleeping on my sister’s couch, and when she kicked me out, I realized I was tired of not having control of my finances. So, I decided to start a side hustle, and within two years, I turned it into a seven-figure income. 

That’s how I learned to earn — through necessity. But what if you’re living with a different circumstance? Say you’re an artist, a thinker, or a planner? Is it possible to learn how to earn? The good news is that you can, and it doesn’t require you to build a company to do that.

“The model that I’m trying to put forward is that there are all kinds of people worldwide who aren’t taking any capital. They’re not going into debt. They’re not spending on their credit cards. They’re finding ways to start their own little business.” – Chris Guillebeau

How will this apply to you? Chris discusses the ways anyone can do to start learning how to earn. I outlined two of them below: 

#1: Identify Your Skill Set

First, Chris advises everyone to identify their skills and what they’re really good at. Begin with asking yourself, “What can you do?” or “What are you curious about?” If you still wonder how this can happen, Chris alludes to the personality of Jake, a character in the book, The Money Tree: Finding the Fortune In Your Backyard.

“Jake has the same situation. He’s like, ‘What am I good at?’ He goes to this group called the Third Way — those who want to earn but don’t take the old path of starting a business via loans (the first way) or the Silicon Valley route (the second way). The group challenged him to make a thousand dollars in the next week. He had no idea until he started selling his old textbooks through online auctions. He started making a little bit of money, and from there, he started to sell more. Before he knew it, he had already done something that helped him reach the challenge.” – Chris Guillebeau

This story shows us that you don’t really need expertise over something to make money. Sometimes, it’s also good to try out different things, such as taking surveys, trying products, and even selling your unwanted stuff. If you keep on doing these things, you’ll eventually realize that there might be something that you’re really good at and can earn a lot of money doing. 

To summarize, the best way to learn how to earn is by being intentional about it, working hard, and gaining experience. Whether you do that through gigs or teaching an online course or something completely different, let yourself explore and be creative! 

#2: Create A Service

Even if you identify your skillset, there may be a moment when you don’t feel like doing it for the rest of your life. That’s why Chris also suggests creating a service. Your service is something you can provide for somebody, and they pay you money for that. It could be some kind of consultancy, coaching, advisory, expertise, or whatever. Chris, however, cautions that there’s something to be careful about in this approach, 

“In the process of providing services, you may realize that you’re not an expert in the service you’re providing in the first place. The product wasn’t specific enough, or the service and benefits you were trying to do weren’t clear.” – Chris Guillebeau

The only remarkable thing about this approach is that you don’t have to lose thousands of dollars. However, you may lose valuable time and effort. On the brighter side, Chris also guarantees that the experience is like taking a master’s degree in business (MBA), where you gain wisdom and eventually apply the lessons you learned in your daily activities.

“Don’t forget why you started.” @chrisguillebeau  

Redefining Impact

What will it take to stand out as an individual or break through as a brand?

Creating an exceptional experience may be a quality that sets your side business apart from your competitors. It can also be your quality products or disruptive marketing approaches. All these are designed to gain more followers for your business and make an impact in a short period. But what if you’ve done everything and still haven’t met a million followers you wanted? Does it mean you have failed in creating an impact for your services? For Chris, the answer is no. As he explains,

“I think we have to think about impact a little bit differently because not everyone will have a million followers, and not everyone will have that kind of breakout success. That’s okay because you can still have a lot of impacts, you know? … A lot of people that have impacted my life are ordinary people. The person that inspired me to think about living in West Africa is a surgeon in California, and it’s been his whole life over there. He doesn’t have an Instagram or YouTube account. But the impact he’s made, not just on me, is far more than what anybody has done” – Chris Guillebeau

Only a few people really stand out and make a significant mark with the millions of entrepreneurs, side hustlers, and freelancers out there. If you’re one of those seemingly “unsuccessful” people, it might be time for you to have a change of perspective on this matter. As Chris explains, certain people have big audiences, and that’s exciting for them. However, you can also impact a few people in a big way that could change the world. 

The Greatest Skill For Every Side Hustler To Master Today

Once you’ve found success as a side hustler, you can most likely earn more. But before you can make this happen, you might want to know the most essential skill you should possess today.

“Curiosity, in the form of asking questions, could be the greatest skill any side hustler can master today. Asking what you know or thinking about the daily annoyances and problems we encounter and asking, ‘What could be a different way to do this?’ can be the answer. … It isn’t so much about being passionate. It’s more like, ‘I am sick of this, and I want something more.’ That’s motivating more than anything else.” – Chris Guillebeau

People pay for a solution to pain, and what Chris advises is for everyone who wants to earn more money to be inquisitive and think about it. Ask questions to get answers, and you’ll probably come up with new ideas or ways of doing things. This can lead to new business opportunities becoming your side hustle and ultimately help you control your finances.

Why You Should Listen to This Chris Guillebeau Podcast Episode Right Now…

Creating a side hustle, or several of them, is on top of many people’s to-do lists. For some, it means earning extra money; for others, it can help overcome financial issues or fund other goals like starting a family or retiring early. Whatever your reason is, this episode with Chris definitely takes the cake when it comes to advising us to be successful with our next entrepreneurial venture.

What we’ve learned today can definitely change us for the better if we apply it in our lives. So, learn more by getting a copy of Chris’s book, The Money Tree: Finding the Fortune In Your Backyard. Also, check out his website, Instagram, Facebook, and Youtube for more of his life-changing financial wisdom!

If you enjoyed this podcast, please share it with your friends and family. Don’t forget to tag Chris, @193countries, and me, @lewishowes, on Instagram with a screenshot of your most significant takeaways from this episode! You may also want to give us a five-star rating on Apple Podcasts so we can spread these powerful messages to more people.

If you want to start learning how to side hustle, don’t miss Episode 937 from the brilliant Chris Guillebeau!

To Greatness,

Lewis Howes - Signature

“You don’t need permission to do big things.” @chrisguillebeau  

Some Questions I Ask:

  • How do we do something in our own backyard that will make us money? (1:00)
  • Why are there not high paying jobs out there for people just graduating? (4:45)
  • What can you do to learn how to earn? (6:21)
  • Why did you start World Domination Summit and why are you ending it? (18:30)
  • What will it take to stand out as an individual or brand to breakthrough? (24:31)
  • How does one find the right mentor? (28:12)

In this episode, you will learn:

  • Why it doesn’t pay off to be cynical (6:00)
  • How curiosity and hard work pay off (9:23)
  • What kind of people impact you the most (22:20)
  • The greatest skill you can have (25:31)
  • Why finding your own way is essential (31:30)
  • Plus much more…
Connect with
Chris Guillebeau

Transcript of this Episode

Music Credits:

Music Credit:

Kaibu by Killercats

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