5 Powerful Lessons From Chris Guillebeau About Lifestyle Design

Chris Guillebeau is an American author, blogger, speaker, and part of a select group of people who have been to all 193 UN countries. His writing inspires millions of people worldwide to channel their inner adventurer and get more out of life. On this basis, here are 5 powerful lessons from Chris Guillebeau about lifestyle design.

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I first came across Chris’s work way back in 2012. 

Somewhere in rural Mexico, a 20-something guy in my hostel was reading The Art of Non-Conformity, Guillebeau’s first book. 

I wasn’t familiar with the concept of “lifestyle design” at the time, but the title caught my attention. I ended up reading the book and instantly fell in love with its message. 

Since then, Guillebeau has published six other books: The 100$ Startup, The Happiness of Pursuit, Born For This, Side Hustle, 100 Side Hustles, and The Money Tree

Most of his writing promotes adventure, entrepreneurship, and personal growth. 

The overriding mantra is simple: Break out of conventional, unfulfilling life patterns and build your fortune to design a life on your own terms. 

5 powerful lessons from Chris Guillebeau about lifestyle design 

Having re-read all of Chris’s books over the last few months, I’ve decided to break down some of their major takeaways. 

As such, here is a concise recap of five powerful lessons from Chris Guillebeau about lifestyle design. 

Panoramic view of Yosemite valley - 5 powerful lessons from Chris Guillebeau about lifestyle design
Picture by Aniket Deole / Unsplash

1. Find a monetizable passion 

In his second book, The 100$ Startup, Guillebeau tells the stories of various entrepreneurs who turned passions into profit by starting small. 

The key message of the book is that almost any passion can become a business venture if you find a way to provide value to your customers. 

Nevertheless, the book also draws a critical difference between raw talent and monetizable skills

Consequently, if you want to turn a muse project into a profitable business venture, you need to identify a passion that can provide value to other people. 

Skills and passion do not suffice in the world of startups. To build a business from scratch, you need to solve customers’ problems. 

In a 2013 American Express interview, Chris uses the following example to explain the difference between a passion and a monetizable skill: “I’ve yet to find someone to pay me for surfing the Internet all day and eating pizza at night, two skills I’ve been developing for a long time.

The lesson here is simple: in the world of startups, passion projects are great, but your passion needs to provide value to other people for it to become a business idea.

2. Use the skills you already have to create assets that work for you

In his 2017 book Side Hustle, Chris explains how you can make an extra income with leisure activities. 

By definition, side hustles are not your main occupation. They are hobbies, passion projects, or past-time activities like writing, photography, and dog walking. 

The primary lesson from Side Hustle is that you do not need to become a fully-fledged entrepreneur to make an extra income. All you need is a way to transform your skills into assets. 

As an example, lots of college students are passable writers. 

Let me tell you a little secret: freelance writing does not require Shakespearean English. 

During my university years, I did a lot of online copyediting, especially for first-year students. I eventually transitioned into freelance writing, but copyediting was the first step. 

There are nowadays hundreds of platforms where you can sell services using skills you already have. You won’t become a millionaire overnight, but the side hustle philosophy is certainly realistic. 

In this context, creating additional income streams without having to learn new skills is a great way to edge closer toward lifestyle design in the 21st century. 

If you’re new to the idea of side hustling, Guillebeau’s book is the ideal place to start. 

3. Your competence is the best job security you’ll ever have

Guillebeau’s first book, The Art of Non-Conformity, was his mainstream breakthrough. 

Published in 2010, its principles still hold their own in today’s world. 

One of the most eye-opening lessons from The Art of Non-Conformity is the importance of building a set of personal competencies

Instead of relying on a company to provide you with regular paychecks, try to build a personal set of skills that transcends your current corporate ecosystem. 

You might love your job. Your boss might be nice and mentoring. And you might enjoy your current office, cafeteria, and coffee machine. 

However, all of these perks are temporary. In 2020, many people learned this the hard way. 

Your current position and status can disappear within the blink of an eye. No matter how far you’ve come, external factors can always influence your job security. 

That’s why the only truly safe option is to build personal competencies over time. 

Imagine knowing that no matter what happens to your professional situation, you’ll have 1,000$ of extra income thanks to your skills. 

You’ll feel much more secure than you could ever feel inside a fragile corporate bubble. 

Chris doesn’t say that you should immediately quit your job and pursue an entrepreneurial route. The entrepreneurial route, while exhilarating, doesn’t suit everybody. 

What Chris wants you to do is to stop putting all your eggs in one basket. 

If you want to design your preferred lifestyle, you need to create a set of competencies that work in any scenario. 

Be it with side hustles, diversification, or other projects, the only way to achieve genuine job security is to be self-reliant in terms of income.

4. Produce work that will outlive you and make the world a better place

Another powerful lesson from The Art of Non-Conformity is legacy building.

Chris writes that most people sleepwalk through life without leaving a mark. 

Routines, random entertainment, and a false sense of security prevent us from questioning our values and doing something truly memorable with our lives.

That’s where “legacy work” comes into play. 

According to Guillebeau, work cannot be a mere vehicle to build your life. Chances are you won’t feel fulfilled if the results of your hard work solely serve your life. 

Everybody has unique skills that can benefit other people. As a consequence, our ideal lifestyle should include a legacy that will outlast ourselves. 

Many people see lifestyle design as a means to live on the beach and escape traditional employment. 

Lifestyle design, however, can have a much deeper impact if we implement Guillebeau’s legacy building idea. 

Whether it’s a charity, a blog, a Youtube channel, or a volunteering assignment, everyone can utilize their skills to have a small but positive influence on the world. 

If you, for instance, help one person out of poverty, you might have changed the lives of that individual’s children, grandchildren, and so on. 

Your small act could have a positive effect that will survive long after you’re gone. 

people mountaineering in Switzerland - Produce work that will outlive you and make the world a better place - lessons from Chris Guillebeau -
Picture by Sylvain Mauroux / Unsplash

5. “Adventure is for everyone” 

Finally, one of the most compelling lessons from Chris Guillebeau’s books is the importance of quests

In his 2014 book, The Happiness of Pursuit, Guillebeau recounts the tales of diverse adventurers, from marathon runners to Panamerica road trippers and Chris’s own 193 country challenge. 

The book analyses the power of quests; personal adventures that take us forward in life. 

In this context, Chris enumerates five main criteria for his definition of a “quest”: 

  • “A quest has clear goals and a specific endpoint.”
  • “A quest presents a clear challenge.”
  • “A quest requires a sacrifice of some kind.”
  • “A quest is often driven by a calling or sense of mission.”
  • “A quest requires a series of small steps and incremental progress toward the goal.”

The best thing about Chris’s definition is its versatility. Anyone can identify their quest and chase goals that will transform their life. 

In the end, that’s what lifestyle design is all about. Pursue quests and adventures, no matter how small, and live a life worth living. 

Without clear goals, challenges, sacrifice, callings, and progress, our lives are nothing but broken cassettes, playing over and over until someone takes them out of the player to be replaced. 

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