The Art of Non‑Conformity | Chris Guillebeau | Book Summary


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The Art of Non-Conformity by Chris Guillebeau



“It’s your own life, so why not set your own rules?”

All about the underlying philosophy behind challenging authority and charting a path for yourself. Setting the terms of your life, overcoming the internal obstacles of fear and insecurity, and taking on the external obstacles of gatekeepers and critics.

Key Concepts

  1. By itself, money has no value.
  2. Choosing between yourself and others is the wrong choice.
  3. Changing the world is not always practical.
  4. You can plan for the future without deferring your life now.
  5. Life is short.


A life of sleepwalking – a contagious pattern of settling for what is “good enough.” Oblivious to the world that surrounds us, the life of sleepwalking offers little risk and little reward. No one will ever fault sleepwalkers for their choice. There’s just one big problem: for those of us who long for a life of adventure, the life of sleepwalking sucks.

We are free to climb the ladder. Have you ever heard about how it’s easier to ask forgiveness than permission? This is completely true, but there’s even more good news: there are very few things you need to ask forgiveness or permission for.

If the sleepwalking life is the “real world” of the unremarkably average, the clear alternative is the living world of adventure.

Setting the terms of your unconventional life

Your dreams and big ideas belong to no one but you, and you never need to apologize for or justify them to anyone. If you already know exactly what they are, great; you’re halfway there. Most of us, however, find that we need to take some time to think about it.

What do you really want to get out of life?

Sit down and figure it out.

  1. Create your ideal world. Write it down, your ideal day, the more detail the better.
  2. Radical goal setting. Have 1 year goals, 5 year goals & lifetime goals. A bucket-list type of goal list.
  3. Planning for serendipity. Have some time for spontaneity, you can’t plan every little thing.

As long as what you want does not cause harm to others, you never need to apologize for pursuing your own dreams and big ideas.

As a general rule, if you don’t know what to do on any given day, spend at least some of your time helping someone else. Instead of having this be an afterthought, you can build a life focused on the relentless pursuit of what you want coupled with the call to make a difference—starting today.



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The principles of unconventional living

  • There is almost always, more than one way of doing something.
  • When faced with a choice between abundance and scarcity, choose abundance.
  • When faced with uncertainty about taking a leap of faith, take the leap.
  • Intelligence is not a pre-requisite. But determination is.
  • You can have unlimited dreams and goals, but not unlimited priorities.
  • If you get a few things in order, the stages of growth are exponential.
  • The pathway to world domination, or whatever it is you want to do, begins with clearly understanding what you want to get out of life.
  • Once you begin taking your ambitions seriously, you can usually accomplish most things in less time than you initially expect.
  • In the end, it’s not all about you. Most of us want a life that leaves a positive impact on others.
  • When you start doing what you really want, not everyone will understand. This is okay.



Fear begins with an undefined worry, a voice in the back of your head that says you’re not good enough, you won’t succeed with anything big or significant, and you might as well give up and stop trying to stand out.

To break the cycle, the fear of the unknown has to become less than the stale acceptance of the current situation. There are two ways to make this happen:

  1. Increase the pain of the current situation
  2. Decrease the fear of the desired situation

Step one: Conquering fear begins with acknowledging fear. Make a list of all the things you’re afraid of at any given time.

Step two: Apply the no-regrets mindset. Accept the worst-case scenario, this helps to put your fear into perspective. Create accountability, tell people, anyone what your planning.

Step three: Smash through the wall of fear. Assuming you know what you want and are just having trouble seeing it through, one thing that helps is to force the active decision. This is where you stop wavering and decide one way or the other if you’re going to take the leap.

How to fight authority and win

Why do people do what other people expect them to instead of what they really want? Sometimes people fall in line because authority figures are very skilled at keeping them in their place. Many of these authority figures are ‘gatekeepers’.

Gatekeepers are a person or group with a vested interest in limiting the choices of other people. They are an obstacle that must be overcome to achieve unconventional success.

When you’re ready to embrace change and challenge the authority of gatekeepers, here’s what you do: deploy the underdog strategy – change the way the game is played. Remember that gatekeepers are all about limiting choices (you can have a or b, but not c or d). The underdog strategy looks for alternatives.


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Changing the way we think about how and where we spend most of our productive time. Deriving security from your own competence instead of an employer, recruiting and deploying your own “small army,” and the important question of money—how much you need and how you can get it.

Taking responsibility by taking action

Your own competence is your best security. Change the way you interpret events, and then take action to change your circumstances. There are a few options in how to tackle this:

  1. The case for self employment – not everyone should be an entrepreneur or small business owner. But it’s fair to say, that a lot of us want to establish “full independence” by taking the leap to self-employment. For many self-employment is the best way to cut the dependency cord.
  2. Become a rockstar and redefine the terms of your job – you have the ability to reclaim independence without completely going off on your own. At your current job, is there an option to work remotely? Try working and living in a different city for example.
  3. Redefine your place of employment by hiring a boss – instead of job-hunting, go boss-hunting. Dare to be different and put yourself out there, give people the option to ask YOU to work with THEM.

Graduate school vs. the blogosphere

The experience of graduate school versus creating an independent career. It won’t be the case for everyone, but for some, the better choice is alternative and independent Learning
Formal education and learning do not always go hand in hand. If your primary goal is to learn instead of to prepare for a career, you may be better off going it alone.

Yes, there are exceptions. If you want to become a professor and work toward innovation in the academy, then you probably need the graduate degree. But the exceptions are greatly outnumbered by the rule that it is often quicker, cheaper, and easier to become your own expert.

  • Relate your education to what you actually want to do when you finish.
  • Don’t use graduate school, or any other course of study, as a form of life avoidance. Pursue the course only if there’s a good reason.
  • Much of higher education consists of learning to make yourself look good. It’s an essential skill, but you might as well learn something else while you’re there too.
  • Regardless of how you feel about college or university, consider some form of alternative learning to increase your knowledge.

The power of your own small army

No matter the goal, you’ll likely discover that you’re going to need some help along the way. If you want to become a working artist, you’ll need fans and patrons to support you. If your plans involve some kind of entrepreneurial project, then you’ll need a group of loyal customers to ensure reliable income over time. Even highly individualistic goals, like writing a book or visiting every country in the world, can benefit greatly from the support of a small army of loyal partners.

If you give people a good enough reason, many of them will stick with you for life, allowing you to scale up your project or move to another goal after you achieve the first one.

  1. Recruit your small army – to stand out from the crowd, you’ll need a platform to speak from, a good reason why people should pay attention to you, and a welcoming environment that encourages prospects to get involved.
  2. Train and reward your army – you’ll want to deepen the relationship. You do this by meeting the needs of your army and helping them get what they want. Consider two things that are inherent in any group of followers: motivation and rewards.
  3. Asking your army for help – ask them to spread the word, or help you to connect with the right people. Ask for financial support, to help grow your business or to join the cause.

The personal finance journey

To state the obvious, personal finance is personal. Just as you shouldn’t let anyone else determine your goals and values, you should also seek to maintain control over your own financial priorities.

The most important part of unconventional life planning is to be clear on what you want. If you don’t know what you really want, how will you know how to get it? Regardless of how much money you have, is that we often discover that the life we want is in closer reach than we initially thought.


Advances the conversation about life and work. We’ll consider the practice of radical exclusion, the pursuit of abundance, contrarian travel opportunities, and creating a legacy no matter how old you are. Tying together the “dangerous ideas” and helping you to consider developing your own.

Radical exclusion and the quest for abundance

The practice of abundance, is all about embracing life to the fullest and ordering your life around a few key priorities. To make that happen, you’ll need to look carefully at all of your current obligations to determine which ones are actually necessary and which can be eliminated.

Part 1: Eliminating the unnecessary

If you want to take on the world and live life your own way, you’ll need to be fairly determined, because there will be no shortage of distractions that crop up every day. These distractions include:

  • The 3,000 marketing messages that most of us take in every day
  • Busywork given to you by others or that you create
  • Unnecessary obligations or responsibilities
  • Social norms and widely held beliefs about work and time

It can be helpful to begin to apply a filter to all the inputs that come your way. Asking two questions—“Why should I do this?” and “What will happen if I don’t?”

Part 2: Enriching our lives through abundance

The acts of decluttering and radical exclusion raise the question of what should stay. After you banish unnecessary or undesirable things from your life, what do you keep?

When you encounter opportunities, distractions, and requests for your time, how do you decide whether to say yes or no?

  • Say yes to legacy work.
  • Say yes to work that leaves a deliverable. (Define work in output instead of time.)
  • Say yes to your kind of fun.
  • Say no to work that doesn’t leave a deliverable (unnecessary meetings).
  • Say no to busywork.
  • Say no to things you would do only out of obligation.
  • Perform an instant gut check: yes or no? If you have a bad feeling about something, say no. If you feel slightly intimidated but also excited, say yes.

A nomadic education

Most people have at least one place in their minds they’d really like to go to “one day.” By saving just $2 a day, you can usually get there within two years or less.

Working on location from anywhere in the world rarely involves sitting in the sand with your laptop. It isn’t for everyone, nor is it always easy—but for me and many others, it’s worth it.

As with most things in life, if you choose to get serious about travel, you can find alternative ways to accomplish almost any specific goal. “Travel hacking” helps to reduce costs and allow for more interesting experiences than conventional travel planning does.

The kind of travel you value is better than anyone else’s idea of fun and adventure. Figure out what you like, and structure your roaming around those preferences.

Legacy work

What do you really want to get out of life?” and “What can you offer the world that no one else can?” Whatever your answers to those questions are, you can likely find the beginnings of your quest to live a full life and make the world a better place for others.

“Legacy” is something that most people don’t consider until they start counting down to the end of something. If you start any earlier, you’re well ahead. When you set out to create something that will outlast you, there are a number of characteristics you need to consider by answering the following questions:

  • Vision—how will the world be different because of the project?
  • Beneficiaries—who will benefit from the project?
  • Primary Method or Medium—how will you do the work?
  • Output—what will be produced as a result of your work?
  • Metrics—how will success be measured?


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Great work

We all know we should cut out the bad work as much as possible, but the key distinction is the difference between good work and great work. Good work is useful, productive work. There’s nothing wrong with it, but the problem is that we have too much good work. Great work, or Legacy work on the other hand, is revolutionary. Great work leads to innovation. While most good work is comforting, great work is simultaneously comforting and discomforting because it pushes us to go further.

A key principle of legacy work is that it usually involves creating something new as opposed to responding to something that already exists. When you create, you initiate a new project or interaction. When you respond, you’re just sustaining an existing interaction.


Be daring, be different. In choosing to live a remarkable life, failure is a real possibility, but regrets are completely optional. If one plan doesn’t work out, you can try something else—but if you never try, you’ll go to your grave with your song still in you.

Be impractical. You don’t have to live your life the way other people expect you to. Most inventions were judged to be impractical at first glance. In the history of the world, provocative ideas that challenged authority were rarely welcomed by the people who controlled access to power and wealth.

Assert integrity against the play-it-safers and slaves of the ordinary. The world has enough sleepwalkers and cynics; the rest of us need your help. Don’t settle.

Taking the road less travelled is a good start, but you can also build your own road.


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