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#102 Chris Guillebeau + Tom Hodgkinson

Episode 102 Tom Hodgkinson + Chris Guillebeau

Have you ever been told you can't expect to make money writing books? Me, too. 

Having heard the refrain that books don't make money over and over, it was my distinct pleasure to speak with two writers who have built careers with books and writing at the center: Chris Guillebeau + Tom Hodgkinson.

I have been reading each of their work for years and was long inspired by books like The $100 Startup and How to Be Idle. These books found me at a particular period in my life when it hadn't occurred to me that I could make choices in life that allowed me to build a career in writing that was not one based on poverty.

So when I had the chance to speak to both of them for one magical episode, I knew it was meant to be. In this essential pair of conversations, we talk about how books can create a larger body of work that you're proud of, and can help you create community, a movement, and create work your proud of. We'll also dive into mistakes both Tom and Chris made in the early parts of their careers and what skills they have found essential to living a successful creative life.

Never has a practical talk been more fun. I can't wait for you to listen to two renegades who have inspired me to ask "who says?" about so many aspects of what a successful life looks like. I hope you get fired up and motivated to take your writing dream further after listening - I know I did.

Chris Guillebeau

Discussed in Episode 102 with Chris Guillebeau:

  • Side Hustle School

  • 2nd year of an everyday podcast. Records every day. Releases every day.

  • Started off wanting to be a writer.

  • Started the Art of Non-Conformity blog, which he then turned into a book. 

  • Book didn’t start off as a marketing plan. He just loved books.

  • “I didn’t really know what I was doing in the beginning.”
    On starting the blog and seeing where it would go.

  • “The more clarity you can have in the beginning, so much the better.”
    On not trying to cram every idea into your book.

  • “If you don’t have intentionality. If you’re not sure what’s important to you, then that’s harder.”
    On looking for your through line.

  • “If you’re going to write a book, make sure you have something to say.”
    On getting started.

  • “I want to break through however I can break through.”
    On publishing his first book.

  • “What you do with your first book is really going to affect the opportunities available to your for your second, and third and so on.”
    On being strategic about your career.

  • “Most things actually didn’t work but a couple of them did.”
    On the hustle of getting his first book out there.

  • World Domination Summit

  • “I do value the connection that comes from writing & publishing something.”
    On the community he’s built around his books.

  • “The greatest productivity hack is to love what you do.”
    On how he gets everything done.

  • “But you have to want it. You have to really want it and if you want it, then great. If not, do something else.”
    On whether you should write your book.


Discussed in Episode 102 with Tom Hodgkinson:

  • Business for Bohemians, Live Well, Make Money by Tom Hodgkinson

  • Was solidly in the middle-class of working writers, successful enough between books and journalism, until the financial crisis of 2008. Then needed to find other ways to start making an income.

  • “A reaction against the Starbucks where everyone’s isolated on their own.”
    On his vision for the Idler Academy

  • “I had to, very, very quickly and not always successfully acquaint myself with the basics of business.”
    On suddenly being a small business owner.

  • “It’s about what I learned over those five years of keeping the shop open.”
    On Business for Bohemians

  • “They really thought they were going to be reclining in a chaise lounge in the window.”
    On hiring staff for a business named “The Idler”.

  • “Have they not read my books? Do they not know that I’m a best-selling author who’s had global success?”
    On taking coffee orders at the end of a long work day.

  • Ran the coffeeshop for five years.

  • Now still doing Idler events, but at other locations.

  • “Something like YouTube or Facebook, Twitter even, we all work for nothing for these companies. We pour all our creativity into them and they give us nothing.”
    On the ‘sharing economy.’

  • “We should be paying creative people and as creative people we should charge money for what we do.”
    What’s at the core of his new book.

  • “We make something and people buy it.”
    On the business model of the Idler magazine.

  • “I think there’s this noble, small shopkeeper class, and musicians, journalists...creative people, people who make and sell things on a smaller level, but who also want to grow, have a lot in common with each other. We have to help each other and this book is for those people.”
    On Business for Bohemians

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