Chris Guillebeau Shares the Game Changing Lessons He’s Learned During His Writing Career

Editor’s Note: I’m pleased to feature this interview with author Chris Guillebeau as part of the Winning Edits Expert Interview Series.

Guillebeau is a travel hacker, entrepreneur, speaker and founder of the World Domination Summit.

Guillebeau is best known worldwide for his writings. His latest book—The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Futureis now available, a must-read, and currently #13 on Amazon in all of books. (Yes, all of them.)

Meet Guillebeau and learn more about The $100 Startup at a book tour stop near you.

Matt Gartland: From blog articles to digital manifestos to published books, your writings are highly proficient and popular. Have you found that developing your writing skills for one form (say books) has informed and strengthened another (say blog articles)? And now, with so much achieved, how are you continuing to challenge yourself to become a better writer?

Chris Guillebeau: I’ve certainly learned that writing books is a lot different from writing blog posts. That’s one of those things that is seemingly intuitive, but until you go through the process you don’t necessarily realize how different it is. I’ve also learned that it’s good to divide the writing and editing process with longer projects, something I tend to combine with blog posts. Thankfully, there are also some similarities, like the need to keep pushing ahead and getting words on the page.

I’m not sure I’ve achieved “so much” yet. Challenge is a good word. I hope to keep writing and making things for a long time.

MG: In The Decision to be Remarkable (one of your original articles) you wrote that “If you want to break out of the mold of average, the first thing you need to do is to make a decision to be radically different.” How has this attitude as operating principle guided your writing career since those early days in 2008? And how do you motivate yourself to stay radically different in the wake of your success?

CG: Fortunately, my writing has improved since 2008—but the core principle remains true. The central message of my blog is “You don’t have to live your life the way other people expect you to.” I’m not necessarily the ideal model for that, but in choosing to be self-employed and crafting a career out from a situation of constant travel, that’s how it looks for me.

As for motivation, I don’t really believe in motivating yourself. Sure, if there’s something you need to do on a particular day, you can probably psyche yourself up to do it. Last month I had to pay my taxes and I put it off until the last moment, but finally made myself sign the forms and go to the bank to get money. But for writing or being different, I’m not sure that approach is optimal in the long term. I tend to do what I want to do most of the time, and fortunately I’m motivated to create.

MG: You asserted your 1,000 words a day rule in your manifesto 279 Days to Overnight Success. Near two and a half years later, you reaffirmed that principle in your article How to Write 300,000 Words in a Year. What other key writing philosophies have become reinforced during your career, and which ones have evolved?

CG: That’s definitely the #1 rule for me. 1,000 words a day, every day. I also like to work on different kinds of writing, since I think most of us have a hard time working on a single project, day in and day out. But in both these self-assigned rules, the key point is to make writing part of my lifestyle. I think of it like exercise: I can skip a day or two of my routine and everything’s fine. But if I start missing several days, I feel bad. I realize something is missing from my life, so I make adjustments to bring it back.

MG: You collaborated with your agent and friend David Fugate on both of your published books. What did you both learn from the experience with the first book, The Art of Non-Conformity, that informed different thinking and strategies for your new book?

CG: I learned to write a more specific book. The first book did fairly well, especially for a debut trade paperback, but one of the challenges for the industry is that it was hard to categorize. Bookstores didn’t know where to put it. Publicists had a hard time pitching it. For The $100 Startup, it’s much clearer: this is a book about creating a new income using a small amount of money and the skills you already have.

It’s also easier for me to talk about. I’ve been doing a lot of interviews lately, and I find that the questions are a lot more predictable (and therefore easier to answer) than the first time around.

MG: In your new book, The $100 Startup, you write: “There’s nothing wrong with having a hobby, but if you’re operating a business, the primary goal is to make money.” Given your advantageous line of sight, do you sense that this necessary attitude is on the rise with indie authors and within the self-publishing world at large? Or is the divide between hobby and business widening?

CG: These days, there’s definitely a blur between activities that were traditionally separate. Organizations of all kinds are hybrids. Some “non-profits” serve their beneficiaries the best by establishing a business model. Many businesses have some kind of charitable component to their for-profit work.

My point in that statement is that many indie authors are simply unaware of how publishing works, and how they can make money through a variety of models. Of course, if you don’t care about making money through publishing, that’s totally fine. But if you do care, you need to learn to think of it (at least in some ways) as a business.

MG: What’s the #1 piece of actionable advice you’d give to writer-entrepreneurs who are in the early phases of bootstrapping their writing startup businesses, and how does this differ from what they should focus on in their growth phase?

CG: Probably the same advice is fundamental to both writing and business: Focus on the takeaways. For whom are you writing? Why should they care? How will the reader (or customer) ultimately be changed by your work?

I’m not sure this focus changes much from the bootstrapping phase to the growth phase, but once in the growth phase, you can then spend more time tweaking and otherwise fixing things you neglected earlier. The process of continuous improvement is especially important. Just keep going! And keep trying to get better every day.

One definition of happiness is “Continuously improving your circumstances.” I take that to mean not only your physical circumstances and way of life, but also the work you do and the impact it makes on those who are connected to it.

Photos taken by Armosa Studios and used with permission.