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Motorcycle Diaries: Woodrow Landfair on 'Land of the Free' (Q&A)

Woodrow Landfair's 'Land of the Free' is available now from the Harbinger Book Group.

Today, Hartford Books Examiner welcomes Woodrow Landfair.

Landfair is the debut novelist of Land of the Free (Harbinger Book Group, $24.95). In 2006, he pawned his belongings and set out on motorcycle. The people and places he encountered along the way, as well as the jobs he undertook—including day laborer, waiter, lifeguard, bartender, bouncer and truck-driver—between that time and 2011 inspired the book. Also a performer, Landfair has entertained in 72 cities throughout 48 states. As a host and speaker, his clients include Fortune 500 companies, government agencies, and non-profit organizations.

Land of the Free was published earlier this month. The San Francisco Chronicle praised Landfair as "… a storyteller in the tradition of the Dust Bowl balladeers like Woody Guthrie and writers like John Steinbeck." Further, Fox News Channel called the book "the ride of a lifetime" while CBS/Richmond heralded it as "an amazing story."

From the publisher:

Entangled in his own tall tales, a traveling laborer and aspiring entertainer cons and claws his way to the cusp of superstardom. Collapsing under the weight of his lies, the protagonist attempts to run from the life he invented only to become a suspected con man, a fugitive, and the subject of a nationwide manhunt. His days numbered, his pursuers closing in, he must discover his identity or attempt a final escape.

Now, Woodrow Landfair invites readers to journey along on a trip down memory lane …

1) What inspired you to write LAND OF THE FREE -- and how did you find the process of writing a novel to compare to other forms of entertainment?

As a child I was told of an America of opportunity and freedom - a place where any individual can start from nothing and make a success of him- or herself. I wanted to write the tale of a person who puts that promise to the test.

I believe there is a tradition in our literature of questioning, defining, or re-examining the American Dream. A tale like this needed to be written as a novel.

2) The book is partly autobiographical. How did you endeavor to balance reality with fiction -- and how important is it to you for readers to distinguish between you and your protagonist, if at all?

A man abandons his identity and hits the road determined to find fortune, fame, and adventure – that was the story I had outlined. I knew it would take a great deal of firsthand knowledge to complete a novel like that, so writing it – or even hitting the road to live and research it – was just a fantasy.

Then, in 2006, an injury ended what I thought was to be my future in the military. Suddenly I had no plans, no job, and no relevant experience at any profession. I felt like the character in the story I had outlined, suddenly faced with the opportunity to hit the road and start from nothing.  

I felt very deeply that this was not just a story I was born to write, but a tale I first needed to live, to survive, and to learn to tell.  I wrote it ambiguously in the first person so readers could live through the protagonist just as I had. It’s hard for me to distinguish between facts and fabrication when I can at all. I left to get lost on the road, to become someone else, and to bring the reader along as my companion.  

3) What are your thoughts on self-fulfilling prophecy -- and how do you believe that this book speaks to that?

What becomes apparent to you, traveling as a lone laborer from town to town, is just how much your own attitude changes every situation. Attitude, outlook, perspective, mindset – it has many names, but it’s the only variable you can control in all circumstances. Have the wrong attitude, and nothing will work, no one will hire you and everyone will give you dirty looks. But the right attitude is what makes miracles happen. In many ways your outlook becomes your reality – I suppose that is a self-fulfilling prophecy. I never fully believed in it but this journey, my life, and this story have taught me better. I wrote and re-wrote this book until it bespoke a philosophy empowering enough for me to believe in it and live my life by it. 

4) In reflecting on your own travels, what lessons do you find to be most profound -- and what message(s) do you hope that readers might take from your book?

I learned that more than any other factor, the most important variable in a person’s success and happiness is his (or her) philosophy on life. Regardless of where you end up, nothing is more important than the story you tell yourself about how you got there. 

5) This book was a labor of love. What about the process most surprised you -- and what advice would you give to other first-time authors?

Perhaps for some people, writing a novel is a joyous undertaking, or maybe a business endeavor. For me it was a demanding and at times desperate journey that I only undertook because I knew I couldn’t face myself otherwise – like some challenge I felt called to accept. I knew that no matter how wonderful or miserable I felt in the moment, there was nothing more worthy of my attention and persistence. I figure any goal approached with that sort of ferocity will be fulfilling in its own right, regardless of what others may consider success. This is the LAND OF THE FREE after all, we are left to define success for ourselves. 

6) Leave us with a teaser: What comes next?  

I’ve never wanted to do anything in life as much as I wanted to research this novel, write it, and get it into bookstores. I was willing to sell everything, to sleep outside, to abandon meaningful relationships and lifelong friends. I don’t know why I felt so strongly about this story or this book, but I don’t expect to feel that way about anything again in life, and I’m okay with that. 

My only goal as an author and storyteller is that readers find inspiration, empathy and entertainment in LAND OF THE FREE long after I’m gone, maybe a hundred years from now or more. I wrote it to be that type of book. There are other books that I may hope to publish later, but none like LAND OF THE FREE. I don’t have another book like this in me. I knew that from the start. I’m fortunate to have written it, lucky to have gotten to live so much of it, and luckier still to be able to share it. 


With thanks to Woodrow Landfair for his generosity of time and thought and to Karen Ammond, President, KBC Media, for facilitating this interview.

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