Freelancers are people willing to take risks, willing to gamble that they can succeed without a steady paycheck. Most of the people I’ve written about have had the confidence to believe in themselves, and most can point to how they maneuvered down precarious and uncertain paths. In my career as a freelance writer, I’ve had moments of doubt. I’ve suffered rejections and cancellations. But there were crossroads along the way that allowed me to continue pursuing my dream of working for myself, doing what I wanted to do, and figuring out how to survive. Freelancing is a lifestyle. In preparing this book, I marvel at how I somehow managed to avoid all the pitfalls and not drown in pessimism. When Alfred Hitchcock, Leonard Bernstein, and Fred Astaire all backed down from interviews they had agreed to, I had to learn how to bite the bullet and move on, how to move forward, and not backward, and that’s what this book is about. It begins with my first byline for an essay I wrote when I was just 15. It continues with articles I wrote when I was in college and then in the Peace Corps. There are pieces I wrote for Newsday and the New York Times that strengthened my resume, and interviews I did with Mae West, Henry Moore, and Hugh Hefner that led to my becoming “The interviewer’s interviewer” for Playboy. I’ve included articles I’ve written about South American cowboys, the first African American pilot, the history of aviation on Long Island, marching with Dr. Martin Luther King Jr. in Mississippi, my daughter’s struggle with infertility, my grandson overcoming a rare disease, Rodney Dangerfield’s lifelong depression, and an in-depth, previously unpublished interview with Tony Bennett. All the pieces in this book were turning points, whether they furthered my writing career, boosted my confidence, made me determined to prove myself, or brought my family closer. Each of the 33 pieces have a preface, explaining why I chose them, and a postscript, summing up the result. This represents one freelance writer’s journey, but it’s intended to inspire present and future freelancers to consider the road less traveled.