When I was young I had the good fortune to travel on one nice trip per year. It wasn’t because my family had the money to- we were just scraping by- it was because my mom had the “luck” to win supermarket and manufacturer contests for free trips.
Now in reality it wasn’t luck at all- it was purely being persistent. She would carefully evaluate local contests that she would find and ones sourced to her through newsletters and zines (this is long before the internet). She would then systematically enter these contests hundreds of times over a few week period- logging the entries in a notebook.
Weeks later she would log whether the entries were a success or failure. The total investment might be two hundred bucks a month in postage but her persistence payed off. Over the five or ten years she was doing this we won trips to Hawaii, Viginia and Disney World (4 times!). Of course the biggest win was a Chevy Astro Van- this actually came about through an essay contest by Stanley Tools. I remember her explaining to me how she was writing what the judges would want- the happy fixer-upper family, ready for their van.
New books like Seth Godin’s “The Dip” are merely ways to convince you of the importance of persistence when I’ve know it all along. I just have to remember that it takes thousands of tries before that trip to Disney World.