Jennifer was standing behind a theater in Winnipeg, Manitoba, frostbitten, her friend long gone, waiting for a movie star she had no appointment with and no guarantee would appear. She had been there for over an hour. What she did in the next five minutes became the clearest illustration of a principle she would spend years refining and eventually name: the 10% target.
The idea that boldness outperforms intelligence as a predictor of success is not intuitive. Most people assume the opposite. But Jennifer’s argument is sharper than a simple ‘take more risks’ pep talk. Smart people, she points out, are skilled at imagining failure. They can catalogue every bad outcome before a single attempt is made. That precision, she argues, is exactly what stops them. Bold people redirect the same mental energy toward what happens when things go right.
A gum wrapper, an eyeliner, and a phone number
When Keanu Reeves finally walked out of the back of that theater, surrounded by cameras and fans, an 18-year-old from a small Canadian city pushed through the crowd and tapped him on the shoulder. She told him he was going to be her ticket to her dream job as a VJ for MuchMusic. He looked, by her account, completely dumbfounded. He offered an autograph. She told him an autograph was useless to her. When he tried to brush her off with ‘give me your phone number and I’ll call when I have a minute,’ she borrowed a stranger’s eyeliner, wrote her name and number on a gum wrapper from her own pocket, handed it to him, and ran.
Her friends mocked her for three days. Then her mother picked up the answering machine and heard: ‘This is Keanu calling for Jennifer.’ Her mother told him Jennifer was at school and hung up.
Two days after Jennifer called him back and explained herself, Keanu Reeves was sitting on her parents’ sofa in their living room, three friends holding amateur camcorders nearby and someone operating a boom microphone that kept hitting him in the face. She got her demo tape. She got the interview. She got the audition. She did not get the job.
The shot you never take
That outcome is the whole point. Jennifer developed what she calls the 10% target: make ten attempts at whatever you want most. Expect nine of them to fail. The goal is not to manufacture confidence before you start. It is to get comfortable with failure through repetition, the same way a body is trained through resistance. As she put it plainly: ‘You chase what you want and you don’t take what you can get.’
The math behind asking for things holds up in ordinary workplaces too. A survey of more than 160,000 people who believed they deserved a raise found that two-thirds never asked. Of those who did ask, 70% received one. The barrier was not merit. It was the attempt.
Practicing at a small scale, she argues, builds the same muscle. Ordering something that is not on the menu at a restaurant is not rudeness. It is a low-stakes repetition of the same habit that once put her in a room with a global film star. ‘When you are comfortable asking for the small things in life,’ she said, ‘it gives you the skills, the habit, and the confidence to ask for the big things.’
The gum wrapper she handed a stranger’s stranger
Somewhere in Winnipeg on a minus-40 night, a woman Jennifer had never met before and never saw again had an eyeliner in her purse.
Jennifer went on to become a best-selling author, an entrepreneur who sold companies for millions of dollars, and a co-founder of a breast cancer charity that raises thousands of dollars each year. She credits 90% failure rates for all of it. The gum wrapper, the frostbite, the answering machine her mother hung up on: none of it was the success. All of it was the path.
