Always a Bridesmaid for Hire by Jen Glantz

Jen posted an ad on Craigslist advertising her services as a professional bridesmaid. When she woke up the next morning, it had gone viral. What began as a half-joke suddenly turned into a lifetime of adventure for Jen–and more insight into the meaning of love than she was getting from OKCupid—as she walked down the aisle at stranger after stranger's wedding.

Non-fiction.

When Jen finally realised that she needed a lesson on how to run a business, she desperately booked a 'free business tutoring' session with a stern business coach, Ray.

What is your greatest failure?

Finally he breaks the silence. "Your problem," he says, "is that you're too scared to fail, so you don't even move."

"You want to be successful? ... You have to fail, fail, fail, and fail until you can sit here, in front of me, and recite every one of them so fluently and quickly that I'll get bored and ask you to stop. That is when I'll know you're ready to learn about success."

"I'm eighty-two years old... There's no time for ultimate dreams. You are either doing it or you're not."