Prologue: The Summer I Stared at the Ceiling

Have you ever made such a mess of things that you were sure there was no way out? That's basically the story of my life. In June 2002, I was in that position: dead broke and $20,000 in the hole. How did I end up that way? Well, I guess you could say it all started three years earlier, during what I now refer to as "the summer I stared at the ceiling."

It was May 1999, and I was twenty-six years old. I was living and working in Chicago. I wasn't unhappy. I was just unfilled. I realized that there must be more to life than what I had experienced so far. I was born in Illinois, raised in Illinois, had gone to school in Illinois, and was working in Illinois. That summer all I did was stare at the ceiling and think. I didn't know who I was. I was the person that my parents raised, but I never felt like my own person. I felt like an extension of them, and an extension of my job. I felt defined by my friends. All I did was stare and think.

At the end of the summer, the conclusion that I came to was this: I had to get the hell out of Illinois. I needed to pack my bags, leave the Windy City, and move to a faraway land. I needed to be alone to figure out exactly who Karyn Bosnak was. And the faraway land that I chose to be alone in was... New York! I had been there once—for a day. But I liked it, and I had seen tons of episodes of Friends and Seinfeld, and decided that it was going to be my new home.

The next year all I did was work and save money. Well, I tried to save money, let's just say that, but I've never been really good in that department. But I saved enough for a one-way plane ticket and a security deposit for an apartment. I had enough for everything except the movers. I had to charge the movers...

Part One: The Rise • May 2000

Chapter One: The Move

I awoke that morning to a buzzing in my ear. My head was throbbing. The night before we had a big party to wrap up the ninth season of The Jenny Jones Show, where I had worked for four years. As desperately as I wanted to leave Chicago, I was sad to say good-bye to all of my coworkers, some of whom I had become very close with throughout the years.

The buzzing stopped and then started up again. I finally realized that it wasn't my alarm clock, but my doorman buzzing my apartment. I got out of bed and went to answer the intercom.

"Karyn, it's Robert the doorman. Your mom's here," a voice said.

Ever since I've lived alone, I've had an apartment with a doorman. It's always made me feel safe. Sure, doorman apartment buildings are more expensive, but how can you put a price on safety? This particular apartment was on Oak Street - the Madison Avenue of Chicago. If you walked straight out the front door of my apartment building, you'd hit Barneys. That was good for me, a girl who grew up shopping.

"Oh, right. Let her up." I was moving to New York the next morning. My mom was there to help me pack and was planning to stay overnight so she could take me to the airport. It was my last day in Chicago.

I love my mom. But she was part of the reason that I decided to move. She'd do anything for me, and I knew that and always took advantage of it. I was hoping New York would make me feel more independent, so I wouldn't call my mother every minute to ask for her help. "Help" to me usually meant "help with some cash," which meant "I spent too much at Marshall Field's and I need help paying the bill." And Mom was always there in that department...