Her life was mostly win-win—so why was it so painfully difficult for Oprah to lose-lose? Then a personal trainer galloped into her world with a life-changing question.
I feel like I've always known Bob Greene, though the truth is it's only been 14 years since we first met. My life has not been the same since.

At the time, I was 237 pounds, miserable, and so ashamed to have joined the ranks of the perpetually obese that I had trouble maintaining eye contact. I couldn't understand why I was able to triumph over so many other challenges and adversities in life, and yet when it came to losing weight I was a big fat failure.

I had spent years bouncing from one diet to another, from the time I was 22. That was when I landed a big job as a news co-anchor in Baltimore and discovered that food—especially corn dogs and six-inch chocolate chip cookies with macadamia nuts—could provide a great deal of solace. I had no friends and no furniture, not even curtains on the windows of my new apartment. My co-anchor seemed to resent me, and I worried that I was in way over my head. I'd had almost no experience as a writer, but every day I was given news copy to rewrite. It's an awful feeling when you know you can't make the mark. No matter how hard I tried, I could not bang out the copy fast enough for my superiors. Every day as we neared the 6 o'clock news hour, I'd hear John, the copy editor, yell across the room, "Winfrey, where's the goddamned copy?!?!"

I was humiliated but put on a smile and got through the days, reading the news and chitchatting with my fellow anchors on air. I felt blessed to have my job, but I truly hated some of the things I was required to do. I always felt as if I were chasing bodies, waiting for the worst to happen. The bigger the fire or collision, the more excited my bosses became.

Working in that environment was an affront to my spirit. The reporter's objectivity I needed to maintain went against everything in my nature. Many times I was an eyewitness to the most devastating moments in people's lives, but I was not allowed to express any emotion. So I ate those emotions, and along with them, just about everything I could buy at the mall food court. I thought I was fine—I just had a little weight problem. Now I realize I didn't have a weight problem.

I had problems that I was burying by eating, but it wasn't until years later, after many conversations with Bob, that I finally made the connection.

When I first met Bob and he asked me why I was overweight, I thought he was being a smart-ass. I was overweight for the same reason everybody else is, I answered smugly. I loved food.

It took me a while to get to the truth. I didn't love food. I used food to numb my negative feelings. It didn't matter what the feeling was—a phone call from someone I didn't want to talk to, a confrontation of any kind, being late, feeling tired, anxious or bored. No matter how insignificant the discomfort, my first reaction was to reach for something to eat, unaware of how much I was consuming. Living unconsciously was like being the walking dead. All my fat years—my unconscious years—are a blur to me now.

I grew up believing that people with money didn't have problems. Or certainly none that money couldn't solve. When I started my working life in Nashville and Baltimore, paying the rent and the electric bill and making payments on my car left me with just enough to buy groceries and get my hair done. Then, in 1986, my show went national. It changed the trajectory of my life. Now I had more money than I'd ever imagined, and everybody wanted some. The first thing I did was to retire my mother, father and a cousin who helped take care of me when I was growing up. My father let me buy him a new house and a Mercedes, but he refused to quit working in the barbershop. He's still there.

Then everybody came out of the woodwork. Distant family members I barely knew wanted me to completely take care of them or wanted to work for me. Relatives I hadn't seen since I was 10 years old showed up demanding thousands of dollars "because we're family." Helping my family was something I wanted to do, but I didn't know how to handle the total strangers who came to Chicago claiming to have spent their last dime leaving a battering spouse, or the teenagers who'd run away from home.

The first year, I helped almost everyone who asked me, family and strangers alike. It was stressful trying to figure out how much to give to whom, and before I knew it, they'd return for more. I was overwhelmed, but I never felt it. Once again, I just ate until I couldn't feel. By the end of the year, I weighed 200 pounds.

In 1988, totally frustrated and up to 212 pounds, I turned to Optifast, a liquid diet supplement program. For four months, I ate not a single morsel of food. I lost fat—and muscle—and I dropped to 145 pounds. Now I know that it's impossible to starve your body for four months, then feed it, and not expect to regain the weight.

It would take seven more years of gaining and countless attempts to follow diets that I wasn't really prepared to stick to before I discovered the truth. In the meantime, I was racing through 200 shows a year, leaving my apartment at 6 a.m. and getting home at 10 p.m. My entire life was work.

In 1992 I won another Emmy for best talk show host. I had prayed that Phil Donahue would win so that I wouldn't have to embarrass myself by rolling my fat butt out of my seat and walking down the aisle to the stage. By now I'd reached the end of believing I could be thin, though I was scheduled to leave for Colorado the next day to visit yet another spa. At 237 pounds, I was the heaviest I'd ever been. I had filled journals with prayers to God to help me conquer my weight demon.

Bob Greene was the answer to my prayers. When I first met Bob at that last-ditch-effort spa in Colorado, I thought for sure he was judging and labeling me as I had already judged and labeled myself—fat and out of control. Bob, it turned out, wasn't judging me at all. He really understood.

But he did have some tough questions for me. One of them was the hardest question that anyone had ever asked me: What is the best life possible for you?

"You of all people in the world can have your life be what you want. Why don't you do it?" he asked. "What do you really want?"

"I want to be happy," I replied.

"Happy isn't a good enough answer. What does that mean? Break it down for me. When was the last time you were really happy?"

"When I was filming The Color Purple, seven years ago."

"What about filming The Color Purple made you happy?"

I didn't have to think to answer. "Doing that work filled me up. I was playing a character who was meaningful to me, surrounded by the brilliance of Alice Walker, Quincy Jones and Steven Spielberg. I was so charged and stimulated every day, I just wanted to do better and be better."

"So what would it take for you to have that feeling again?"

In answering that question, I realized that the show had gotten away from me. In order to stay competitive, we had become more and more salacious, covering topics like "My sister slept with my husband" and "Is my husband or my boss my baby's father?" I didn't want to put junk on the air that perpetuated dysfunction instead of resolving it. It wasn't who I wanted to be.

And so, while I worked out and changed what and how much I ate, managing the rest of my life became my real focus. I started asking myself the same questions Bob had asked me. For every circumstance, I asked myself:

"What do I want?"
"What kind of show do I want?"
"What kind of body do I want?"
"What do I want to give to all the people who are asking me for my attention, my time, my money?"

I finally made a decision about that last one. I set up trust funds with a finite amount of cash for the people to whom I wanted to give money. And to those with whom I had no connection, I said no and meant it. And just to be sure, I changed my home phone number. I've never visited a psychiatrist, but working with Bob has been priceless therapy.

One thing I know for sure now is that you've got to ask yourself: What kind of life do you want and how close are you to living it? You cannot ever live the life of your dreams without coming face-to-face with the truth. Every unwanted pound creates another layer of lies. It's only when you peel back those layers that you will be set free—free to work out, free to eat responsibly, free to live the life you want and deserve to live. Tell the truth and you'll learn to stop eating to satisfy emotional hunger and to stop burying your hopes and dreams beneath layers of fat.

The Best Life Diet plan mirrors the way I eat and live now. I lost weight in stages. First, I became active. I still work out, even though I really hate it. But I know if I don't, I will end up 200 pounds again. Then I started working on my eating. I stopped eating past 7:30 at night. When Bob told me it would make a big difference in my weight, I resisted. I thought it was going to be too hard. It was at first, but it gradually got easier and turned out to be one of the most effective changes I made.

I've now taken most of the unhealthy foods out of my diet and replaced them with better choices. I eat smaller portions and healthful foods as a way of life, not as a diet to go on and off.

I still work constantly at not repressing my feelings with food. If you turn on the TV and see that I've picked up a few pounds, you'll know that I'm not managing and balancing my life as well as I should.

I pray or meditate—or do both—every day. I pray to be used by a power greater than myself. It takes consistent effort to live my best life. The mistake I've made in the past is not realizing how constant a struggle it really is not to turn to food for comfort. It all comes down to another question Bob asked me years ago. "How much do you love yourself?"

"Of course I love myself," I'd snapped. "It's the first law of self-preservation. I firmly believe in it."

"You may believe in it, but you don't practice it," he said. "Otherwise you couldn't let yourself be 237 pounds."

I wanted to cry, and later I did. He was so right. I cared more about everyone else's feelings than my own. I'd overextend myself to do anything anyone asked, to honor his or her feelings. I didn't want anyone to think I wasn't "nice," or worse, that "the money has gone to her head."

This, too, I know for sure…loving yourself means honoring yourself and your own feelings first.

My hope is that you can learn from my mistakes and liberate yourself from this struggle. I finally know it doesn't have to be so hard. Make a decision. Know that you deserve the best life possible. It's there for the asking, the answering, the taking. Go out and get it!

As a reminder, always consult your doctor for medical advice and treatment before starting any program.


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