Confidence makes all the difference. (1/2006)


I almost threw it away, hardly glancing at the return address and logo on the envelope. In fact, it wasn’t until an hour later that I finally ripped through the envelope and read the invitation. It was a week later that I finally decided to attend.

It was my high school ten year reunion. I didn’t go to the one five years earlier; I just couldn’t bring myself to go. I was petrified by the idea that she might be there.

‘She’ is Anne Glass, my high school class’ dream girl. Back in high school, she had it all: beauty, confidence, intelligence, charm. Back in high school, I didn’t have any of those things.

I remember once in twelfth grade… Anne was in my social studies class. Mr. Hogan, the teacher, was a portly fellow with thinning hair and watery eyes, but he had a deep, booming voice that commanded our attention. One day, he posed a question to the class and called on me. I don’t remember the answer I gave or what I was thinking at the time, but I sure remember Mr. Hogan’s reaction. Apparently, he believed my answer was, basically, stupid. To make this point to the class, he wiped the chalk board clean and then proceeded to draw two sets of two buckets. He wrote my name over one pair and Anne’s name over the other pair. Then he labeled the left bucket in each pair ‘Intelligence’ and labeled the right ones ‘Common Sense.’ Finally, he completely filled in the two Intelligence containers as well as the Common Sense bucket under Anne’s name. He left the Common Sense bucket under my name empty. As subtle as the U.S. dropping an atomic weapon on Nagasaki, Mr. Hogan publicly humiliated me in front of the whole class. In front of Anne.

Even before the empty bucket incident, I never talked to Anne much. She was way too pretty and I was way too shy. After the incident, well, let’s just say I did my best to become invisible for the rest of the year. I even started coming to class late just so I’d have to sit in the back row, as far away as possible from her—and my usual—seat.

Now, ten years later, I was staring at the reunion invitation, just like I had stared at the one five years earlier. Only this time I had my life together, sort of, and this time I made a different decision: I was going to the reunion. And I was going to see Anne.

I landed at Detroit Metropolitan Airport around 7:00pm Friday night. I felt my t-shirt moisten and begin to stick to my back as I walked from the terminal to catch the rental car bus. The oppressive heat was a quick reminder of one of the primary reasons I’d moved out to California immediately after graduating from High School. I drove my dorky rental—a maroon Ford Taurus—up I-96 and got to my hotel about an hour later. I crashed after first calling my mother to tell her I got into town successfully and that I’d see her in the morning. My conversation with her was another reminder why my move out west was a good one.

I woke up early, went for a run, showered and drove to my mother’s house. She had gone to town: her table was overflowing with bagels, lox, white fish, four different kinds of cream cheese, various kinds of vegetables, and more.

There are people who succeed in life and there are people who fail in life. I was one of those people who didn’t just fail; I failed spectacularly. After college, I started a dot com company, which got real big real fast and then got real small even faster. I was on the covers of a few national magazines, each pointing out the dozens of things I’d done wrong as CEO of my company. All total, I lost my investor’s over $20 million.

For almost a year afterward, I drifted. I traveled some, wrote some, had lunches with my friends who were still lucky enough to have stable jobs and reliable paychecks. Without my company—a way to pursue my passion—I was lost.

After I’d smeared cream cheese on my bagel, my mom brought it up immediately.

“Do you ever talk to Dan?” she asked. Dan was Dan Emory, the managing partner at the venture capitalist company that was the “lead investor” in my company.

I shot my mother a look that said, “Why? Why on earth do you always feel compelled to rehash my failures?” Of course, she didn’t seem to comprehend my meaning this time any more than she ever had in the past.

As calmly as I could, I said, “No, but I wrote him a letter the other day.” Before she could reply, I added, “I told him about a new company I’ve started, asking if he wants to be an investor.”

I thought I had earned some kind of acknowledgement for holding my head up high, being determined, for not giving up, and all that. Instead she looked at me like I was an idiot. She said nothing in return, didn’t even ask me about my new company. A strained hour later, I kissed her on the cheek and told her I’d call her when I got back to California.

Another run and another shower helped me shed the stress of my visit with my mother. Around 5:00 PM, I donned my tuxedo and drove to the hotel where our reunion party was being held. I sat in the car, parked in the parking lot for twenty minutes. Just sat there. No radio, no fidgeting. Just sat there. Would she even remember me? What would I say to her?

I finally screwed on my courage cap and walked in. After signing in, I quickly surveyed the room. She wasn’t there. My heart sank.

I felt people’s eyes on me as soon as I walked into the banquet hall. Most were probably wondering how I had the nerve to show up. After all, I was the most famous screw-up in the school’s history.

A few old friends were nice, or at least tried to be nice. They tried so hard to avoid talking about the proverbial elephant in the room. A few old friends weren’t so nice at all, asking me about it right off, not caring that the subject might be uncomfortable for me.

I was sitting with and running out of things to say to Jeff Rogers, an old classmate, when someone tapped me on the shoulder.

Jeff was nowhere near finishing his humorous (to him) tale of how he’d fallen into the carpet and floor tile business when I turned and realized it was her.

“Hello Derek,” she said.

Her voice was quiet and calm. Her eyes glistened. Wearing a black pleated skirt and a starched white blouse, she looked even more beautiful as a woman than she did as an 18-year-old ten years earlier.

“Hello Anne,” I managed. Then with a burst of courage I added, “It’s nice to see you.”

She reciprocated the feeling, and by this time Jeff, who’d finally realized I was no longer listening to his treatise on why vinyl was such a miracle material, excused himself. I didn’t notice him leave.

Anne made sure our conversation wasn’t awkward, didn’t lag. She told me things about her life: cities lived in, jobs held, bosses hated. I told her things about mine, at least my life after my dot com bomb.

The entire time, I lived in two worlds, along both forks in the road: the road I’d taken and the road not traveled.

“Are you married?” I asked her.

“Yes,” she answered after a heart-beat of a delay and with eyes that I swore I thought dropped with… what?… regret? “And you?” she asked.

“Yes. Four years this May,” I replied, queasy from my intermingled feelings of pride and regret.

“That’s great,” she said. “What’s her name? What’s she like?”

I told her some. Enough to be respectful of my wife, not so much that I would have become ill.

Decorum would have me return the questions about her husband, but I just couldn’t bring myself to do it. She noticed my failing but graciously let me off the hook.

“Did you have a crush on my in high school?” She asked the question so matter-of-factly that I sat there blinking. That’s it, just blinking.

“Should I take that as a yes?”

“Uh, yes. That’s a yes,” I said. “Yes I had a crush on you in high school. Like every other guy in school.”

“Oh, please.”

“I’m serious. I didn’t know a single guy that didn’t think you were the cat’s meow. Well, maybe Quinn but I think he’s gay.”

Anne smiled. Her white teeth were perfect. Her red lips shone.

“Tell me what happened,” she said quietly. It was the first time someone asked me to talk about that time out of genuine interest. And kindness.

I told her everything, leaving nothing out. It was painful but cathartic at the same time. She asked questions; I answered them. I told her too about my new company.

We chit-chatted a bit more, then she stood up. I stood too.

“Goodbye Derek,” she said. “It was really nice seeing you.”

“Goodbye, Anne,” I said. I took one last look, trying to memorize everything about her, then she turned to walk away.

“You should have said something,” she called out over her shoulder. She looked at me, eyes moist, voice wavering slightly, and added, “I would have said yes.”

I nodded, then mouthed, “Thank you.” I walked away, hoping she wouldn’t see my legs wobbling.

It felt good to know.

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