Chapter 5

How I Spent My Summer Before Law School

I was running through O’Hare Airport, trying to make my connecting flight from Chicago to Los Angeles. My flight from Charlotte to Chicago had been delayed, and I hoped I would have enough time to catch my next flight. My checked baggage had been processed and was being loaded onto the plane as I rushed from one end of the huge airport terminal to the other. If I made the flight, I would have three days of meetings with company executives, updating them on the changes my father-in-law had mandated in company policy.

This all stemmed from the celebration dinner my mother, Mr. Olson, Karen, and I shared on the day of our university graduation. We had our “family celebration,” as Mr. Olson called it, at an upscale steakhouse, where one of Mr. Olson’s assistants was able to secure us a reservation at the last minute. The food was excellent, and I was glad to see Karen and my mother getting along so well. Then again, I can’t ever recall my mother not getting along with anyone she was paired with. They chatted away about things I had no knowledge of. I only spoke when addressed directly, responding with as few words as possible.

Everyone was getting along just fine, and it felt like everything was perfect—until Mr. Olson asked what Karen and I had planned for our future as a married couple. The moment I responded, the mood at the table shifted, and it was like I’d just ruined everyone’s Baked Alaska. The chatter stopped, and suddenly, all eyes were on me. I told Mr. Olson that I hadn’t made any plans yet; I was still waiting on the marriage annulment Karen had promised.

My mother shot daggers at me, and I could see both anger and disappointment in her eyes all at once. Mr. Olson fell silent, and I could tell he was about to point out the flaw in my thinking. Karen burst into tears and ran off to the bathroom, sobbing, with my mother trailing after her—but not before casting one last dirty look at me, one that seemed to say she was ashamed to have me as a son, waiting on the marriage annulment.

I have to give Mr. Olson credit for not raising his voice and for staying calm as he laid out the facts of life. I had committed the greatest sin in his eyes: I had made his daughter cry.

“You care to explain yourself, Mr. Freytag?” he asked in a cold, impersonal tone. “I understand the circumstances under which you two were married. Until now, I thought you would make the best of an unusual situation and learn to love and respect each other, building a successful marriage. But now you bring up the annulment. Would it be so bad to be married to Karen, love her, and make her happy?”

I voiced my concerns about why this wouldn’t work and why it was bound to fail.

“Mr. Olson, there are countless reasons why this won’t work. First, Karen and I come from completely different worlds. She grew up in an affluent family, always having everything she wanted, never having to go without. I, on the other hand, didn’t have a lot of luxuries, though I always had the essentials. How do you think Karen would handle not getting something she wanted because I couldn’t afford it? Then there are her friends. Take her ex-fiancé, Michael Stanley—he’s the epitome of entitlement. And her girlfriends? They’re all the same: spoiled, self-absorbed divas. I’m not saying Karen’s like them, but most of her circle definitely is. I don’t fit in with people like that, and if we’re being honest, Karen would be much happier without me around. That’s why I keep bringing up the annulment.”

My candid response surprised Karen’s father. I’m sure he was expecting a response from me that focused on my happiness, but it didn’t. I believe that caught him off guard.

Karen and my mother returned from the women’s restroom. Karen had stopped crying, but her eyes were still red, a clear sign she had been upset. When they sat down, Karen and my mother had switched places. My mother sat beside me, while Karen took a seat on the other side of the table, closer to her father and as far from me as possible while still remaining at the same table.

Karen didn’t look at me, and I could sense she wanted to leave as soon as possible. My comment had hurt her, and she seemed to want to be as far away from me as she could.

Before anyone else could speak, Mr. Olson said, “William has expressed his reasons for not wanting to marry you, Karen. While I don’t agree with his stance, I can understand why he feels the way he does. What he shared with me wasn’t a selfish reason, as you might expect. Instead, he thought about you first, before himself. Karen, William doesn’t think he can make you happy or keep you happy. That’s why he keeps asking about the annulment. He mentioned the difference in your backgrounds and your choice of friends. He claims your friends are shallow, and I have to agree with him. So, Karen, he cares enough about you that he wants to sacrifice being your spouse so you can be happy with your life choices and not feel held back or left out because of him.”

I have to say, I see why Mr. Olson is successful as a businessman and billionaire. He knows how to present a situation that no one wants to hear, but he makes it sound like an opportunity for change and improvement. Karen listened to her dad and, at least, glanced in my general direction.

Mr. Olson then asked, “How do we fix this? Do we agree to the annulment and move on, or is there a way to find a solution where you two can have a successful marriage, built on love and mutual respect?”

I didn’t have an answer, but I glanced at Karen, and she was giving me that look again—the same one she gave when I told her she was the most beautiful girl on campus.

So, that’s how I ended up working for Mr. Olson as his assistant and messenger. I traveled wherever his company had a presence, delivering whatever materials he had for each division and reporting back on how they were received, noting any opposition. It only took one instance when I wasn’t well-received because I was the boss’s son-in-law. That management team was let go and replaced. Lesson learned: I was the surrogate for the boss and needed to be treated accordingly.

How I came to have this position was after dessert, when Mr. Olson asked Karen and me questions about what we knew about each other and how we had grown up. It turned out that neither of us knew that much about the other. I knew Karen had grown up in a privileged family, and she knew that I came from a lower social class than she did. That was when Mr. Olson came up with the idea that Karen and I would not live as husband and wife that summer. Instead, we would live in each other’s households. I would stay and work with Karen’s father, while Karen would live with my mother. I would work as his assistant, and Karen would find a job that my mother would arrange for her. He thought that would give us a better understanding of each other’s backgrounds and lifestyles.