“When can I visit your office?”

In almost every conversation with my mother, I would get that question.

While many Jewish parents wanted their kids to be doctors, my mom always wanted me to be a lawyer. The most successful guy she knew (which in this case meant the guy with the nicest car and biggest pool) was a lawyer. She wanted the same for me.

And she got it. Two months after I turned 25 I found myself working as a first-year lawyer at a top-tier law firm specializing in litigation in downtown San Francisco.

My office (yes, offices then) at 4 Embarcadero had great views of the San Francisco Bay. On a clear day, I could see the UC Berkeley campus. I was paid well. I had a secretary, parking, great health insurance and many of my expenses were paid by the firm. I was on track.

There was just one catch.

I was miserable.

My firm specialized in “insurance defense.” Basically, this meant that we represented insurance companies when they got sued - often for not paying on a claim. In short, our work was focused on helping insurance companies make more profits.

This work seemed excruciating to me. But I didn’t have an alternative plan. This was the only plan.

“When can I visit your office?” she would ask.

“Soon,” I would say. “Soon.”

While I liked many of the lawyers at the firm, the office was stiff. Law firms hadn’t gone casual yet. Men wore suits and ties to work every day except the last Friday of the month. That day was “Casual Friday,” but even then we couldn’t wear jeans.

It was hard to fish a personality out of many of the partners. It started at the top. You lived most days in fear of the managing partner getting into the office elevator at the same time as you. Unless you were particularly good in conversations about how much you loved insurance companies sticking it to the insured, it was pretty difficult to have a conversation with the guy.

Almost all the partners ever talked about was their work, and when you ran into them it felt like you had to pretend to share their interests.

You could hear people say things in the halls like, “I’m pretty excited about this summary judgment motion we’re about to file,” or “I think we’re going to get our temporary restraining order.” It was sort of like L.A. Law, but without the sex or anything interesting.

Yes, the hours were long. But the hardest part (at least for me) was trying to pretend to the others that I was into it.

I had rent to make and student loans to pay. Those suits I had to wear didn’t come cheap. So I learned to fake my interest in some arcane argument that may help our client. “I think I found a circuit court case that will help us!”

I had a good sense I wasn’t going to practice there forever, but I needed to do it until I had a better option.

In our regular conversations, I told my mom how unhappy I was. I told her about the work we did and how uninspiring it was. I told her about the long hours including the many weekend days that had to be given up for our cases. She was empathetic, but inevitably she would ask the question.

“When can I come see the office?”

“Soon,” I would answer. “I promise.”

I was stalling.

I understood my mother’s interest in seeing the office. She was a single-mother and a school teacher. She raised my brother and me mostly by herself and she supported us by teaching learning disabled children in very tough neighborhoods like Detroit, Michigan and Richmond, California. I knew that having her oldest son working in a fancy law firm was her dream - even if it was feeling like a nightmare to me. At some point, she deserved to at least come in and see the place. I knew she would love it.

And yet, my intuition told me it would not end well.

“When can I come see your office?” she asked.

“How’s next Thursday for lunch?”

“I can’t wait!”

I had a strategy. First, I thought that if she came around lunchtime, there would be less people in the office than usual - and less of a chance for something to go wrong. Also, if we planned to have lunch rather than just an office visit it would be easier to cut her stay short so that we could go out to eat. In other words, I wanted an excuse to leave when things went bad.

In other words, my strategy was that she would come, I’d quickly show her around an empty office and then we would leave and have lunch. Easy as pie.

A little over a week later, the office receptionist said those words that made me sense impending doom.

“Your mother is here.”

She looked nice. I told her how people dressed in the office and she dressed the same. She actually wore a suit and heels. I could see that she was trying to act professionally. I quickly greeted her. Even before anything happened, I felt panicked.

I wanted the tour to be over fast so I started right away. “You have already seen our reception area.” “This is one of the conference rooms.” “This is my office.” Occasionally we would pass my colleagues (why were so many people in the office during lunch?). I would try to act calm and introduce her. She was always very polite. You could tell she was trying to be on her best behavior.

The more I tried to move quickly, the more it felt like she was slowing down. She stopped to look at the views from every corner of the office. From each window, it was the same thing. She would look out the window at the view and then she would look at me and say, “Wow, David.” She was really proud.

And then it happened.

I planned to close the tour in the library. For starters, all of the legal volumes there really gave you the sense that you were in an important place. It wasn’t true, but it would feel that way to her. Also, the library had huge windows and some of the best views of the whole office. I knew she would like it.

But for some reason, the library was packed with lawyers. I think some of the other lawyers were facing a deadline for a huge motion and so they were all there doing research. Even some of the partners were in the library - which was very rare.

My mom walked ahead of me to get to the window and look out at the expansive view. She looked at Coit Tower. She looked at the San Francisco skyline. She looked at the Bay. She really couldn’t believe that this was where her son worked.

After admiring the view for awhile, she turned and saw me standing on the other side of the library. Because it was crowded, she made sure to speak loudly so her voice carried over the heads of the other lawyers and across the room.

“My god. It’s beautiful here. I don’t understand how you can hate it so much.”


Nobody ever commented on what my mother said. I left the firm within a year.