Reflections on My Experience as a 1992 Summer Associate in Sidley & Austin’s LA Office

I recently blogged about my 1993 summer associate class at Cooley Godward. I would love to do a similar roundup of my peers’ careers from my other summer associate experience at Sidley & Austin’s LA office in summer 1992, but I have not yet found the class facebook/directory in my archives (it may be gone forever).

As I’ve been thinking about that time period in my life, I realized that I have rarely publicly discussed that I spent a summer at Sidley. Unless you knew me 30 years ago, you probably have no idea about this stop in my journey. This post will explain why.

A reminder: As a JD/MBA student in the class of 1994, I had 3 summers: 1L summer in 1991, 2L summer in 1992, and 3L summer in 1993.


In the late 1980s, I worked in a real estate brokerage firm representing tenants in commercial leasing transactions. In 1990, it was clear that the Los Angeles real estate market would crash due to the savings & loan scandals of the late 1980s. I figured I would get my JD/MBA during the crash, so that after graduation I would be well-positioned to find a job as a real estate developer in Los Angeles when the economy rebounded.

As you may recall, summer 1991 was a nadir for summer associate jobs at law firms. Few firms were hiring 1Ls into their summer associate classes. I sent out 100+ resumes to firms all over the West Coast, got a few interviews, and no offers. Frustrated by my strikeouts, I explored markets where I thought I could be more competitive. My mom had a condo in Palm Springs that she rented seasonally, but it was vacant in summer for obvious reasons. I figured that there wouldn’t be much competition for a summer job in the desert, so my application would be more likely to stand out there. Indeed, I sent three applications and got three interviews, including an offer from a small tax and litigation firm, Sanger and Stein. I still talk about that experience today as an anecdote about aggressive job searching.

How I Got Hired at Sidley

My 1992 summer job search inevitably was going to better than my 1991 summer search. First, the economy had rebounded slightly compared to 1991. Second, my resume improved in the first half of 1991. In my first 1L semester, I had 2 Bs and an A (an AmJur) on my transcript–a decent start, but not compelling in the down market of summer 1991. I got all As in my second 1L semester, including 2 more AmJurs, plus I wrote onto law review in Spring Break 1991. By July 1991, I had the standard academic credentials prized by most firms at the time.

Third, for summer 1992, I could apply as a 2L instead of 1L…but this was a bit of a cheat. In 1991-92, I did the standard first-year MBA curriculum and only took 1 law school course beyond my 1L classes. More importantly, I had two summers left, which for most firms classified me as a 1L. Indeed, many firms politely rejected my application with a suggestion to reapply for summer 1993. However, a few firms treated me as a 2L for summer 1992 purposes.

I sent letters directly to firms in July 1991, before OCIs started, and I got at least two callbacks in July/early August before school started, with Sidley & Austin and Proskauer Rose. Both firms extended offers before OCIs started. Proskauer Rose focused on employment law, which didn’t interest me. I preferred Sidley because they seemed to have more real estate-focused work. Also, they were well-known at the time (and still?) for being snooty about grades, so I figured the firm’s prestige would benefit me no matter what. Having the Sidley offer in my hands before OCI allowed me to cut loose other firms I wasn’t interested in.

My dream firm that summer was O’Melveny & Myers. I liked it due to its prestige, the amount of real estate work it was doing, and a great screening interview with a UCLAW alum, Kim Wardlaw. (You may recognize her name: she was appointed to the Ninth Circuit in 1998 and is still on the bench). However, my callback interview was disastrous. For the lunch portion of the interview, the partner drove me to the Santa Anita racetrack to watch the horse he owned run a race. “Lunch” at the racetrack–if you can call it that–was on the firm, but the partner reminded me that all bets were on my own dime. He may have forgotten that many students don’t have a budget to play the ponies. After the race, we walked down to the track to greet his horse, meaning that we traipsed through the mud and horseshit in my finest clothes. I’ve never conclusively determined if the partner genuinely thought the racetrack outing was a good idea or if he was just a narcissist, but I’m still shocked that the recruiting department approved it. In any case, the firm no-offered me. I have occasionally wondered how my career trajectory might have changed if the OMM offer had come through.

I also considered summer 1992 jobs on the business side. Most of the formal MBA summer programs were with consulting firms or investment banks, neither of which I wanted to pursue. The real estate market was still in the tank, so real estate developer summer jobs were going to be rare or nonexistent. As a result, Sidley & Austin was my best available option at the time.

The Work and Culture

I wanted to do real estate work that summer, but I got more environmental litigation work, a big part of the office’s practice. I also worked on a couple of entertainment financing projects, such as those forgettable early 1990s direct-to-video productions. I preferred the transactional work, but entertainment financing wasn’t a core part of the office’s practices, and I couldn’t tell if there would be an option for me long-term. Plus, I now know the entertainment work would have put me on the wrong side of the copyright debates. In any case, based on the projects I got and how I evaluated the office’s priorities, I didn’t see a good fit for my professional goals.

I also struggled with the office culture. I’m usually a steady stream of self-deprecating and sarcastic attempts at humor, which I don’t think fit the office norms. I remember, in particular, a recruiting dinner with the office managing partner on a Friday night, which you’d think would be a relaxed affair. For a couple of hours, I did my standard shtick but not a single joke appeared to have landed. NOT ONE. I wondered–is this my future? To work with colleagues who don’t share my humor? Maybe I would lose my sense of humor?

My Denouement With Sidley

At the end of the summer, Sidley invited me to return for 3 weeks in summer 1993, when they would potentially give me a permanent offer. This was standard practice at the time (and may still be?). I think the idea was that the student, after sampling another firm, would fall back in love with the first firm, plus it gave the firm a strong position to close the deal.

As expected, when I interviewed as a true “2L” (really, 3L), I had many more options. Some of the offers I took most seriously were Cooley (Palo Alto), Wilson Sonsini (Palo Alto), Irell & Manella (LA), and Skadden Arps (LA). As you know, I chose Cooley–a decision I’ve never once regretted.

Due to UCLA’s wacky course scheduling for the JD/MBA program, my summer break in 1993 started in May and ended in September. As a result, I had time to return to Sidley without reducing my time with Cooley. Yet, I couldn’t justify going back. It just wasn’t what I wanted out of my career. I decided that if Cooley didn’t work out for whatever reason, I would seek jobs on the business side rather than accept a fallback permanent offer with Sidley. As a result, I declined the offer to return to Sidley in summer 1993, and my contacts with the firm quickly faded.

I can’t recall when Sidley dropped off my resume, but it was within a couple of years. It was only a summer position, and my experiences at Cooley were so much more important to my story. That’s why my Sidley stint has become a lost/secret piece of my history.

Summer 1992 Was a Pivotal Period in My Life

When I started searching in July 1991 for 2L summer jobs, I still planned to pursue a career as a real estate developer. Two major things changed between my Sidley offer in August 1991 and when I showed up at the law firm in June 1992. First, during my first year of business school, I became excited about venture capital, innovation, and entrepreneurship. That sparked my interest in the Silicon Valley. Second, I got my first email account in Fall 1991 through the business school, and it blew my mind. I became fascinated with Internet law.

While browsing the stacks in the Sidley library after hours (yes, law firms used to have physical libraries, and browsing stacks was how we discovered new content before RSS and social media), I stumbled across this Computer Lawyer article that changed my life. It was a routine summary of the Cubby v. CompuServe opinion, but I became obsessed with the issues it raised. I pivoted towards the legal issues of UGC, and I wrote my law review note on the law of BBSes. Working on that paper in December 1992, I decided that I wanted to become an Internet lawyer. I’m still pursuing that ambition 30 years later.

You can see how my Sidley 1992 summer experience was a key piece of broader transitions in my life. By October 1992, I had the “place”–Cooley in the Silicon Valley. By December 1992, I had the “plan”–Internet law. The third and final piece came a year later, in December 1993, when I met Lisa–the daughter of my boss at the Palm Springs law firm–and I had the “partner.” (Yes, I married the boss’ daughter. Such a cliché). There’s evidence that men’s brains complete their maturation at age 25, and I turned 25 in April 1993. I strongly believe those last bits of maturation contributed to the whirlwind of crucial life decisions I made in 1992 and 1993.

At Santa Clara University, we often talk about making our educational programs “transformational experiences” for students. Some of that may be marketing rhetoric, but it’s my personal aspiration as a professor. You can see how my graduate school training, and the associated professional experiences it unlocked, transformed my life. I hope to do the same for my students.