Although Stein has not practiced law for years and does not plan on doing so again, he believes, and exemplifies, that law graduates, in addition to being prepared to practice law, have a myriad of options available to them when it comes to making career choices. The talent and skill that one needs to become a successful lawyer can take young and eager professionals many places far beyond the courtroom. Fully embracing the road less traveled, Stein has responded to a continual hunger for exploring uncharted territory, demonstrating that bookworms and wallflowers can unleash their personal and professional capacities to blend their smarts with witty, clever, and outspoken ideas.
Stein attended Yale Law School during the late 1960s, right when the Vietnam War was inspiring the rebellious behavior that his generation is known for—and the campus at Yale University was not exempt from being influenced by the spirit of the times. When asked about his experience at Yale Law School, Stein's entire tone and expression brightened, illuminating his fond memories as he said, "Oh, we had fun at Yale. It was great; it was absolutely great. It was paradise there in those days."
Professors and faculty might have referred to the late 60s as the "dark ages," but Yale was a breeding ground for learning and expression; Stein and other students were able to freely speak their minds about the school and the world outside of it. With genius professors, such as prominent law professionals Robert Bork and Harry Wellington, Stein learned from the best and spoke out to the ones who were, well, less-than-best. "If we had professors who were great, we could appreciate and laud them, and if we had ones who we didn't like, we could let them know of our displeasure. We could go down and demonstrate for the Black Panthers, we could smoke dope—it was great; it was absolutely great," he reminisced.
"Please, please, please, lawyers out there, there's a whole big world of things you can do. Your legal training has made you, presumably, a sharp, acute, analytical thinker and a good writer—use that training to do something other than be a prisoner of law," Stein said.
Stein's drive to venture out and strive toward self-satisfying career goals, regardless of what may stand in the way, is a wake-up call for those who settle and become stuck in the humdrum of careers they hate.
After the recent passing of former President Gerald Ford, Stein paid tribute to him on CBS Sunday Morning, saying, "The man I knew when I wrote speeches for him, the man the nation and the world knew, was the Grand Rapids boy who worked his way through the University of Michigan washing dishes in the Deke house, worked his way through Yale Law School coaching football, fought and nearly died on an aircraft carrier in the Pacific in World War II. He was molded of Michigan iron—a Ford, not a Lincoln, but what a glorious Michigan-made vehicle of the human spirit."
After living and working on the East Coast for his entire life, Stein began to get anxious for a change of pace—and scenery. "I was traveling around on a subway—this was before the subways in New York were air-conditioned—and it was hot and miserable, and I was really, really unhappy being in these hot, miserable, smelly subways. I sat at a gray, gunmetal-colored desk at The Wall Street Journal in a very dreary atmosphere, and I hated it."
By the time Stein made it to Hollywood, he had already developed a multifaceted career comprised of his work as a reporter, a poverty lawyer, an economist, a trial lawyer, a university professor, a speech writer for two U.S. presidents, a columnist and editorial writer for The Wall Street Journal, a novelist, and a nonfiction book writer. While he was working as a screenwriter in Hollywood, Stein realized that he needed more aggressive talent representation to take him where he wanted to go professionally. When he met Michael Ovitz at a charity lunch, his opportunity arrived. At that time, Ovitz was starting up a new talent agency called Creative Artists Agency (CAA)—now one of the few giant powerhouse agencies in Hollywood. After hearing stunning reviews of Stein's work from legendary producer Norman Lear and executive producer and writer Al Burton, Ovitz took Stein to his agency and started selling his scripts as fast as he could produce them.
In 26 Steps to Succeed in Hollywood...or Any Other Business, Stein extensively discusses the value of personal connections, saying, "Connections are everything, absolutely everything!" Stein's connections date back to the 1930s, when his father, economist and writer Herbert Stein, befriended Milton Friedman, a future Nobel Prize-winning economist who would influence three U.S. presidents, at the University of Chicago. Friedman later became the head economist on Richard Nixon's transition team and eventually recommended Stein's father to Nixon. After Stein's father was called to serve as Chairman of the Council of Economic Advisors, Stein's connections to the White House were secured. Stein also had connections at The Wall Street Journal because his father frequently wrote for the publication. All of Stein's relationships and connections have been built on his father's friendship with Friedman, which has functioned as a valuable foundation for his success.
When Stein settled into Los Angeles years ago, he said to himself, "This is the way to live!" After moving to Hollywood, where he found palm trees and swimming pools and purchased his own Mercedes convertible, he was a "happy camper." All of that glamour began to turn stale when he found that screenplay writing was nothing like novel writing. Stein was not prepared for the never-ending revisions and the sea of criticism and opinions that he had to take into account. "I had no idea that you had so many people able to criticize and modify your work or what a collaborative process it was."
Since that time, Stein has branched out into a more performance-oriented sector of the industry, claiming huge credits in all arenas, from commercials to voiceovers to television to film. With appearances and voiceovers in television and radio commercials for Murine Clear Eyes, the Alaska Seafood Marketing Institute, and former California Attorney General candidate Chuck Poochigian; appearances on television shows like The Drew Carey Show, The Man Show, and The Wonder Years and a myriad of talk shows and specials as himself; performances in films like A Smile Like Yours, The Mask, My Girl 2, and Dave; and voiceover work on animated series and movies such as King of the Hill, Family Guy, and Disney's Hercules (not to mention television and film producer credits), Stein has achieved an unusually wide-ranging entertainment career. His quirky attributes and personality, combined with his unique reserves of experience and pure genius, make him one of those performers who is not necessarily Brad Pitt but who is always, always working and in demand.
One of Stein's latest writing endeavors involves educating the United States' 78 million baby boomers—and younger generations to come—on saving for retirement. Stein has speculated that in the coming years, our economy will endure very alarming economic hardship because most Americans simply have not saved enough money to comfortably retire. With Social Security benefits and pensions being whittled down quickly, people are not going to be able to solely survive by such means. The problem is that the average saving rate in this country is less than zero...-0.5%, to be exact.
In Stein's financial advice books (co-written with noted investment advisor Phil DeMuth), Yes, You Can Get a Financial Life!: Your Lifetime Guide to Financial Planning and Yes, You Can Still Retire Comfortably!: The Baby-Boom Retirement Crisis and How to Beat It, he addresses lifelong saving and how it can easily be accomplished. Stein advises all people to start saving as soon as possible, saying, "Let's say that you are able to save, as soon as you get out of law school, 10% of your after-tax income in a broadly diversified mutual fund. If you keep doing that, if you start at 26, you will, by the time you are 66, have enough money to retire comfortably. But if you start when you are 56, you're not going to."
One of these options was teaching in law schools throughout the country. In past years, Stein has taught classes on political and social content of mass culture at American University in Washington, DC, political and civil rights under the Constitution at the University of California, Santa Cruz, and libel law and securities law and ethical issues at Pepperdine University in Malibu, CA, giving him considerable perspective on the educational side of law. Stein said that the best combination of two types of law work that he knows of is being a law professor and expert witness.
Combined with his network of connections, Stein's education has allowed him to dip his toes into an array of job pools, diving into those he has fallen in love with and straying away from those that have not won his creative and personal interest. "There's just a big, wide world out there. I was very lucky; I had great, great connections, and I had a little bit of talent in many areas."
Through his various areas of study at Yale and throughout his career in general, Stein has developed priceless relationships and has been guided by incredible mentors. His father is at the top of his list of influential people, as he taught Stein through his love as a father and his creative genius as a writer and economist. "My father was a very kind human being and a very generous human being and a brilliant-beyond-words human being. He was really my mentor in the sense that he was an economist, which you think of as being a dull, boring job, but he made it very interesting by writing about it in a very interesting and amusing way."
While in school, Stein also learned from fellow classmates Duncan Kennedy, now a law professor at Harvard University, and Peter Broderick, now a producer, a writer, and the president of Next Wave Films. Broderick was one of the first people who urged Stein to explore a career in film and television. In law school, Stein met professor of finance Harry Wallich, who inspired him to further his aspirations in financial planning and other related areas. Another Yale professor who, along with immortal television producer Norman Lear and famed producer, director, and writer John Hughes, played a large part in molding Stein's creative career was theater professor, accomplished critic, and writer Stanley Kauffmann. Having such a vast group of mentors and friends has further fueled Stein's compelling and long-lived career.
Stein is also a family man. He married his wife, Alexandra Denman, in 1968; the couple divorced in 1974 and remarried in 1977. 10 years later, their adopted son, Tommy, was born. Dealing with a new life and first-time dad insecurities, Stein released a book in 1998 on his parenting experience entitled Tommy and Me: The Making of a Dad, in which he reflects on his struggle to acclimate to being a father. Being a wise investor and economist, Stein recognizes a good investment when he sees one—and his son is his most valuable asset to date. In an interview with CNN, Stein shared what he has learned from parenthood, saying, "If you pay attention to your kids, they will pay it back to you a thousand-fold. If you give them some of your esteem and status and share yourself with them, they will double, quadruple it for you." Currently, Stein lives with his wife and son, four cats, and two large dogs in Beverly Hills, CA.
Today, Stein is pleased to have evolved into a speaker, commentator, and columnist. His refusal to settle for a mediocre or unfulfilling career will likely encourage many to go out on limbs to hunt down the most satisfying professional pursuits available. As Stein has steered his way through many different career paths over the years, he has opened many doors to opportunity, providing himself with a multitude of choices. He has shown us that it is possible to stick to one's guns and still master the worlds of law, politics, writing, entertainment, and journalism—all in one lifetime.