Maybe you’ll work on a railroad and then become a famous writer. Or maybe you’ll be a prostitute and then create a TV show. Or maybe you’ll buy a car alarm company and run for Congress. You just never know, man.

Nicholson Baker

By then Baker already had notions of becoming a writer, even though one of his teachers put this comment on a story he turned in: “This, to be frank, is boring.” (Margaret remembers that he had a chart keeping track of all the rejection letters he received.) Before he became a full-time writer, though, Baker had a misguided interval of trying to be a businessman, and briefly even became a neoconservative.

Tom Cruise

Tom Cruise dreamed of being a priest when he was a teenager. The Hollywood star—now a devout follower of Scientology—was so sure religion was his calling he even left home to live in a Catholic seminary. He revealed: “I looked at the priesthood and said, ‘Listen, this is what I’m going to do.’ They (the church) would pay for the boarding school for a year. I knew being there would help my family financially. The school also had hobby shops and remote-control boats and planes.”

Roseanne

Roseanne worked as a waitress, a window dresser, a maid, and a prostitute, and then began to write comedy, often in the closet, at night, with a flashlight. Trapped at home, bored, frustrated, Roseanne started listening to the feisty talk-show host Alan Berg, who was later shot dead by the Aryan Brotherhood.

Darrell Issa

Issa acquired Steal Stopper in February, 1982, began to run the company himself, and turned it around. That year, he sold 200,000 car alarms to Ford, and was planning to sell Ford a million the following year.... In 1985, he sold his company to a California firm that made home alarm systems, and he moved to San Diego to work for the new entity. Soon afterward, he left to start another car-alarm company, called Directed Electronics, Inc. D.E.I. shared Issa’s initials and his voice, which he recorded for the company’s signature product, the Viper, an alarm that warns potential car thieves (as well as passing trucks and bursts of wind), “Please step away from the car.”

Alec Baldwin

Alec Baldwin began at George Washington University in 1976, with the idea of going into law and becoming President of the United States. At the end of his junior year, he split up with a girlfriend and lost a student-body election. Feeling underappreciated, he transferred to NYU and began studying at the Lee Strasberg Theatre Institute.

Condoleezza Rice

DU Magazine: The story goes that you were set to have a career in music. And then one day you wandered into a course with Josef Korbel (founder of what was then DU’s Graduate School of International Studies). That must have been some course.

Rice: The truth of the matter is that I was a failed piano major by the time I wandered into Dr. Korbel’s course. I had studied piano from age three; I could read music before I could read—I was really headed for a career at Carnegie Hall. And then, the summer of my sophomore year, I went to the Aspen Music Festival school. I met 12-year-olds who could play from sight what it had taken me all year to learn, and I thought, “Uh oh, I’m going to end up teaching 13-year-olds to murder Beethoven, or maybe I’m going to play [in a] piano bar, but I’m not playing Carnegie Hall.”

Janis Joplin

Briefly, she’d been an art student at the University of Texas, Austin. She’d come up to the semi-bohemian college paradise—where there were 20,000 students—from her native seacoast ground of Port Arthur, Tex. In Port Arthur, she’d been a misfit: ever the right thing in a wrong place. She never really fit in at Austin, either, except with her fellow hippies—which was a word nobody had heard yet. Austin in the early ’60s was a bohemia only by degree. The frat boys who ran the place orchestrated a campaign to get her named “Ugliest Man on Campus.” They succeeded.

James Baldwin

During this early part of his life, he followed in his father’s footsteps and became a preacher. Of those teen years, Baldwin recalled, “Those three years in the pulpit—I didn’t realize it then—that is what turned me into a writer, really, dealing with all that anguish and that despair and that beauty.” Many have noted the strong influence of the language of the church on Baldwin’s style, its cadences and tone. Eager to move on, Baldwin knew that if he left the pulpit he must also leave home, so at 18 he took a job working for the New Jersey railroad.