CHAPTER 6

Focusing on Success While Remaining Open to Iteration

Featured Narrative: Tom O’Keefe, Actor, Bedlam Theater Company

REM’s song This Could Be the Saddest Dusk was playing on Tom O’Keefe’s Walkman as he made his way to the mailbox. On lunch break from his summer internship at the attorney general’s office in Massachusetts, he was thinking about what he’d tell his father, the man who’d poured equal amounts of tuition and pride into his son’s future as an attorney. The last of six children, Tom knew the cost of attending Boston University’s law school. He’d seen how hard his parents had worked to attain their financial security, how they’d started out with nothing. And as he took the T back to his apartment that day, he was panicked. Grades were in. Despite the nightmares he’d been having about exams, he’d liked the first year of law school, the rigor of studying. Criminal law was particularly appealing for its rhetoric and drama and the opportunity to be in the courtroom. But if he’d flunked his criminal law exam, he was decided: He’d let go of becoming a prosecutor, a U.S. attorney, and quit law school to become an actor. Bracing himself, he opened the envelope and started to laugh. He’d gotten the highest score in the class.

“Well,” he thought, staring down, incredulous, “this is what I’m supposed to do. I’m supposed to be a lawyer.” That first year, Tom received the Book Award for his highest grade and finished number two in his class overall. At the end of his three years in law school, a hair separated him from graduating summa cum laude, finishing, as he did, among the top 10 students out of approximately 350. He took the distinction of magna cum laude with him to the associate job waiting at the Boston law firm of Goodwin, Procter, and Hoar. He’d worked there as a summer associate after finishing his second year. That same year, while fielding multiple offers from big firms, he joined a band as its lead singer. It was also the year he’d had a failed audition for Legal Follies, the group at Boston University that put on an annual variety show. Before his third year of law school was complete, he had an offer from Goodwin.

He’d chosen Goodwin because, he tells me, “It seemed the best of all worlds.” Not only was it a “respected firm with great people doing some great corporate litigation work,” but a number of the firm’s lawyers were former U.S. attorneys, including two of Tom’s mentors. The firm had a program with the Middlesex District Attorneys (DA’s) office where they’d send a couple of second-year associates to work for six months while still collecting their salaries from Goodwin. It was, Tom remembers, “a good way to make money, get experience, make connections, and then move on and become a US attorney, if that was still my dream.” More than a decade would pass before he would make “the very distinct connection between lawyering and Shakespeare” and a couple of years after that when he would be in rehearsals for a production of Hamlet in New York City.

Tom first considered the notion “to take on acting” in high school. He’d auditioned and performed in a few shows. At that time, there was also the “side note” of considering the Air Force Academy. Participating in band, rather than acting, was likely a better fit for the Air Force track. But, as the next step toward his future came into focus, Tom recalls, “In the end, it was to go to college and become a lawyer.” During college, there were a handful of acting classes, the thought to add theater as a minor, and the Shakespeare class where the words were spoken aloud and he was utterly captivated. But law school would not only provide him with the “financial stability” that he’d seen his parents valiantly achieve, but Tom thought, “That’s the career path that fits me.” When we look back together during our interview and I ask him about that time, he doesn’t recall wondering about what he’d do. “To be honest,” he says, “I didn’t really struggle with it.”

At Goodwin, he was hardly miserable as an attorney. Was acting knocking at all, I want to know? Was it whispering? “I don’t recall thinking about it,” Tom tells me in all candor. He was working, fulfilling his “dream of becoming a prosecutor.” But then, what came next was “really wacky,” he remembers. His girlfriend had gone to a tarot card reader. She called Tom afterward to report that when the reader discovered that Tom was an attorney, the tarot reader blurted out, “How dare he!” Looking back, Tom says that reaction could have meant any number of things. Perhaps the tarot card reader had been sued or had an ex-husband who was an attorney. Or just hated lawyers. But when Tom heard those words, he blurted out in response, “Yeah, I should be acting.”

Despite the just-below-the surface immediacy of his response, what followed could best be described as “gradual with stutter steps and lots of tripping,” he tells me. No sooner did he get off the phone with his girlfriend than Tom did an Internet search and e-mailed an acting school in California. He gave them a sketch: Twenty-eight years old and an attorney, he’d acted a bit in high school and college and wanted their suggestions. Within an hour, a response. The school was holding an intensive seminar the following weekend. In Boston. He shares with me that while he “had a good time with it,” he didn’t make any big changes to his life.

But he was taking steps. At the conclusion of the weekend intensive, the instructors pulled him aside. “You have something,” they said. Those words at that juncture. They provided some reassurance, some reflection. “This passion of mine that’s been hidden away and keeps popping up at the interesting moments,” he recalls thinking, “is grounded in some reality.” He’d needed that. Because wrapped around the pursuit of acting were a series of strung-together questions that plagued him: “Should I really be doing this, or is this just ego? Who do I think I am? Am I fooling myself?” That nod toward his talent prodded him to further action, nudged him along. He took a few more acting classes near Boston. He remained at Goodwin but downsized from his solo one bedroom to sharing an apartment with a roommate to save money. He was looking into acting, dipping a toe in the water, but wasn’t about to plunge in full-time.

But now, at this place, there is “something of a struggle,” Tom recalls. He was toggling, caught between “am I going to do this, am I not?” He had one foot each in two worlds. And he remained in that place of back and forth for almost two years. The world of the law had its prescribed track, a well-marked route. And, while not guaranteed, the hard work it demanded likely granted ascension. That path came with “its set of accolades or respect in traditional society.” It was acceptable. The world of acting, however, only promised to fulfill his passion. He knew one thing: If he did it, he would go to Los Angeles (LA). New York, while closer and likely a very good place to begin acting, was dangerous. It would put him in the same city where Goodwin had a branch office. He would be in proximity to family in nearby Connecticut. The next step would have to be big, he knew. It would have been easy to just “give up acting and go back to my job,” he remembers. Reflecting during our interview, Tom’s relays that “the only thing that was getting in my way” was how unsure acting was. But there was more. There was the practical. It wasn’t as if he had a map for launching an acting career. “How do I do it?” was another hesitation. And, then, perhaps the question that held his greatest reluctance: “How do I tell my Dad?”

It would be Tom’s father who would inform his son that it was time. Still at Goodwin, Tom had a week’s vacation planned for LA. With friends living there, the idea was to go “just to look around” and continue his inch-by-inch exploration of acting. But he did not make that trip. Instead, he flew home to be with his mother who was dying. A woman who’d once wanted to act, herself, Tom recalls a moment between them when she was still lucid, before the Alzheimer’s made her seriously ill. He’d shared what he was considering and she shared her cautious excitement for him. A week after her death, Tom’s toggling ceased and the struggle was over. With his father’s blessing and gentle push, he returned to Boston, to Goodwin, and as colleagues were offering their condolences, he walked into the office of the partners, closed the door, and offered his resignation. He was leaving for Los Angeles. For acting.

With the savings he’d socked away, Tom felt confident that he could sustain himself for two years while he attempted to get himself established. And it would be that long before he began booking commercials. But he found opportunity in LA. There would be at least one national spot in commercials each year, even some guest spots on TV. While he hadn’t found extraordinary success, and there were times when he didn’t have work, he’d gained a foothold. But after almost 10 years in LA, something eluded him. He’d begun to feel “stagnant.” Despite the hard work and reward of launching his acting career, he “wasn’t feeling really fulfilled.” Most of his time was spent auditioning for commercials or preparing to audition. He was doing one play a year, at most. “I wasn’t spending my daily life as an actor,” Tom explains to me.

Performing a scene from Tennessee Williams’s Orpheus Descending would change that. On stage during a weeklong intensive class, Tom was instantly reunited with why he’d gone to LA in the first place. “This is why I became an actor,” he recalls thinking. Theater. He went home to find his copy of King Lear. Reading it again, he was transported back to the college class where he’d first been “so moved” by Shakespeare, by hearing it read aloud. At that moment, he knew: “That’s the stuff that I want to do.” It would be New York, after all. But not before immersing himself in classical theater.

Leaving LA, Tom focused on Shakespeare. He sought out training at weekend intensives, spent time at the theater company of Shakespeare and Company, and worked in plays throughout New England, practicing his craft. Law school, it turned out, had not been in vain, had not been an error. Despite the difficulty often associated with its first year, he’d had a passion for learning the cases and discovered a “real love for rhetoric, for words, for using the right words.” During his first weekend Shakespeare intensive after leaving LA, he saw it. Law school, with its emphasis on argument and word precision, had not only been excellent training for reciting and performing Shakespeare, it made perfect sense.

After a year of “living like a nomad,” of going from play to play to learn and train, it was finally time for New York. But arriving “was kind of like a slap in the face,” Tom tells me. The promise of doing great work might have been waiting, but so was a New York winter. And the fact that he knew no one. And that no one knew him. It was demoralizing that he needed to find an apartment with a roommate at that stage in his life. He was starting over again. And “starting over much older,” he emphasizes. The first year in New York he characterizes as “very rough.” In darker moments, the questions came: “Why did I become an actor to begin with? This is just silly. Why didn’t I just stay in LA? I was making a living.”

This second leap was more difficult than when he set out for LA. It asked that he relinquish the success in LA to embark on another route that once again had no defined guideposts or markers. It required that he confront that he “still had the mindset of being someone who is on the traditional path” and attempt to let go of it, at least temporarily. Even if he hadn’t been performing theater in LA, at least, Tom relays, “I had been making money on commercials, so it was easy to call myself an actor.” In New York, he was redefining what it meant to be an actor. “It sounds a little pretentious to me,” he relays, “but I have to convince myself that it’s the work that’s the most important.” New York asked a lot. But there was a cadre of support: his dad, a sister in nearby Connecticut, and dear friends from law school and childhood he calls “bedrocks.” All provided infusions of encouragement and sustenance.

As Tom tells me about beginning all over again, I wonder if Los Angeles, like law school, wasn’t a fundamental and necessary step toward performing classical theater, rather than a warm-up or derailment. I wonder if for him to get to New York, he had to go to LA and succeed for almost 10 years to then discern that it wasn’t merely acting that he wanted, but Shakespeare. And, I wonder if his ability to leap, not once but twice, exemplifies a seemingly contrasting, yet essential, merging of two ingredients necessary for full prosperity: a deep and fixed determination for success with an openness to what presents itself, to iteration.

Temporarily setting aside material gain was, Tom tells me, “one of the more difficult things” for him during this time. I ask if he was able to change his perspective on New York and starting over. And if so, how? “I started doing plays and feeling like I was doing the right work,” he says. He was working with people he admired, doing the kind of theater he’d yearned for. One thing led to another. At the time of our interview, Tom had been in New York for two years. He was “deep in rehearsals” for Bedlam Theater Company’s second production, Shakespeare’s Hamlet. The year before, he’d performed in their inaugural show, George Bernard Shaw’s Saint Joan. Bedlam was brand new to the New York theater scene, a start-up, and a “tiny, little theater company with no money” launched by two friends he met during his time spent studying theater in the year between LA and New York. Saint Joan, a play in which “every scene is an argument,” drew on Tom’s love of law school. Brought in as one of four actors in the production, he played 11 of the 25 characters. There were frequent character changes, often without costume, in the span of a few minutes. It was risky. He worried if the audience would buy it.

The contrast between working in New York and LA was not lost on Tom. At the time of our interview, he had fulfilled his reason for moving to New York, to focus “mainly on theater” and found himself a combination of happy and exhausted. Time spent in LA auditioning for commercials had been replaced by rehearsals for Bedlam’s follow-up to Saint Joan, with a few actors taking on many different parts once again in Hamlet. Rehearsals typically ran 8 to 10 hours a day. “At last count,” he tells me, “I’m playing nine characters.” He is finally on stage, finally with Shakespeare. How was Saint Joan received, I want to know? “It was really kind of comforting,” he says candidly. The New York Times named it a Critics’ Pick. The Wall Street Journal praised it as the best revival of the year. And the most exciting revival ever.