For the last five years, the Cafe Carlyle, perhaps the premier cabaret venue in New York City, has devoted the month of November to an act featuring John Pizzarelli, a jazz guitarist and vocalist, and his wife, Jessica Molaskey, a Broadway actress and singer.  My year wouldn’t be complete if I didn’t go. Their exacting musicianship; their ability to weave the Beatles and Sondheim, Jobim and Cole Porter into a seamless set; and their hilarious banter (John is a born ham, Jessica a born foil) invariably make it a memorable evening. I admire the way they make it look easy.  I also admire something else about them: the way they have built their careers. In their late 40s when the Carlyle first booked them, they are the opposite of “overnight sensations.” They have been working at their professions since they were teenagers.  They have had their setbacks. The one time Jessica thought she had landed a breakout role in a musical, the show failed to make it to Broadway. The one time John got a big push from a major record label, the record flopped. But they persevered, never mailed it in and, eventually, were rewarded. From where I’m sitting, their careers can serve as a model for a lot more people than just musicians and actors.  Jessica was 19 when she moved to New York from the small town of Wolcott, Conn., determined to be an actress. Her first audition landed her a role in the ensemble of “Oklahoma!,” which was being revived. “I thought it was going to be like that forever,” she recalls.  But, of course, it wasn’t. Although she had roles in many of the big-budget musicals that rolled through New York — “Cats,” “Les Miz” and the like — the parts were small, and the work ultimately stultifying.  So, in her late 20s, she stopped auditioning for can’t-miss musicals and gravitated instead to the riskier work of younger composers who were building their own careers. She remembers doing shows for $200 a week — and loving it. “I was a lot more broke, and a lot happier. I was learning things.”  John, meanwhile, had grown up around jazz. His father is Bucky Pizzarelli, the great guitarist. Bucky “didn’t teach me how to play the guitar, but he taught me how to love the guitar,” John says. As he got good, his father would take him on the occasional gig, but John was also playing in rock bands and writing songs.  “I thought I was going to be the next Billy Joel,” he says.  The light bulb went on when he started listening to Nat King Cole recordings. “I sorta said, ‘I’m gonna play this music,’ ” says John. That’s what he did in his 20s and early 30s — playing in bars in New Jersey, where he grew up, and in New York City for $40 a night, “barely paying the bills.”  His father would still sometimes employ him — and that would earn him a real paycheck. When I asked John what he learned from playing with his father, his answer was immediate: “Every gig counts.”  John and Jessica met in 1997, when they were both cast in a short-lived musical called “Dream.” They married, had a daughter, and built a life together.  For the most part, they continued their separate careers: John toured constantly with a quartet that included his brother Martin on bass, and Jessica began cutting records in addition to taking the occasional part in a musical. There was never a moment when their careers took off, but slowly, steadily, they each built a substantial, praise-worthy life in music and acting.  John knows that he is never going to be as rich or as famous as Billy Joel. He says he is O.K. with that. Jessica still yearns for that breakout Broadway role. But if it doesn’t happen, she says she’ll be fine.  When she first came to New York, Jessica recalled the other day, her brother dropped her off and then drove back home to Connecticut.  “He told me recently that he felt so guilty leaving me there,” she said. “He wasn’t sure I was going to survive. And there were days when I wondered that myself. I remember going to an audition and thinking, ‘If I don’t get this job I’m going to die, because I only have a dollar to my name.’ But guess what? I didn’t get the job, and I didn’t die. Kids get bailed out now,” she added. “There is something to be said for the resolve it takes to make it on your own.”  She thought about that for a minute. John, who was sitting next to her, looked over at her with a smile.  “There is something really lovely about putting one foot in front of the other,” she said, finally. “You wake up one day and you have a nice career, and a 13-year-old daughter and a house in the country. There is something about the way you earned it that is gratifying.”
The slow and steady careers of two great musicians provide some meaningful life lessons for the rest of us.