From Learjets to Love Songs: Judy Whitmore Talks New Album, Lifelong Creativity and Why It’s Never Too Late
“You know what? I think people used to have one lifelong job back when they only lived to 40. But now we’re living longer, and we can afford to change… It takes courage, though. There’s safety in the familiar, and stepping away from that to follow a dream takes bravery. But people do it. Many people do it. Every time I’ve made a change, I’ve been happy I did.”
I had the pleasure of talking with Judy Whitmore. Judy is a California-based vocalist whose circuitous professional journey spans the arts, aviation, psychology, and literature. Known for her nuanced interpretations of the Great American Songbook, Whitmore’s return to music after decades away from the stage represents a lifelong engagement with creative pursuits and a willingness to reinvent herself. Her latest album, ‘Let’s Fall In Love,’ produced by GRAMMY-nominated composer and arranger Chris Walden, continues a series of solo projects that reflect both personal passion and musical precision, offering orchestral renditions of classic romantic standards.
Born in Brooklyn, New York, Whitmore moved to California as a child and was raised in Studio City, where music was a constant presence in her household. Her grandfather was the first violinist in the MGM studio orchestra, playing on iconic scores including ‘The Wizard of Oz,’ while other family members were trained pianists. This environment steeped her in classical and American popular music from an early age, leading her to piano lessons at five and later to voice training in adolescence. By 13, she had begun formal singing lessons, driven by an emotional response to music that she described as both joyful and overwhelming.
Her first foray into the music industry came unexpectedly during a summer break from college when she auditioned for a vocal group being assembled by Capitol Records. Though unfamiliar with rock music, the genre at the heart of the project, Whitmore was hired, marking the beginning of a short but formative stint in professional singing. The momentum was halted when she married young and became a mother. Over the following years, her professional life would expand in multiple directions, including a career as a psychologist, a licensed pilot with a Learjet rating, and a theater producer.
Whitmore’s return to music occurred later in life, catalyzed by a casual performance at a friend’s birthday party. The experience rekindled her love for performing and eventually led to the formation of a vocal trio, Act 3, with her brother and a close friend. Their debut show was met with enthusiasm, and a suggestion from their music director to record an album led them to Capitol Studios in Hollywood. While Act 3 eventually disbanded to allow each member to pursue solo paths, it set Whitmore on a new trajectory.
Her solo career launched in 2020 with her debut album ‘Can’t We Be Friends’ and has since included multiple albums, with each project deepening her exploration of the American popular song tradition. Her most recent work, her fourth album ‘Let’s Fall In Love,’ focuses entirely on love songs and includes orchestral arrangements that she describes as both emotionally resonant and celebratory. The project reunites her with Chris Walden, whose orchestral sensibilities have become a signature of her sound. Recording with a full orchestra at East West Studios, Whitmore cites the experience as one of the most thrilling of her career, calling it “electrifying.”
Beyond her performance work, Whitmore is an active supporter of the arts in Orange County, California. She serves on the boards of the Pacific Symphony and the Pacific Jazz Orchestra, reflecting a long-standing commitment to arts advocacy and community involvement. Her background in psychology also informs her view of the arts as a healing and unifying force, one she believes has the potential to bridge cultural and political divides.
Throughout her varied career, Whitmore has navigated challenges that span both the personal and professional. One of her earliest lessons in music came from a misunderstanding during a voice lesson, where a misinterpretation of the term “piano” led to confusion with her German vocal coach. Later, as a pilot training for her Learjet rating, she encountered skepticism upon landing a plane in the Mojave Desert, where a refueling technician refused to believe she was the captain. Such moments, she says, highlight the importance of preparation, self-assurance, and adaptability.
Her work as a theater producer began during a period of personal transition when she was encouraged by a director friend to take a chance on producing a new musical. With no formal background in production, she relied on her experience as a theater board member and her intuition. The production faced challenges, most notably a lack of budget for rehearsal space, which led to rehearsals taking place in her mother’s garage, but ultimately received critical acclaim and opened doors to further theatrical collaborations, including in London.
Whitmore is candid about the emotional and logistical demands of returning to the stage after decades away. She describes early performances as nerve-wracking and emphasizes the perseverance required to sustain a creative career later in life. “Every time I’ve made a change, I’ve been happy I did,” she says, framing reinvention as both an opportunity and a personal challenge.
Health and self-care are integral to her routine. Daily exercise, healthy eating, and walking meditations are among her methods for managing the stresses of a busy professional and artistic life. She also cites her father’s nightly encouragement to pray for perseverance as a guiding principle that continues to shape her approach to work and life.
With her fourth solo album now joining her growing discography, Whitmore remains focused on the enduring power of music to uplift and connect. Drawing inspiration from the resilience and optimism embedded in the Great American Songbook, she hopes to not only preserve the genre’s legacy but also introduce its emotional richness to new audiences. For Whitmore, each performance and each project is another chance to do what she has always done: follow her passion, challenge herself, and keep going.
Yitzi: Judy, it’s a delight to meet you. Before we dive in deep, our readers would love to learn about your personal origin story. Can you share with us a story of your childhood and how you grew up?
Judy: I was born in New York. My family lived in Brooklyn. My father met my mother in California, and she convinced him that California would be a much better place to raise children than New York. So when I was very young, we moved to California, and I grew up in Studio City.
My grandfather was the first violinist in the MGM studio orchestra. He started working there — I think his first film was ‘The Wizard of Oz’ with Judy Garland. Our house was filled with music. My grandmother was a pianist, my grandfather was a violinist, my mother was a pianist, and my aunt was a pianist. So I started taking piano lessons — it was mandatory. Everybody had to take piano lessons when they were five years old. The house was just filled with music, and I was very lucky. I had a pretty great childhood.
Yitzi: You have an amazing career. Can you share with us a story of how you first entered the music industry?
Judy: When I was young, I loved all kinds of music. My father gave me a record player when I was about six, along with an LP of the Nutcracker Suite, and I would play that music, dance around my bedroom, and cry because it was so beautiful. I always thought, I love music so much, I want to have a music career.
I knew how to play the piano and thought I was going to be a singer. When I was 13, I started taking singing lessons. One summer when I was home from college, a friend of mine who worked on the periphery of the music business told me that Capitol Records was looking for a background singer for a group they were forming. She gave me a number and said, “Why don’t you go audition?”
I thought it was exciting, so I called and scheduled an audition. It was for a rock band, and the only music I knew was the Great American Songbook. I took one of my piano pieces — it wasn’t even in my key — and went to the audition. Miraculously, they gave me the job. That was my first entry into professional singing.
I did that for a while, then I finished college, got married very young, and had two children right away. That was the end of my career for a while. I put it on hold and did a lot of other things in between.
About 12 years ago, a friend of mine was turning 50. She knew I had sung when I was younger and asked if I would sing with her for her birthday. I said sure. We did the show at my house with about 50 people, and we had such a good time. We enrolled in musical theater classes at South Coast Rep, a local theater here, and started doing small concerts in our area.
After about two years, we were in New York walking by Carnegie Hall. She said, “You know, they have a recital hall here. We could rent it and do a show.” I thought she was crazy, but that’s exactly what we did. I remember saying, “Who’s going to come to our show in New York? At least we know people in California.” But believe it or not, people came, and it was thrilling.
From there, my girlfriend Lynn, my brother Bill, and I formed a trio called Act 3. That was about 10 years ago, and that’s when we started taking it seriously. Our first show was a huge success. The musical and vocal arrangements were beautiful, and our music director suggested we record an album. We thought, why not?
We recorded that album at Capitol Studios in Hollywood, and shortly after, all of us decided to pursue our own careers. The following year, I did my first solo album. Now, this is my fourth solo album. It’s been a whirlwind — a 10-year whirlwind.
Yitzi: You’ve reinvented yourself in the second chapter — or maybe the third chapter — of your life. What would you say to other people who would love to reinvent themselves, but feel like they’re already typecast in a certain image or way?
Judy: You know what? I think people used to have one lifelong job back when they only lived to 40. But now we’re living longer, and we can afford to change. You can do a job or have a career for 10 years, then have the option to say, “You know what? This isn’t really for me anymore.” If you have the ability to make a change — and maybe a partner who’s willing to support you through it — you can do that.
It takes courage, though. There’s safety in the familiar, and stepping away from that to follow a dream takes bravery. But people do it. Many people do it. Every time I’ve made a change, I’ve been happy I did. I’ve enjoyed whatever I was doing at the time, and then I moved on to something else when it felt right.
Yitzi: I’ve heard that you’ve been a psychologist, a pilot, an author, a producer, and now a music artist. That’s incredible. You must have some amazing stories from your various careers. Can you share one or two that stand out most in your mind?
Judy: I remember when I was a pilot, I was the captain and I had a female co-pilot. This was during my training to get my Learjet rating. We flew from Orange County to an airport in the Mojave Desert. After we landed — I landed the plane — we needed to refuel. This was in the middle of nowhere, so we parked, and I opened the door and stepped out.
Usually when you land a private plane, someone from the local FBO comes out to meet you. A guy was standing there, and I said, “I need 500 pounds of fuel in each tank.” He looked at me and said, “Well, as soon as the pilot comes out, he can tell me himself.” I said, “No, you’re looking at the pilot.”
At the time I got my Learjet type rating, there were a lot fewer female pilots than there are now. Of course, there were some, but apparently out in the Mojave Desert, they hadn’t seen one yet.
Yitzi: It’s been said that sometimes our mistakes can be our greatest teachers. Do you have a story about a funny mistake you made when you were first starting — either in the music industry or another part of your life — and the lesson you learned from it?
Judy: I can think of a mistake I made when I was very young. I don’t know what I learned from it at the time, but it’s kind of a funny story.
When I was taking singing lessons, I had a variety of vocal teachers. One of them was German, and he was very strict. I was probably about 15 years old when I went to my first lesson with him. That was around the time I had decided I wanted to be an opera singer, and he was a coach for opera.
At that first lesson — we were doing scales — he told me, “I want you to sing piano.” To me, at the time, “piano” meant a piano. I didn’t realize he meant to sing softly — pianissimo. I didn’t know any of that yet.
So I said, “Piano?” And he was furious. He kept repeating, “No, no, no, sing piano, piano, piano!” And I just kept saying, “Piano?” He was livid. Finally, I guess he realized I didn’t know what he was talking about, and he said, “No, sing softly. Softly.”
The lesson from that is: be prepared. Whatever you’re going into, at least do some reading. Know the basics before you start.
Yitzi: You’ve had so many different roles. What’s been the most challenging role or the most challenging project you’ve ever taken on and why?
Judy: Raising my children.
Aside from that, deciding to be a theater producer was probably the scariest. I was living in Aspen and was the president of the Board of Directors of a regional theater there. I met a director from California who came up to work with the theater. We became very good friends.
At one point, I had decided I was going to get a divorce and move back to California. I was talking to him on the phone and he said, “I just wrote a new musical. Why don’t you produce it?” I said, “I’ve never produced anything. I don’t know how to do that.” He told me, “You’ve worked in theater, you’ve been around theater people, you’ve been backstage, you know how shows work. You can do this. And I’ll help you.”
I thought, why not? To me, it felt like jumping off a cliff. Being involved in a nonprofit theater as the president of the board is one thing. Being a producer of a show is something else entirely.
But I thought, what’s the worst that can happen? So I did it. And we had wonderful adventures with that show. It got great reviews, and that experience eventually led to me working on a show in London. I was always so happy I made that decision. It was a hard one because I had no experience as a producer.
I remember just before we started rehearsals — we’d already secured a theater, hired PR people, cast the actors, hired set designers, costume and lighting people — all incredibly talented professionals, many of whom had worked on Broadway. Truly amazing artists.
We had even brought in Hugh Martin, who had been the lead vocal arranger at MGM for decades. He was retired at the time, but he came out of retirement to work on our show.
Then, about a week before rehearsals were set to begin, the director called me and said, “Judy, you didn’t put any money in the budget for rehearsal space.” And rehearsal space in LA is at a premium.
We ended up rehearsing the show in my mother’s garage because we had no money left for anything else. But it was such a fun, exciting time. I was always glad I made the decision to take on something completely new. I love the excitement of a challenge, and this one was worth it.
Yitzi: Judy, you have so much impressive work. Can you share with our readers this exciting new album? Tell us what’s unique about it, and why we have to listen to it and buy it.
Judy: I was so excited to do this album. I had looked on Spotify to see which of my songs had the most streams, and I noticed they were mostly love songs — tender, emotional love songs. So I thought, let’s do an entire album of love songs.
We had so much fun putting the song list together. I literally Googled “Great American Songbook love songs,” and all these beautiful songs came up. In the studio, we tried them out one by one to see which ones fit best together. It’s a wide variety of love songs. There are some upbeat numbers like “I’ll Take Romance,” and the orchestrations and arrangements on this album are stellar.
I’m so lucky to work with Chris Walden, who is a composer, arranger, and conductor. I think he’s had seven or eight GRAMMY nominations. He does such amazing work. The arrangements on this album will make you smile, they’ll make you want to dance, and they might even make you cry. It covers a whole range of emotions, and that was exactly the intention.
I’ve loved all the albums I’ve done, and I’ve worked with different arrangers and conductors over the years, but I think this album might be my favorite.
Yitzi: I read that you’re named after Judy Garland. How would you say you’re similar to her, and how are you different?
Judy: When I was a little girl, I had a Judy Garland album, and I would play it in my room and sing along, trying to sing like her. Of course, nobody can sing like her — she was just so fabulous.
I guess I’m like her in that music is now my life. It’s so important to me. And it’s important to me that young people listen to this music, because the Great American Songbook is made up of the most important composers and lyricists in our country’s history. You’ve got George and Ira Gershwin, Cole Porter, Johnny Mercer, Irving Berlin — these are people who wrote during some of the darkest times in history.
Much of this music was written after World War I, during the Great Depression, through World War II, and afterward. These were times when people desperately needed to be uplifted. That’s why I love this music so much. When I was a little girl listening to Judy Garland, I felt uplifted all the time. And now, what I want to do is uplift people too.
Yitzi: Amazing. What was it like recording with a full orchestra at East West Studio?
Judy: It was unbelievable. It was so exciting. The very first album I did, I worked with John Swosky, who produced that album. John is just fabulous, and I love working with him. We decided, since it was the first album, we had to be really careful about expenses. We recorded it at Capitol Studios in Hollywood, but it was just too expensive to have strings on the album. So when the album was finished, he said, “We really need some strings.” We ended up using strings from an orchestra in Budapest because it was about a quarter of the price of doing it here. The album came out wonderful, and I loved doing that, but I had never sung with a full orchestra. I don’t know how many strings they had — maybe about 15. We did it on the last album, and we did it on this album too. It was electrifying to be in the studio with so many musicians and to hear the strings along with the rest of the instruments. I’m speechless. I don’t even know what to say. It was so exciting.
Yitzi: This is our signature question. You’ve been blessed with a lot of success. Looking back to when you first started in music, you must have learned a lot. Can you share five things you’ve learned that you wish you knew when you were starting out in the music industry?
Judy: Let’s see. Five things I wish I had known.
- I wish I had known how nice everyone was going to be. I wouldn’t have been so scared. Everyone I’ve worked with has been so supportive, and that’s been a real blessing to have around me.
- I wish I had known how hard it is to fill a theater when you’re just starting out. I was really lucky, but every time I did a show, I was constantly checking to see if people were coming. I was always worried. I wish I had known to tell myself, “Things will work out.” Just like people came to Carnegie Hall, they’ll come to the local theater too. I wish I hadn’t carried all that anxiety. And I don’t play big theaters — just small clubs — but still, getting 150 people to fill a club is scary. Now, it’s not so scary.
- I wish I had known how important it is to be present every minute you’re on stage. One time, I forgot the lyrics to a song during a show because I was looking out into the audience and lost focus. Luckily, it only happened that once, but it taught me something.
- I also wish I had known — this may sound silly — how easy it would be. And by “easy,” I mean, once you make the decision, you do it, stay on that path, and don’t get distracted. If you have perseverance, you can do it. When I was a little girl, my dad would come into my room every night. We’d say our prayers, and afterward, he’d say we needed to pray for perseverance. I was five years old, praying for perseverance — I didn’t even know what it meant! But I know we prayed for it every night. My dad was such a great role model. He grew up in a tenement in New York City and became successful. His whole life was about sticking to your path, putting one foot in front of the other, and just keeping going.
- I wish I had had more faith in myself. It would’ve saved me a lot of anxiety. But I just keep going, like the Energizer Bunny.
Yitzi: Can you share with the readers the self-care routines that help your body, mind, and heart thrive?
Judy: I go to the gym every day. I used to hate it, but now I love it because the bicycle I ride has a video screen, and I can play backgammon the whole time I’m on it. I actually look forward to going now. I usually go around 6 PM, after I’ve been working all day. I used to think of it as something unpleasant, but now it’s like a reward at the end of the day. I sit on the bike, play backgammon, then move to the treadmill and play Mahjong.
We eat very healthy in our house. I’ve always been conscious of eating a low-fat diet. My grandmother, even way back then, used to say fats weren’t good for you, so we got used to eating lots of vegetables. We don’t eat red meat — just chicken and fish — and we keep a very healthy diet. I might have a glass of wine every couple of weeks, but I don’t drink much.
I’m really conscious of what I eat, I make sure to get a lot of exercise, and I try to manage stress. Sometimes life is so complicated, and it’s hard to keep your stress level down. When I feel overwhelmed, I’ll leave the house and take a walk. I find that walking is like a meditation. If you’re by yourself and just walking, one foot in front of the other, it calms your mind. That works really well for me. I think that’s what I do.
Yitzi: This is our final aspirational question. Judy, because of your great work and the platform you’ve built, you’re a person of enormous influence. If you could put out an idea or inspire a movement that would bring the most good to the most people, what would that be?
Judy: Oh, you know what? I have this fantasy that the world could heal itself. If I could do anything, I would love for there to be a way for people who think differently to come together — some kind of big movement where people who are at each other’s throats could find common ground. That’s the most important thing to me.
There’s so much violence in the world — what’s happening in Ukraine, the hostages in Israel, all the violence here in the U.S. I know that if you can get two people in a room together — having been a therapist and worked with couples who wanted to kill each other — and help them reconcile, there is a way. I know it’s possible. I just wish there were a way we could do that on a grand scale.
Yitzi: Amazing. How can our readers purchase your new album? How can they listen to your music? How can they support you in any possible way?
Judy: I’m on all the streaming platforms. You can listen, stream, or buy it on Spotify, Apple Music, Amazon, YouTube, Tidal, and probably a few others. That’s a good place to start.
Yitzi: Judy, it’s been so delightful to meet you. I wish you continued success, good health, and blessings. I hope we can do this again next year.
Judy: Oh, I hope so. Thank you so much for talking to me.
From Learjets to Love Songs: Judy Whitmore Talks New Album, Lifelong Creativity and Why It’s Never… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.