How Judy Whitmore Handles 3+ Careers (Vocalist, Therapist, Jet Pilot)

by | Oct 28, 2022

Meet Judy Whitmore. She is a multi-careerist based in California. I first knew her as an acclaimed artist whose new album Isn’t It Romantic? is remarkable. And then I learned about her many fascinating journey.

Judy’s careers:

  • Theater Producer
  • Jet Pilot
  • Marriage and Family Therapist
  • Writer
  • Vocalist

On her motivations for having many careers

My curiosity and sense of adventure have always been driving forces in my life. With each career change, I would imagine myself in a new role, weigh the pros and cons, and then “jump in.” I love the excitement of new experiences. My personality is not suited to one long-term career.

Advice to aspiring multi-careerists

Each career (except writing and singing) lasted around eight to ten years, but not in succession. While a theater producer, I developed a passion for aviation and became a licensed Learjet Captain. By that time my interest in producing had waned, so I went back to graduate school for a degree in clinical psychology. I gave up my ten-year private practice, along with flying, to become a writer. Ten years ago I returned to my first love, singing…so now I am a writer and a singer.

Advice to aspiring multi careerists

Juggling two or more careers demands focus and dedication to each. This is difficult to do if you are not truly organized — make lists, keep your calendar up to date, keep your desk free from clutter. Manage your time well. Don’t accept a lunch date if your current project has a deadline!


On overcoming obstacles

The biggest issue I have had to deal with is a current one. My singing career takes up so much of my time, the book I have been working on for the last several years is still not finished. I have decided to postpone working on my new album until this Spring and, instead, to dedicate the next several months to completing my new book.

On how multiple careers are beneficial

My experiences as a jet pilot were vitally important to the plot of my best-selling novel Come Fly With Me. The degree in Clinical Psychology has been helpful in all my endeavors because it has enabled me to communicate more effectively with people.

On personal time

I’m busy and my husband and children are busy…but on Sunday night, everyone comes home for family dinner. Quality family time is more important than quantity time!

On what she wishes she had learned earlier

Although it would not have stopped me, I wish I had known and been prepared for the negative perception some people would have of this choice.

What to read

My two favorite books related to creativity are Big Magic: Creative Living Beyond Fear, by Elizabeth Gilbert, and Bird by Bird by Anne Lamott.

Although these books address careers in the arts, I suspect the wisdom and suggestions these books offer would be applicable to a person engaging in a portfolio career.

On the stigma of having many careers

Having more than one career invites people to brand you as a novice, a “wannabe,” or a dilettante. Years ago I was asked to introduce myself at a new writing group. I mentioned I had been a theater producer, a pilot, a therapist, a singer and a writer. One of the men in the group chimed in, “What a showoff.” As part of my path to success, I had to learn to ignore these people.

On what to share with others

I’m always careful about sharing information with anyone I don’t know well.

On sublimating ego

Since I have always worked for myself, and since I’m my biggest critic, I’m not allowed to have an ego at my day job!

A Day in the Life

  • 7:30am – Wake up, make tea, read newspaper
  • 9:30am – Drive to L.A. for voice lesson, or sit down at my computer and start answering emails, handle personal business affairs, pay bills, make phone calls, do research for new book, an hour a week spent on Pacific Symphony business.
  • 1:30 – Lunch
  • Afternoon – More computer time: work on upcoming and current projects, calendar scheduling. Writing time, rehearse a few songs.
  • 5:30 – Work out at Gym
  • 7:00 Dinner
  • 8:30 – Answer more emails
  • 9:00-10:00 Watch TV
  • 10:00 Do New York Times Wordle

Where to find Judy


Kabir Sehgal is a Multi Grammy & Latin Grammy Award winner, as well as New York Times bestselling author.

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