Meet Penny Orloff

We’re excited to introduce you to the always interesting and insightful Penny Orloff. We hope you’ll enjoy our conversation with Penny below.

Hi Penny, we’re so appreciative of you taking the time to share your nuggets of wisdom with our community. One of the topics we think is most important for folks looking to level up their lives is building up their self-confidence and self-esteem. Can you share how you developed your confidence?

No one can “give” you confidence or self-esteem. Developing confidence and self-esteem is an inside job.
Having watched way too many Fred Astaire/Ginger Rogers movies on TV with my mother, by the age of eight I had decided I would grow up to be in Show Business. I began writing and starring in little plays, enlisting other children in the neighborhood as my supporting cast. When my theatrical ambitions persisted, my parents chided me, telling me that I would never be able to earn enough money to make a living.
“You’ll wind up alone and in poverty,” they said.
“I don’t care about money,” I replied. “I would be happy to be poor if I can be an actress.”
Shortly after high school I fled to New York, living alone for years in a cockroach-infested tenement. I strummed my guitar and sang on the street to earn rent money. I never applied for jobs in restaurants or offices. My thinking was that if you wait tables, you’re a waitress. If you work in an office, you’re a secretary. If you sing on the street, you’re a performing artist!
It was, perhaps, a bit unconventional, but it worked to build my self-esteem—without which it is virtually impossible to face the endless auditions. The auditions are murder. Although I auditioned for and sometimes won low-paying roles in small professional theater companies, like almost all other Showbiz hopefuls, mostly I heard:
The face is okay, but God! That hair… Next.
Too short, next.
Too tall. Next!
Too young, too old, too thin, too FAT … NEXT!
It’s almost enough to crash an arrogant little nobody’s self-esteem.

By habit, it’s way too easy to criticize our own appearance, feel shame for our thoughts or actions, second-guess our decisions. Most folks are more than eager to focus on—and loathe—perceived “flaws” in their own physical being. Early on my bushy, frizzy hair was a major source of self-loathing. As a young ballerina, the radical changes to my body at puberty were hugely shocking in that inescapable wall of mirrors. All these decades later, at 77 years of age and 102 pounds, I confess that there are days when that little ballerina inside still feels intolerably FAT. Self-esteem collapse.
This untoward proclivity to negative self-appraisal is actually a product of evolution. Most mammalians are social animals that take ranking and status very seriously. Such societies constantly compare, evaluate, and judge the status of individuals. It’s a matter of survival. In humans, a preoccupation with self-esteem and fear of judgment are the prehistoric residue, amplified by a culture that emphasizes being a Winner.
Social media has the unfortunate tendency to make this limbic propensity worse. Constant comparisons of our own small, colorless lives with those of flashier online Winners (with their designer bodies and dogs and careers) bring us crashing into the cellar of low self-esteem with soul-killing self-judgments, while an increase in our “likes” and “followers” produces a sudden burst of dopamine, like a gambling win or hit of cocaine. And more is never enough.
But, our experience of life is almost wholly dependent upon our focus. And that is certainly something we can control. Here’s an example: There was a childhood game we played when bored out of our minds on a long automobile trip: Find the Yellow Volkswagen. We spotted every single one. Note: We never saw blue Chevys. They were there, certainly. But we were not scanning for them, so blue Chevys didn’t exist. Outer reality is a reflection of our inner seeking (as ever, the elegant quantum theory reigns).
The good news is that we actually can learn to focus on our best moments and greatest gifts. Like any skill, practice increases our competence. We get better at confidence and self-esteem with exercise and focus.
My upcoming book, “Who Would You Be If You Had Nothing to Bitch About,” explores questions of self-image, authenticity, confidence, and self-esteem in detail. Here are some guidelines:
Stop comparing yourself with others. Put down that phone!! Do not be distracted by what or how others are doing.
Better beats “perfect.” Eat the whole elephant one small bite at a time.
Minimize or eliminate whatever disturbs your peace–especially with regard to any self-limiting beliefs or self-negating behaviors.
Break free of courting the good opinion of others.
Take time in nature. For 17 years I lived in a cabin on a stream in a forest. I was befriended by trees, who silently witness without evaluation or judgment. The very concepts of self-esteem and shame disappear in nature.
Deliberately be present in your five senses.

The following questions can get you started. They have no right or wrong answers.
1. What are some of your favorite scents? Some of mine are freshly-ground coffee; gardenias and roses; ocean air; newly mowed grass; horse manure (YES! Really! “There must be a pony in here somewhere!”); raspberries.
2. Favorite sights. Mine include colorful sunsets, the first star of evening, fluffy cumulous clouds, horses running in a field, lush gardens…
3. Favorite sounds. Who doesn’t love hearing a child laugh? Wind chimes. Bird songs. A running stream. Slow movements of Baroque concertos. Classical guitar music.
4. Favorite tactile experiences. Puppies’ ears. Diving into cool water on a hot day. A deep massage. Digging in my garden. Stretching.
5. Favorite flavors. I love tart flavors like citrus and vinegar. Dark chocolate. Roasted meat! Raspberry frozen yogurt. Peppermint.

Watch for and notice when ANY of your personal favorites are present. Really notice. Appreciation and gratitude are the chief ingredients of happiness. Like the yellow Volkswagens, deliberately watching for and being aware of these simple, beautiful aspects of your life means that the blue Chevys – those issues that disturb your peace – cease to exist, at least for a timeless moment of bliss. Who would YOU be, if you had nothing to bitch about?
Take it further:
6. Your Mental Self: What are your greatest intellectual abilities? When are they active?
7. Your Emotional Self: What are your most powerful (NOT “most acceptable”) feelings? When do these feeling rise?
8. Your Spiritual Self: What are your least-limiting, most self-empowering beliefs?
9. Your Physical Self: What are your greatest physical attributes? Come up with AT LEAST FIVE! (PS: Your physical self is more than your appearance. Do you possess super-acute hearing? A kick-ass immune system?)
10. Your Potential Self: What do you do best? (List at least five specific things)

When you experience an unexpected crash of your self-esteem, read your lists and think on these things…

Thanks, so before we move on maybe you can share a bit more about yourself?

I am by nature a Storyteller. I spent a lifetime in Show Business–I was a working actor/dancer in Los Angeles when a Juilliard scholarship took me to New York. I played featured roles on Broadway and sang more than 20 Principal Soprano roles for New York City Opera. In a career spanning more than 50 years, I have starred in over 100 productions off-Broadway, regionally, and internationally. My first solo show, “Jewish Thighs on Broadway” (based on my award-winning, #1 best- selling novel of the same name, available at Amazon.com), toured the U.S. for a decade, including a successful off-Broadway run in 2005. Having outlived most of my early competition for Babe roles in movies, since 2012 this old gal has enjoyed acting in a range of interesting shorts, Indie, and feature films (silver-white hair and a Botox-free face are in short supply in LA…).
By about a dozen years ago, I had outgrown performing “Jewish Thighs,” and I started work on another show. The new one, “Songs and Stories From a Not-Quite-Kosher Life,” premiered in Seattle in 2019. Then the COVID lockdowns hit, and my 2020 tour was cancelled. I resumed performances recently around the Western US and, at 77 years of age, I am doing the best work I’ve ever done. I’m finally the Old Storyteller I always knew I could be. My next performance is January 10, 2026, in Surprise, AZ. Tickets are available on Eventbrite.com… Please come.
When my parents died 20 years ago, they left me some money with which I went to college and earned a Psychology degree. In a blinding synchronicity, I spent 10 years as the Art Therapist at a residential drug and alcohol rehab in Malibu. In addition to fool-proof art projects, and with the wholehearted support of the Executive Director of the facility, I offered Tarot readings–actually, Tarot-based counseling which, largely due to the “magical” nature of the process, produced some astonishingly positive results. I continue with Tarot-based counseling to this day, with clients from all over the US checking in via FaceTime! I also have done mini-readings at private parties — it’s always a thrill to see the long line of people lined up waiting for their turn. As a Tarot reader for over 60 years, I still find this process magical.
The big question for my counseling clients is, “Who Would You Be If You Had Nothing to Bitch About?” After decades of dedicated experimentation, rather than being an “expert,” I consider myself a living example. I’ve minimized or completely eliminated whatever disturbs my peace, and increased exponentially that which gives me joy. I remain on a constant lookout for my “yellow Volkswagens,” and I find them everywhere!

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

Imagination, curiosity, and fearlessness are, perhaps, the three qualities that have made my life so interesting and fulfilling. The “What-If” of my natural curiosity opened an unlimited playground for my imagination – and fearlessness meant I had no problem leaping into experiences I wanted to explore.
I believe that people who want to develop more colorful and exciting and pleasurable lives have only to remember moments from their childhoods — painting a picture, making up a poem, singing and dancing for NO REASON AT ALL, without judgment or expectation.
What did you want to do, who did you want to be when you were seven years old? When you were ten? When you were fourteen?
In the next few days, make a list of everyone you know who is engaged in any sort of creative activity that holds any interest for you. These might include the old gent who sings bass in your church choir, your nine-year-old’s ballet teacher, the lady down the street who grows such amazing dahlias. The recovered alcoholic who is getting her BA at the age of 62.
Take a deep breath. Take five minutes to ask one of these people how they got started in the activity.
Take a giant step. Take a look at the Continuing Education course catalogue from the local Community College. Take a moment to consider one course that looks interesting or fun.
Take a chance. Take advantage of the opportunity. Take the course. You will find that almost all the other people, instructor included, are there for shared support, encouragement, communal fun.
Take heart. Success breeds success.
Take notes–I need stories for my book!

How would you describe your ideal client?

I love working with clients who are willing to remember their childhood dreams and aspirations. Until we’re about 8 or 10, our self-image emerges without fear of others’ opinions–we get to imagine being a bus driver, a cowgirl, a forest ranger, an old storyteller… I like taking people back to the innocent time before fear of judgment rears its formidable head, before the mask hides the authentic Self.
I enjoy working with curious and imaginative people willing to at least explore the idea of their own power to guide their focus, their choices, their interpretations of “reality.” Who are open to the concept that we are creators and our lives are artwork–a result of myriad choices and actions, conscious or unconscious.
It’s always a pleasure to have the deep conversations that elicit a client’s own wisdom regarding workable solutions to perceived problems, and manifestation of dreams.

Contact Info:

• Website: penny orloff.com
• Facebook: https://www.facebook.com/penny.orloff.7/
• Youtube: https://www.youtube.com/watch?v=RanMdQxAwPY
• Other: https://www.doniscasey.com/?p=2308

  https://www.eventbrite.com/e/wham-presents-penny-orloffs-songs-and-stories-from-a-not-quite-kosher-life-tickets-1946658801879?aff=oddtdtcreator

  https://www.wnbnetworkwest.com/featured-author/Penny%20Orloff

Image Credits

Penny candid shots: Charles Long; Portraits: Mike Orloff; Pen’s house and Cisco the Donkey: Penny Orloff; Kosher Life logo: Virginia Downs