• OAK Street Initiative

Discovering Your Passion- A Toolbox for Reinvention

OAK Street Initiative Board Member Phyllis Pastore is a working actress and world class cabaret singer, but her path to performance was far from straightforward. From her childhood in Colorado to her move to New York City, Phyllis’ journey has been filled with reinvention.


Phyllis shares her life experiences and how career changes have helped her to follow her passions. And this new year, Phyllis encourages everyone to explore what reinvention could mean for them and reminds us it’s never too late to start a new chapter in life.



Retirement is strange. On Friday you go to work as normal and on Monday you have no place to be. You begin your work life with the goal of retirement. And when you retire, you spend your time looking for something worthwhile to do – which sometimes turns out to be another job.


Girls in my family didn’t go to college. We married young and raised babies. But growing up in my Italian family in Colorado, I was different from my cousins.

After I graduated high school in 1967, my parents did send me to college. But honestly, I think they hoped I would attend college to find a husband, but instead I earned a degree and then attended graduate school where I earned an MS degree in Vocational Rehabilitation Counseling. I did meet a boy and followed my heart, and a job, to Oklahoma. At 23, I was Director of Rehab for Goodwill Industries in Tulsa where I helped clients build their “vocational toolboxes” for job success. I had a beautiful apartment which I shared with the love of my life and felt that this was it…I was finally going to be married and my life would begin. That didn’t happen. I remember folding his underwear one day and consciously thinking, “Is this it? Is this my life?” I left the boyfriend, I left my job, I left Oklahoma and moved back to Colorado.


My life was a blank slate: no job, no boyfriend, no permanent home to speak of, so I did what any self-respecting social worker/rehab counselor would do: I took stock of my skills and interests. I began building what we call in the vocational rehab field, my “vocational toolbox” - an exercise used to outline a person’s skills and interests to point them in the right direction.

In the Skills column I put my education, my work history and people skills. I had worked in my aunt’s pizzeria in high school, so I added food service to the Skills column, too. Thankfully, “the boyfriend” was a computer programmer and through his work I became interested in computers. I found a job as a vocational counselor that enabled me to assess the skills and abilities of my clients through testing and the use of the computer and from there I went on to work for Royal Business Machines, allowing me to further use and add to my computer skills. Sadly, I was a dismal failure at business machine sales. I was GREAT at demonstrating and teaching the uses of the product, but my counseling background failed me when it came to closing the sale. I had picked up a waitress/bartending job for a lark at a small par three golf course restaurant/bar called the Twilight Lounge. When I decided that selling business machines was not for me (and please let me tell you that I left that job in a most dramatic way) I began tending bar and waitressing full time at The Twilight.


I had always loved music, theater, and singing (though my parents never really encouraged that as a vocation) and that went to the top of the Interest column. Coincidently, my cousin had started a children’s theater company in Denver, and I auditioned for her. She hired me (she had to, really) as a singing, dancing duck in a Mother Goose production.

I went on to be involved in many other productions through the years, including one that would give me my first singing solo as Little Bo Peep, playing guitar and singing parody lyrics which we had written for the song “Inch Worm.” It was a stunning moment in the show, if I do say so myself. It was during this show that I was given the best piece of performance advice that I have ever received. My cousin the director said to me, “Phyllis, if you don’t get that folk-singer look off your face, you’re out of the show!” So, I started to smile and happily began to sing. Performing was now in my Interests column.


My “toolbox” was filling up and it seemed that all of my skills and interests were working together for me. It was at the Twilight Lounge that I really started singing. My boss loved music and hosted jazz jam sessions every Monday night- all of the best musicians in Denver would turn up. They heard me singing along from behind the bar and invited me to sit in with the band. My own personality and ability to “read the room” from my counseling years were great assets to me when singing in that small room. The guys in the band taught me so much: how to use the mic, how to communicate with the band, and how to read the audience. Before I knew it, I was a singer embarking on this next new chapter.


I was fortunate enough to meet several great pianists in Denver and around Colorado. I worked regularly in the Denver clubs, primarily gay clubs, with my pianist and musical partner. We had created a “cabaret scene” in the city. We had a regular gig at The Brown Palace Hotel and another restaurant owner built a cabaret room for us where we performed every week. We met the legendary Barbara Cook and Wally Harper and I can proudly say that they invited us to perform with them while they were doing a concert in Denver. I sang a duet with Barbara Cook. It was an incredible experience. I also sang a request from actor Gene Hackman and opened the show for Grammy nominated entertainer Michael Feinstein – more wonderful experiences. It all seemed to be going very well until my pianist decided that he wanted to move to New York City to conduct and be a part of the musical theater scene. This left me, once again, with a decision to make. Stay or go?


The decision was tortuous. I spent a year laboring over it. I began making the lists again – pros and cons of staying or going. I went to group therapy to help with the decision and finally, after hammering this topic to death, one woman said, “Nobody really moves to New York. When you get there you are at the doorway to the world.” And that was the phrase that got me out of Denver and onto my next phase of reinvention.


I opened my “toolbox” again, began counseling at Rusk Institute during the day and singing in the piano bars at night. It was a grueling schedule. The thing that had become most apparent was that singing made me happy. It filled a void in my heart that had been waiting to be filled. I could not give it up. After a year I realized that I had not moved from Denver to be a counselor. So, I quit my day job (again, not without drama) and became a full-time piano bar singer/waitress/bartender.

It was at Don’t Tell Mama on W. 46th Street in New York that I met Jody and Nikos, the owners of The Piano Bar in Mykonos Greece and the door to the world opened. In 1993 they found themselves in need of a girl singer. My friend David Dyer from Aspen had been playing there and with David’s recommendation, they asked me if I would like to come to Greece for one month. Why not? So, I packed my bags and off I went. It was a life-changing decision.


After years of having several jobs at one time, I found myself with only 1 job: to be “the singer.” I had found my passion. One month became 2 months and then 4 months. And that continued for 27 years.

I had also been fortunate enough to get a great job at a small law firm that allowed me to use my computer skills, gave me financial stability, and afforded me the flexibility to go to Greece every summer. All of my skills, interests, and abilities came together and as an added bonus I met a young intern who would become a lifelong friend and now the co-founder of the OAK Street Initiative, Dr. Kevin Baumlin.

I worked at that law firm and sang in Mykonos every summer for over 25 years. After years of doing both of these jobs, it was time to retire from the firm. Though the decision to retire came easily, I struggled with the reality of being retired. I went through the stages of grief at the loss of both of these jobs. I felt that my identity had been so wrapped up in both of them that I wasn’t sure who I was any more.


The most interesting part is, that with age, came a fearlessness. I have dared to try things I would never have tried in my youth for fear of failure. As an example, I began writing songs. I needed a song to celebrate my 20th anniversary in Mykonos and I wrote one, and then I wrote 6 more.

I began singing with a standard jazz band in Brooklyn and doing a lot of computer work, resumes, website design, and more.


And now, my greatest reinvention of all: with the help of an amazing mentor, at age 70 I have become a working actress!


This new phase has brought commercial and voice-over work and look for me in The Many Saints of Newark, the feature film based on The Sopranos.


Everyone has a story to tell and skills to mine, shaping retirement into whatever we choose it to be. Each twist and bump in the road led me to another situation, presented another door, and mentors to help guide me along a new path. I merely opened the doors. There were risks, there were tears and stumbles, but I was able to find the joy that made all of that worthwhile. I found a world full of travel, adventures and wonderful friends who have become my family. If you’re wondering what’s next, I encourage you to build your own vocational toolbox to help you find your next open door. Sort through all of the skills, interests, and experiences that you have acquired that make you the unique individual you are. Write a new chapter. It could be the most satisfying chapter of all.




A world-class cabaret singer and life-long advocate of non-profit organizations, Phyllis Pastore is Secretary of the Board for OAK Street Initiative. She resides in New York City.


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