Author Tom Ingrassia: Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life

An Interview With Jake Frankel

Authority Magazine Editorial Staff
Authority Magazine
15 min readFeb 8, 2024


Don’t listen to the naysayers. So many people told me that I was crazy to give up my university job. Even my mother asked, “Can you really make money doing THAT?” And it did put doubts in my mind.

Many successful people reinvented themselves in a later period in their lives. Jeff Bezos worked on Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Kroc was a milkshake-device salesman before starting the McDonalds franchise in his 50s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Tom Ingrassia.

Tom Ingrassia is an award winning author, motivational speaker, radio personality and, now, documentary film producer. His 2013 book, One Door Closes: Overcoming Adversity By Following Your Dreams was recently adapted as the documentary film, One Door Closes: Korey’s Courage, which is currently on the film festival circuit. In 2014, he achieved yet another childhood dream, whe he started hosting The Motown Jukebox with “Motown Tom,” on WCUW 91.3FM in Worcester, MA.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

Thank you for this opportunity. I love sharing my story of Reinvention. In fact, I firmly believe it is vitally important that we share our personal stories of struggles, tragedy, triumphs. You never know when your story will touch another person and help them to change their life.

I grew up in a small town in upstate New York in the 1960s. I was a typical “white bread boy,” and totally caught up n the Beatlemania craze then sweeping the country. Then, in the summer oif 1964, I was lying on the beach in Sea Bright, NJ, when I heard the most exquisite sound coming out of my ever-present transistor radio. It was The Supremes’ “Where Did Our Love Go.” I was in love — head-over-heels in love, and my life changed forever. The Beatles were out…The Supremes and Motown were in! And then it happened. December 27, 1964. I was watching The Ed Sullivan Show — as we all did on Sunday nights in the ‘60s — and there they were. Right in my living room. These 3 goddesses whom I idolized. And they were singing just to me!! I remember as if it was yesterday — turning to my mother and sayingf, “I’m gonna meet them someday!” Yeah, right kid. I was 11 years old. What did I know about meeting celebrities? But the seed was planted. I knew I wanted to be a part of the show business glamour and glitter. But how? I didn’t know anyone in show business. The school music teachers told me I didn’t have any talent. So I followed a “traditional” career path. I went to college and graduate school. Got married at age 22. Pursued a career in higher education. Safe. However….

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I have 2 quotes that I live by every day — and they are related. One comes from a Native American proverb — “Learn from the turtle. It only makes progress when it sticks its neck out.” The other comes from Mary Wilson, of The Supremes, who toild me many times, “Have the courage to follow your heart. Dreams DO come true!”

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much?

Even though, initially, I followed a “traditional” lifestyle, I have never seen myself as “traditional.” I have always –always — done things my own way. I now my own mind and what I want. For example, my mom always reminded me that, on my first day of kindergarten, she layed out my clothes for me. I said, “I don’t want to wear that,” and went to my closet and picked out my own clothes. Second — and perhaps most important — I AM a risk taker. Just like the turtle, I stick my neck out in order to move closer to my goals…no matter the obstancle. Everything I have achieved in the past 25 years has involved risk…and it has all paid off in ways I never imagined. People thought I was crazy when I left my university job to go to work for Mary Wilson, when I was 48 years old. Third, I am patient. I understand that I can’t rush things. For example, I needed the 25 years I spent working in higher education to develop the skills that I now use every day in my Second Chapter. If these opportunities had happened earlier, I would not have been ready.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

I always knew that I wanted to be connected to show business — ever since I was 11 years old in 1964. Music was all I ever wanted. However, when the school choral director and band director told me that I “wasn’t good enough,” I thought that dream was gone. It seemed like a pipe dream — better yet, an imp[ossible dream. So, yes, I followed a traditional career path. I earned my undergraduate and graduate degrees in History (State University of NY at Geneseo, and the University of Connecticut), and in 1976, I started working in higher education. Looking back, I now realize that I always worked in the role of helping others achieve their goals and live into their dreams — academic advisor, student services, career development. And I was good at what I did. I loved it. It was fulfilling. I rose through the ranks, ultimately achieving the position of Assistant Dean at the Graduate School of Management at Clark University, in Worcester, MA. I developed excellent organizational, communication, research and management skills. But, still…that “other” life was calling my name….

And how did you “reinvent yourself” in your Second Chapter?

I think I actually started reinventing myself before I even started my First Chapter! Remember my saying that I told my mom that I was going to meet The Supremes in 1964? Well…8 short years later, when I was a 19 year old college student, I met Mary Wilson, when she agreed to be interviewed for a project I was working on. And believe it or not, we formed a wonderful, warm friendship that lasted almost 50 years (until her death in 2021). Mary Wilson had this amazing ability to see things in people — especially young people — that we didn’t see in ourselves. As she did with so many other young people, she took me under her wing. She nurtured me. She became my mentor and my inspiration. And, recognizing my academic skills, over the years she asked for my assistance on projects she was working on. I assisted in writing the script for her lecture programs — and then she asked me to help her book lecture dates at colleges. I helped with research for both of her books. I sometimes traveled with her and helped out at concerts. I actually did some TV interviews with her. I started writing magazine articles about The Supremes and Motown. So, while maintaining my full time, “safe,” “traditional” job in higher education, I felt that I had achieved my dream of working in show business. I was fulfilled. I thought that was the best I could hope for. Little did I know….

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

My life truly changed forever in early 2001, when Mary Wilson asked me to help her launch a merchandising business — Supreme Legacy. She said, “I have the creative ideas. You have the business experience. Will you work with me as the Creative Director of Supreme Legacy?” This was my dream come true. However, I didn’t give up my university job…just yet. I was still too afraid to give up that security. So I managed the business on the side — taking Mary Wilson’s ideas and designing products around them, promoting them, marketing them. Working with vendors and suppliers. Sometimes even hawking the products at her concerts. I LOVED it!! Then…in September of 2001, Mary Wilson asked me to also serve as her Executive Assistant. She was preparing for a 6 month, cross-country tour in the stage show, “Sophisticated Ladies.” 6 months in Europe was to follow. She wanted someone on the road with her full time, to handle business, the merchandise, etc. I knew that if I didn’t jump, I would never have this opportunity again. And…can you believe this?! — the next day, I marched into my office at Clark University and told the dean (remember, I was the assistant dean of the business school!), “I’m leaving. I can’t even give you 2 weeks notice. I am leaving today.” That was September 10, 2001. The tour was scheduled to begin on September 16. Well, we all know what happened on September 11, 2001, and the chaos into which the entire world was plunged. Cast members couldn’t fly in for rehearsals. Theatres were cancelling engagements. The world, the tour…and my life were in shambles. But, you know, it all worked out eventually. The tour finally launched in early 2002. I spent the next 4 years working for Mary Wilson. Traveling with her. Meeting people. Before I knew it, I was also working for people like Arlene Smith of The Chantels, Barbara Alston of The Crystals, June Monteiro of The Toys, The Velvelettes, Sarah Dash of LaBelle, Carl Gardner of The Coasters, actress Dee Wallace. The very people I had grown up listening to and idolizing. And I have never looked back.

Mary Wilson opened so many doors. She taught me to believe in myself — to believe that I CAN do it. She once told me, “I know there are great things in your future. Go for it. Don’t let anyone stop you.” With her support and encouragemt, I launched my own business as a motivational speaker — telling the incredible story of how I made my dreams come true…against all odds. I travel the country with the lecture program, “Motown and The Civil Rights Movement.” I have written 2 award winning books — “Reflections Of A Love Supreme: Motown Through The Eyes Of Fans,” and One Door Closes: Overcoming Adversity By Following Your Dreams” (co-written with Jared Chrudimsky). Me…that little boy with little boy dreams. Doing the work I was born to do!

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

As I said earlier, I wanted to be in show business. But I didn’t really have performing talent…and, as a child, I was painfully shy. However, when Mary Wilson offered me that job — and then when other celebrities started saying, “I like what you have done with Mary, would you work with me, too?” I realized that I had management skills — and entertainers need people to manage various aspects of their careers. THAT was my way into the show business world that I had strived for since childhood. Yeah, I am NOT a singer — but I can promote your products and sell your merchandise! And I can use my story of reinvention to motivate others to follow in my footsteps.

How are things going with this new initiative? We would love to hear some specific examples or stories.

Oh, my goodness! Where to begin. My book, One Door Closes, has just been adapted as a documentary film — “One Door Closes: Korey’s Courage.” The film premiered at The Hanover Theatre, in Worcester, MA, last October. In 2024, the film will be on the film festival circuit — with an eye to having either PBS or a streaming service pick it up. I served as Executive Producer on the film. The fil features Scherrie payne, Formerly of The Supremes, and June Monteiro of The Toys, sharing their stories of overcoming adversity in their lives and careers. Mary Wilson was going to do the narration for the film. Sadly, we had to shut down production during the Covid 19 pandemic, and Mary Wilson died — unexpectedly — in early 2021, before we had production back up and running, and before we could film her scenes. The documentary is dedicated to her memory and inspiration. I will be 71 years old this yuear — and I am busier — and more fulfilled — now than ever before. I am doing all the things I love.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Obviously, THE person was Mary Wilson. I have shared the story of how she guided and mentored me. I also am VERY grateful to my wife of 49 years, Barbara. When Mary Wilson offered me that job, Barbara knew it was my dream come true — AND that it was a risk. It woulld require a great sacriface on her part. However, without hesitation, she said, “I know this is what you want. Go for it. I’ll do whatever I need to support you.”

Can you share the most interesting story that happened to you since you started in this new direction?

This is a good example of one open door leading to another open door. In late 2013 — right after One Door Closes: Overcoming Adversity By Following Your Dreams was published,” I was at radio station WCUW 91.3FM, in Worcester, MA, doing an interview to promote the book. When the interview was over, the station’s Executive Director, Troy Tyree, pulled me aside and asked, “Tom, are you interested in doing a radio show at ‘CUW?” “I’ve only wanted my own radio show since I was 11 years old. When do I start?” And 3 weeks later, I was in the studio, at the sound board, hosting The Motown Jukebox with “Motown Tom.” It is a live, 4-hour show — part music, part education. I share the stories behind the music. I am now in my 11th year. Have won 2 Best Radio Personality awards. Who knew? So, I also have to give props to Troy Tyree for giving me the opportunity to fulfill yet another childhood dream. Remember I said that I am patient? It took me 50 years to land that radio show!

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

When Mary Wilson offered the job to me, I KNEW that was what I had wanted since I was a child. But…could I really do it? What did I know? Those voices — the elementary school choral director and band director — echoed in my head, “You’re not good enough.” What if people laughed at me? What if I failed? But I knew I had to go for it — and that Mary Wilson would not have offered that precious opportunity to me if she didn’t believe in me. And that helped me believe in myself. Then, in 2013, when I was offered the radio show, I said to myself, “How are you going to fill 4 hours of live radio? You’ll screw up the controls.” Again, it was Mary Wilson who told me, “You’re gonna be great at this, Tom.” This is what you’ve wanted since you were a kid. Do it!”

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I truly had to trust my own instrinct. I didn’t know anyone who had done anything like this. However, I looked to my friends for support and encouragement. I joined networking groups. I continued to rely on my contacts in higher education for support and encouragement. Bottom line, though — I had to do this my way and in my own time.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

Working in highed education was “safe.” For me, it was natural. It was what I had gown up around all my life. And I had a VERY good, secure salary, with amazing benefits. When I went to work for Mary Wilson, I gave up all that security. While I had the “safety net” of my wife’s job to provide a steady income, I really risked everything to live into my dreams. At one point, I had just $300 left in my bank account. THAT was uncomfortable. I gritted my teeth and pushed through the fear. Now, I am VERY comfortable!

There is one other aspect of my Reinvention — dare I say, Transformation — that I would like to share with your readers. Growing up, I was that kid who no one wanted on their team in gym class. I was bad at every sport — more of a book work. And I was bullied because I didn’t do what the other guys did. In adulthood, I stayed actgive and took care of myself — but I never did anything athletic. Well…in 2010, I was in a deep depression. My dad had died in November, 2009 — followed just 4 months later by my mom. In betweek their deaths, my mother-in-law died. 3 parents lost in 4 months. I was physically and emotionally exhausted, sinking deeper into darkness. I knew I had to do something. My best friend, Jared Chrudimsky (who co-wrote One Door Closes with me, and served as Associate Producer on the documentary), convinced me to start running. I was 57 years old, and had never run even ¼ mile in my life! But he coached me, and was VERY patient. 4 months after taking my first tentative — and pathetic — run with Jared, I entered my first 5K race…and finished in just over 24 minutes. In less than a year, I ran my first half marathon — finishing in just under 2 hours. I ran my first Boston Marathon in 2013 — the year of the Marathon Bombings — at age 60. I ran Boston again in 2014. I have run ultra-marathons — running in 24-hour races…and completing over 80 miles. It was all a matter of mind over body. I pushed myself. I set goals. I told myself I COULD do it. And I did it. This was WAY beyond my comfort zone. And running the Boston Marathon twice remains one of my most satisfying accomplishments.

What are your “5 things I wish someone told me before I started” and why?

  1. Don’t listen to the naysayers. So many people told me that I was crazy to give up my university job. Even my mother asked, “Can you really make money doing THAT?” And it did put doubts in my mind.
  2. Related to the above — never let anyone tell you that your dreams are silly or unimportant.
  3. You will reach your goals…just give it the time it needs. At the beginning, I wanted everything all at once. It doesn’t happen that way. Step by step….
  4. Be grateful for ever opportunity and experience — even the negative ones. When I started out in this Second Chapter, I never imagined that I would be writing books and producing movies. Keep your mind — and your options — open.
  5. You may have to sacriface some personal relationships along the way. That is perhaps the saddest part of my journey. There have been those who are jealous of what I have achieved, who tried to undermine what I was doing. I have had to let go of those relationships.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Simply this — live into your dreams with vision, courage, determination and passion. Everyone deserves to be happy and to live their best life. We all need the encouragement…and that open door. Imagine what the world could be if we ALL are living our dream lives!

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. :-)

Well…obviously, with the One Door Closes documentary, I would LOVE to have breakfast with the head of Netflix or Amazon. Or (maybe first and foremost) the head of programming for PBS!

How can our readers further follow your work online?

My website is I have a Facebook page for the documentary: And I am on LinkedIn.

Thank you so much for sharing these important insights. We wish you continued success and good health!