Rae Woolpy (50 over 50 Vol. 2)

During my junior year of high school, Rae became my swim coach. After having had a less than motivational coach, Rae’s enthusiasm and energy was a breath of fresh air. Our team wanted to do well for her, swim harder for her, and make her proud. And she in turn instilled in us the desire to reach for our personal best, not just in the sport of swimming, but in life.

“I am passionate about changing lives. Coaching was teaching about life through swimming. Then I became athletic director—the first female AD at Richmond and in the North Central Conference, and one of few in the state in 1996. I loved this new role at Richmond High School (RHS) and was so proud to be moving up in leadership where I felt I could make a difference in the lives of more athletes. Discovering that women were still not respected in roles often touted in a ‘good ole boys’ world, I took the approach of showing my abilities of leadership and hard work ethic. I became a well respected athletic director. My thought was that I would be able to affect more athletes in this role. I started “R” Club for athlete leadership, kids going to games to cheer as a block, leading and professional development for all coaches in regular monthly meetings, and changing the culture where all athletes, coaches, and teams supported each other. It was first steps but then I understood there were so many students who didn’t have the need for an athletic coach but still needed an advocate. I switched from coach to athletic director to assistant principal to principal and never looked back. I love RHS, and I love my kids. And I want every teacher I hire to love our kids too,” said Rae.

“I have a quote hanging up on my office wall, ‘Every child is a story yet to be told’. What you show on the outside isn’t whats always going on in the inside. Given my own story, I try to look at everyone keeping in mind we don’t always know what’s going on behind the scenes of that person. I may meet someone who at first glance appears less desirable—maybe they’re abrasive, rough or rude. And I remind myself it’s their armor. And there are so many people walking around with their armor on. We have to be willing to look deeper.”

Little did I know during my high school days, Rae was in the midst of her own journey of discovery. And Richmond High School was beginning to reveal to Rae her purpose. 

“In my 20s I was lost and didn’t know who or what I wanted to be when I grew up. Throughout my childhood, my dad really never knew how to have a loving relationship with me. At times it was horrible—he was horrible. There were lots of lessons and times I felt broken. 

‘Who was I’ was a question I often asked myself. My time at Indiana University fighting for civil rights, women’s rights, Title IX, equal rights for ALL people, protesting in Dunn Meadow at IU to change the world was my foundation,” she said.

I have a quote hanging up on my office wall, ‘Every child is a story yet to be told’. What you show on the outside isn’t whats always going on in the inside. Given my own story, I try to look at everyone keeping in mind we don’t always know what’s going on behind the scenes of that person.
— Rae Woolpy

In her 30’s Rae found her grounding and centering through coaching, and a welcoming place at school. “It starting with coaching. This was where my fire started. I felt loved and successful. It was my safe place where I could allow myself to blossom amidst a shaky personal life” , Rae said. 


“The many awards and accolades I received helped sustain my confidence, which I always questioned in myself. The old ghosts my father had created would come out and haunt me with self-doubt, telling me I was stupid, not deserving or good enough. But fortunately I was surrounded by strong women who held me up and helped me focus on who I really was.

I had reached the lowest point of my life during my second marriage. I was married to a man who became more and more verbally and emotionally abusive. I hated going home not knowing what to expect. My savior was RHS. I would walk into the building each day and feel valued, loved and appreciated—feelings that were absent at home. A student saying, ‘Hey, Ms. Woolpy’ would make me smile and was a constant reminder that I was making a difference. RHS and the family that I helped create there helped me get through the lowest point of my life and eventually through an ugly divorce. I’m not sure everyone there knows how important that was to me!”

Fast forward from my swim team days to years later, I’ve had the good fortune to watch four Richmond High School commencements. You might be furrowing your brow at my use of the word fortune. Not a lot of people enjoy sitting through multiple graduation ceremonies. But for me, has been an opportunity to listen to Rae—now as principal and currently at the age of 75— address the graduating class with her words of wisdom. Words that mean just as much to me as an adult as to the students walking across the platform. Watching her hug each of the 300+ graduating students with equal intensity—and realizing that for some of those students that might be the most affirming encounter of their day—it occurred to me that this was the phenomenon I call “being Ms. Woolpy-ed” in action. 

Not too long ago I observed this phenomenon again. My friend, a Richmond native now living out of town, and I ran into Rae (I can call her that now that I’m an official adult). In true Rae fashion, a giant heartfelt hug was given along with a big smile, dancing eyes, and inquiring questions proving a genuine interest in my friend’s life. 

Later, over coffee, as I sat across from my friend I noticed she turned quiet. Her nose became pink and her eyes filled. She turned to me and said, “I can’t believe after all these years Ms. Woolpy remembers me.” Tears started to brim in my own eyes because I knew what my friend was experiencing. I had experienced this myself the first time I saw Ms. Woolpy after many years—to be looked at with her bright eyes, to feel genuinely remembered, to be deeply hugged by her and felt truly seen.


Maya Angelou said, “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” Rae Woolpy is the embodiment of this quote—because anyone lucky enough to feel her embrace will always know that they matter and that they can do great things.


Advice to her 20 year-old self: Love yourself, Love others, Serve others, Don’t let anyone ever define who you are, Always be kind, Equal justice for ALL—treating every human being with respect, dignity, and value, It’s ok to fail as long as you learn and grow from it, Remember it will be okay, BUY THE TICKETS__don’t wait, go for it, Let that fire inside of you get stronger and brighter, There’s always HOPE, Be the light in the darkness, Never give up, Get up, dust off, yell “F” and start again, Always be humble, Good is the enemy of being great - be great in all you do, Do what you love and love what you do.

Strong women aren’t just born that way. We are forged in the fires and strengthened in the storms. We are made of the stuff that should have broken us but never did.
— Alysia Helming
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Ginger Roberts (50 over 50 Vol. 2)