Finding the Silver Lining at Every Age: The Extraordinary Wisdom of 94-Year-Old Trailblazer Gwen Borden

Some conversations stay with you long after the microphones turn off, and this week’s interview on my *Living Ageless & Bold* podcast is one of them. At 94 years old, Gwen Borden has lived through nearly a century of world events, personal challenges, reinvention, loss, and extraordinary resilience. She and her daughter, leadership strategist and entrepreneur Amy Goober, recently co-authored *My Mother Always Says: 25 Lessons for Finding the Silver Lining*, a book that blends memoir with life lessons Gwen has passed down through four generations.

Gwen’s story is as rich as it is inspiring. She lived through the Great Depression, World War II, her sister’s polio during the height of the epidemic, the sudden loss of her first husband at age 49, and a completely unexpected second chapter that included directing one of the first bereavement centers in the United States. And through it all, she has maintained a deep belief that joy always returns, that resilience is within reach, and that life continues to offer something good—even after heartbreak.

Below, I’m sharing the highlights and lessons from our conversation, all taken directly from the transcript of our interview.

Growing Up in “Interesting Times”

When Gwen reflects on her life, the first thing she talks about is the era she was born into. “I think I was born in interesting times,” she told me. She arrived in 1931—at the height of the Great Depression—while her mother was in the hospital giving birth. At the same time, her four-year-old sister was at home battling polio during the major epidemic in New York.

Gwen’s mother returned from the hospital to a dangerously ill child and made a life-changing decision. Instead of allowing doctors to put her daughter in braces, which often left children crippled, she read about Sister Kenny’s alternative treatment, which wasn’t yet widely adopted by doctors in New York. Her mother filled the bathtub, organized a round-the-clock “water brigade” of family members, and moved her daughter’s legs in warm water for hours at a time. She recovered fully—walking, dancing, and living without any fallout from the disease.

Because of this crisis at home, newborn Gwen was handed to teenage cousins who cared for her as her mother focused on saving her sister’s life. She describes herself as a happy, resilient baby surrounded by love, which set the tone for her outlook on life.

Gwen’s early years also included living through World War II, and she later witnessed the events of 9/11 firsthand while working on Long Island. She sees each chapter not as hardship, but as privilege—“a privilege to be present and participating in the most exciting historical times in this country.”

A Devastating Loss and an Unexpected Pivot

Gwen married her first husband, a vibrant and successful businessman, in 1956. Their life together was filled with happiness, but everything changed in 1975 when he died at age 49 from a brain tumor. It happened in just 10 weeks. Although the tumor wasn’t malignant, it destroyed the frontal lobes of his brain—and Gwen and her children were left reeling.

Her daughter Amy was just 15. In the interview, Amy shared that she was always an “old soul,” even bringing a handkerchief to the appointment where the doctor delivered the devastating news. In a touching moment, Amy ended up handing that handkerchief to the doctor himself as he cried while explaining the situation.

Gwen describes this time as traumatic, but she also talks about what happened next. After returning to teaching, she realized the classroom no longer fulfilled her the way it once had. So she made another major life transition: she enrolled in graduate school to become a social worker.

While in school, she wrote a paper imagining a bereavement center—a concept that hardly existed in 1979. Her professor encouraged her to show it to the director at the Family Service office where she interned. They loved the idea, and before she knew it, Gwen was directing one of the first bereavement programs in the country.

She supported parents who had lost children, widows and widowers, and siblings grieving the deaths of brothers and sisters. She learned on the job because the people she served taught her everything she needed to know. Her clients became her greatest teachers.

This transition became one of the most meaningful chapters of her life.

Reinvention After Loss—Again

In 1980, Gwen married again. This second marriage lasted nearly 50 years. Her husband passed away just a month before our interview, at age 98—exactly twice the age of her first husband at the time of his death.

Now, at 94, she is learning to live alone again, something she hasn’t had to do since her 40s. But in true Gwen fashion, she sees this new season not with fear, but with curiosity. She told me, “I really believe since I am so programmed to enjoy myself, something good’s always going to happen.”

A 21-Year-Old Trailblazer Traveling Europe Alone

One of Gwen’s most cherished memories—and one that became a key lesson in the book—is when she traveled to Europe alone at 21. This was decades before young women traveling solo was common or encouraged.

She had just broken off an engagement because she had “bad vibes,” and suddenly the money saved for a wedding became the money she used for a 10-week trip abroad. She met a friend in Paris, and together they traveled through France, Italy, Spain, Copenhagen, and England. She described it as the most valuable educational experience of her life.

This adventure became the inspiration for one of the book’s core lessons: **Spread your wings and learn to fly.**

Gwen returned more confident, more mature, and more certain of who she was—an inner strength she would lean on throughout her life.

Lessons Passed Down Through Generations

When I asked Gwen about her favorite lesson in the book, she hesitated—not because there weren’t many, but because she had never thought of her life as producing lessons. Yet her stories do just that.

Amy also shared her favorite lesson: **You can’t put your head on someone else’s shoulders.**

This is such a powerful reminder that we can’t force people to see the world the way we do. Whether it’s adult children, friends, or colleagues, their experiences shape their choices, just as ours shape ours.

Gwen also shared a central belief that runs throughout her life: **There are no bad experiences—only the ones you don’t learn from.**

She is clear, however, that you don’t find the silver lining while you’re in the middle of pain. You reflect on it later. You survive, you grow, and only then do you look back and understand what life was teaching you.

A Family of Strong Women

Listening to Gwen and Amy together, it becomes obvious that their family is rich with strong women across generations. Gwen’s mother stood up to the medical system to save her daughter from a life in braces after polio. Gwen reinvented herself after loss and pushed forward with courage time and time again. Amy built a successful bakery at age 26 with no business experience and now runs two companies—one creating women’s events and another leading women’s travel groups.

Amy also has two daughters of her own, and both show the same strength and independence. Their family is a testament to how one woman’s resilience can ripple outward for decades.

Staying Curious and Connected at 94

One of my favorite moments from the interview was when Amy shared how her 24-year-old daughter’s friend often visits Gwen. This young woman told Gwen, “I wait all week to talk to you.” She finds comfort, joy, and wisdom in Gwen’s presence, and the feeling is mutual.

Gwen shared another beautiful insight: older people are often told to focus on their aches and pains—what she calls the “organ recital.” But she believes the secret to thriving at any age is to invest in the next generation. Engaging with young people brings purpose, joy, and connection instead of isolation.

What’s Next for Gwen and Amy

Even at 94, Gwen is looking forward. She’s about to become a great-grandmother for the first time, adding yet another generation to her family’s remarkable line of strong, determined women. Amy continues to run her women’s events and travel company, as well as promote their book through speaking engagements and appearances.

In fact, Amy says that at her events, no matter how many speakers are on the agenda, women always want to hear more from Gwen. Her authenticity and wisdom resonate with everyone in the room.

A Legacy of Optimism and Silver Linings

What touched me most during this interview was Gwen’s unwavering optimism. She has lived through some of life’s most challenging experiences, but she continues to believe that something good is always approaching.

At 94, she is not slowing down emotionally, intellectually, or spiritually. She is still curious. Still engaged. Still generous with her stories. Still teaching all of us how to live with grace, gratitude, and resilience.

Her message is simple but profound: **Life will break you open, but it will also rebuild you—and often into someone wiser, stronger, and more joyful.**

It’s a reminder for all of us, especially those of us in midlife and beyond, that there is always something left to learn, to do, to teach, and to love.

Watch the full episode here: