Elaine Benfield

Finding Her Voice Through Reinvention

I met Elaine Benfield through an introduction from Meg Bear, and from our first conversation I knew I had found a kindred spirit. Like so many of the people I've interviewed, Elaine is driven by curiosity and a desire to make a meaningful contribution. What particularly resonated with me was her commitment to telling Herstories—celebrating the journeys of inspiring women leaders whose voices are too often overlooked.

What I didn't expect was the extraordinary series of life events that would become the catalyst for her own redirection. Within a remarkably short period, Elaine's child came out as transgender, her husband of more than twenty years came out as gay, she lost her job, and she broke her ankle. Any one of those experiences would have been life-changing. Together, they forced her to reexamine everything.

Instead of defining herself by what she had lost, Elaine began building something new. Through entrepreneurship, consulting, writing, and storytelling, she rediscovered not only her voice but a life that reflected who she had become. Her story is a powerful reminder that our most difficult chapters sometimes create space for our most authentic ones.

Elaine Benfield turned 50 expecting it to be her best year. Instead, her life unraveled.

Within months, her child came out as trans, her husband of nearly 20 years revealed he was gay, and she faced the collapse of the future she thought she’d built. “It was like everything I believed about my life just fell apart,” she recalls.

But from the ashes of that upheaval, Elaine began a journey of rediscovery. It was one that led her to entrepreneurship, self-reliance, and a voice she hadn’t realized she’d lost.

Catalyst for Change

Throughout her 20-plus-year tech career, Elaine excelled by keeping personal struggles separate from work. Even as her marriage dissolved and she processed her child’s transition, she showed up every day in her corporate role. Work was her steady place. But a cascade of events forced her to pause. In 2023, she fractured her ankle and spent ten weeks bedridden, confronting feelings she’d long suppressed. “That was the first time in my life I had to sit still,” she says. “It gave me clarity I’d never had.”

As she recovered from surgery, her employer of 16 years eliminated her role. After an initial wave of disbelief, she saw it differently. “It was the universe telling me: this was not the path I was supposed to be on.” She let herself question what she truly wanted and whether she was willing to bet on herself.

Her Transformation Process

Elaine began with small but powerful steps: claiming her voice through a podcast she’d dreamed about for years. Herstories became a platform for amplifying women’s experiences—divorce, loss, reinvention. In telling their stories, she reclaimed her own. “I realized I was always the wife, the mother, the employee first,” she reflects. “This was about finally being me.”

With encouragement from a mentor, she launched The Benfield Connection, an advisory business helping small and mid-sized tech companies align their brand, communications, and growth strategies. Where others see silos, Elaine sees opportunities to weave cohesive narratives that move companies forward. At the same time, she cultivates Herstories into a professional extension—interviewing women leaders, building a following, and exploring sponsorships.

This dual path of consulting and storytelling gives her both purpose and financial footing. Still, she admits the risk is real. “I’m always nervous about money,” she says. “But I’ve spent my whole life betting on others. It’s time to bet on myself.”

Current State and Reflections

Today, Elaine is balancing both sides of her professional identity. The Benfield Connection helps tech founders grow their businesses, while Herstories fuels her passion for elevating women’s and men’s voices. Her goal is clear: over time, to shift her energy more fully into storytelling and thought leadership.

She’s also learned to embrace what once terrified her—being alone. “I used to be devastated thinking I’d have no one to travel with,” she says. “Now, I’ve done trips by myself and with friends. I’m back to hiking, back to the version of me that I lost somewhere along the way.”

Meditation and daily reflection have become practices that sustain her. “Everyone has their own way of finding stillness,” she says. “For me, it’s sitting in my sunroom with a cup of coffee, just breathing.”

Above all, Elaine has discovered that reinvention doesn’t come from running faster. It comes from sitting still long enough to hear what your heart wants next.

Advice to Others

Elaine offers this guidance for those contemplating entrepreneurship especially after major life change:

Find Your Circle: Surround yourself with people who challenge and support you. “I have a handful of advisors who act as my mirror, reminding me who I am when I forget.”
Know Your Finances: Budget carefully, track your expenses, and set clear thresholds. “Know when the risk is too much—and when it’s worth it.”
Plan and Dream: “If you’re a visionary, have a plan. If you’re a planner, make sure you have a vision,” she says. “Write it all down. You never know when that small idea in a notebook will become your next big thing.”
Don’t Be Afraid: Fear doesn’t have to be a stop sign. “Every time I’ve questioned whether I could do something, I came out stronger.”

In a world quick to discard experience, Elaine Benfield proves that reinvention isn’t just possible. It’s often the most powerful chapter yet.