There are some conversations that stay with you long after the microphones are turned off.
My interview with entrepreneur Claudia Harvey was one of them.
I’ve known Claudia for years, and I was thrilled to finally have her on Living Ageless and Bold. I thought we’d spend most of our time talking about entrepreneurship, Dragon’s Den, and building successful businesses. We did talk about all of those things. But what surprised me was that the conversation wasn’t really about business at all.
It was about reinvention.
It was about learning that the life you carefully build may not be the life you’re ultimately meant to live.
And it was about discovering that some of our greatest opportunities arrive disguised as our greatest disappointments.
For women navigating empty nest, career changes, divorce, retirement, or simply wondering what’s next, Claudia’s story is proof that there is no expiration date on starting over.
The Best Pivots Are Rarely Planned
When I asked Claudia how she had built such an impressive career, I expected a carefully mapped-out strategy.
Instead, she smiled and admitted something that immediately resonated.
“The pivots happened because I had to adapt,” she explained. “I wanted to simplify my life and live in strength, balance, and harmony.”
Those three words—strength, balance, and harmony—have become the lens through which she now makes every major decision.
She didn’t always realize it.
In fact, she said it wasn’t until her forties that she recognized those values had quietly guided her entire life.
What struck me most was that Claudia never described her career as a straight climb upward. Every major move came because something no longer fit.
Sometimes we picture successful women as having an elaborate ten-year plan.
Claudia’s experience suggests something very different.
Success often comes from recognizing when your current life no longer matches who you’ve become.
That idea resonates with so many women I interview.
Whether someone is leaving corporate America, becoming an empty nester, or recovering from a health crisis, the women who thrive aren’t necessarily the ones with the perfect plan.
They’re the ones willing to adapt.
Reverse Engineer the Life You Want
One sentence from Claudia immediately became one of my favorite quotes from the interview.
“I reverse engineered where I wanted to be and then figured out how to get there.”
Simple.
Powerful.
Practical.
Too often we focus on the next step instead of the destination.
Claudia does the opposite.
She first imagines the life she wants and then works backward, identifying every step required to reach it.
She was also quick to point out something we don’t hear enough in today’s culture of overnight success.
Sometimes those transitions take years.
We’re constantly bombarded with stories of entrepreneurs who seem to explode onto the scene overnight.
What we don’t usually see are the years spent quietly preparing.
That message is especially encouraging for women over fifty.
Maybe you’re building something after decades in another career.
Maybe you’re finally pursuing a dream you’ve postponed while raising children.
Maybe you’re reinventing yourself after a divorce or loss.
Your timeline doesn’t have to look like anyone else’s.
Progress is still progress.
Why Motherhood Changed Everything
Claudia’s first career was impressive by anyone’s standards.
After graduating from university, she quickly landed a position on Bay Street, Canada’s equivalent of Wall Street. She immersed herself in the financial world, studying how successful people built wealth before moving into sales and climbing rapidly through the ranks. Within just a few years, she had become Vice President of Sales at Citibank Canada.
From the outside, it looked like she’d made it.
But then life happened.
She became a mother.
While traveling constantly for work, she found herself standing in a freezing Chicago winter, exhausted and pulled in every direction.
She had the title.
She had the income.
She had the beautiful home.
She had the family.
Yet she wasn’t enjoying any of it.
I think so many women know that feeling.
On paper, everything looks perfect.
Inside, you’re running on fumes.
During our conversation I mentioned another guest, ESPN’s Hannah Storm, who once told me that anyone who claims you can effortlessly balance a demanding career and raising three children isn’t telling the whole truth.
That honesty matters.
Social media often shows polished highlights.
Real life is far messier.
Sometimes success requires redefining what success actually means.
Building a Business at the Kitchen Table
After stepping away from corporate life, Claudia accepted an operations role that gave her valuable insight into how companies actually function. She learned about profitability, systems, scaling, and the behind-the-scenes mechanics that keep a business alive. But even that role eventually stopped aligning with the life she wanted. She was earning less than she had in sales while still feeling pulled in too many directions. Something had to change.
One afternoon, she looked at her husband and said the words that would change the course of her life.
“I just can’t do this.”
That simple statement became the beginning of Dig It, the gardening glove company that would grow into an internationally recognized brand.
What I love about Claudia’s story is that she doesn’t romanticize entrepreneurship. She wasn’t sitting in a trendy coffee shop sketching business ideas on a napkin. She was a mom raising three young children.
She got up at 5:30 every morning to work before the kids woke up. She squeezed in business tasks while they were at school. She worked again after they went to bed. Her office wasn’t some glamorous headquarters. It was her kitchen table.
I think so many women underestimate what can happen during those seemingly small moments. Thirty minutes before sunrise. An hour after everyone else has gone to bed. Those little pockets of time can slowly become a business, a book, a podcast, or an entirely new career.
Looking back, those years weren’t glamorous.
They were simply consistent.
A Simple Product That Solved a Real Problem
As a fellow product entrepreneur, I was fascinated by how Dig It came to life.
At first glance, it sounds almost too simple.
Gardening gloves.
But Claudia didn’t invent just another gardening glove. She identified a specific problem that women were experiencing and solved it. Her gloves included a patented fingertip design that protected manicures while still allowing women to garden comfortably. It was functional, innovative, and designed for a growing market of women who wanted to stay active without sacrificing self-care.
That’s one of the biggest lessons I took away from her entrepreneurial journey.
Successful products don’t have to be complicated.
They simply have to solve a problem.
Too often entrepreneurs chase revolutionary ideas when what customers really want are practical solutions that improve everyday life.
Dig It did exactly that.
The Pitch That Changed Everything
Because I’m a lifelong Shark Tank fan, I couldn’t resist asking Claudia about Dragon’s Den, the Canadian version that actually predated the American series. Six weeks after launching Dig It, she and her business partner stood before the Dragons to pitch their company.
What happened next changed everything.
Kevin O’Leary invested.
Even more remarkable, years later he would describe their presentation in his book Cold Hard Truth as the perfect pitch.
That doesn’t happen by accident.
Claudia told me they practiced relentlessly before stepping into the studio. Over and over again they refined every answer, anticipated every question, and prepared for every possible scenario.
Preparation creates confidence.
As she talked, I found myself laughing because her story reminded me of my own Shark Tank journey.
Years ago, I made it all the way through the producer rounds with my fashion accessories for medical walking boots before ultimately being turned down. At the time, I was devastated. I cried the entire weekend after getting the call.
Looking back now, I realize it was one of the best things that ever happened to me.
I wasn’t ready.
I didn’t understand the financial side of running a business nearly as well as I thought I did. Had I walked into the Tank back then, I probably would have become one of those memorable pitches for all the wrong reasons.
Sometimes the opportunity we desperately want isn’t actually the opportunity we need.
Sometimes rejection is simply preparation in disguise.
Success Doesn’t Mean the Story Is Over
One of the most powerful moments in our conversation came when Claudia shared something many entrepreneurs would rather hide.
After years of growth, thousands of retail locations across North America, and a successful partnership with Kevin O’Leary, Dig It filed for bankruptcy in early 2024.
Retail changed dramatically after COVID.
Costs increased.
Margins disappeared.
Consumer buying habits shifted.
Like thousands of businesses, Dig It faced circumstances completely outside its control.
Claudia didn’t sugarcoat how painful it was.
This company had been part of her life for more than a decade. She had poured herself into it.
Of course she grieved.
As she joked during our conversation, there were a few nights filled with wine, ice cream, and tears. But after that, she made a decision.
She refused to let one chapter define the rest of her story.
That mindset may be the greatest lesson of all.
So many of us believe failure is final.
Claudia sees it differently.
It’s simply another pivot.
Watch her full episode here:
https://www.youtube.com/watch?v=rPDPJkyBgCU
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