Is It Too Late to Start Over at 50? Short answer? Nope. Not even close.
I just wrapped up recording the latest Diana Prince Lives Next Door episode for our Angela Atelier blog, and wow, do I feel fired up. The question circling in my head—is it too late to start over at 50?—got torched right to the ground by our guest, Tina Yao. If anyone’s proof you can build a business you love and a legacy worth bragging about at any age, it’s Tina.
Let me set the scene. Tina Yao is a retail and e-commerce executive who did the unthinkable—ditched her 25-year corporate career (after stints at places like Armani Exchange and Uniqlo, by the way), and launched her own women’s travel bag brand, Tyvy. At fifty. With two kids. A Manhattan zip code. And a no-nonsense love for running, travel, and the occasional killer cocktail.
So, yeah—if you’re breathing, you’re not stuck.
Why Do We Wait So Long?
I was dying to know what pushed Tina out of corporate security and into the wild world of entrepreneurship—and the answer was honestly so real, I wanted to high-five my headphones.
Burnout. But not the headline-grabbing kind, the slow-leak variety. The relentless, post-pandemic pressure snuck up and body-slammed her—losing her voice, getting sick for two winters, realizing the pace had become unsustainable. “I didn’t really feel it until after,” she told me. Sound familiar?
But here’s the kicker: she’d always wanted a second act. She just needed the right nudge (ahem, burnout wave crashing down) and the right idea. For Tina, it came from lugging her life around Manhattan in a not-quite-right bag and thinking, “You know what, I’m just going to create the solution.” More punch, less pouch.
H2: Is It Too Late to Start Over at 50? Here’s What No One Tells You
It’s so easy to think, “I can’t possibly start from scratch now. Not at my age.” I sure did. Tina did, too. But here’s what really landed during the episode—if you can lean into your expertise, do your homework, manage your risk, and tap your support system (and by God, network, ladies!), you can do that crazy thing. Whatever “that” is.
Tina didn’t have every detail locked down. She just started. She bet on what she KNEW—her product chops, her retail network—and found a new community along the way. Did she get it all right? Not even close: the process of finding a factory to manufacture her dream bag almost broke her. The first few samples? “Horrible,” in her own words. She had to become a nerd about recycled nylon fabrics and international manufacturing just to get Tyvy off the ground.
But she kept at it. Because the idea wouldn’t let her go.
Confidence Looks Different at 50
Here’s the gem I pocketed from our chat: confidence isn’t loud. It’s not about charging the boardroom or snagging another corporate win. Sometimes, it’s quietly betting on yourself—again, maybe for the first time since your twenties.
Tina’s bags are more than organized, gorgeous accessories. They’re a physical reminder that you can design a life that fits you. You—itty bitty hidden keys pocket, brain fog, Bluetooth chaos, needs-five-lipsticks you. You at 27, 47, or 67.
What I’m Taking Forward
- Your next move doesn’t need a roadmap—just movement.
- Perfection is a trap. Make the Ziploc-bag-mistake first if you need to, then fix it.
- Find your people, ask questions early, and let go of needing “the right time.”
- Life isn’t linear. Careers, especially not. Try surprising yourself.
Before I sign off, here’s the book that changed everything for Tina
Book: Bringing Up Bébé by Pamela Druckerman
Yep, it’s technically a parenting book, but it’s the “let them explore, don’t over-control, unlock your own adventure” approach that stuck with Tina for life. Sometimes permission to experiment, to NOT be perfect, is what unlocks your next big leap.
Want to hear Tina’s full story (and score early dibs on a Tyvy bag before I snatch them all up myself)?
Listen to the full episode here!
Stay bold. Stay curious. And remember—it’s never too late to claim your wonder.
— Angela
This post is part of The Gal Project—amplifying women’s voices, one real story at a time.
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