Die Invisible or Live Unforgettable

Its Your Call

Most women receive training on how to blend in.

We train them to be quiet, agreeable, and predictable. Ann Taylor? She did the opposite. She piloted planes when society advised women to remain grounded. At a time when most housewives were preoccupied with cooking, she excelled in skiing. She built a fashion empire from nothing, then walked away from it on her own terms. And when life knocked her down—when her husband ran off, leaving her with two kids and no money—she didn’t beg; she didn’t break. She reinvented herself.

Who was Ann Taylor?

Ann Taylor was a woman who defied conformity. Born into wealth in 1910, she could have lived a comfortable, predictable life. But that wasn’t her style. She was a nationally ranked tennis player, an alternate for the U.S. Olympic Ski Team, and one of the first female aviation instructors in the country—all at a time when women weren’t even expected to have careers. However, her life drastically changed. At the age of 18, she entered into a marriage with a Princeton man who met all her expectations, but he left her feeling bored. By the time she was 28, she found herself ensnared in a marriage devoid of love. Then, the ultimate betrayal: her husband ran off with one of her closest friends, another skier on the U.S. team. In the 1930s, divorce wasn’t just frowned upon—it was a scandal. Women didn’t just “start over.” There were no support groups, no hashtags, and no empowerment movements. Divorce meant disgrace. And worse? Her wealthy family wasn’t there to save her. Her father was an addict. Her grandfather had lost the family fortune. She was truly on her own.

Most women in her position would have folded.

Ann Taylor fought. She sold her jewelry, put herself through aviation school, and became one of only 25 female flight instructors in the country. While other women were sewing and baking, she was training military pilots during WWII. But Ann was never just one thing. After the war, she reinvented herself again. She took her passion for skiing and built a high-end skiwear brand—designing clothes so bold they landed in Vogue and Harper’s Bazaar. She talked her way into the biggest fashion magazines, made the cover, and turned her name into an empire. Ann Taylor was not just a woman but a formidable force. She dominated in a man’s world before anyone handed her permission. She moved through high society not as a guest but as royalty. She married Texas oil magnate Vernon “Moose” Taylor, and together they built a life of opulence, throwing legendary parties that brought the world’s elite to Vail. She made Vail a destination for the powerful, the stylish, and the untouchable. And let’s talk about style. Ann didn’t dress to fit in—she dressed to be remembered. She wore bright yellow Mongolian wool coats. On the slopes, she donned military headgear. In her mansion, fur capes hung like trophies. People didn’t just see Ann Taylor—they felt her.

But here’s the part nobody wants to talk about.

Regardless of her boldness, power, or exuberance, time ultimately caught up with her. The parties ended. The ski house was sold. The world moved on. Nobody tells you that truth. Even if you adhere to the rules, lead a quiet life, and exercise caution, you still risk disappearing. The difference? No one will remember your name.

So here’s the real lesson:

Be unforgettable while you can. Wear what you want. Take up space. Speak louder. Dream bigger. Live with such boldness that your name remains in the air even after your departure. This is because the world only remembers the women who refuse to be ordinary. Embracing fearlessness in the face of adversity requires more than just a catchy mantra; it demands actionable steps and resilience. It means finding the courage to advocate for yourself, even in a stifling work environment, and seeking opportunities that align with your passions. It involves making small, intentional choices each day that reflect your worth, whether that’s budgeting wisely to ease financial strain or surrounding yourself with people who uplift and inspire you. Living boldly is not about the absence of fear, but rather about moving forward despite it, reclaiming your space and your voice in a world that often tries to silence you.

Here's how to succeed despite the challenges you face:

1. Stop Waiting for Permission.

Nobody is going to hand you a megaphone and say, “Hey, it’s your turn to be outstanding now.” Had Ann Taylor waited for others to validate her decision to fly planes, teach men how to fight wars, or run a business, she would have become a footnote rather than a force.

• Do the thing you’ve been hesitating on. Start the business, pitch the idea, and end the toxic relationship. No one's coming to save you.

• Ignore the ‘Who do you think you are?’ voices. The louder they are, the more you're onto something.

2. Embrace the Pivot.

Life will present unexpected challenges to your plans. Your marriage might implode. Your career might stall. You might have to start from the beginning while everyone else appears to be thriving. Guess what? Reinvention is your superpower.

• Ask yourself: What can I build from the rubble? Ann Taylor didn’t sit in the ashes of her old life—she grabbed a shovel and built a new one.

• Don’t be afraid to look ridiculous. Beginners always look clumsy. Whether it's learning to trade stocks, lift weights, or negotiate salaries—keep going.

3. Take Up Space—Loudly and Unapologetically.

We train women to be agreeable. Women are conditioned to be likable and approachable. Avoid causing offense. Forget that.

• Speak in meetings. Speak confidently, even if your voice is shaking.

• Negotiate everything. Negotiate your salary, your time, and your boundaries. The biggest lie? That asking for more makes you greedy.

• Make people uncomfortable. That means you’re disrupting the status quo. And the status quo was never built for women like you.

4. Look Like You Belong—Even When You Feel Like an Imposter.

Ann Taylor entered rooms full of wealthy individuals, CEOs, and elite athletes, acting as if she belonged there. And guess what? That made it true.

• Walk in like you own the place. This should not come across as arrogance but rather as a sense of belonging.

• Adorn yourselves accordingly. It's not about impressing others but about commanding the presence you deserve.

• Fake confidence until it’s real. If you wait until you feel ready, you’ll die waiting.

5. Build Your Own Damn Table.

Tired of being excluded from opportunities? Stop knocking. Start creating.

• Start the business. Start the business, regardless of its size. This holds true even when it's disorganized.

• Launch the newsletter, podcast, blog, or brand. If the industry won’t recognize your talent, let the public do it instead.

• Surround yourself with rule-breakers. Energy is contagious—make sure you’re catching the right kind.

6. Play the Long Game.

Nobody tells you this: You won't win easily in this world. You will face setbacks. Rejections. Laughs. Maybe even public failures.

• Success is persistence over time. Keep showing up. Keep refining. Keep adjusting.

• Your legacy is built one day at a time. Ann Taylor wasn’t remarkable because she had one good year—she was remarkable because she kept showing up for decades.

Let’s talk about what this means for mothers.

The cycle of smallness starts young. If we don’t raise our daughters to take up space, who will? If we don’t show our sons what strong, unapologetic women look like, how can we expect them to respect us?

Raise too many girls to be "nice" instead of bold, "helpful" instead of ambitious, and "likable" instead of powerful. And too many mothers are reinforcing this without realizing it. We teach our daughters to be polite, to be accommodating, to smooth over tension—while we teach our sons that their voices matter, that their opinions count, that their anger is valid.

Enough.

Raise your daughters to be leaders, to demand excellence, and to set such high standards that the world must rise to meet them. Teach them that their voices are meant to be heard—not just in whispers, not just when asked, but always. Let them be difficult. Let them be defiant. Let them be the kind of women who refuse to fade.

Do our sons need to witness this? They need to see this too. They need to learn that women don't exist to serve them, soften their edges, or shrink them for more space. Raise sons who admire powerful women, who respect boundaries, who understand that a strong woman isn’t a threat—she’s a necessity.

The future does not require more well-behaved girls. It needs women like Ann Taylor. Ann Taylor is an example of a woman who defies conventional norms. These are women who seize their own opportunities. Women who are remembered.

What kind of legacy are you building—for yourself, for your daughters, for your sons?

Final Truth: If You Play Small, You’ll Be Forgotten.

Ann Taylor didn’t follow the rules, and people are still talking about her. Women who live fearlessly don’t get erased. Their impact lingers.

Therefore, ask yourself: Are you leading a life that ensures your legacy will endure?

If the answer is no, then it's time to revise your own rules.

What’s one bold move you’ll make today?