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Badass Women in History with Kerry Chaput · Jul 29, 2026

The Doors That Won't Open

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Kerry Chaput · Badass Women in History with Kerry Chaput

Studying women’s history isn’t just about the incredible stories—the big hits that make sensational headlines and hook algorithms—it’s about the small moments. The very human side of a woman’s life that makes someone in modern times feel seen.

This week, one of those small moments hooked me. It paralleled my life. A woman from history gave me perspective on something every author must learn to embrace: the necessity of the pivot.

I could go on for days about Virginia Hall.

Her bravery as a WWII spy is the stuff of legends. She organized entire spy networks of thousands of people, rescued downed airmen, organized supply drops, gathered intel necessary for D-Day, and became one of the Gestapo’s most wanted. She hiked fifty miles over the Pyrenees Mountains in a blizzard with a wooden leg to escape Nazi capture.

To fully appreciate the beauty of Virginia’s life, you first need to understand her greatest aspiration. The goal she worked toward for decades. Young Virginia dreamed of becoming a diplomat. At the time, out of fifteen-hundred foreign service officers, six were women. And none were ambassadors. She knew she was up against a male-dominated system, but she wanted adventure. She was going to be the exception.

She applied to the State Department and bounced around various embassy jobs, but all she could get was secretarial work. Over the years, she took the Diplomatic Corps entrance exam multiple times but never passed. They denied her repeatedly, claiming this wasn’t women’s work. At twenty-seven, during a hunting expedition, she sustained a gunshot to her foot, which resulted in gangrene and an amputation. Undeterred, she rehabilitated with her cumbersome eight-pound prosthetic, determined to finally pass the diplomat exam.

She learned about an obscure State Department rule that excluded anyone with an amputation from serving as a diplomat. Her dream of twenty years went up in flames. When the war broke out, her offers to volunteer received multiple refusals. No one wanted a disabled woman.

The system she tried so hard to win over rejected her once again. Locked doors everywhere.

Virginia found her calling in the unbelievably dangerous world of espionage. A place outside the system, where they were desperate for anyone smart and brave who could handle the stress of an experimental program with little oversight.

Virginia thrived outside the system she had always fought for.

After years of daring escapes and clever disguises (once selling cheese to German officers while on their most wanted list), the end of the war brought a new challenge. The wilds of wartime vanished. The world ran on systems again. She helped establish the CIA—a time she called the saddest of her life. She was trapped in a rigid architecture that still didn’t want women. They didn’t see her for the war hero who won the Distinguished Service Cross. They saw a nag who hadn’t spent prep school with them or graduated Harvard.

The system had excluded her once again.

Studying Virginia Hall for an upcoming writing project coincided with my own moment of awakening. I’m facing letting go of the dream I’ve held for over a decade. When I began seriously writing, I dreamed of landing a literary agent. Sure, getting the big publishing contract was in there, but I wanted the agent. The one email that said, I love what you’ve done and I want to be a part of it.

Ten years ago, that was the answer to writing success, and approval from an industry insider felt like the only thing that mattered.

I’ve spent most of my forties publishing with a small press, hustling, devoting seven days a week to storytelling. I’ve won multiple awards and been a bestseller. My latest book was featured in People magazine, and my work has been shared by famous names like Rosie O’Donnell, Queen Latifah, and George Takei. I go viral on the regular, and have built a platform of hundreds of thousands of engaged followers.

Still, I wanted the agent. Misguided as it may have been, it was my only bar for success.

After my 400th rejection across six manuscripts (yes, I’m getting real with you all), I cried at midnight in a Northern Idaho hotel room, accepting my crash-out was about more than one rejection. I had hit the reality that it may be time to give up the dream I always believed I could accomplish. If I just worked hard enough, remained tenacious enough (it’s kinda my superpower), I would beat the odds. I would force the system to see me.

It began to feel like approaching the cool kids’ table day after day while they shooed me away. At some point, don’t we need to stop walking up to the table? Accept the closed doors and stop expecting whatever is on the other side to make us relevant?

Virginia Hall didn’t find her moment to shine in the conventional world. She found it outside the walls. In the dark. On her own, following her instincts.

All these years I’ve felt like a failure as dozens of requests flooded in, and the inevitable responses always followed: they never know how to sell my work. Meanwhile, I’m doing the work. Selling thousands of books, building a platform, getting messages from readers who love my stories.

I came across a substack this week from a literary agent who said: if you have a publish-ready project and a strong hook, you won’t have any trouble finding an agent.

Ouch.

In eight years, I have had several “almosts.” One said she was heartbroken to pass, but she couldn’t sell it. Another set up a call then ghosted me. Twice. And still, I never had that moment, the one that unlocked the doors I’d knocked on for years.

Maybe I’m not meant for the system.

And maybe, that’s okay.

I will write forever. I know that. But somewhere in reading about Virginia Hall and examining my own idea of success, I realized chasing something that wasn’t working felt comfortable. Letting go of approval and loving where I am? That feels far scarier. Building a life where I don’t need that unlocked door is downright terrifying.

I don’t know who I am without the chase. Reaching for a goal, fighting for my place—something about it feels like my birthright. Nothing is supposed to be easy, and isn’t acceptance settling?

No one knew about Virginia Hall. Even her closest friends were clueless about her accomplishments. It wasn’t until her records were declassified around 2008 that the archives exposed how badass she really was. Her greatest purpose was never accolades. It was in herself.

The box she wanted inside would have stifled her. She would have never found her greatness without those rejections. Her life held bravery beyond our comprehension—bravery that only existed in the face of decades of denials and heartbreak.

I will never give up on my love of storytelling, but how I get to my destination isn’t always up to me. Perhaps, I’m already living the dream, and that has to be enough. I’d like to believe the rejections have directed me to a better place, where I learn to be enough through my words my stories, and my message, regardless of what doors remain locked.

Thank you for reading. I don’t monetize my substack, so if you’d like to support me, please buy my book, or click the link below.

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Read the original on kerrychaput.substack.com

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