Early report cards called me "obedient." Teachers meant it as a compliment. I hated it. I wasn't a puppy being trained—I was a person in progress. Obedience felt like a leash.
I fit the good student mold. I followed directions, got good grades, and avoided trouble. But my mom didn't tell me to "follow the rules. "She taught me to question stupid rules and to stand up to authority when it's wrong. One of my earliest memories is of her nose-to-nose with a detective who had falsely accused my brother of stealing a gun. It turns out the officer had misplaced it.
I'm often asked what my parents did that led three of their kids to start companies so young. There's no perfect formula, but a big piece was this: they raised us to question established rules and to act anyway.
Even in elementary school, my mom made sure we knew when not to follow rules. Our school had a rule: you needed a pass and permission to go to the bathroom. I remember my mom telling me, "Ask first, sure. But if they say no and it's an emergency, go anyway." Getting "in trouble" wasn't a big deal if the alternative was wetting yourself.
In middle school, I challenged a choir teacher who marked me down for not skipping other classes to attend extra practices. I got my grade changed and called out how absurd it was that a music teacher thought she outranked math.
In high school, when the normal channels stalled on approving a press visit after we raised our Series A, I skipped the middleman and went straight to the superintendent.
We weren't disrespectful. Our parents taught us to evaluate the rules, not just follow them. And if the rule was dumb, we were taught to push back.
That mindset is the foundation of entrepreneurship. It's also a part of why so many women hesitate to use tools like AI. They're waiting for permission.
A few months ago, I was conversing about AI and schoolwork. A friend suggested that "good students" may be less likely to use tools like ChatGPT—not because they don't see the value but because they're afraid of being seen as cheaters.
The research supports his theory.
Harvard Business School research by Michael Blanding and Rembrand Koning found that women are adopting AI tools at a 25% lower rate than men—largely because they worry more about ethics and fear judgment.
"Women face greater penalties in being judged as not having expertise in different fields," Koning says. "They might be worried that someone would think even though they got the answer right, they 'cheated' by using ChatGPT."
We teach girls to be "good, " to be liked, and to follow the rules. But when the rules haven't caught up to the world, that training becomes a cage. To stay competitive, we all need to learn and experiment constantly and have the agency and empowerment to do that.
One of the most important skills in startups and life is initiative. In a recent piece for
, writes about how companies that produce 10x more changemakers give people the agency to act without waiting for permission.And yet, we often celebrate compliance as a virtue in children, especially girls.
The goal isn't to raise rebels. It's to raise people who can think, act, and know when rules serve a purpose and when they don't.
My two-year-old daughter's teacher recently told me she was "feisty." She meant it as a compliment. "She's so vocal about saying no," she told me with a smile. It's such an important milestone."
I hope she keeps that voice. " No" is one of the first tools of autonomy. And in a world that still celebrates obedience in all the wrong ways, she will need it.
Scream on, little hell cat.
Thanks for reading!
🕜 Come to my free office hours! The next one is on 4/25 at 1:30 pm ET. More info here!
🚀 Need help with performance marketing or GTM strategy? Sign up to be notified when my new marketing course for entrepreneurs and small teams is available.
🔌 Or book a power hour
📖 Grab a copy of my book! Amazon | Barnes & Noble | Signed Copy