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You run a high school in Brooklyn. Be honest…what's something students think they're getting away with that you definitely already know about?
Students think they're masters of subtlety. They're not. We know when someone is "going to the bathroom" for the third time during the same period. We know when there's drama brewing before it hits social media. We know when a student is suddenly sitting in a different section of the cafeteria because of a friendship issue. The funny part is that most of the time we're not trying to catch them—we're trying to give them room to figure things out while keeping them safe.
What's one lesson being a principal has taught you that no degree or training program ever could?
Relationships drive everything. You can have the best systems, the best curriculum, and the best strategic plan, but people don't care what you know until they know you care. Leadership is far more about human connection than management.
You're shaping the next generation every day. What's one thing you wish more adults understood about today's teenagers?
Today's teenagers are often misunderstood. They're growing up in a world where they're constantly connected, constantly evaluated, and constantly exposed to information. What looks like indifference is often anxiety. What looks like defiance is sometimes a search for belonging. They need accountability, but they also need grace.
Do you keep up with student slang and trends, or do you let them think they're getting it off? What's the last phrase you had to Google?
Honestly, I don't keep up with student slang nearly as much as people assume I do. The trends change so quickly that by the time I learn one phrase, they've already moved on to the next. What I find even more challenging is keeping up with all the shorthand they use in texting and on social media. Sometimes I'll see a string of letters and have absolutely no idea whether it's a compliment, an insult, or a complete sentence. I've definitely found myself Googling acronyms more than once. Fortunately, I don't need to speak their language to connect with them—I just need to understand them.
You're an avid traveler and a property owner in Cape Town, South Africa. What drew you there, and what does that space represent for you personally?
Cape Town captured me immediately. The beauty is undeniable, but what stayed with me was the feeling. It's a place where mountains meet the ocean, where cultures intersect, and where life feels expansive. As an African American woman, there was also something deeply meaningful about standing on the African continent and feeling a connection to a history much larger than myself.
Owning property there represents freedom, possibility, and the fulfillment of dreams I know my ancestors could scarcely have imagined. For me, it's symbolic of how far we've come—from a people forcibly separated from their ancestral lands to a woman who can choose to own a piece of property on the continent by choice. In many ways, it feels like reclaiming a connection that history tried to sever.
That space is more than an investment; it's a reminder of resilience, legacy, and what's possible. It's proof that a woman who became a teenage mother, put herself through school, earned multiple advanced degrees, built successful businesses, and dedicated her life to serving others can create a life that transcends circumstance. I often think that I am living what would have been my ancestors' wildest dreams, while honoring the sacrifices that made those dreams possible.
What's your “I've arrived” travel ritual? (The outfit, the meal, the first thing you do when you land.)
Once I check in, I unpack immediately. I don't live out of a suitcase. The outfit is usually something monochromatic and chic. Then I find a beautiful place for a meal with a view, order a glass of wine, and take a moment to simply be present. Before I start exploring, I always pause in gratitude—gratitude for the opportunity to see another corner of the world, for the experiences I've worked hard to create, and for the journey that brought me there. Travel is a celebration for me, not just transportation. It's a reminder that life is meant to be experienced, and I never want to take that privilege for granted.
What destination is still sitting on your bucket list that you have to check off soon?
The Seychelles remains high on the list. I've spent a lot of time researching it and imagining it. There's something about that combination of luxury, nature, and serenity that keeps calling me.
Traveling as a woman, as a leader, as you, what has it taught you about freedom and identity?
Travel has taught me that my identity is bigger than any title I'll ever hold. I'm a principal, a mother, an entrepreneur, a traveler, and a woman who is still evolving. Seeing the world has taught me humility, curiosity, and the importance of creating a life that feels authentic rather than simply successful.
It's also taught me the value of independence. I genuinely love solo travel. There is something incredibly restorative about navigating a new city, enjoying a beautiful meal, watching a sunset, or sitting with a glass of wine overlooking the ocean completely on my own. In a life where I'm constantly making decisions, solving problems, and pouring into others, that peace is a gift.
I think many women are conditioned to believe that certain experiences should be postponed until they have someone to share them with—a partner, a spouse, or a companion. I've never subscribed to that mindset. I don't wait on anyone to live the life of my dreams. If there's a destination I want to see, an experience I want to have, or a memory I want to create, I go. Travel has reinforced that happiness, fulfillment, and adventure are not things that should be deferred.
For me, freedom is having the courage to build a life that reflects who I am today, not who others expect me to be. And every passport stamp is a reminder that some of life's most meaningful journeys begin when you're willing to go, even if you're going alone.
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Let's talk style. How do you balance being taken seriously as a principal while still expressing your personal fashion sense?
I don't think professionalism and personal style are opposites. My clothing communicates confidence, attention to detail, and self-respect. You can lead effectively while embracing fashion.
Have students ever commented on your outfits? Be honest…are they your toughest critics or biggest fans?
Students notice everything. Surprisingly, they're often my biggest fans. Teenagers can spot authenticity immediately, and they appreciate when adults show personality.
What's one fashion trend you secretly love but aren't sure you can pull off in the building?
Honestly, I don't know that there's a trend I can't pull off. The real question is whether my school community is ready for it. I love sleek monochromatic dresses, bold tailoring, and elevated pieces that can take me from a leadership meeting to a rooftop dinner without missing a beat. My fashion philosophy is simple: professional doesn't have to mean boring. It can be powerful, polished, and just a little bit sexy.
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When you pour into everyone else all day, what helps you pour back into yourself?
Travel, reading, meaningful friendships, prayer, meditation, reflection, and intentionally creating beautiful experiences for myself. I've learned that restoration isn't selfish—it's necessary.
I also prioritize feeling good in my body and my environment. That means always looking put together in a way that feels like me, and always smelling good—because those small rituals of care are part of how I stay grounded and confident throughout demanding days. There's something powerful about taking a moment for yourself, even in the smallest ways, that signals you're still choosing you.
At the core, it's about replenishment. Whether it's stepping off a plane in a new city, getting lost in a good book, laughing with friends, or sitting in stillness with my thoughts, I've learned that I have to actively create space to refill my own cup. When I do, I show up better for everyone and everything that depends on me.
Finally….If you had to name this chapter of your life like a candle scent, what would it be called?
"Golden Hour: Grace, Growth & Global Dreams."
The notes would be champagne, sea salt, sandalwood, white florals, and a touch of amber—warm, sophisticated, and full of possibility.
Because this chapter feels less about proving and more about enjoying what I've built while remaining open to what comes next.
There's something about this conversation that reminds us…
You can lead, nurture, explore, and still find your way back to yourself.
And wherever you are…home, car, classroom, or halfway across the world…your environment should feel like you.
We have enjoyed our time with Dr. Penn. Wishing her much success for the school year. She doesn't subscribe to social media, but if you would like to get more information about her travels and her Airbnb in Capetown, I can connect you.
This is your September Monthly Pour. Thank you for reading.
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