We’re looking forward to introducing you to Courtney S. Jenkins. Check out our conversation below.
Courtney S., really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: What do the first 90 minutes of your day look like?
My mornings always start with gratitude. Before I touch my phone or think about the day, I take a moment to say thank you and acknowledge life itself. Then I sit in silence for a bit, no rushing or pressure, just letting my mind and body fully wake up. Once I’m grounded, I get up and move through my morning self-care routine. After that, I make breakfast and go straight into my morning affirmations. Once I’m settled, I put on one of my favorite podcasts, usually something about finances, personal development, business, or investing. From there, I shift into strategy mode to start on my “daily three” the actions that move me 1% forward that day.
Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Courtney S. Jenkins, and I am a wealth strategist, investor, author, and founder of Legacy Under Oak, a brand dedicated to bridging the gap between financial strategy and personal evolution. I help ambitious individuals move beyond surface level money management into structured, long term wealth. What distinguishes my work is that I don’t simply teach concepts, I apply them daily. As an active investor, I understand the emotional control, strategic focus, and long term vision required to grow sustainable wealth. My approach combines practical investing experience with structured financial systems and mindset refinement because I believe wealth is strongest when strategy and self-mastery move together.
My story is rooted in lived experiences. I’ve navigated financial uncertainty, entrepreneurship, and rebuilding phases that shaped my belief that wealth isn’t built through motivation alone, but through consistency, systems, and intentional decision making while staying emotionally sound. That journey led me to create Legacy Under Oak, launch my podcast, and author Improvement Begins With I: 31 Gems To Become Your Best Self, a transformative book designed to strengthen mindset, elevate discipline, and intentional personal development.
Today, I work with people who want to gain control over their money and build wealth in a strategic way that aligns with their goals and values. I am expanding my coaching work, creating digital tools, and facilitating powerful conversations that challenge how people engage with money, power, and legacy. My mission goes beyond building wealth. It is to create change, disrupt limiting systems, and redefine what true financial empowerment looks like for this generation and the next.
Amazing, so let’s take a moment to go back in time. Who were you before the world told you who you had to be?
I’m going to redefine this question because what really matters is understanding who I was when the world tried to tell me who I was supposed to be.
When the world told me who I had to be, I became shaped by pressure, responsibility, and expectations. I followed systems and standards that were never designed with my freedom or fulfillment in mind. I learned how to perform, how to carry weight, how to survive even if it meant silencing parts of myself just to fit what looked acceptable. Over time, I realized that society teaches people to follow paths that benefit conformity, not individuality and when you live by those rules, it doesn’t create genuine happiness. It creates a survival, routine, and dissatisfaction that never really leaves. I decided I wasn’t going to live that way.
Through self education, I started understanding life on a deeper level and what it truly means to live on your own terms. I began noticing the unspoken rules around money, success, and identity, all the things that keep people boxed into systems that reward those who never challenge the norm. I saw that most of those rules protect the status quo, not the individual spirit. Learning became my freedom, but I also learned that knowledge only matters when you use it. Staying educated keeps you informed. Actions change the game. With that awareness, I stepped outside of what was expected and chose a life built on intention, not conditioning. I follow my own vision, create my own standards, and happiness. I choose alignment over approval, truth over tradition, and growth over comfort. I am who I consciously chose to become.
What did suffering teach you that success never could?
Suffering taught me who I am when nothing is certain, when comfort is gone, and when the applause disappears. It showed me resilience before confidence, clarity before certainty, and strength before recognition. Success can make you feel validated, but suffering is what actually reveals your foundation. It taught me patience at times when I wanted answers, humility when I wanted control, and discernment when I wanted relief. It pushed me to listen to myself, confront my truth, and sit with discomfort long enough to understand it instead of running from it.
Suffering showed me that real growth is quiet. It’s uncomfortable. It’s repetitive and it’s transformative in ways you don’t fully appreciate until you’re on the other side of it. Now on the other side of suffering is the direction you move in. Healing starts with awareness and growth follows intention. You can let that pain define you, or you can let it become the catalyst that reshapes and strengthens you. Success may validate your progress, but suffering refines your character.
Next, maybe we can discuss some of your foundational philosophies and views? What important truth do very few people agree with you on?
I believe society can be a trap, and most people are too conditioned to ever question the comfort walls around them. We’re taught to accept what’s considered normal without stopping to ask who that “normal” actually benefits. The systems we move through were built around control, compliance, and repetition. They reward obedience more than originality, and comfort more than consciousness. A lot of what we see around us is designed to trigger reactions instead of reflection. Outrage, fear, division, and blind loyalty keep people busy, emotional, and distracted. So many people end up defending positions instead of seeking clarity.
One of the most dangerous parts of the system is the illusion of progress. Surface level changes get celebrated, but the core stays the same. Words change, branding changes, leadership rotates, but the power remains exactly where it’s always been. Many of the people presented as leaders were never actually leading. They were holding space, maintaining the structure, and calling it progress. While a lot of people are scared to challenge what feels familiar, I see the system clearly enough to know that compliance has never created liberation.
Okay, so before we go, let’s tackle one more area. What do you think people will most misunderstand about your legacy?
My legacy was never meant to be understood or put into familiar narratives. It’s an energy you feel, a movement you witness, and a presence you remember. People might try to define it or even shrink it, but my legacy doesn’t live in comfort. It lives in the spaces where truth matters more than applause. It wasn’t created to be understood. It was created to awaken. I don’t move through this world trying to be understood. I don’t soften my truth just to make other people comfortable. I move unapologetically, rooted in who I am. Anyone trying to understand me from the outside will always miss the point, because I’m not here to fit into definitions. I’m here to embody my purpose, honor my voice, and exist as my whole self.
Contact Info:
- Website: https://courtneysjenkins.com
- Instagram: https://www.instagram.com/courtneysjenkins
- Other: Legacy Under Oak Podcast
https://open.spotify.com/show/1rGAZyubEiNLvi04fD1qna?si=8279d11441074867
https://podcasts.apple.com/us/podcast/legacy-under-oak/id1821997420
