The Miseducation of Self-Elevation

When Lauryn Hill asked, “How you gonna win when you ain’t right within?” in “Doo Wop (That Thing),” she was speaking to something deeper than success. So much of our lives revolves around achieving—securing the dream job, building a family, buying a home. We all want to win. But I’m learning that winning isn’t limited to just what’s tangible. 

Sometimes winning looks like doing the inner work: seeking God, going to therapy, choosing discipline over comfort, or finally booking the workout class you’ve avoided. Lately, my victories have looked more like these quiet commitments. They’re less visible—but far more transformative—and far more uncomfortable than I expected.

My 2026 has been great, and still is. Yet, the past month has brought unexpected twists and turns, similar to how I felt riding Superman for the first time as a child at Six Flags (even after watching it for minutes while waiting in line). The self-work has been no joke, between letting go of toxic work habits and healing from a traumatic dating experience; that literally brought me to my knees and realigned me with God. 

Things accelerated in the early hours of February 2nd, as I woke to devastating news: a man who was like a grand-uncle to me—and a father figure to my parents—had passed away. I still hear my brother and dad’s cries as they couldn’t even say the words. He was family in every way but blood—married to my grandmother’s lifelong friend from their Jamaica days. Every Sunday at church, he was the head deacon who’d take our gum if he caught us chewing. A steady pillar throughout my entire life, suddenly gone.

The days between his passing and homegoing felt both fleeting and endless, a reminder of how much my relationship with God, community, family, and life offline truly matters. When celebrations for his life coincided with New York Fashion Week, I didn’t hesitate to take the time off—and I didn’t feel guilty about it. One day, we were sitting in my room when my dad was shocked to learn I wasn’t attending anything for fashion week because of the funeral. “Really?” he asked. “Yeah—this is DaDa we’re talking about,” I replied. There was a time I would have found a way to do both. But not this time. Suddenly, the dream life I had been living didn’t hold the same weight. I didn’t care about showing face, seeing new collections, or interviewing my inspirations. All that mattered was being with family—and simply being. 

For a long time, I equated elevation with the visible: Instagram posts, LinkedIn updates, compliments, or some coveted fashion buys I once dreamed of owning. Now, I see elevation in discomfort and struggle—and I understand their purpose. Every beautiful thing begins with an ugly stage: olives are beaten and pressed for oil, caterpillars hide before becoming butterflies, and construction sites are messy before the road is smooth again. 

I am still elevating and will continue to, but I no longer misunderstand what that requires of me. Experience has shown me that change isn’t optional, but inevitable.  Whether we resist it or embrace it, life moves us forward. And while it’s okay to feel the feels, you can’t stay there. 

Like an elevator shifting floors, growth demands movement. You cannot rise and remain unchanged. There are seasons when that ascent feels isolating and uncomfortable, when the silence is loud and the uncertainty heavy. There are also seasons filled with clarity, connection, and joy. Both are necessary. Both shape you. I have learned that elevation is not about avoiding discomfort, but is part of the transformation. In the end, every shift, stretch, and moment of solitude contributes to who you are becoming. And when you finally arrive at the next level, you realize the journey—no matter how difficult—was preparing you all along.

“¹⁸For I consider [from the standpoint of faith] that the sufferings of the present life are not worthy to be compared with the glory that is about to be revealed to us and in us!

“²⁸And we know [with great confidence] that God [who is deeply concerned about us] causes all things to work together [as a plan] for good for those who love God, to those who are called according to His plan and purpose.”

                            Romans 8:18 & 28 {AMP}

Much love and peace,

Nay.