When Winning Didn’t Feel Like Winning: A Lesson in Redefining Success

I know it’s been a while since I’ve posted, and I’ve missed this space more than I realized. Life has been moving fast, and I’ve been doing my best to keep up. But today, I want to share something real with you, a story about a “success” that didn’t feel like success at all and why that matters more than we think.

Some time ago, I was allowed to be the sole head of my department. Typically, the department is run by two people, evenly splitting the twenty teams. Once my cohort departed, the agency elected to make me the sole head instead of backfilling the position, something that had never been done before. On paper, it was everything I had been grinding for. People congratulated me. Some even said they were inspired by it. But here’s the truth, I didn’t feel anything. No joy. No pride. No sense of fulfillment. I smiled through it, but deep down, it felt empty.

I expected to feel proud, empowered, and maybe even relieved. Instead, I felt drained and disconnected. I remember sitting at my desk after the announcement and wondering why I wasn’t more excited. Why didn’t it feel like the win I thought it would be? For a while, I couldn’t understand why. I told myself maybe I was just tired. Maybe the excitement would catch up later. But it never did.

After some serious reflection, I came to realize the truth. Somewhere along the way, I had outgrown the goal. I was so focused on chasing that title that I didn’t stop to question whether it still aligned with who I had become. Yes, I earned it. Yes, I was capable. But deep down, it no longer reflected the kind of impact I wanted to have or the life I wanted to lead.

This moment taught me something I’ll never forget. Success isn’t just about reaching the goal. It’s about how the goal fits into the bigger picture of your values, your purpose, and your well-being. If it costs you your peace, your passion, or your joy, then it might not be a success at all.

Becoming the head of my department looked great on paper, but it forced me to re-evaluate what truly matters to me. I started asking deeper questions: Am I fulfilled in this work? Do I feel seen and supported? Is this the kind of leadership I want to embody? And the answers surprised me.

That “successful” moment helped me reconnect with what I actually want: meaningful work, intentional living, and the freedom to define success on my own terms. It reminded me that fulfillment isn’t about external validation. It’s about feeling in alignment with your truth.

So, if you’ve ever hit a milestone and felt nothing, you’re not alone. And you’re not broken. You’re just evolving. Keep going, not toward what looks successful, but toward what feels right.

Thank you for reading and for still being here. I’m excited to share more with you, honestly, intentionally, and with an open heart. Let’s keep growing together.

With love. ❤️