The Confidence to Choose Freedom Over Familiar Paths in Leadership

Written by Orvin Kimbrough | May 01, 2026

What would you do if life handed you more time tomorrow?

Not for work, not for obligations just for you. For almost four years now, I’ve been navigating life as an empty nester. Even before my kids officially moved out, they were already finding their independence. In those last two years of high school, they didn’t want much to do with me my son was deep into sports, and I supported him by showing up to basketball games. That time was precious, but fleeting.

As the kids prepared to leave for college, I got asked a lot of questions: “What are you going to do with all this newfound time?” And once they actually moved out, the questions shifted: “Aren’t you sad?”

The answer to both questions required reflection. When people asked what I was going to do, my first thought was about work. My role at the Bank and my community commitments could easily expand to fill every available hour. But that didn’t feel right. This was a rare opportunity to intentionally decide how I wanted to spend my time not just for others, but for myself.

Finding Joy and Reimagining Time

I started asking myself: What brings me joy? I knew reading and studying were already integral to my routine they helped me grow as a leader and a person. But I realized that the one area in my life that needed attention was my relationship with my wife. After years of raising kids and prioritizing other commitments, we needed to rediscover what we had in common. That went on my list of priorities.

Beyond that, I reflected on what truly fulfills me. Helping others find the best version of themselves brings me joy. Writing brings me clarity, and nothing breaks my heart more than seeing people unoptimized lacking confidence in their potential. That’s when I realized: I needed to do something bigger to articulate my story, share my lessons, and help others.

I decided to write books and develop courses, even though I’d been teaching and creating for years. To ensure I did this well, I hired a coach. Writing a book wasn’t easy it required confidence I didn’t know I had. Every blank page was a challenge, but as I leaned into the process, something incredible happened.

Growth Through Confidence

Writing became an act of faith. Each late night spent grinding, each morning spent refining, built my confidence. Sharing chapters with my editor and receiving encouragement like, Your story is going to change lives,” kept me moving forward. My wife, often my first reviewer, offered advice that still echoes in my mind: “Don’t worry about the audience just say what’s on your heart.”

This year, I was approached by a major university to develop a leadership curriculum. Having done this successfully in the past, I knew the drill: significant time invested, yielding what often feels like minimum wage when all is said and done. The prestige of the university’s brand and the built-in audience of motivated leaders made it tempting to say yes. It offered an easy, streamlined path to visibility and impact.

But as I thought it through, I realized that saying yes would come at a cost my time, my creative freedom, and my ability to shape the course on my terms. I began to ask myself, What do I truly want to accomplish? If my goal is to make the greatest impact and have the freedom to evolve the curriculum as needed, the better option was to develop the course independently.

This decision wasn’t easy it required another leap of faith and, yet again, a test of confidence. Could I create something just as compelling without the backing of a well-known institution? Could I reach the same audience on my own terms? I didn’t have all the answers, but I leaned into the challenge.

I sought out a course and a community to guide me, understanding that growth often requires collaboration and learning from others. Now, I’m stretching myself into new territory designing a program that aligns fully with my vision and values. It’s a risk, but one I’m confident will yield a more meaningful and lasting impact.

A Universal Truth

One of the biggest lessons I’ve learned is this: Time is fixed, but how we use it determines our growth. It’s not about creating more time it’s about prioritizing what matters. Whether it’s a new phase of life, a professional challenge, or a personal goal, the key is intentionality.

As I’ve stepped into this new chapter, I’ve discovered that growth doesn’t just happen it’s designed. Confidence isn’t something you wait for it’s built through action. And fulfillment comes when you align your time with your purpose.

Your Turn

So, what’s next for you? What’s one step you can take today to step confidently into your next phase? Write the first page of that book. Say yes to that opportunity or maybe say no to make room for something better.

Time won’t make room for you you have to claim it.