Leading With Conviction, Living With Fulfillment

My original plan was law school. In undergrad, I studied philosophy and followed a pre-law track, not because I had a clear vision of being a lawyer, but because I was drawn to big questions about how people think, make decisions, and define fairness.

But when it came time to go to law school, it just didn’t feel quite right. I had this realization that law tends to look back into the past, and that I wanted something that was more oriented in building a future vision. That’s how I ended up in an MBA program.

But even in business, something felt off and I wasn’t happy. I hired a coach to help me figure out what was missing, and I fell in love with the work we were doing together. We explored what energizes me, what I value, and where I felt most fulfilled. 

Very early on in that process, it clicked: This is what I want to do. So, I followed advice from a professor I admired: “Just because you can, doesn’t mean you have to.” 

It was then that I decided to keep following my gut, even if it meant walking away from multiple paths that I thought would be right for me, and become a coach.

Following Conviction: Choosing Freedom and Fulfillment

Making a major career pivot can be difficult to explain, especially when the path you’re leaving is one that others might see as successful. But for me, it came down to conviction.

Two values that have always guided me are freedom and fun. Freedom in the sense that we always have the agency to choose how we respond, how we lead, and how we live. And fun not in a frivolous way, but as a reminder that we deserve to enjoy our life’s work. I didn’t want a career that felt like I was ticking boxes. I wanted one that gave me meaning and enjoyment.

That’s ultimately what led me to coaching. I launched my own practice and began working with high performers, lawyers, ex-military leaders, and other professionals who were outwardly accomplished but inwardly disconnected. They weren’t looking to fix résumés. They were looking to reconnect with meaning.

After all, isn’t that what conviction is really about?

At The Humphrey Group, conviction is one of the six core principles of the Leader’s Mindset. We define it as more than just holding beliefs. It’s about having the courage to live those beliefs consistently, to express them clearly, and use them to them to guide decisions, even when it means walking away from the familiar.

For me, choosing conviction meant choosing a career that aligned with my values. And now, I help others do the same.

Creating a Career that Feels Like You

One of the most common challenges I see in my clients is not that they lack skill, but rather that they don’t feel connected to their work or at ease and confident in their role. Many have built impressive careers, taken on big responsibilities, and checked all the right boxes, but somewhere along the way, they lost sight of what energizes them.

That’s where we start. I’ll often ask them which parts of their work gives them energy or excites them. It might be mentoring junior colleagues, making strategic decisions, or telling stories that spark change. Whatever it is, we find the moments that light them up, and then get curious about why.

Behind the energy, there’s usually a value. Maybe mentoring lights you up because you believe knowledge should be shared. That was the case for one of my clients, a high-performing executive who was already widely respected in his role. Still, he felt something was missing.

When we explored what gave him the most fulfillment, he kept returning to the informal mentoring conversations he had with junior colleagues. He enjoyed the technical aspects of his work, but mentoring offered something different.

So, he decided to lean into that. He joined a professional mentoring program outside of work and eventually stepped into a leadership role within it. It didn’t require him to change his job, but it did enhance his experience of it. By acting on his conviction that knowledge should be shared, he added a new layer of purpose to his career.

That’s the power of conviction. It helps you make small shifts that create big changes in how you feel, how you lead, and how you show up.

Career Fulfillment Starts with What You Like

In many traditional approaches to leadership development, the focus is often on what’s lacking: gaps to close, skills to fix, and other areas for improvement. While there can, of course, be value in focusing on growth, I’ve found that meaningful change doesn’t have to start with what’s wrong. 

What about focusing on what’s working? When I begin with a client, one of the first things I ask is what parts of their work they genuinely enjoy. And I don’t just mean what they’re good at. It’s about what gives them energy and helps them to really feel engaged. It’s important to anchor into the reason why they may have started on their career path in the first place.

A good way to demonstrate this is to think about public speaking. Most people feel some degree of anxiety around it. At The Humphrey Group, we coach leaders to speak from conviction, to connect with their audience, and to transform information into inspiration. 

That process starts with recognizing what already lights you up and finding ways to do more of it. That’s why it’s so important to not only focus on the negatives, nerves or perceived weaknesses, but to instead drill down to the why. 

Most of the time, the answers are rooted in conviction. People believe in the message they are sharing, and they want to inspire change. Anchoring to those beliefs makes everything shift. Suddenly, it’s less about fear and more about impact.

The same can apply to your career. A massive overhaul to your role or career path isn’t necessarily what is required to feel more fulfilled. Sometimes the most powerful change begins by reconnecting to the part of your work that feels most like you.

You Always Have a Choice

One of the most powerful shifts we can make in our work (and in our lives) is to realize that we always have a choice. Even when we don’t control the circumstances, we can choose how we respond and show up.

That’s what I discovered when I stepped away from paths that didn’t align with me, and moved toward what felt right. But fulfillment doesn’t have to come from waiting for something new to arrive. 

At the core, it’s about living your life through the lens of your own conviction. Is life just happening to you, or do you play a role in co-creating it? When you drill down into what you value and begin to lead from that place, real change and fulfillment become possible, no matter the circumstances.