The What If Journal
I’m convinced of this: the moment a leader believes they’ve “arrived” is the moment their leadership is done.
Leadership isn’t a destination. It’s not a point on the map where you finally get to kick back and say, “I’ve made it.” It’s a constant journey of curiosity — of staying open, asking questions, and wondering, “what if?” What if there’s a better way? What if this could be clearer? What if…
That’s really what this column is about. It isn’t a tidy list of leadership formulas or a claim to expertise. It’s more of a confession that I’m still learning, still stumbling, still curious. My hope is that by putting words to what I’m noticing, it might spark reflection in you too.
Some weeks the story may come from a strategy session with a team. Other times, it might be a moment in the church — something from ministry life that sparked a reminder or a lesson. And often, it will come from home: a conversation with one of my kids, an everyday challenge in family life, or even something as ordinary as working outside. Because leadership isn’t just about boardrooms and budgets. It’s also about guiding your family, serving your church, and influencing the people who are closest to you.
And if I’m honest, reflection has never been a natural strength for me. I’m wired to move forward quickly, to think about what’s next, and to get things done. Slowing down to ask, “What did I learn this week?” doesn’t come easily. In many ways, this journal is an exercise for me — forcing myself to pause, look back, and name what I’m learning in my own life and work.
That’s why the format will be simple and repeatable. Each post will follow the same rhythm:
A short story or observation from my week.
The leadership reflection it sparked.
A “what if” question or challenge that you can carry into your own leadership.
My hope is that these reflections feel more like invitations than instructions. They’re not meant to be a manual. They’re meant to give you a window into my journey, while giving you space to consider your own. If something here helps you think differently or lead more intentionally — whether in your nonprofit, in your church, or in your home — then that’s a win.
And maybe it helps you the same way it helps me: by reminding us that leadership is less about having all the answers and more about asking better questions.
So, welcome to The “What If” Journal. Thanks for joining me in this practice of curiosity, reflection, and progress.
What if the best leaders aren’t the ones who declare they’ve arrived, but the ones who keep asking “what if” — in the office, in the church, and at home?