Over the past 30 years, I’ve learned that most people, myself included at times, find it easier to fit into a mold someone else created. It feels safer to follow someone else's playbook than to step out in faith and become the person God uniquely designed us to be. But I’ve also learned that when you play someone else’s game, you’re already at a disadvantage.
Sure, there are macro rules we all operate under. But there’s room, and a need, to play the game differently. And some people won’t want you to. They’ll discourage you from leveraging your unique value proposition, your gifts, your perspective. But I believe each of us has something deeply valuable to offer. When we lean into that uniqueness, we create differentiation. We write new rules. We shift the game.
When I reflect on my time at United Way, it was an extraordinary journey of learning. I had the privilege of learning from one of the best, the former CEO who taught me how to build relationships and stay focused on the scoreboard to drive impact. But even from day one, I was clear: I wasn’t there to merely follow the rules. I was there to learn, build, and iterate on what came before me. That’s the choice we all face: know when to stay in bounds, and know when it’s time to stretch. Growth comes when we stretch. Innovation comes when we challenge the rules. And advancement comes when we dare to see things differently.
Trying to play someone else’s game often costs more than it seems. You sacrifice your peace, your authenticity, your time. And even if you "win," you may look around and realize you never actually wanted the prize. Real winning is measured by alignment, not approval.
Early in my career, I had the privilege of interning with the National Benevolent Association, one of the largest nonprofits of its kind in the country. That opened doors into the vibrant community and economic development ecosystem in St. Louis. If you were paying close attention back then, you could see the structures, incentives, and systems at play, who held the power, who controlled the money, and who had influence.
I saw firsthand how certain neighborhoods, like Jeff-Vander-Lou, were subjects of repeated revitalization efforts. Every 20 to 30 years, someone came in with a new vision, largely because of its proximity to more affluent areas of the city. But what remained unchanged was the underlying game, a power structure that had not yet conceded that these communities must thrive for the region to thrive.
I remember being in rooms back then, asking uncomfortable questions about whether certain initiatives were even intended to succeed. Some didn’t appreciate the challenge. I was directly discouraged from speaking up. But my conscience wouldn’t let me be silent.
Over the years, I’ve seen how easily we lose track of what matters. We pour charitable dollars into communities with noble intentions, yet the outcomes often don’t match the original goals. We owe it to ourselves and the next generation to reflect on the systems, the incentives, and the history, so we don’t just repeat the same cycles. Because if we don’t reflect, we become exhausted, overwhelmed, and short on memory.
No matter your background, urban or rural, Black or white, nonprofit or business, we all want the same things: safety, opportunity, dignity. And we’re all playing a game within a larger system of incentives and structures. Those of us with a higher level of consciousness must ask: Are our actions helping or hurting the communities we serve?
I often reflect on the erosion of the tax base in our neighborhoods. Charitable organizations do important work, but we also need to re-center our efforts around entrepreneurship, small business ownership, and economic vitality. Not just because they create jobs, but because they sustain communities. We need more storefronts engaged in commerce, not just charity. That’s how we restore the tax base, grow the employment base, and reimagine what’s possible.
So, here’s the final question: As you climb the ladder, are you sure it’s leaning against the right wall?
Are you measuring your life by someone else’s metrics?
We should learn from others, absolutely. But ultimately, we must own our path. We must play our game.
For this next generation of leaders: the game isn’t imitation. The game is alignment. The game is ownership. The game is building something that lasts. And as we thrive, we create the kind of communities, and country, that thrive with us.
Grow in your lane. Play your game. And write your rules.