Run Your Own Race: What the Kentucky Derby Reminded Me About Leadership, Fundraising, and Big Dreams

Every year, people tune into the Kentucky Derby looking for the favorite. The horse everyone expects to win. The safest bet. The one getting all the attention.

But every now and then, a different story unfolds.

This year reminded me of something I talk about constantly with nonprofit leaders, entrepreneurs, and even myself: sometimes the winner isn’t the loudest, most polished, or most expected contender in the race.

Sometimes it’s the one that stayed focused.
The one that kept moving.
The one that ran its own race.

And honestly? That lesson applies everywhere.

I see so many nonprofit leaders carrying big, bold visions for their organizations while quietly wondering if they’re really capable of getting there. They look around at larger organizations with bigger staffs, stronger donor bases, larger marketing budgets, and more established networks, and they start questioning themselves before they’ve even fully stepped into the race.

But comparison is dangerous in leadership.

Because when you spend too much time watching someone else’s lane, you lose focus on your own strategy, your own momentum, and your own mission.

The organizations making meaningful progress right now are not necessarily the ones with the most resources. They are often the ones willing to consistently do the work day in and day out. The ones showing up when nobody is clapping yet. The ones building relationships before results appear. The ones willing to keep moving even when the finish line still feels far away.

That’s true in fundraising.
That’s true in business.
That’s true in leadership.

I can apply this lesson directly to my own life and businesses.

There have been seasons where growth felt slow. Seasons where it seemed like other people had more momentum, more visibility, or a clearer path. But over time, I’ve learned that success usually doesn’t come from one dramatic moment. It comes from consistency. From discipline. From continuing to move forward long before the results become visible to everyone else.

Winning often looks boring before it looks impressive.

It’s the daily work.
The hard conversations.
The follow-up.
The planning.
The repetition.
The willingness to stay in motion when doubt creeps in.

And sometimes, if we’re being honest, leadership requires believing in yourself before other people fully do.

That may be one of the hardest parts.

When you’re building something meaningful — whether it’s a nonprofit, a business, a campaign, or a vision for your future — there will be moments where the external validation hasn’t caught up yet. The results may not be obvious. The support may not feel overwhelming. But winners keep going anyway.

Not because it’s easy.
Because they believe the vision is worth pursuing.

That’s what I try to instill in the organizations I work with. Big dreams are allowed. Ambition is allowed. Growth is allowed. But none of it happens accidentally.

You have to run your race.

Not someone else’s timeline.
Not someone else’s strategy.
Not someone else’s definition of success.

Yours.

The Derby is exciting because it reminds us that outcomes are not always determined by expectations. Sometimes the horse nobody predicted simply refuses to stop running.

There’s something powerful in that.

So if you’re in a season where the vision feels big, the path feels long, or the odds feel uncertain, keep going. Stay focused. Do the work. Trust the process. Build momentum.

Because sometimes the ones who win are simply the ones who never stopped believing they could.