You Don’t Make Progress by Standing on the Sidelines

“You don’t make progress by standing on the sidelines.” — Sonia Sotomayor

Leadership is not a spectator sport. Yet, too often, I see talented founders, nonprofit leaders, and business owners hesitating — watching from the edges, waiting for the “right” moment to jump in. The truth is, the right moment rarely arrives perfectly packaged. It arrives when you decide to show up, fully, with all the doubts, fears, and imperfections that come with it.

Where Are You Standing on the Sidelines?

The question I want to ask you today is simple but challenging: where are you silently stepping back instead of stepping up?

This is not a call to reckless action. It’s an invitation to honest reckoning. It’s about identifying where hesitation or discomfort has kept you from fully owning your leadership role and, in turn, limiting the growth of your organization.

The cost of staying on the sidelines is real. It’s not just your missed opportunities — it’s the momentum stalled, the voices left unheard, the vision left half-birthed. It’s your team waiting for you to lead with clarity and courage, and your mission waiting for your bold commitment.

From Hesitation to Intention

Leadership requires messy, unglamorous work. It requires stepping into uncertainty and making decisions that might feel uncomfortable or vulnerable. But this is where real progress happens — not in waiting, not in perfection, but in movement.

This week, I challenge you to break the pattern of hesitation. Reflect deeply on the ways you might be holding back and ask:

• What is the real cost of this hesitation to my team, my vision, and my growth as a leader?

• What is one bold, intentional step I can take to move from observer to active leader?

Owning Your Seat at the Table

Showing up fully means owning your place — your seat at the table. It means recognizing that leadership is messy and imperfect and that your presence, commitment, and voice matter deeply.

No more sidelines. No more waiting for perfect conditions. The moment to lead is now.

If you’re ready to lean in — to lead with intention, purpose, and real impact — I invite you to start today. Make that bold move. Your organization, your team, and your mission are counting on it.

Ready to own your leadership and build a stronger, more intentional organization?
Let’s talk. At BlackOak Consulting, we help nonprofit and small business leaders move from hesitation to impact — with clarity, strategy, and rooted leadership.

What step will you take this week to leave the sidelines behind?
Journal your thoughts or connect with me directly.