Lead Like a Leader

Personal Leadership Mastery

Blog Post #16 — Find Your Cool Series

Title: How to Cultivate Everyday Courage
by Tom Reynolds

When most people hear the word courage, they think of the big, dramatic moments — standing on stage, making a life-changing decision, taking a leap into the unknown.

But over the years — from operating rooms to boardrooms, and later in my own journey to rebuild health and purpose — I’ve come to understand something much deeper:

Courage isn’t a single big act. It’s a daily decision.
And often, it’s quiet.

It’s the decision to speak up in a meeting when staying silent would be safer.
It’s the choice to walk for 30 minutes when your energy says, “Skip it today.”
It’s owning a mistake before anyone finds out.
Or saying, “This isn’t working anymore,” when the world expects you to smile and push through.

The most courageous leaders I’ve known didn’t shout.
They showed up.
Even when it was hard. Especially when no one else did.


A Personal Reflection: Speaking My Own Truth

I spent decades in a corporate system where strength often meant silence. You kept pushing, kept winning, kept performing.

But many years ago, I hit a wall. Physically. Mentally. Emotionally. I’d lost over 100 pounds, reshaped my life — and yet, the hardest thing I had to do wasn’t physical.

It was admitting out loud that I was struggling. I had that voice in my head that would not quiet.
I was rethinking my identity. I needed a reset.

I’ll be honest, that was one of the most difficult acts of my life. Not because I didn’t know what to do next, but because I finally told the truth to myself.

And that truth? It cracked the door open for everything that followed.
Cool isn’t built by being perfect.
It’s built by being honest, and brave enough to change.


A Lesson from the Headlines: Brittany Force and Quiet Courage

Racer.com feature from March 22, 2024, discusses Brittany Force’s plan to “reset” at Pomona after a tough, winless 2023 season, emphasizing her mental and emotional recalibration heading into 2024

We all need to step back at times and recalibrate.

It’s not always about charging forward. Sometimes, it’s about choosing yourself in a world that demands your hustle.

I personally reset at least once a year


Cool Exercise: Name the Next Brave Step

Ask yourself right now:

Where in my life have I been playing small to avoid discomfort?

Write it down. One area. One situation.

Then answer:

  • What’s one small act of courage I could take this week — even if it’s awkward or scary?
  • How will I feel if I don’t take it?

Now commit to that one act.
You don’t have to fix the whole situation — just move one inch closer to truth.


Innovation Insight: Quiet Courage Builds Culture

When we ran leadership transformation sessions, we noticed a pattern:

  • The loudest person in the room got attention.
  • But the person who told the hard truth with the ability to share it in a way that draws people in and not push then out changed the conversation.

Courage in innovation wasn’t flashy.
It was the one nurse who admitted the system wasn’t working.
It was the executive who said, “We’re measuring the wrong things.”
It was the mid-level manager who tried something new without asking permission.

You want to transform your life?
Start by doing the thing you’ve been avoiding.

That’s how cool is built — not in the big win, but in the brave moment.


Quote to Reflect On

“Courage doesn’t always roar. Sometimes courage is the quiet voice at the end of the day saying, ‘I will try again tomorrow.’” — Mary Anne Radmacher


Final Thought

If you’re waiting to feel ready before being brave, you’ll wait forever.

Courage doesn’t show up first.
You go first — and courage meets you on the road.

Start small.
Start honest.
Start where you are.

That’s how you become the kind of person who builds momentum not through force, but through truth.

The coolest people I’ve met weren’t the loudest. They were the realest.
And real always requires courage

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Embark on an extraordinary journey with John Dempsey and Tom Reynolds at “Lead Like a Leader,” where 80 years of collective wisdom meets a passion for Self-Discovery in Leadership. Dive into our blog, where we unravel the secrets of success from the corridors of one of the world’s largest healthcare companies to the dynamic world of start-ups. Join us in reimagining personal leadership and well-being, as we blend timeless insights with cutting-edge strategies. This is not just a blog; it’s a beacon of empowerment, a sanctuary for truth-seekers, and a roadmap to your fullest potential. Welcome to the straight-talking zone, where learning and sharing never stop.