Fear of Failure in Leadership
Ever had a big idea that made your heart race, and not in the good way?
That shaky mix of excitement and terror when you’re standing on the edge of something that really matters. A promotion. A presentation. Starting something new. Speaking your truth. You feel the pull… and then the fear floods in.
I know that feeling. And so does Franklin Esau.
Franklin shared his story with me in a raw, honest conversation on my podcast, Let’s Talk Courageous Communication. And it has stayed with me for years. Not because he had some perfect, polished “success story”. But because he’s walked the road of real, gritty courage. The kind that comes with trembling hands, not superhero capes.
Let me tell you about it.
When everything in you says “Don’t speak”
Franklin has lived a life many of us can’t imagine. As a young man, he was pulled into gang culture. By his early 20s, he was in prison. And for a long time, silence was his survival strategy.
“In prison, the belief was: you don’t speak about emotions. You don’t ask for help. You keep your mouth shut and your guard up.”
But deep down, he knew something needed to shift. When he was exposed to emotional development programmes during his sentence, it cracked something open.
He then started doing the hard work. He started to heal old wounds, learn to name his feelings, and to face his pain.
Still, when he was released, the idea of sharing his story publicly was terrifying to him.
“For a long time I was ashamed of who I was,” he told me. “I thought people would judge me. I had this fear that they wouldn’t take me seriously.”
That fear could’ve stopped him. Easily.
But Franklin said something significant:
“I realised if I didn’t speak, I’d be going against everything I now believe.”
And that right there is what helped him do something big. Not because the fear went away, but because his purpose got louder than his fear.
The fear is real. But so is the cost of silence.
We need to remember that feeling scared doesn’t mean we’re weak. It means we’re human.
When you’re standing in front of a meeting room, wanting to pitch an idea… when you’re holding back on asking for a raise… when you know you need to give honest feedback but your voice catches in your throat… that’s not failure. That’s just a response from your nervous system to what it perceives to be a threat.
But if you always let fear win, then you end up with regret.
Franklin said it better than I ever could:
“If I had kept silent, I would have stayed in that prison internally.”
What an image. A man who physically walked out of prison… still feeling emotionally imprisoned, just because fear told him to stay quiet.
That’s what so many of us are facing. Not bars, but boxes: of politeness, of fear, of imposter syndrome.
And here’s the lesson: You don’t need to be fearless to do something brave. You just need to take one step.
5 Things that helped Franklin speak up (and might help you too)
- He got clear on his “Why”
Franklin realised that his story could help others. That he could be a mirror to young men going down the path he once walked.
He asked himself: Is staying safe worth more than making a difference?
That one question can change everything.
Try this: Write down 3 reasons why your voice matters. Read them before every scary conversation.
- He built emotional literacy
This is something I talk about often in my coaching work. If you don’t have the language for what you’re feeling, and a framework to understand your emotions, then the fear just keeps you trapped.
Franklin went through an emotional development programme inside prison, and later helped facilitate it. He learned how to name emotions, process them, and choose how to act (rather than react).
That gave him the confidence to face emotionally risky moments.
Tip: Start with the basics. Print a list of emotion words. Use it to check in with yourself daily. I have a list I can email you , if you would like it? Just contact me and ask for it.
- He didn’t do it alone
One of the most powerful things Franklin shared was the impact of being seen.
“Having people believe in me, and say ‘you’ve got something worth sharing’… that mattered more than they realised.”
We all need cheerleaders, not to hype us up with fake confidence, but to remind us of our truth when fear makes us forget.
Ask yourself: Who can I talk to when I’m scared? And if you don’t have someone, let’s change that. Join a community. Book a session. You don’t have to white-knuckle your way through.
- He took one small step
Franklin didn’t start by standing on a TEDx stage.
He started by sharing his story in a safe space.
Then another. Then a school. Then a podcast. Then more.
Courage compounds.
What’s one tiny action you can take toward your big thing? A draft email. A phone note. A 5-minute rehearsal in the mirror. That’s how it starts.
- He told the truth, not a perfect version
One of my favourite moments in our conversation was when Franklin said:
“I’m not saying this because I’ve got it all together. I’m saying it because I remember when I didn’t.”
That kind of honesty builds trust.
If you’re worried about how you’ll be perceived, try aiming for honest, not impressive. People connect with real.
If you’re scared… Good.
It means you’re standing at the edge of something that matters.
You don’t need to feel ready. Or confident. Or perfect.
You need to decide: Is this silence costing me too much?
Franklin could have stayed quiet, safe and unseen.
But he didn’t.
He spoke. And now, his story is changing lives.
Maybe yours will too.
If this stirred something in you and you’re ready to take your first step, I offer private coaching and group programs to help you speak up with courage and clarity. You don’t need to do this alone.
Let’s start where you are.
Your voice matters. Even if it shakes.
