ABOUT 1 YEAR AGO • 2 MIN READ

The leadership stories no one tells you

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The Monday Manager

For health and social impact founders stuck in operational firefighting. Every Monday, one dispatch from inside health and social impact organisations — what's breaking, why, and what actually fixes it. P.S. Lookout for the confirmation email.

You know that sick feeling when a decision doesn't work out?

It's not just disappointment about the outcome. It's something deeper.

A voice that whispers: "Real leaders would have seen this coming. Real leaders would have made it work."

That voice? It's been trained by years of consuming leadership content that only celebrates the wins.

Here's what happened to me: One of my bosses once had a eureka moment and asked me to implement it.

I along with my team created a detailed, well thought out plan to pilot the idea. After three months the pilot revealed many shortfalls with the idea, one of them being the need for much greater workforce which made it unfeasible.

Yet the result was met by a look of disappointment and the comment that "I still think this is a great idea, we just need to find 'someone' to make it work."

The decision process for the pilot was solid. But that night, I lay awake scrolling through LinkedIn posts and Youtube videos about "visionary leaders who saw around corners" and "bold decision-makers who always find a way."

Each success story felt like evidence of my inadequacy.

This is what survivorship bias really costs us:

Not just bad decision-making (though that happens). It's the slow erosion of our leadership identity every time reality doesn't match the hero narratives we consume.

Almost every business book follows the same pattern:

  • Leader X makes bold decision Y
  • Amazing result Z follows
  • Implied message: "This is what good leadership looks like"

But what about:

  • The equally bold decisions that failed due to market shifts?
  • The visionary moves that were right but mistimed?
  • The careful choices that got derailed by factors no one could predict?

Those stories don't get told. So when our thoughtful decisions meet bad luck, we don't think "that's leadership in the real world."

We think "I'm not cut out for this."

Today's Permission Slip:

You have permission to stop measuring your leadership against carefully curated success stories and start recognising that even your "failed" decisions might be exactly what good leadership looks like.

Why this feels uncomfortable: We've been conditioned to believe that if we were truly competent leaders, we'd find a way to make every decision work. That failure to deliver results reveals some fundamental inadequacy.

But here's what survivorship bias hides: The leaders in those inspiring case studies have graveyards full of excellent decisions that didn't pan out.

They just don't write books about those.

The Hidden Damage: When we constantly compare ourselves to these polished narratives:

  • We lose confidence in our decision-making ability.
  • We start avoiding necessary risks.
  • We second-guess ourselves into paralysis.
  • We carry shame about outcomes beyond our control.

This Week's Practice:

This week, try this mental shift:

Instead of asking "Would a great leader have made this work?" ask "Did I make this decision the way a great leader would?"

Focus on:

  • The quality of information you gathered.
  • How thoughtfully you weighed trade-offs.
  • Whether you considered key stakeholders.
  • How you communicated with your team.

The market can shift.

Competitors can surprise you.

Pandemics can happen.

That's not leadership failure. That's just the world we lead in.

This Week's Question:

What decision are you still carrying shame about, even though your process was sound?

Here's to leading differently,

Raghav

P.S. I've made plenty of excellent decisions that looked terrible on paper afterwards. The shame took longer to heal than the business impact. If you're carrying that weight too, hit reply – you're not alone in this.

P.P.S. Know someone who might need to hear this? Forward them this email. They can also subscribe here.

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The Monday Manager

For health and social impact founders stuck in operational firefighting. Every Monday, one dispatch from inside health and social impact organisations — what's breaking, why, and what actually fixes it. P.S. Lookout for the confirmation email.