Why the optimists didn't survive the POW camp

Hey - it’s Tom.

Welcome to this week’s Freedom Friday edition of Ctrl+Shift, where we unpack one core psychological challenge of leadership, and leave you with a single (sometimes challenging) question to ponder.

Est. time to read: 5 minutes.

Many founders ride a wave of relentless optimism. It's a necessary survival trait, but it can also blind them to the cold, hard fact - a dwindling cash runway, a failing product, or a toxic culture.

This edition explores the paradox of holding unwavering faith while simultaneously confronting the most brutal facts of your reality, a discipline that separates the businesses that endure from those that do not.

A note from Tom: 'I once ignored three straight months of declining sales because I was 'certain' our new feature would turn everything around. I was so high on my own optimism that I didn't see the most brutal fact: our core service was no longer competitive. I was selling a fantasy while my business was sinking in reality. That optimism nearly killed the company.'

This psychological duality is known as The Stockdale Paradox. In his book Good to Great, Jim Collins profiles Admiral Jim Stockdale, who survived seven years in a Vietnamese POW camp. Stockdale observed that the first to die were the pure optimists. They'd say, "We're going to be out by Christmas," and Christmas would come and go, leaving them devastated. They died of a broken heart.

The survivors, Stockdale noted, were different. They maintained an unwavering faith that they would get out and prevail in the end, but they also confronted the brutal, soul-crushing reality of their day-to-day existence.

As a leader, your job is to embody this paradox. It’s the discipline to say two seemingly contradictory things at once:

"We have the vision, the talent, and the grit to become the #1 player in this market" (the faith),

while also saying:

"And right now, our churn rate is 15%, our top competitor just raised $20 million, and our product has a critical bug we must address" (the brutal facts).

When you are only an optimist, you create a culture where no one can bring you bad news. When you only focus on the brutal facts, you create a culture of despair.

The magic happens when you hold both. It gives your team the confidence to believe in the future, and the permission to be honest about the present.

For you to ponder:

What is the single most brutal fact about your business right now that you have been avoiding?

Want to read more? This edition was inspired by learnings and insights from Good to Great by Jim Collins.

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That’s it for this edition, see you next Tactical Tuesday!

Cheers,

Tom

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