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Stockdale Paradox — Why optimists don’t survive software projects
When projects plans go wrong, face the brutal truth and deal with reality.

Plans are optimistic, you have to be realistic to deliver a project
In Love and War is the story of Admiral Jim Stockdale, who was the highest-ranking military officer in the Hanoi Hilton. They imprisoned Jim for years and tortured over 20 times. What is amazing is James Stockdale said he was stronger when he came out of the prison camp than when he went in.
How do you avoid losing belief when things don’t go to plan and problems keep appearing?
- Have unwavering faith that no matter what, you will deliver this project
- Face the brutal truth of the situation, no matter what the plan says
This was useful advice for enterprise software projects which can last for years and sometimes feel like they will never end.
Optimists
We start IT projects as optimists and finish them as pessimists #HoskWisdom
Jim Collins has a blog post on the book called the The stockdale Paradox, and video here — Stockdale Paradox: A Message for Uncertain Times
When asked who didn’t make it out of the prison camps, James Stockdale answered.
“Who didn’t make it out?”
“Oh, that’s easy,” he said. “The optimists.”
“The optimists? I don’t understand,” I said, now completely confused,
given what he’d said a hundred minutes earlier.
“The optimists. Oh, they were the ones who said, ‘We’re going to be out by
Christmas.’ And Christmas would come, and Christmas would go. Then
they’d say,’We’re going to be out by Easter.’ And Easter would come, and
Easter would go. And then Thanksgiving, and then it would be Christmas
again. And they died of a broken heart.”
Most projects will disappoint because the project plan underestimates the effort, uses high-level…