The Stockdale paradox refers to Admiral Jim Stockdale, who was the highest ranking United States military officer in the “Hanoi Hilton” prisoner-of-war camp during the height of the Vietnam War. Tortured over 20 times during his eight-year imprisonment from 1965 to 1973… in Jim Collins book “Good to Great” chapter 4 page 83 (which is by no-doubt a must book) he is quoting Stockdale saying: “You must never confuse faith that you will prevail in the end – which you can never afford to lose – with the discipline to confront the most brutal facts of your current reality, whatever they might be.”
The Stockdale Paradox have much deeper implications than I present in this post and I am only using it to shed some light on The Pessimistic Developer Paradigm
I truly believe that in software projects, the pessimistic developer will win 80% of the software “battles” over an optimistic one (which is more than enough for me as a true believer in the pareto principle).
Don’t be confused with the semantics of what I am saying; we are not talking about this-can’t-be-done developers! – the best developers will keep an “optimistic attitude” (a.k.a. can-do spirit) with an “pessimistic mindset” (a.k.a. what could possibly go wrong?)
A “pessimistic mindset” will bring you to double-check, anticipate and be pro-active in mitigation of possible points of failures.
Saul Lieberman said ”The difference between a smart man and a wise one is this: A smart man can work his way out of a difficulty that the wise man will not get into in the first place”
I heard it many times and saw it in real life more than once so don’t “kill” the pessimistic messengers in your organization…
Keep being pessimist in the tacticalities (I want to patent this term :-) and insure your strategic success.