A common pitfall I see everywhere in our culture is judging the success or failure of a strategy through outcomes.
You might win with an inferior strategy, or lose with a superior strategy, so disregard results from your judgment.
All of us are operating on a daily basis with incomplete information, unlike chess, which is a game of perfect information.
In sports and business, you can have a good strategy and still a bad outcome. There’s luck involved, a mirage of factors that are outside of your control, and many unknown unknowns that handicap your ability to anticipate.
When evaluating if a strategy was good or bad, don’t look at the outcome, instead, evaluate what the strategy is trying to accomplish in light of the strengths and weaknesses that could be known at the time, anticipation is an art because you can never know for sure what other parties will do unless you’re cheating—winning strategies share anticipation as their main tenet, the ability to anticipate and navigate the unknown is everything but easy, and will never be perfect.
Don’t be results-oriented. Instead of saying “the strategy was good” or “the strategy was bad” by merely looking at the outcome, look deeper, understand what information the players had, and evaluate in lieu of that—could they’ve anticipated more than they did? What could they’ve done differently?
This framework will allow you to craft winning strategies in the long run, because if the strategy is sound, and your ability to anticipate was on point, eventually the outcomes will start to align.