Context is not a well understood concept in context of decision-making:-) By context, I mean a set of conditions (mostly interconnected) under which something works or occurs.
We go to school (higher education) and learn theory which tells you how the world should work and not necessarily how it actually works. Subjects are taught in universal terms and not in relative (or context-specific) terms. How many classes have you seen on mastering context? So, how do you learn context? Mainly, by experience and thinking. However, most people are mentally lazy and they don't think about why something worked. One of my heroes, George Bernard Shaw, famously said, " Few people think more than two or three times a year
. I have made an international reputation for myself by thinking once or twice a week."
We tend to think that success was because of our actions and failure was because of others' actions. We like simple rules of thumb which don't require us to think much and to react quickly. I have seen many successful entrepreneurs go to big organizations and fail and many executives from big organizations go to start-ups and fail. They replicate their decision that worked for them in the past and in a different context the same decisions produce different results.
The idea of being successful for many people is to do what the other successful people have done to become successful. However, we fail to understand the conditions that made someone successful and those conditions may not be available to us. It would be much more fruitful to understand how the successful people approached decision making, what skills did they have and analyze if you have those skill or could you acquire those skills.
The Golden Rule in most religions is "Do unto others as you would have others do unto you." It is a good rule in most cases but what if the others don't want what you want? Our social conditioning also encourages context-free rules and thinking. We tend to replicate the behavior of people we like. The other problem is communication and memory. It is really hard to communicate and make people remember, "well, this rule only works in conditions x,y,z".
The coming years represent an interesting problem. The world is getting more interconnected, there is too much information available, and everything is moving faster. So, we need to get better at understanding context but we may not have time to analyze the conditions. People who may do well are the ones who understand systems (which by its nature teaches you context) and those who effectively use machine intelligence for decision making.