John Kay argues against my naive five-year strategy in his book Obliquity. Our finest preparation can't keep up with the complexity of the world. Attempting to directly approach amorphous aims such as profit or happiness is a fool's way. A better strategy is to approach the object from the side. Take modest steps and iterate, making course corrections as you go. Kay's writing is simple and straightforward, making it a pleasure to read. He gives numerous examples of how direct planning fails and how obliquity succeeds. This book becomes tedious after a while, especially if you've already bought into the basic premise.
Obliquity is a term that represents the process of achieving difficult goals in a non-directive manner. Oblique approaches understand that complex objectives are sometimes imprecisely definedand contain numerous parts that are not always or obviously compatible with one another, and that we learn about the nature of the aims and the means of achieving them via experimentation and discovery. Oblique approaches frequently take a step backward in order to go forward. The belief that practical knowledge resulting from a process of adaptation and discovery might be superseded by rational design by an omniscient planner surged across many fields during the twentieth century. Modernism was the term used to define this approach.
Oblique problem solvers do not consider all available options; instead, they make a series of decisions from a limited set of options. Effective decision makers distinguish themselves not so much by the breadth of their knowledge as by their awareness of its limitations.
Rather than being direct, problem solving is iterative and adaptive. The ability to deliver persuasive narratives of how they arrived at their findings does not distinguish good decision makers. The most sophisticated systems emerge and function without anyone having a complete understanding of the system. Consistency, rather than being a virtue, is seen as a sign of stubbornness or ideological blindness by good decision makers. Rationality is not defined by good processes; irrationality is defined by sticking to ways and acts that are clearly ineffective, including those that are widely mislabeled as rational.
We learn about the structure of a problem as we solve it in obliquity. Begin by doing anything when confronted with a daunting task. Select a minor component that appears to be important to the goal. Oblique issue solution is the most reasonable approach to problems. Obliquity does not imply that we should cease thinking about goals, ignore alternatives, or refuse to seek knowledge and learn as much as we can about the complex systems we work with. When complex systems operate in an unpredictable environment and the impact of our activities is dependent on how others respond to them, obliquity is the ideal option.