Overly Complicated Plans Subtopic

In a bold move, we've decided to create an entire subtopic dedicated to the art of overthinking things. Because, why not?

Subtopic: Overthinking 101
Subtopic: The Overthinker's Dilemma
Overthinking 101 | The Overthinker's Dilemma

Warning: excessive overthinking may lead to spontaneous combustion, spontaneous combustion, or spontaneous combustion of your social life. Proceed with caution.