Title text: Of course, "Number of times I've gotten to make a decision twice to know for sure how it would have turned out" is still at 0.
This is a chart showing the outcomes when Randall was confronted with situations he wasn't happy with. It counts 13 situations which he realizes, in retrospect, he should have left sooner than he did, and only 2 situations where he should have stayed. The implication is that, in his experience, it's generally better to leave a situation you don't like, rather than stick with it in the hope that it will improve.
People often stick with situations they are not happy with (a broken relationship, an unfulfilling career, a stale piece of cake) because they think sticking with the situation is better than throwing it away, and fear that they won't find something better if they leave. This is sometimes referred to as "settling", thus the title of the comic. This risk aversion can lead to people sticking with something a lot longer than they ought to if they want to be happiest. Humans' aversion to loss is common; you, being at the necessary reading level for this wiki, can surely easily recall many times when you feared to lose access to something or someone you valued.
Economists and behavioral scientists refer to this behavior as the "sunk cost fallacy", more formally known as Escalation of commitment. Colloquially, this is a situation where resistance to change is justified by the amount of effort or time already expended. A proverb recognizing the error in this thinking is "Throwing good money after bad", while a competing proverb seemingly justifying the behavior is "In for a penny, in for a pound". The popular book "Thinking, Fast and Slow" by Daniel Kahneman details many "errors" in human decision-making, like our aversions to losses, the sunk cost fallacy, and others.
The title text references a common thread in human regret, which is wondering whether we should have turned the other way when making a choice ("I would have...", "I could have...", "I should have...", et al). Randall points out that it is literally impossible to know how it would have turned out, perhaps urging readers not to regret their decisions, and to live in the moment. It also points out that the previous "scorecard" cannot be regarded as certain, since a person is not given the luxury of knowing what would have happened if they had made a different choice. Thus, one can think that they made the wrong choice and would have been better off if they had left sooner, but in actuality, it may have turned out even worse. It is impossible to know, and therefore he can't be positive that he didn't actually make the right choice in the situations where he "should have left" .
Although knowing individual outcomes is impossible, and although it is difficult to separate correlation from causation when analyzing large numbers of decisions, rigorous attempts have been made. Notably, a paper titled "Heads or Tails: The Impact of a Coin Toss on Major Life Decisions and Subsequent Happiness". The paper confirmed that "For important decisions (e.g. quitting a job or ending a relationship), those who make a change (regardless of the outcome of the coin toss) report being substantially happier two months and six months later."
Times when I thought...
"I'm not really happy here, but maybe this is the best I can expect and I'll regret giving it up."
...It turned out I...
Should have stayed: 2 (in tally marks) Should have left sooner: thirteen (in tally marks)
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