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You make countless decisions every day, and most of them come easily. But the few that could change the direction of your life can leave you stuck for months. The Stoics had an interesting explanation for why these decisions are so difficult, and why preparing for them begins long before the moment you have to choose.
We get better at most things through practice, and everyday decisions are no exception. Over time, you learn how long things usually take, whose promises you can trust, and which risks are worth taking. You make a choice, see what happens, and adjust the next time. Eventually, much of what you’ve learned becomes instinct.
Major decisions rarely give us that kind of practice. You might change careers or decide whether to leave a long relationship only a handful of times in your life. Even then, it can take years to see how things turn out, and the result doesn’t always tell you whether you chose well. A careful decision can end badly because of circumstances you couldn’t predict, while a careless one can work out through luck. This makes it difficult to learn from experience when the decisions matter most.
So when a major choice comes along, we try to make up for that lack of experience by thinking harder. We gather more information, ask more people, and wait until we feel certain. Sometimes that helps. But the Stoics understood something we often overlook. Long before a major decision arrives, we’ve already developed beliefs about what is safe, what failure would mean, and what we’re capable of doing. Those beliefs influence how we see our options, often without us realizing it. And if we want to make better decisions when it matters, we need to start paying attention to the judgments we’re making today.
Continue reading with a paid subscription to learn where the Stoics believed our biggest decisions are really made, why so much careful deliberation is fear in disguise, and how to judge a decision fairly once you have made it.