Jesse ran across a quote from one of his favorite authors, Nassim Taleb. In his book Antifragile, Taleb advises "invest in preparedness, not prediction," which also neatly describes the goal of YNAB. We cannot predict the future with any certainty, so it's folly to behave as if we can with our spending habits. What we can do, however, is prepare for the future by embracing our future expenses, and even though we don't know exactly when (or how much) those future expenses will occur, we can save up a pile of cash to handle them.
Jesse gives the example of an old car. As his early 2000's Toyota Camry aged, he started dutifully socking away $150/mo to cover inevitable repairs as well as a replacement vehicle. Years later, he had enough for a replacement, but the car was still humming along. So in this case he did not successfully predict the future. He could have held off on saving that money and directed it toward something else. At the end of the day, however, by preparing for the day he needed a new car, Jesse had a pile of cash in his bank account. When that day didn't come, he still had lots of options, because he had the cash. If he hadn't prepared, and the car died earlier than expected... then he likely would have ended up having to borrow money for the car.
This gets back to the idea of being "antifragile." Owing money is a state of fragility, because someone else has a claim on your future cash flows until you pay off the debt. It prevents you from using your cash to prepare for the future.
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