
Flying airplanes is serious business. Mistakes are costly, not just because of the cost of the aircraft; if you're flying people, their lives are on the line. Jesse knows this better than most, having two brothers who are pilots. One day he overheard them talking shop and narrowed in on a common occurence they had teaching student pilots to fly -- these pilots were afriad of "hooking," that is, making a mistake on a flight and having to redo the assignment.
Jesse realized that everyone, including people who work high stress, high stakes jobs, learns through making mistakes. He quotes his favorite definition of intelligence, which "error correction." We learn by making mistakes then fixing them. And this must happen even for the most critical jobs like flying airplanes.
The same applies to money. Can you afford to make mistakes? Of course! You will mistakes, it's all about how you error correct after the fact. That's what the Five Questions help you do. They help you clarify what you want your money to do for you, and when you make a mistake with money, they help you correct your path and get you back on track. So, ultimately, you can live spendfully, loving the way you spend.
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