Sun Tzu's six rules for identifying rewarding position generically based upon timing.
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This article explains that the advantages of new positions come in a variety of flavors. The problem is that we can only judge the value of new positions once we have moved into them, not before. We cannot know if we have actually improved our position until it proves to be more rewarding than our previous position. Some forms of rewards, especially financial rewards, are quantifiable and theoretically easy to compare, but most of us don't keep detailed ledgers. We keep mental ledgers that record a wide variety of things. Other forms of rewards, such as wasting our time, are difficult to compare because they are measure in quality of the experience rather than a comparable quantity. Most situations are a trade-off between quantitative and qualitative values.