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Most people judge their happiness during the extreme moments, when positive or negative things happen to them. This is a statistical no-no, since these events are typically referred to as outliers. The best time for measuring happiness is actually when you're at neutral. When you have a moment of solitude between your distressful (or eustressful) day at work and before you take on the responsibilities of the home later in the day, you should take this important measurement. How do you feel when you aren't acted upon by the circumstances of your life? If you feel fulfilled and validated, you are probably leaning in the direction of what I'd consider "a happy person." If you feel deflated, defeated and weary with the world, you are probably closer to "an unhappy person."
I try to take circumstances out of the equation when measuring happiness because while they certainly can affect emotion, they don't tend to have nearly as large an impact as people think. In a study I read about in Happy for No Reason by Marci Shimoff, people who had won the lottery and those who had become paraplegics had rises and drops in happiness right after their events occurred to them. About a year later, however, despite these life changing events, the lottery winners and paraplegics returned to roughly their original levels of happiness. The pessimistic lottery winners returned to a relatively negative viewpoint while the optimistic paraplegics came back to their positive world view. The key then isn't about changing your circumstances; it's about changing your deep down levels of happiness.
This is why you must measure happiness when you are at neutral so you can know if you need work on it or not. If you tend to have trouble keeping optimistic, grateful and peaceful when no outside circumstances are acting on you, it is likely that you must work on your happiness levels through frequent happiness exercises like the ones I discuss in my new book. Learning about the true causes of happiness and how to go down an optimistic path will ensure that your future measurements are much more in keeping with those of a happy soul.