In his book, Barry Schwartz talks about some of the reasons why modern Western societies suffer from ever increasing trends of depression and unhappiness. While the "grass is always greener" view of human nature is something we have all thought about and hold to be self evident, Schwartz takes this discussion a step further and makes his conclusions personal with simple examples of everyday situations that contribute to unhappiness in our lives.
In a speech he gave in 2005, Schwartz describes how even the simple act of buying salad dressing - of which his local grocery store has over 75 options - can become a source of stress or negativity if the wrong choice is made. It is this excess of options, this extreme freedom of choice in our lives, that creates a pressure to choose correctly and ultimately leads to an acute awareness of when we fail to make the right choice. By understanding all too clearly the opportunity costs of our decisions (which in large part is propagated by the marketer's goal to "inform" us the consumers - if interested in this topic read Buyology by Martin Lindstrom) we become critical of ourselves when the wrong choice is made.
Not only applicable to the trivial things such as choices in food or clothing in our lives, the paradox of choice extends to our decisions regarding career and social setting. From the ever present dissatisfaction that many have with their current jobs to wondering if you have chosen the right partner, it is our awareness of the alternatives that has corrupted our ability to be happy. In essence happiness is settling on something. Basically nothing more than an appreciation - based on ignoring everything else - of what we have over what we could have. Maybe this is why divorce is so prevalent in the United States today, because married people know that at the flick of a switch they can be single testing all of the options that are available to them.
The issue is one worth thinking about and meditating on because by all current measures our options our only going to continue to increase. Whether it happen to you while on a vacation or while sitting at your new job, it would be smart to stop yourself from ruminating over all of the other things you could have done. Although there is a fine line between optimizing your choices versus obsessing about your failures maybe just maybe you would be happier if you stayed put.