According to a podcast by Stephen J. Dubner on Freakonomics.com, there are upsides to quitting - if you do it for the right reasons. Other than the often cited career changing quits, one may quit a band, a bad habit, a sports team, a community and even a religion.
In evaluating the dilemma between staying or going, a common consideration is the balance between sunk costs and opportunity costs. This a trade-off between what you've spent (time, money, energy) in any endeavour, and what you're foregoing if you do choose to continue in that trajectory.
Often, people end up sticking to what they're doing because of the blood, sweat and tears that they've already invested in any activity. Indeed, Dubner shared that humans are psychologically wired to avoid waste, and quitting would seem counter-intuitive.
However, failing to recognise that one is on wrong path may sometimes be an emotionally and psychologically damaging exercise if one recognises, many years later, that one has been flogging the wrong horse. By then, it may be too late to unravel the years of lost youth and opportunity.
This problem is further compounded by the issue of knowing when to quit. According to Seth Godin's book "The Dip", one shouldn't simply bail out at the lowest point of one's career/relationship/project/whatever if pushing it for that much longer will yield the results that one desire.
In other words, don't quit when you're feeling down, crappy, or embattled. Instead, quit when you're clear that you're running the wrong race, headed to a destination that is uncertain to bring forth personal fulfillment.
Of course, the question is further worsened by the difficulty in measuring success and failure.
Does rising to the top of the organisational food chain constitute self actualisation? Is material achievement the only yardstick? On the flipside, is success measured only by your own happiness as opposed to your influence on the lives of others?
In the arena of one's mind, played between one's dreams, goals and ideals, one also needs to consider the harsh realities of life. Repeated quitting may give one a temporary psychological boost, but does nothing for one's financial situation. And we all know that inflation isn't going to go away anytime soon in a growing economy.
As we consider once again this age-old question, let me leave you with a song that perhaps best characterise the issue of whether one should stay or one should go: