Why Selling feels Uncomfortable?

Selling requires of us a significant change in our thinking - indeed a complete reversal! 

When we bought that stock, its prospects were wonderful, and it represented value and opportunity.  Now, whether our investment has since done well or not, to sell requires closing down hope and perhaps admitting defeat.  And it is possible that our defeat may have been created by faulty initial thinking, meaning we can place no blame externally since we were actually wrong all along.  Not a realiszation we savour.

Buying involves the opening o f possibilities of great things.  Buying represents open-endedness; continued holding maintains such hope for gain and pleasure (or, when we have a paper loss, hope for recovery and the righting of a temporary wrong).  Selling carries a finality with it because, by definition, it closes the book or ends the game and establishes a final score.  We prefer to have our options open rather than foreclosed, to retain chances for improvement and betterment rather than to know that the verdict is sealed and no chance for change exists.  We have great difficulty coming to closure since it cuts off further possibiiities; it ends hope for any better outcome.  Closure includes such experiences as

• cleaning out great grandmother's attic;
• graduating and leaving school and friends;
• acknowledging a failed marriage by concluding a divorce;
• burying a dear friend or loved one;
• seeing winter come;
• leaving an employer and valued colleagues;
• retiring and therefore wrapping up business. 

Those are heavy and sad passages, so we are predisposed to resist voluntarily creating any closure expereinces that we have power to avoid.  Holding does exactly that.

Holding keeps our options open, while selling clearly brings closure and finality.  (With surprising myopia, we ignore the fact that once we sell a stock we can just as easily repurchase it.  Viewing repurchase as a very real antidote to our revulsion against closure, however, raise visions of again going through that agonising process of reversing our opinion by 180 degrees, which is painful for all the reasons noted above.) 

• So we hold rather than sell because, at the very least, holding postpones coming to closure. 
• Many a bad stock is held (into an uncertain yet not hopeless future) with palpable likelihood of further financial loss because the (presently avoidable) emotional cost of coming to closure is perceived as so heavy. 
• Investors pay in dollar losses to avoid emotional pain from a closure process; often, as losses get worse, they will later need to pay a higher price in both lost dollars and eventual pain by imposing self-punishement over major mistakes. 

The closure aspect of selling is a powerful deterrent, one requiring both strong will and courage to overcome.