A character is driven to become the best there is — the richest man in town, the best martial artist in the world, the emperor of the galaxy... and succeeds.
But, along the way, the character winds up abandoning or betraying everyone and everything that character ever valued. These sorts of characters will inevitably wind up bitter and alone, having fulfilled their great obsession, but pondering everything they lost in the pursuit — just before losing the thing they obsessed over too. ("If only I'd never left the family farm/talked to that man/become a model/signed that contract/etc.")
This is often a form of reversed Wish-Fulfillment for the viewer, as average people want to be able to think that the things they don't have (such as an abnormal amount of money, power, skill, or beauty) won't lead to happiness, conveniently forgetting how, in real life, there are plenty of poor, enslaved, stupid and ugly people that are unhappy. But since not everyone wants the same things out of life, the Aesop doesn't always work that way.
A variant is for a character to achieve immortality, i.e. Who Wants to Live Forever?, and/or ultimate power i.e. God for a Day, and become suicidally bored over how meaningless everything is when it's so easy.
This phrase originates from the Chinese proverb "高處不勝寒/高处不胜寒"Note , which literally means "the top (of a mountain) cannot defeat the cold". It is commonly used to describe people of high positions may feel lonely at the top. Though that is not all to this proverb, it also means that individuals of high positions gradually become suspicious of those around him/her, thus feeling shivers running up and down their spine constantly. A similar proverb, huipulla tuulee, "it's windy at the (mountain) top", exists in Finnish, implying being on the top is both lonely and precarious.
Dying Alone is often threatened, though if they learn An Aesop it may be averted. A common component of a Pyrrhic Victory.
Often ends in a form of Karmic Twist Ending.
The natural conclusion of Ambition Is Evil and Being Evil Sucks. May overlap with Everything but the Girl. Contrast Celebrity Is Overrated, In with the In Crowd, and The Last DJ. Characters who are Married to the Job are especially at risk of having this happen to them. If the character merely gets a whole load of mental problems from trying too hard, he'll become a Broken Ace.
May overlap with Et Tu, Brute?, Victory Is Boring, I Just Want to Have Friends, God for a Day, Wanting Is Better Than Having, The Perils of Being the Best, No Challenge Equals No Satisfaction, and And Then What?.