It's no doubt quips such as these which are why Kierkegaard is seen as a bit of a Four exemplar. Truth to be told, if Kierkegaard was a Four, he was one who expended most of the Four issues in his youth and, developing a profound sense of humor about himself, saw the dangers of aesthetic self-indulgence in one's spiritual development.
It is not my intent to advise him as a tool for Fours today, however. Today, I would like to draw your attention to his work, Sickness Unto Death, which I believe could be highly helpful to type Twos.
Twos, for those of you familiar with the Enneagram, tend to be oriented towards being loved and being seen as lovable. It's often been said that if Fours want to be rescued, Twos want to be a rescuer. Twos, like Fours, are highly emotional, although it is positive emotion that they like to convey. Underneath this, however, is a profound neediness and a desire to be seen as caring, loving people. Twos can be dramatic, just like Fours can be, but they are typically less conscious of it. The drama of Twos manifests in effusiveness and often maneuvering for greater contact and closeness. Typically, this closeness is sought through good deeds--the loving spouse, the teacher with the "calling" to help others, the nurturing friend--although Twos, especially with a dominant Sexual instinct, can be seductive and flirtatious as well.
When Twos are healthy, they go to Four, becoming more introspective, more willing to spend time reflecting on themselves, and more aware of negative--as well as positive--feelings. To aid in going to Two, I think some reflections on Kierkegaard might be helpful.
Sickness Unto Death talks about people being in despair, although Kierkegaard lays out two types of despair: Earthly and Eternal Despair. Despair in this sense refers to trying to find the self through the wrong kind of relationship. For Kierkegaard, it is only in a relationship that a self can be found, but the problem is that most people go astray by looking in the wrong place for this. It is only with God that the right relationship can be achieved and the self realized.
In Earthly Despair, the person seeks a relationship with society to find the self. There are two ways in which this typically manifests: one is the affected individual, who seeks to replace herself by adopting a completely false self that is some sort of societal ideal. She never wants to reflect on herself, and tries to be someone else. In the second case, the person may engage in self-reflection for a time, but invariably lands upon undesirable, unflattering aspects of the self and experiences a bit of moral horror. Unable to face the dark side of the self, she distracts herself through involvement with the community: volunteering with one's church, giving to the arts, being a caring spouse and so forth. In short, the person is an upstanding member of society, all the while with the unconscious intent of avoiding reflecting on the negative aspect of oneself.
In Eternal Despair, the person realizes that nothing can be gained through involvement with society and withdraws, becoming aware of the dire situation, and staying in a reclusive, self-enclosed state. When this happens, the person may realize it is a relationship with God that is necessary. However, it is equally possible that the person will go mad in this isolated state, and engage in self-destructive behavior, ranging from addiction to suicide. Kierkegaard considered Blake and Shelley to both be in this kind of despair.
While these were intended to be universal and not type-specific, one can no doubt see the presence of the image triad types in Kierkegaard's account. The first kind of Earthly Despair reminds me a bit of the issues Threes are most vulnerable to, while the second kind of Earthly Despair reminds me a bit of type Two, and Eternal Despair contains definite similarities to Type Four.
For Twos, I think this is especially powerful. First, Kierkegaard presents a deeply spiritual account which, while certainly not applicable to every Two, still may appeal to a number of Twos. Kierkegaard presents a helpful reminder that society can often have elements that, while giving a sense of community, can interfere with the quest for self when gone too far. While I wouldn't go so far as to say that Twos should withdraw completely from society, I do think that by learning about the differences between the types of despair, could inspire Twos to explore spiritual techniques that require more solitude. These techniques could be anything from taking a bit of time each week to engage in spiritual practice to long walks in nature, to simply securing an hour a day in which they can close the door and practice a creative pursuit. The first step is to realize that too much involvement in the community can be a kind of despair or misrelation, and a distraction from facing the more unpleasant aspects of the self.
If you're a Two and philosophically inclined, you might find it helpful to read Kierkegaard's Sickness Unto Death. Try reading it in conjunction with journal keeping, where you read one hour a day, then write your reflections on what you think it means and how it might help you come to your security point, Four.
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