An ongoing life challenge for human beings is to face suffering, various sorts of loss, and life itself, that ultimately leads to death. This paper is an attempt to reflect on these existential givens from a psychoanalytic perspective.I will begin this paper by sharing a personal experience about my observing myself getting older, both on an ontic and ontological level. I also reflect on how the people around me react painfully and squirm on coming face-to-face with this natural life process. This reaction in turn, leads me to investigate how psychoanalytic contributors, not least, the founder, Sigmund Freud, together with modern contributors like Adam Phillips and Matthew von Unwerth, perceive and interpret beauty, joy, and life in relation to loss and transience. Under Phillip’s influence I again ask two fundamental, recurring questions, namely: ‘Is there the right amount of suffering in the world?’ And, ‘Does life ask more of us than we can bear?’In this paper, I am focussing exclusively on how we tend to perceive beauty and joy as tarnished and destroyed by transience, loss and death. Moreover, I will focus on our difficulty to endure the constant tensions and conflicts that life bestows on us, especially with regard to the process of mourning. More specifically, I will draw on my experience as a counselling psychologist in training, my work with a particular client, and the affects this triggers in me. I conclude this essay by quoting Phillips’ contention about the uncanny paradox of suffering.