The psychotherapist Irvin Yalom, in his book Staring at the Sun, points out that many of us live with the dim fear that on our deathbeds we’ll come to regret how we spent our lives. Remembering our mortality moves us closer to the deathbed mindset from which such a judgment might be made—thus enabling us to spend our lives in ways that we’re much less likely to come to regret.

Truly to confront your own mortality, Yalom argues, is to undergo an awakening—a total shift in perspective that fundamentally transforms how it feels to be alive. […] To make that switch, Yalom insists, is not merely to ratchet up the intensity with which you live, but to alter your relationship to life. It is a transformation he describes, borrowing the language of the philosopher Martin Heidegger, as a move from focusing on ‘how things are’ to the fact ‘that things are’—on the sheer astonishing is-ness of existence.

[…] When you really face mortality, the ultimate and unavoidable worst-case scenario, everything changes. ‘All external expectations, all fear of embarrassment or failure—these things just fall away in the face of death, leaving only what is truly important,’ Apple’s founder Steve Jobs once said, in a speech that was speedily co-opted by several gurus of positive thinking, though in truth its message struck fatally at the heart of theirs. ‘Remembering that you are going to die is the best way that I know to avoid the trap of thinking you have something to lose. You are already naked.’

Start thinking this way, Yalom points out, and it becomes a virtuous circle. Living more meaningfully will reduce your anxiety about the possibility of future regret at not having lived meaningfully—which will, in turn, keep sapping death of its power to induce anxiety. As he puts it, there is a positive correlation between the fear of death and the sense of unlived life. Live a life suffused with the awareness of its own finitude, and you can hope to finish it in something like the fashion that Jean-Paul Sartre hoped to die: ‘quietly … certain that the last burst of my heart would be inscribed on the last page of my work, and that death would be taking only a dead man.’