Either/Or and the Question of Regret

There Is No Regret-Proof Life

No matter how much you plan, no life strategy can eliminate regret.

Let’s talk about regret as an existential condition.

Most of us assume regret is something we can outgrow. We tell ourselves that with enough foresight, enough discipline, enough patience, we will eventually make decisions that do not disturb us later. As though regret is a sign we miscalculated.

Soren Kierkegaard does not see it that way. In Either/Or, regret is not treated as an accident of poor judgment but as something built into the human condition. To be free is to stand before alternatives. To choose one is to let others go. That loss is unmistakably real. Regret grows steadily and persistently from that reality.

Kierkegaard describes two broad ways of living: the aesthetic and the ethical. They are not personality types. They are orientations toward life.

The aesthetic life is organised around experience: what feels vivid, stimulating, meaningful in the moment. It resists binding commitments because commitment feels like narrowing. To decide firmly is to accept that some versions of yourself will never exist. The aesthete prefers to keep the field open.

That is very understandable. Who does not want room to move? Who does not hesitate before closing doors?

But over time, the refusal to settle produces a particular kind of regret. It is not even always conscious. It is the steady awareness that life is being compared against other possible lives. You enjoy what you have, yet part of you is measuring it against what might have been. Even satisfaction feels provisional.

Kierkegaard captures this tension with unsettling simplicity: whatever you choose, you will regret it. The point is not that all choices are equally bad. The point is that choice itself carries exclusion. When you commit to one path, you cannot simultaneously inhabit another and the mind does not forget that.

The aesthetic response to this is often rotation; changing circumstances when they grow heavy, reframing disappointments as stories, keeping things fluid enough that nothing defines you for long. It can look sophisticated. It can even feel free. But the self remains loosely assembled. Regret lingers in the background because nothing is ever fully owned.

The ethical life begins when a person decides to live in continuity rather than in episodes. Here, one chooses commitments: to a person, to a vocation, to a way of being , and accepts that these commitments will shape the future. The ethical individual does not pretend that other possibilities cease to exist. He simply agrees not to live in constant comparison with them.

Regret changes form here.

Instead of regretting entire unlived lives, the ethical person confronts particular failures within the life he has chosen. The question is no longer, “What if I had taken a different road?” It becomes, “Did I act well within this road?” That shift is subtle but decisive. Regret becomes tied to responsibility.

While there is weight in that, there is also stability.

When regret is connected to responsibility, it can teach. It can lead to correction. It can deepen character. It assumes a self that persists through time; someone who can look back and say, without theatrics, that action was mine.

Kierkegaard’s larger insight is that regret reveals our relationship to freedom. We regret because we can imagine alternatives. Every choice contains a quiet farewell. You do not notice it at first. Years later, you might.

This is why attempts to eliminate regret often fail. Keeping all options open does not remove regret; it multiplies it. A life built entirely around possibility never consolidates into anything solid. The self remains hypothetical.

To live ethically is to accept finitude. You cannot be everything. You cannot test every identity. You cannot preserve every potential version of yourself. Some doors will close because you closed them. Others will close because time did.

That acceptance is not heroic. It is simply sober.

So when regret surfaces, the question is not whether you should feel it. The question is what kind it is. Is it the restless sense that you never fully committed anywhere? Or is it the steadier recognition that, within a life you chose, you sometimes fell short?

The first leaves you drifting. The second can make you wiser.

Kierkegaard does not promise relief from this tension. He suggests that tension is part of becoming a self. Regret is not proof that you have failed at life. It is evidence that you are living it as a free being rather than as a spectator.

You cannot design your way out of that condition. What you can do is choose carefully, accept the limits that choice brings, and remain accountable within them.

That is less remarkable than the fantasy of a regret-proof life. It is also more realistic. And perhaps, in the long run, more peaceful.