The Benefit of Accepting Our Regret — A Lesson from Kierkegaard

And yes, we all have regrets

You know the drill. Ask someone if they have any regrets and nine times out of ten, you get a polished “No regrets!” or maybe an honorable mention regret — something that has a round-about way of making them look good. 

The reason why many of us do this is because regret has a stigma. It’s similar to the ones around mistakes and failures. And in the same way that our stigma toward failure can keep us from avoiding challenging opportunities (lest we be seen as failures), so too can our stigma toward regret stifle our progress.

The Danish philosopher Søren Kierkegaard noted this trouble as well in not facing up to regret. Whether we like it or not, this is the conundrum we all have before us:

Marry, and you will regret it; don’t marry, you will also regret it; marry or don’t marry, you will regret it either way. Laugh at the world’s foolishness, you will regret it; weep over it, you will regret that too; laugh at the world’s foolishness or weep over it, you will regret both. Believe a woman, you will regret it; believe her not, you will also regret it… Hang yourself, you will regret it; do not hang yourself, and you will regret that too; hang yourself or don’t hang yourself, you’ll regret it either way; whether you hang yourself or do not hang yourself, you will regret both. This, gentlemen, is the essence of all philosophy.” 

From this, it sounds like Kierkegaard’s got a pretty bleak outlook on life. But there’s a deeper lesson here that’s incredibly relevant to us. It’s partly to do with not taking life too seriously; not getting so hung up on a decision (which naturally conflates to one’s existence) as all-important.

Another takeaway from Kierkegaard is more obvious. It’s in his explicitness that every decision comes with regret. So whether you laugh at the world’s foolishness, weep over it, or even do something drastic like believing in love or contemplating offing oneself, regret is inevitable. It belongs in the same category as the realities of death, freedom, ego, anxiety, and responsibility — that is, as an existential given of life. 

Also, I think it’s worth clarifying: having a regret isn’t necessarily the same thing as saying I wish I didn’t have the reality I have. It’s coming to terms with mourning the death of a certain version of yourself that never got to live (e.g., becoming a parent).

Thus, with every choice, we face potential regret because we can never fully predict the outcomes or understand the paths we didn’t take. This is one of the burdens of human freedom and ego.

So what do we do?

Like mistakes or failures, it’s not just about avoiding regret. It’s about understanding and accepting that regret is part of the human condition. 

But of course, way easier said than done right? 

In fact, this is probably the existential challenge I’m most sympathetic to. I deeply understand the temptation to create a self-delusion out of the need to tell oneself and others, “I have no regrets.” The difficulty in avoiding regret arises from the difficulty in confronting what the regret becomes on second thought: The Great “What-If.” A haunting of narrative(s) spun in different directions, all seemingly effortless by your own mind, and all seemingly without regard for your own mental health. 

Add also that the benefit of accepting our regret isn’t at all clear after the first pass. Philosopher Simone de Beauvoir grew to understand this and poignantly expressed her anguish from regret and the what-if experience:

I want everything from life. I want to be a woman and to be a man, to have many friends and to have loneliness, to work much and write good books, to travel and enjoy myself, to be selfish and to be unselfish… You see, it is difficult to get all which I want.

De Beauvoir’s longing for everything life has to offer complements Kierkegaard’s views on regret. Her desire to experience the full spectrum of life’s possibilities underscores the inevitability of missing out on certain experiences. The more you want, the more you have to accept that you can’t have it all.

Acceptance, then, is still the key.

By accepting the inevitability of regret, we can hope to find a kind of freedom. Freedom in making choices. Freedom in knowing that they’re imperfect trade-offs. Freedom in embracing the unforeseen realities that, for better or worse, come as a consequence.

In the end, Kierkegaard isn’t telling us to be pessimists. He’s urging us to live authentically. To make our choices with the understanding that regret is part of the deal.

But despite that being the case, we don’t have to let regret define us. Whether you decide to marry, go to university, start a business, or simply take a walk along the coast, even though regret will meet you in some form or another on the other side, it’s a byproduct of a choice we get to accept as just that. It’s simply the cost of taking action. A small part of what it means to belong to this beautiful complexity of life — a life that, as Kierkegaard says, “isn’t a problem to solve, but a reality to be experienced.”

When we do this well — accept our regret — the benefit comes in eventually learning what it means to accept ourselves.