Chapter 1: Understanding Regret

What if experiencing regret is a fundamental aspect of life? The philosopher Søren Kierkegaard suggests that regret is simply unavoidable. He famously stated, “If you marry, you will regret it; if you don’t marry, you will also regret it; regardless of your choice, regret is a certainty.”

In his work Either/Or: A Fragment of Life, Kierkegaard articulates,

"I perceive it clearly; there are two possible paths — one can either choose this or that. My sincere opinion and friendly counsel is this: proceed with your choice or abstain — either way, you will experience regret."

Kierkegaard referred to this as “the essence of philosophy.”

In a discussion with Oliver Burkeman, author of Four Thousand Weeks, several key insights regarding time management emerged. Burkeman emphasized that,

Four Thousand Weeks is not just another time management guide; it’s written with the understanding that traditional time management approaches have largely failed, and we must face this reality.

We must confront some stark truths about our time. As Burkeman points out, “The average lifespan is absurdly, terrifyingly short.” However, this shouldn't lead to despair but rather offer relief. It allows you to abandon the futile pursuit of becoming the ideal, endlessly capable individual society often expects.

“The moment of ultimate control will never come — when the torrent of emails is under control; when your to-do lists cease to expand; when you’re fulfilling all your commitments.” — Oliver Burkeman

This perspective resonates with entrepreneur Derek Sivers, who shared, “If I’m not exclaiming ‘Hell Yeah!’ about something, then I decline.” However, in practice, there often isn’t enough time to accommodate everything that falls within the “Hell Yeah” category. Time represents an opportunity cost, meaning each affirmative choice implies saying no to something else.

In my conversation with Dr. Dilip Jeste, author of Wiser, he noted,

As life progresses, there’s often a moment of clarity. During this period, individuals tend to become more discerning about what holds significance in their lives and how they wish to utilize their limited time.

As finite beings, the impossibility of doing everything leads to regret. Similarly, our inability to foresee the outcomes of paths not taken leaves us ruminating on “what-if” scenarios.

To quote Kierkegaard, “Life can only be understood backward, but it must be lived forward.” In a reflective moment toward the end of his life, Christopher Hitchens remarked, “One will always harbor some regret; it’s essential to pre-determine what those regrets will be.”

How might your regrets influence the decisions you make moving forward?

Thank you for engaging with this reflection; I hope you found it insightful.

You can listen to similar brief reflections or interviews on one of our podcasts. Additionally, subscribe to our free weekly email meditation to receive three timeless insights delivered directly to your inbox.

Chapter 2: Embracing Regret as a Guide

The video titled "The Most Depressing Philosophy | Soren Kierkegaard Either:Or" delves into the profound insights of Kierkegaard, exploring the complexities of regret and decision-making in life.