Soren Kierkegaard famously wrote, “Marry, and you will regret it; don’t marry, you will also regret it.” He kept going—“do this or that, either way you’ll regret it.” Why? Because most regret doesn’t come from making the wrong decision. It comes from simply making a decision.
That insight feels relevant today because modern life is engineered to keep every alternative visible. Like getting “outordered” at a restaurant. You order the fish and regret it when the other entrees you didn’t choose hit the table. Suddenly you’re questioning your life’s decisions. At any moment, you can open Instagram and see friends traveling to Europe, running marathons, celebrating anniversaries, retiring early, or somehow doing all of those things at once. How absurd. Life becomes an endless digital comparison trap.
That comparison trap trains us to compare reality against fantasy all day long. Reality loses every time, because no life feels extraordinary from the inside…all the time. Every meaningful life eventually becomes ordinary, because ordinary life is where human beings actually live. I suspect that even the Pope occasionally gets bored with his life.
Much of modern dissatisfaction comes from a refusal to accept this basic truth. People keep searching for the choice that eliminates regret altogether—the perfect partner, the perfect city, the perfect career, the perfect setup. It’s a recipe for disaster.
Every meaningful decision costs something. The goal isn’t to find a life with zero tradeoffs. The goal is to choose tradeoffs you can live with. You do not get to avoid sacrifice. You only get to decide which sacrifices are worth making.
Wisdom has less to do with making flawless decisions and more to do with learning how to stop idealizing the alternatives. Because perfect choices are a fantasy. You have to notice when your imagination is distorting reality. You have to catch yourself when you start worshipping the road not taken.
Psychologists have found that people are often less satisfied with decisions that can be reversed. Because reversibility keeps alternative realities alive in the mind. You buy a new piece of clothing that is returnable. Prior to wearing it, you obsess about taking it back to exchange it for something else. But once a decision feels final, something surprising happens. The noise begins to quiet. Not because the choice became perfect, but because commitment changes attention. Instead of obsessing over alternatives, we begin to commit to the life directly in front of us.
Kierkegaard understood that regret is not a sign of failure. Sometimes it’s simply proof that your decision mattered. Proof that you are alive enough to feel the weight of both what was gained and what was lost.
Peace doesn’t come from finding a regret-free life. Maybe peace comes from accepting that every intentional life contains both a sense of gratitude and a sense of loss. You can deeply love what you chose while still feeling the occasional ache of what you left behind. It’s human. That tension is not a flaw in the system. It’s just human beings—being human. See what I did there? And here is the strange truth: the road not taken is often an imaginary one. The intentional life must bear the full weight of existence—the compromises, disappointments, sacrifices, and responsibilities that come with being alive.
Maybe maturity is learning to love the life you have. So that you stop wondering whether another path would have made you happier.
Because no path saves you. You didn’t make the wrong decision. Your regret comes from simply making a decision.
Ever made any decisions you regret? I want to hear about it. Email me at [email protected]. I promise you’ll hear back from me.
