How to Make Difficult Decisions in Life: A Brief Applied Philosophy

There are decisions that are easy even though they seem large. And there are decisions that are difficult even though they seem small. The former are resolved with an Excel sheet; the latter are not.

If you have spent weeks turning something over in your mind —changing jobs, ending a relationship, moving to a new city, saying no to a very good opportunity, saying yes to a simpler life, taking on the care of an aging parent, breaking off a fifteen-year friendship— you have probably already discovered something: the decisions that truly matter are not made by comparing options. They are made from another place. And most modern decision manuals, those advising pros and cons lists, Eisenhower matrices, and five-whys methods, offer little help precisely when you need them most.

This is going to be a different conversation. Slower. More philosophical. And, I hope, more useful.

Why Difficult Decisions Are Difficult

The first thing to understand is that difficult decisions are not difficult due to a lack of information. Almost never. When you have spent three months pondering whether to leave your job, it is not because you lack data. You know what you earn, you know what you would lose, you know what you like about it and what you do not. What you lack is not information. It is a framework. A place from which to decide.

Higinio Marín, a philosopher, says it in a way that sticks with you. Human beings, he says, cannot act without a framework of meaning. "Frameworks of meaning do not point to good, evil, truth, or falsehood. They point to the fact that we as humans are incapable of acting, incapable of living, without an assumed framework of meaning". That is to say: even when you are not aware of your framework, you have one. Deciding from an implicit framework —which almost no one examines— is what causes most of us to make decisions that seem reasonable at the time but then do not hold up.

The first task, therefore, is not to decide. It is to look at the framework. From where am I looking at this decision? Am I deciding from the person I want to be in ten years or from the person I was ten years ago? Am I deciding from the fear of losing what I have or from the desire for something that truly matters to me? Am I deciding from what my parents would say if they could see it or from what I would say if I could see myself with honesty?

That first question —from where am I deciding— is worth more than ten lists of pros and cons.

Three Modern Pitfalls When Making Decisions

The first: confusing indecision with prudence. Pondering something for months is not being prudent; it is often the opposite. Classical prudence —vigorously revived by Ricardo Calleja in his work on virtues in professional life— is not waiting. It is deciding well with the information one has, accepting that it will never be complete. There are decisions that remain in limbo for years not because they are complex, but because the person who has to make them has confused postponing with discerning.

The second: treating the decision as an optimization problem. There is no hidden "correct answer" waiting to be calculated. There are possible paths, all with costs, none with guarantees. Treating a vital decision as if it were a logical problem is one of the great formative mistakes of young professionals with stellar records.

The third: asking too many people for advice. Talking to fifteen people about a difficult decision usually paralyzes more than it helps. Each person hands you back their own framework, and in the end, you have accumulated fifteen foreign frameworks without having built your own. It is wise to talk about it, yes. With two or three people who know you well. The quality of the interlocutors matters a hundred times more than the quantity.

Prudence as a Virtue: Deciding with Incomplete Information

Ricardo Calleja insists, in his work on business ethics, on something that applies to all serious decisions —not just professional ones—: deciding well is more of a virtue than a technique. That means two important things.

First, it requires training. Just as any virtue is trained. By deciding, making mistakes, gathering what has been learned, and deciding again. The person who, at forty-five, makes difficult decisions well is not the one with the best method: it is the one who has spent twenty-five years deciding, failing in some, succeeding in others, and paying attention to what happened afterward.

Second, that prudence is not the opposite of audacity. This is a modern distortion that paralyzes many people. Classical prudence —that of Aristotle, that of Thomas Aquinas— necessarily includes taking action. It is deciding well and deciding when. The prudent person is not the one who doubts most; it is the one who knows when to stop doubting.

If you have spent more than three months turning something over in your mind and no new information has appeared, you are not being prudent: you are procrastinating. And procrastinating also has consequences. The life you do not decide today, you continue to live: the default decision is to stay as you are, and that is also a decision.

The Threshold Before the Decision

There is a movement prior to deciding that almost no one makes, and it changes the entire process.

Higinio Marín, speaking about how human beings organize life, says there are two fundamental verbs: to leave and to return. Every serious decision is, at its core, a small departure. A crossing of a threshold. Before the threshold, there is one life; after the threshold, another. "Human life depends, to find itself and to achieve itself, precisely on finding the threshold", writes Marín.

What is interesting is what comes next. Marín adds that no threshold is crossed alone. Every departure calls return into question. And that helps immensely when deciding. Before making a difficult decision, it is wise to ask oneself two questions that almost no one asks.

One: where am I departing to? It is not enough to know what you are leaving behind. You must be able to describe, even if imperfectly, the place you are going. If you cannot do that, the decision is not yet mature.

Two: what home do I have left if this goes wrong? Every serious departure assumes it might not go well. The question is not only "what do I want if it goes well", but "what relationships, what habits, what people, what inner place will sustain me if it goes wrong". If the answer is nothing or almost nothing, it is wise to reinforce that home before departing. Not to avoid deciding, but to decide well.

That prior gaze at the threshold —that recognition that every serious decision is a crossing with a possible return or none— makes you decide with a different weight. Without drama, but without frivolity.

Three Movements for a Difficult Decision

If I had to summarize, almost reluctantly, what making a difficult decision well consists of, I would do so in three movements. They are not sequential steps. They are three gazes that should be crossed before acting.

Look at the framework from which you are deciding. Ask yourself, with honesty, who is deciding within you. Is it the child who wanted to please their parents? Is it the adult who wants to resemble someone you admire on LinkedIn? Is it the self of the next ten years, or the self of next week? If you cannot name who is deciding, you are not ready. It is not necessarily that you have to wait; it is that you have to look first.

Look at the consequences for those who depend on you. Serious decisions almost never affect only the person who makes them. Your partner, your children if you have them, your parents if they need you, your team if you have responsibilities, close friends. Not so that they decide —you decide— but so that, in deciding, you do so having looked at what your decision will do to them. Decisions made looking only inward almost always age poorly.

Look at what your future self will tell you. This is the most useful test. Imagine yourself, not young, but old. You are seventy years old. You are sitting somewhere quiet. You have had a reasonably successful life. You see yourself today, with this decision before you. What would you tell yourself? Not what others would tell you. What would you tell yourself, viewed with the distance that only time provides. That voice —which exists, even if you cannot hear it clearly now— is usually the wisest one you have.

After Deciding

Once made, most difficult decisions continue to hurt for a while. Not because you have decided poorly, but because serious decisions always leave something behind. To decide is to renounce, and to renounce hurts. The idea that a good decision makes you feel immediately good is one of the most harmful modern myths.

What does distinguish a well-made decision from a poorly made one is what happens over time. A good decision, viewed from two or three years of distance, holds up: you would make the exact same choice mentally. A bad one —made due to pressure, fear, or to avoid difficult conversations— erodes. When you look at it from afar, you realize it was not yours to make.

Therefore, after deciding, it is wise to endure the initial discomfort without turning back prematurely —three months is short, a year is reasonable, two years begins to be a verdict— and to look from time to time, slowly, to see if the decision is still yours. Not to reverse it every week. To accompany it with honesty.

What Is Learned by Deciding

I conclude with an idea that captures the spirit of everything said.

Each difficult decision well-made trains you for the next. It does not make you immune to pain, or to error, or to doubt. It simply makes you someone more capable of looking directly at what lies before you. That, accumulated year after year, is what in other times was called having character. And, viewed closely, it is probably the only thing you will truly take with you at the end of your life.

Difficult decisions are not avoided. They are walked through. And by walking through them with honesty, one by one, you build that which no test, no method, and no manual can give you: a self that has decided its own path.

It is the work of years. It is worth it.