In practical matters, we are always happening upon the one-in-a-million and the could-have-been-otherwise. These encounters introduce uncertainty into our choices. Having only explored a few options, aren’t we bound to wonder if the best may be found elsewhere? How can we know that we’ve seen all that there is to see? This is a real fear that many experience. Fortunately, it’s a fear that prudence addresses. How? By insisting on the difference between what we can know and what we can’t, and by seeking the certainty of a virtuous life squarely within the bounds of human possibility.

How then are we to proceed? Furthermore, what are we to do with our uncertainty? Should we hold off on the decision until we’re really sure? Or open the Bible randomly and look for a sign? Or something else entirely? The answer has become familiar by this point. If we want to choose well and be certain, we have to grow in prudence. This means, first, cultivating genuine moral maturity — persevering in prayer, making good use of the sacraments, seeking to grow in virtue, introducing some penance in your life, cultivating healthy friendships, studying the faith. It also means reimagining what we mean by certainty. Decision-making simply has to get away from evaluating tortured psychological states. The “correct” answer isn’t a matter of performing the right mental gymnastics. Decision-making will continue to remain difficult, but that difficulty needn’t disconcert us. Rather, it ought to draw out an increasingly free and generous response. And, since prudence perfects our use of practical reason, making us both whole and bold, it is the key for bringing about this transformation and readying us for a life of concrete choices. Only in this way do we derive certainty.

In short, we don’t need to know everything there is to be known about a choice before we choose. The only prerequisites are knowing what can be known and acting in accord with virtue. Prudence, with the certainty it affords, accomplishes both of these things. Ultimately, the goal of a prudent life isn’t to avoid all mistakes or to guarantee all successes; it’s to live one’s life well and become a saint. As it turns out, a touch of uncertainty and a glut of errors are entirely consistent with that goal. This side of eternity, we can only achieve the uncertain certainty of prudence, but that’s enough to choose well and to do the good with what we’ve got.

There are different kinds of certainty to be had in life, depending upon what kind of knowledge we’re working with. Usually, when we think of certainty, we think of absolute or mathematical certainty, sometimes called speculative certainty. This is the certainty we have that 2 + 2 = 4. This is the domain of the virtues of understanding, knowledge, and wisdom. Prudence can’t give this kind of certainty, because it doesn’t deal with the same subject matter. Prudence deals with the uncertain truths of human action. The certainty it gives is an uncertain certainty, sometimes called moral or practical certainty. Moral certainty is basically the certainty we have of something that happens for the most part.

Moral certainty is the certainty that a jury is looking for before they rule on the guilt of the defendant. As they hear a variety of witnesses, they are looking to find a preponderance of evidence. Once they have it, they can be certain of their ruling. Prudence works a bit like this. Prudence’s certainty, though, is not based on the testimony of witnesses. Rather, it’s based on the testimony of the moral virtues. Effectively, when lining up an action, prudence checks in with justice, fortitude, and temperance. The prudent person asks, would a just, courageous, and temperate person perform this action? If the answer is yes, then he or she can be certain. That’s roughly all that moral certainty entails. Why, though, the testimony of the moral virtues? Why not something else?

The moral virtues give prudence its principles for action. As we have seen, the moral virtues clarify our appetites, providing us with insight into human goods. As the moral virtues make us to be better, they cause us to see better, and with that comes certainty. The more robust our formation in the moral virtues, the more certain is our footing in practical matters. Take the example of a battlefield commander. Neither a cowardly nor a rash captain has surety of his commands. A cowardly captain can’t be certain when he thinks his company should retreat. His inclination might just indicate that he lacks the fortitude to take the requisite measures. The rash captain can’t be certain of his action either. He may feel impelled to take a risk, but, then again, he always does. Perhaps he simply doesn’t value his life or the lives of his soldiers. A courageous captain, though, can afford to be certain. He knows that he wouldn’t ask anything of his soldiers that he doesn’t first ask of himself. He also is able to see what is called for in the circumstances. As a result, he sets out boldly. In the case of the captain, moral virtue is the key to moral certainty. When he knows that his action arises from a courageous character, he can be certain that it is a prudent course.

Not only does prudence take its cue from the moral virtues when formulating the action, it also checks in with the moral virtues when performing the action. In this exchange, the moral virtues let prudence know whether its judgment is sound or not. If it is sound, the judgment translates to virtuous action. If it isn’t, then it doesn’t. Take the example of a soon-to-be college graduate. She has big plans for the future. She wants to make it as a writer, launch a periodical, and work for social change. At this point though, she doesn’t know how best to go about it. Should she look for jobs in creative writing? Should she apply to graduate school? Because her path will be arduous and long, it’s hard to say which will contribute best to the realization of her big plans. Still, she can have a kind of certainty. She knows that if she is going to succeed, she will have to grow in virtue. She will have to grow in truthfulness (justice), magnanimity and perseverance (fortitude), and humility (temperance) — just to name a few. With this in mind, she can approach her decision with an eye toward growth. Which will challenge her more, contribute more to her formation in character? Ultimately, she can be certain of her choice, provided it is just, courageous, and temperate. Here, again, moral virtue is the key to moral certainty. When she knows that her action bears out and contributes to a just, courageous, and temperate character, she can be certain that it is a prudent course.

Prudence is situated “between” the moral virtues. On the one hand, prudence receives its principles from the moral virtues. The more morally virtuous one is, the clearer those principles are. On the other hand, prudence applies its judgments to the moral virtues. The more prudent one is, the more consistently one’s judgments translate to morally virtuous action. Prudence and the moral virtues are mutually reinforcing. They grow together. Where the moral virtues are, there too is prudence. As a result, the moral virtues secure prudence’s objectivity. In answer to the question, “Is this a prudent choice?” one can respond with greater certainty provided that he or she is just, courageous, and temperate. The key to prudence’s certainty is the unity and integrity of the human person ordered to action by a life of virtue.

Prudence isn’t bound to a hypothetical best possible state of affairs. Instead, it seeks what fits with a virtuous character.

Notice that this doesn’t mean that one is always searching for a single correct answer. In fact, it leaves a lot of room for variety. Prudence isn’t bound to a hypothetical best possible state of affairs. Instead, it seeks what fits with a virtuous character. The goal is to choose means that accord with virtue and promote virtue. There are always better and worse means to a given end. Of course, one seeks to identify the best, but it may not always present itself. Say, for instance, that you’re choosing a Christmas present for your goddaughter. You ask her mom what she wants. You ask her what she wants. You shop around, make purchases, wrap the gifts, and present them. As she opens them up, it’s clear that, while not displeased, she’s not blown away. You got some B+ gifts. Better luck next year. After the fact, you can evaluate whether there were better options, and maybe you approach it differently next year. Frankly, though, the main point is that you love your goddaughter and that your gifts tried to convey that. That’s enough.

The prudent person can’t treat morality as if it were a deductive science. Human life is too complex, and it takes more than intelligence to figure it out. Truth be told, trying to get the correct answer in every choice may actually paralyze prudence. If only the hypothetical, best possible solution were sufficient, you couldn’t ever be certain that you had happened upon it. In practical matters, there is simply no speculative certainty to be found. Making a choice isn’t like solving a math problem. Certainty in a choice will never be such as to remove all anxiety, and so you have to learn to live with it. All you get in practical matters is the uncertain certainty of prudence. In time though, the life of virtue imparts its own confidence and certainty. Moved by the moral virtues and applied to the moral virtues, prudence’s judgment begins to take on the aspect of surety. Ultimately, the real human certainty derived from prudence lies in its power to make one good.

Think of how this applies to Natural Family Planning. How do a mother and father know for sure that they are ready to welcome another child? Short answer: They don’t. Long answer: Couples may consider a variety of reasons for waiting to conceive. There may be serious financial constraints; they may have children with special needs who demand much of their energy; the mother may have grave complications with each pregnancy. In their thought and prayer, they weigh these factors prudently, with an openness to God’s will, and eventually come to a decision. Still, they will never be absolutely certain of their choice. If they seek such certainty, they may risk overplanning in search of the hypothetical, best possible solution. Whatever they choose though, when they choose prudently, will give them sufficient surety. Though they cannot know beyond any shadow of a doubt, they can know enough. Their family plan will not disappoint, provided only that it is shaped by virtue and genuinely open to life.

We are responsible for becoming good and acting well. We are not responsible for weighing every possible factor that may contribute to a choice. We can neither know those factors nor act upon them. Limitation is baked into our human reality. Acknowledging and accepting that fact doesn’t amount to resignation; it is actually a source of empowerment. Consent to the limitations of what prudence can and cannot do brings with it the wholeness and boldness of real human certainty.

Human certainty comes from what we can really know, but in practical matters there are a lot of unknowns. Real certainty is found within those limits, within the terms set for us by our actual lives. When it comes to limits, we first have to be reconciled to the inscrutability of human affairs. In a given situation, there are any number of ways that you can legitimately act. And with each of these ways, there are potential consequences, both good and bad. Once you begin to entertain all of these consequences, the prospect of making a decision may become overwhelming.

For instance, let’s say that a friend recently hosted you for the weekend while you were in town for business. You are grateful and want to communicate that. You could buy her a little house plant, for instance, or give her a gift certificate to a local restaurant. In truth these are both good options. But might there not also be unforeseen complications that render them unfitting? On the one hand, she might be hyper-pragmatic and see a house plant as just something else to take care of in her already busy life. On the other hand, she might see a gift certificate as evidence that you’re not comfortable receiving without repaying, causing her to question the authenticity of the friendship. So, what do you do? Get bent out of shape at the thought that she might be less than pleased and choose to do nothing? No. The point is that you do something that expresses your appreciation and attempts to deepen your friendship. Depending on how well you know her, you might be able to anticipate potential sensitivities, but you also might not. You can only act on what you can know. You are not responsible for reading her mind, and it’s not reasonable to expect that of yourself. What is reasonable is that you act virtuously. Provided that you do, you can be certain that the act is good. Might it have bad consequences? Perhaps, but truth be told, that’s not your business.

Even though human affairs are inscrutable, we have what we need for choosing well. Prudence sees to that. First, it gathers the variety of our moral experience, drawing upon our successes and failures and taking its cues from law and grace, custom and culture. Then, it condenses that experience into a rough working model, one reflecting what happens always or for the most part, which then serves as the basis for present and future endeavors. This working model gets the job done as well as it can be done. Errors crop up, but they’re rare. In the case of selecting a gift for your host, your response is shaped in part by your virtuous formation, by the setting in which you live, and by the peculiarities of this particular friendship. For most people, a small gift will do the trick perfectly. Every once in a while, you’ll be thrown for a loop, but you needn’t brace yourself against that chance occurrence. You take it in stride.

Practically speaking, we cannot live in perpetual fear of the consequences of our choices, nor permit them to keep us from acting. Negative consequences will inevitably arise from our decisions. This is especially true when it means confrontation with another person. Perhaps you are thinking about suggesting to your friend that he see a counselor or therapist, but what if he takes it the wrong way? Or maybe you are thinking about alerting your boss to some financial irregularities, but what if some of your colleagues get fired? What do you do?

If you are dedicated to living in truth and abiding in love, it’s practically guaranteed that you will upset other people. That’s very stressful, but it shouldn’t keep you from acting. You are genuinely able to testify to the truth and encourage others in virtue. You may be uncertain of your ability to do so, but you can’t let that get in the way. With each interaction of this sort, you can simply ask yourself: “Does this actually matter? Can this actually change? Am I actually motivated by love?” If the answer to those questions is yes, then it’s just a matter of timing. Do your best, and don’t beat yourself up if the other person reacts poorly.

Over the course of a lifetime, interactions like this should get easier, and occasions of stress and perplexity fewer. As your working model gets fine-tuned, it draws more readily from a richer store of experience. This isn’t simply to say that by experiencing more things, you will automatically become more prudent. There are plenty of “experienced” people who live imprudently until their last breath. This goes back to the integral part of memory. What is important isn’t so much a breadth of experience as a depth of experience. The prudent individual might never leave his zip code, but he can nonetheless discover what is in the heart of man. So, while he might not see everything there is to see, he can come in time to experience everything there is to experience. With that comes a greater moral certainty, even in difficult encounters. That is what lies in store. That is what is expected of us.

That accounts, then, for the things below us — the inscrutability of human affairs. But, what about the things above? Many experience God’s designs as maddeningly mysterious. The Psalmist sings, “Such knowledge is too wonderful for me; / it is high, I cannot attain it” (Ps 139:6). Saint Paul muses, “O the depth of the riches and wisdom and knowledge of God! How unsearchable are his judgments and how inscrutable his ways!” (Rom 11:33). God’s ways are so far beyond us. Despite our best efforts, they seem to always elude us. Though one might peer behind the veil at times, the common lot is one of general bewilderment. To what extent, then, can we really know his plan?

Imagine someone who reasons about a decision along the following lines: God is eternal, so he sees everything — past, present, and future — in one gaze. In that one gaze, he sees my life, my future, my flourishing. God knows it all. What is more, he knows this choice — how it should go, how it will go. But, for whatever reason, God has not seen fit to reveal to me what he knows. Perhaps he will reveal it at some future date. In the meantime, everything else remains on hold. After all, I don’t want to mess it up.

While some of this thinking is true, it represents a flawed way of understanding and interpreting God’s providence. What is more, if endorsed, it can seriously hamstring our efforts at living a virtuous life. There are four basic tenets at work in this position:

1. God knows the plan.
2. I am capable of knowing the plan.
3. In order to act, I need to know the plan.
4. It’s up to me to know the plan and to act upon it.

Each tenet is true on the surface, but underneath a few of them is just enough error to skew one’s understanding of divine providence.

God knows the plan.

If God created it, he knows it. Since he created it all, he knows it all. Since God is the author of all creation, his providence encompasses every imaginable aspect of things visible and invisible. Nothing escapes his gaze. There’s nothing here that’s objectionable.

I am capable of knowing the plan.

Indeed, we have intellectual natures capable of receiving God’s revelation. By faith God gives us his very own knowledge of himself. Faith, though, is a virtue on the way. “Faith is the assurance of things hoped for, the conviction of things not seen” (Heb 11:1). Faith isn’t yet the vision of heaven. “For now we see in a mirror dimly, but then face to face” (1 Cor 13:12). While on earth, there will always be limits to what we know. Even in heaven, we still won’t know the plan exactly as God does. To comprehend the plan perfectly, we would have to comprehend God perfectly. But God is infinitely greater than our minds and hearts. As human beings, we can only know his plan to a limited extent, according to our limited capacity.

In order to act, I need to know the plan.

It’s true that we can’t choose what we don’t know, but we don’t need to know all of the details, just some of them. We need to know what pertains to us, and that is for God to decide. Often enough, God chooses to show us the next step and little else. We have to be content with that. As St. John Henry Newman writes:

Lead, Kindly Light, amid the encircling gloom
Lead Thou me on!
The night is dark, and I am far from home—
Lead Thou me on!
Keep Thou my feet; I do not ask to see
The distant scene—one step enough for me.

One step is enough. While it might be nice to have a sense for the whole of one’s life within the broad sweep of salvation history, such vision awaits us only at the general resurrection. As for now, “Thy word is a lamp to my feet / and a light to my path” (Ps 119:105).

It’s up to me to know the plan and to act upon it.

The healthy emphasis on acting is well-placed, but we often look in the wrong direction for marching orders. Many people seem to think that they can’t proceed without explicit directions. “I’ll do whatever you ask of me Lord, I just don’t know what it is.” But God’s plans are not often communicated with crystalline clarity, like the onrush of prophetic insight. Instead, they are given in the quiet certainty of prudence:

God’s plans are not often communicated with crystalline clarity, like the onrush of prophetic insight. Instead, they are given in the quiet certainty of prudence.

For this commandment which I command you this day is not too hard for you, neither is it far off. It is not in heaven, that you should say, ‘Who will go up for us to heaven, and bring it to us, that we may hear it and do it?’ Neither is it beyond the sea, that you should say, ‘Who will go over the sea for us, and bring it to us, that we may hear it and do it?’ But the word is very near you; it is in your mouth and in your heart, so that you can do it. (Deuteronomy 30:11–14)

God’s plans are at work in our own ability and desire. They arise organically from the outworking of the life of grace and virtue.

God alone sees the plan in its plenitude. It is for him to give and for us to receive, and we receive it by prudence. Prudence is just our created share in God’s providence. By providence, God takes care of the whole world, orchestrating the movements of all the creatures that fall within his power. Some of those creatures fail; some of those creatures sin; but God is able to incorporate even failure and sin into a work of great glory. By prudence, we take care of our world, orchestrating the movements of everything that falls within our power. Sometimes we fail; sometimes we sin; but we, by God’s grace, are able to incorporate even failure and sin into a work of great glory.

Prudence gives us the insight to see who we are and where we fit, helping us to flourish within the bounds of human limitations. Prudence empowers us to know our part and to play it well. Think of human life as a role in a stage play. The actors in the play need to know something of the playwright’s intention and the director’s vision to interpret their part well, but they don’t need to know all the details. They just need to be good actors. If an actress felt that she had to know what Shakespeare had for breakfast on the morning of April 29, 1578, and the precise reason why he named his children as he did before acting the part of Desdemona, that’d be a bit excessive. Certainly she needs to know something of the context and setting of Othello, but not all there is to know. She needs to know her movements and her lines, and she needs to deliver them beautifully. So too in human life. Like the actress, we have enough to go on. Sure, we may not know the whole of God’s plan, but, frankly, we don’t need to. We were made to learn our movements and our lines and to deliver them beautifully. While we may chafe at being so bound, we can be certain that the script is good and that it leaves nothing out. What is more, we are amateurs, and so we can’t reasonably expect to deliver our lines flawlessly. We can reasonably expect to deliver them with our best effort, recognizing that our every word and work is under the care of he who is at once playwright, director, and principal actor. And so we needn’t call the play into question or write our own. We trust that we’ve tried our best to do the good and that our happiness lies in just such a pursuit.

Though the inscrutability of human affairs and the mysteriousness of divine providence may give rise to frustration at times, it is within these bounds that we find freedom and certainty. To say, though, that these bounds are good isn’t to say that all bounds are good. The limits to our knowledge of human affairs and of divine providence are part of being human. They are given by God, by reality. We receive them; we don’t invent them. In addition to the bounds that we receive, though, there are other bounds that we invent for ourselves. Some are good: “I have to stop rebound dating. I’ll give myself at least a month after each relationship.” “I can’t accumulate any more debt. I’m freezing the credit cards and dealing in cash.” Some are bad: “I don’t really keep up with friends; it’s a detachment thing.” “This sin, it seems, will be with me until I die.” Bounds of this sort impose false limits on life and make it harder to find freedom and certainty. To flourish, we need to address these falsehoods, specifically those that surround our choices.

On a particular day, you might do any number of things: wake up, brush your teeth, take a shower, eat breakfast, go to work, plug away at spreadsheets, drink coffee, check emails, take a few calls, go to Mass, go back to work, sit in on some meetings, update your computer, check the news, sit in traffic, prepare dinner, watch a show, pray a bit, think about the next day, and go to bed. In the course of the day, you may only make a couple of momentous choices where you work through the three acts of counsel, judgment, and command in a conscious way. Do I go to midday Mass or work through lunch? Do I ask my boss about a raise or do I put off the conversation? Because these kinds of choices occur only at intervals, we often experience them as perplexing. We feel surprised by them or impressed by their consequence. Though we choose all day long, most of the time we know perfectly well what we should do or recognize the choice as a mere matter of preference. Why is it then that these momentous choices stress us out so much? Have we put them in a different category? Have we labeled them as meaningful and the other choices as unmeaningful? Have we bounded our experience such that everything seems to hang on a few choices that matter?

Strangely enough, the best way to choose well in these instances is not by doubling down and reaffirming your resolve. In fact, it’s probably not healthy to assign any more importance to these momentous choices than you already have. By focusing too narrowly on them, we risk imposing an artificial bound on our experience, that of limiting our “moral lives” to the occasional and infrequent. Even if only slight, there is a subtle snare at work in this logic. Often, those who entertain it start to believe that their lives aren’t really meaningful except at crisis points, as if there were but two settings: cruise control and chase scene. This is an artificial boundary, a false characterization of the moral life, and by conceiving of our choice in this way, we miss out on all the joy of living.

The moral life and its resources are not intended exclusively for crunch time, nor are they addressed principally to solving one’s most difficult problems. The meaning of our moral lives is distributed among the various experiences that make up our daily fare. The moral life is not first about problems; it is first about persons. How we make a choice (how we even approach a choice in the first place, for that matter) is a fruit of who we are and who we want to become.

In any decision, the question is not so much about whether I do this or that, but who I am before this choice and who I want to be on the other side of it. One’s life isn’t principally about results to be realized in the world. That’s the domain of the artist. An artist is successful if he makes good and beautiful things, and his standing as an artist is relative to the things made. When it comes to the prudent person though, one’s standing as a human being is relative to character. A person is successful if he or she becomes good and noble. The results, the consequences of action, are, in a certain sense, beside the point. As St. Teresa of Calcutta once said, “God has not called me to be successful; He has called me to be faithful.”

Within this setting, the big choices assume the right kind of importance. They are part of the story of who we are and who we are to become, but just part of the story. Beyond the bounds of the momentous choices, there is a whole moral universe in which to grow as a person and fill out what is lacking in character. From this vantage, we see that we aren’t just helpless individuals stumbling from isolated bewildering choice to isolated bewildering choice. We actually shape our future choices, both in how they are presented and in how they are resolved.

Our choices are shaped by our character, and our character gives us the certainty we need. We will never be sure beyond any shadow of a doubt, but neither should we seek to be so. There is much we do not know, but there is also much that we do. We are not robots operating by machine logic. We are human beings acting by prudential logic, which is our small share in God’s perfectly providential logic. While cultivating a virtuous life, we can grow ever more rooted in the uncertain certainty of prudence that empowers us to live courageously the life set before us. Before the choices of your life, both great and small, ask not whether it is the theoretically best possible decision or one completely void of bad consequences. Ask instead whether it is good with what you’ve got. Ask whether it makes you and those whom you love to be good, too.

Think back to a good choice you’ve made. What identified it as a good choice before, during, or after? In the future, how might you be able to better identify the certainty that prudence affords in your practical decision making?

Are there any bounds you have set for your life which you suspect may be false? Have you cordoned off your important choices in some way? What are some steps to reclaiming the whole of your life for happiness and holiness?

Can you think of a choice you have been deferring for a while? Are you conscious of the reasons why you have been deferring it? Are there aspects of the choice or its consequences that you fear? How might this choice offer an opportunity for new-found freedom and certainty?