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Helping Your Son Discover the Meaning of His Life
The following essay first appeared as an article in Alvaro de Vicente’s Substack publication, Men in the Making. For more articles like this one, you can visit his page here. Subscribe to the publication to stay up-to-date on Alvaro’s writing.
This essay is part of a series entitled “Life Prep.”

I have my mission—I never may know it in this life, but I shall be told it in the next. … I am a link in a chain, a bond of connection between persons. He has not created me for naught.
St. John Henry Newman
Oliver Wendell Holmes Jr., the well-respected supreme court justice who served nearly thirty years in the first decades of the twentieth century, though a sharp legal intellect, was famously absent-minded. As the story goes, Holmes was riding a train one day when the conductor came through to check tickets, and the justice realized he’d misplaced his own.
As the conductor made his way down the aisle, Holmes searched his pockets frantically, then his briefcase—without success. By the time the conductor reached his seat, Holmes still hadn’t found it.
Seeing the man’s frustration and recognizing him as the famous Oliver Wendell Holmes Jr., the conductor reassured him with a smile: “Justice Holmes, don’t worry. I know who you are. Everyone in this train knows who you are. You do not need to show me your ticket.”
“No, sir, you don’t understand; that’s not the problem,” replied Justice Holmes. “The issue is that without my ticket, I don’t know where I’m going.”
Drifting between Dreaming and Dabbling
Many young people today find themselves in a position analogous to Justice Holmes’s—except their problem is worse, because the destination they lack isn’t a stop along a train line, but the very point of their life itself.
The research of William Damon, a Stanford psychologist and author of The Path to Purpose, sorted 12- to 26-year-old Americans into four groups based on their sense of purpose: the disengaged, the dreamers, the dabblers, and the purposeful. Only about one-fifth qualified as purposeful—having found something meaningful to commit to and sustained that commitment over time. Roughly a quarter fell into the disengaged category: no real interest, no consistent action, and not even actively searching for a direction. The remaining majority drifted between dreaming—holding vague, shifting ideas about a future without acting on them—and dabbling in one interest after another without settling on any.
Data from the CIRP College Freshman Survey—also known as “The American Freshman”—has tracked students’ changing priorities for decades, and points in a similar direction. Since the late 1960s, college freshmen have steadily ranked developing a meaningful philosophy of life as less important, falling from over 80% to roughly half today, while ranking being financially well-off as more important, rising from under 45% to above 80%. Perhaps many young people aren’t finding meaning in their lives in part because fewer of them are treating the search for it as a priority.
What Does Meaning Mean?
You can’t help your child find meaning in life unless you yourself have a good sense of what meaning even means in the first place.
Researchers like Frank Martela and Michael Steger, whose work has been popularized by Arthur Brooks, define meaning as the combination of three factors: coherence, purpose, and significance. Coherence is the ability to gather the parts of one’s life into a sensible whole; without it, the events of your life feel random, disconnected. Purpose is the direction of one’s life, the goal toward which your efforts aim. And significance is the sense that your life matters—that it actually makes a difference.
I find this framework helpful. Though I didn’t have it in mind at the time, it fits well with a talk I gave years ago on the moral imagination, in which I used the metaphor of a book—could be a movie or a play as well—to describe life. If your life is a story, then it has coherence—a narrative arc that draws together its various scenes. It has a purpose: the protagonist has some goal to accomplish. And it has significance: it matters whether you, the protagonist, accomplishes the mission that has been given to you.
Developing a Life Plan
Practically speaking, you can make these ideas concrete for a high school student by helping him develop a “Life Plan.” The plan will likely change as he matures and the particulars come into focus, but drafting a first version is a valuable step toward getting him to think reflectively about his life as a story of consequence.
There are three steps to formulating a life plan.
The first requirement of any plan is knowing the end goal. Life is a series of journeys, and unlike Justice Holmes, you shouldn’t set out on one without a sense of the destination—to do so is meandering, not journeying. What is the goal of your life? What do you believe happens after you die? You cannot arrive without a destination.
And once you have a destination in mind, it matters that you aim for it from the very beginning. The moon is hard to miss, given its size, yet all it takes for a rocket to miss by thousands of miles is to be off by a few inches at launch.
The second step is asking: How am I going to get there? This is a hard question for a high schooler to answer. A better way to frame it might be: Who will be on my team? Friends, mentors, spiritual directors—a kind of board of directors for your life. No one arrives at a worthwhile destination alone; the people you choose to walk with you shape whether and how you get there.
The third step relates to significance. Ask yourself: What do you want to leave behind? We tend to think of plans in terms of action—what we’re going to do in life. That matters, but it matters more to first decide what you want to leave behind, because that’s what motivates and guides your actions in the long-run.
What Parents and Educators Can Do
There is no hack for teaching something as important and as big as the meaning of life. The only way to teach this kind of subject is through modeling—in word, in action, and in disposition. It happens through many small comments made over time, responses to events as they occur, a steady disposition that only reveals itself gradually.
So what does that look like in practice for a parent or an educator?
First, clarify for yourself what you believe the purpose of life actually is. As a Christian, this is simple in outline, if not in practice: to go to heaven—or, more specifically, to learn to love on earth so as to love God forever in heaven. You must have a destination in mind before you can help someone else find theirs.
Clarifying that purpose requires time for reflection and self-examination—dedicated moments of quiet that create space to honestly consider your own motivations. Why do you do what you do? Why do you work? Why do you relate to people the way you do? What do you want to be remembered for? What do you believe happens to you after death? These are the questions that help you identify what you actually believe the purpose of your life to be—because you can’t convincingly hand a boy something you haven’t first worked out yourself.
Second, you have to believe it deeply. Boys are experts at detecting insincerity—especially when what’s being conveyed is a deep truth.
Third, the actual teaching happens in two registers: active and passive.
Active teaching consists of talking to your son or student directly about the things that matter most—religion, family, work, virtue. This does not need to involve long, planned lectures. A short, unplanned comment about the importance of faith, or heaven, or God, often lands with more force than any formal talk would. As Seneca put it, “The greatest benefit is to be derived from conversation, because it creeps by degrees into the soul. Lectures prepared beforehand and spouted in the presence of a throng have in them more noise but less intimacy. Philosophy is good advice; and no one can give advice at the top of his lungs” (Moral Letters to Lucilius, no. 38).
Passive teaching is what a boy absorbs simply from watching how you react to events, since that reveals what you actually value, regardless of what you say. What are you visibly disappointed by? What makes you angry? What excites you? What do you seem to value most? How do you respond to the death of someone you loved?
Passive teaching also involves modeling: how you practice your faith, how you treat other people, how you approach your own work—the ongoing demonstration of what you actually believe is important in life. Modeling includes both what you do and the manner in which you do it. As St. Teresa of Calcutta put it, “The miracle is not that we do this work, but that we are happy to do it.”
Discovering Your Life
Finally, though I’ve spoken about developing a life plan, I should clarify: we don’t create it on our own. We discover it in dialogue with others—and with God, who is the Author of our story.
About the Author
Alvaro de Vicente
Headmaster of The Heights School, and an advisor to hundreds of school leaders, both of start-up schools and established schools seeking to revamp their offerings, especially for boys.