“By their fruit you shall know them…”

The world is full of organizations that seek to transform character and improve lives, but how can you tell which ones are successful and which ones aren’t?

The following questions should provide a guide to help you make these judgment calls. They fall into 16 categories, corresponding to the 16 crucial features that truly formative institutions tend to possess:

Does the organization have a clear, strong reason for being in the world, embraced and pursued by all of its members? Does it give its members organizing criteria for what to love?


If you have a why to live for, you can withstand any how.
~Friedrich Nietzsche


If there’s one thing that marks today’s erosion of institutions in civil society, it’s a loss of what the Greeks called telos. Aristotle conceived of telos as that why and to what endone is living and laboring—a purpose beyond self. As many traditionally formative institutions have struggled to relate to an increasingly individualistic, consumerist, and utilitarian culture—be they churches, universities, voluntary service associations, or something as intimate as marriage—they have tended to lose sight of a transcendent mission as they’ve scrambled to meet the goals of their individual members. In the process, they often wind up losing both goods.

Ideally, a strong sense of telos unites people and raises them up out of themselves. It orients their energies and yokes their actions to their beliefs, often in the company of others. The most effective mission statements imply something normative, and they allow for a common frame of reference that creates a standard to abide by, leading naturally to a structure of accountability, a sense of responsibility, and an enduring moral identity. A strong institutional telos joins individuals to an arc beyond themselves. That sense of belonging leads people from small conversations about safety and comfort to large conversations, such as our relatedness and responsibility to one another and to a larger cause or community. A strong telos protects against selfishness, cynicism, and distrust. It allows for genuine, robust inquiry and free individual action. It lends meaning to struggle and pain, fostering individual grit and interdependence.

Take the U.S. military. Its mission places the individual in existential service to the country at large. With the stated end being to protect the U.S. and to fight and win the country’s wars, a list of core values naturally follows: loyalty, duty, respect, selfless service, honor, integrity, and personal courage. The military’s compelling purpose attracts people from vastly different backgrounds, chiseling one another and learning how to work together in the process.

Religious universities are another example. A school like Yeshiva, Notre Dame, or Brigham Young University has the advantage of locating itself in a larger tradition centered on deeper truths. Insofar as universities were founded to protect and facilitate a shared quest for truth, today’s more rigorous religious colleges actually have a head start compared to their secular counterparts, which have come to understand learning merely as a means to one’s career, nothing more uniting or inspiring. Wheaton College, for instance, exists “to integrate faith and learning” in the service “for Christ and His Kingdom.”

A strong telos doesn’t need to be as exclusive in its beliefs as ­Wheaton’s is, but it does need to be sufficiently specific in its implications that all of the institution’s activity, culture, and logic are informed by a clear direction. Universities that have maintained their original motto and consistently measure all activities and changes against it tend to maintain their capacity to form—even amidst today’s distractions and moral cacophony.

The Latin motto of the University of Chicago is Crescat scientia; vita excolatur. “Let knowledge grow from more to more; and so be human life enriched.” The school took an independent stand in 2016 against “safe spaces” and “trigger warnings” in a letter to its incoming freshman class. This letter, followed by a matriculation speech from law professor ­Geoffrey Stone, explained clearly the reason for protecting the free exchange of ideas. “Academic freedom is, in fact, a hard-bought acquisition in an endless struggle to preserve the right of each individual, student and faculty alike, to seek wisdom, knowledge, and truth, free of the censor’s sword,” said Stone to the freshmen. A university’s role is to “instill in its students and faculty the importance of winning the day by facts, by ideas and by persuasion, rather than by force, obstruction, or censorship.” He knew what the University of Chicago was about—­seeking truth as a community of learners—and thus had ground to stand athwart prevailing collegiate winds.

Every strong telos of a character-building institution should have an expression in a mission statement, but not every mission statement implies a strong telos. Some missions are deeper or more focused than others. The key is to see if the statement answers three tests: (1) Is it in service of something beyond the individual member’s own development? (2) Does the mission statement have a clear moral purpose embedded within it? (3) Is it rooted in an identifiable tradition, even as it strains toward the unpredictable demands of the future?

Is there a covenant or creed that is affirmed regularly as a community, in word and deed? Are there communal rhythms, routines, and rituals?


Liturgies aim our love to different ends precisely by training 
our hearts through our bodies.… Liturgies make us certain kinds 
of people, and what defines us is what we love.

~ James K. A. Smith


As human beings we’re a strange blend of individual agency and interdependence. As unique as each of us is, we are also built to mimic others, from birth to adulthood. We find meaning by locating our lives within a broader context, which in turn grants direction and purpose.

But we live now in an age that glorifies the unfettered rights of the individual, his or her moral responsibility defined only by temporal group identity, not a transcendent moral creed. We balk at the idea of deferring to a set of rituals or committing to an organizational routine. We fear giving away our own power, and assume that freedom of conscience means standing apart from institutional overhead, from hierarchy, from a set of absolute proclamations about what is good or true.

Considered reaction against empty forms and abuses of power is commendable. But today’s trust in the individual’s capacity to find his or her own flourishing is extreme. An older wisdom says that real liberty involves paradox: Tie yourself down to the right things, and you will find true freedom. Commit to a set of repeated rhythms in the company of others, and gradually, if mysteriously, a deeper personality will bloom.

There are a variety of longstanding institutions that stake their success on this theory. Liturgies and rituals are of course the basic ingredients of all the historic religions, with regular recitations of creeds, cycles of fasting and feasting, liturgical calendars and concentric circles of sacred daily, weekly, monthly practices.

The military is another example. From the morning bugle to evening taps, salutes to covering each dead soldier’s casket with a flag, rituals speak to the institution’s ultimate telos: to serve and sacrifice for one’s country. Even when informal, “off-the-book” rituals get established—fighter pilots getting hosed down after their final flight, Marine infantrymen shaving their heads for their first deployment—the point is the same: Develop a set of traditions, and you will find yourself not only further bonded to your comrades, but the conscious heir of a heroic lineage.

Williamson College of the Trades is a vocational and character-­building training school in Pennsylvania that relies upon a carefully structured environment of daily chapel, work details, a dress code, and clearly defined rules and responsibilities. The goal is to produce “The Williamson Man” in each graduate, known throughout their future careers as crewmen of integrity and humble leadership.

Five out of the six narrative features in this very book rely on a set of rituals to orient the community and grant it an identity and purpose. The Scouts from their founding have revolved around an oath, a law, a motto, a slogan, and an outdoor code, all of which are recited aloud and reflected upon at various junctures. The Oaks Academy begins each day with songs in the foyer, the parents standing side by side with their children. The Other Side Academy is defined by ritual and monument. From the confessional “Games” to the matriculation and expulsion Bench to the 12 Beliefs that line every wall to the opening and closing ceremonies, everything is anchored in set scripts, their truths revealed over time and through personal discovery. The Positivity Project schedules a 30-minute slot every day before the lunch hour for groups of students to dissect their character strengths.

The point is, liturgies and rituals form us, and when they’re taken seriously and followed by both leaders and members, they are also a sign that an institution wields a well-earned authority, that its leadership is trusted, that its members are humble and teachable, and that the institution at large believes in something beyond itself—something deep enough, and existential enough, to create ritual, and to sustain its practice. Rituals root us, remind us of who we are and why we are here, and also give us the resources from which to innovate and live authentically in a world of uncertainty.

Are all members of the organization, regardless of position or stature, engaged in the mission and aware of the significance and contribution of their roles?


To belong to a community is to act as a creator and co-owner 
of that community. What I consider mine I will build and nurture. 
[Our task today] is to seek in our communities a wider and deeper sense of emotional ownership; it means fostering among all of a community’s
citizens a sense of ownership and accountability.

~ Peter Block, Community: The Structure of Belonging


Steven Reinemund, former CEO of PepsiCo, once observed that “the organizations with the best cultures encourage full engagement up and down the company hierarchy.” He was talking about for-profit behemoths like Southwest Airlines, Chick-fil-A, and Zappos, but the same principle applies to nonprofit organizations in the character-­forming business.

Organizations that engage every member of their staff in their mission, and win their full-throated investment, tend to foster a widespread sense of ownership and accountability.

As everyone participates willingly, even joyfully, a mutually enriching culture emerges—one that’s intriguing to outsiders, that is trusting and transparent, that encourages personal responsibility, and that forms people’s ethos in a consistent, recognizable way.

Take Wake Forest, for instance. Every person you talk to, whether it’s a janitor, professor, student, or administrator, emanates a sense of pride in the institution he or she is serving. Wake’s identity is rooted in an ethos of service and personalism, how you treat others is the mark of the well-formed man or woman. The school is small enough that each individual has the chance to know and be known, large enough that each can be challenged to stretch and mature. President Nathan Hatch comports himself in a way that matches his belief in the innate dignity of each person, and he has hired people of similar conviction. Employees at all levels and across Wake’s undergraduate and graduate education, as well as its schools of business, divinity, law, and medicine, affirm their commitment to Wake’s mission of developing the whole person, ensuring that knowledge, experience, and service are consistently reinforcing one another as the training pathway to a meaningful, responsible life.

Community Renewal also inspires this kind of all-in commitment and personal transformation. One person after another, whether rich or poor, white or black, has found a deeper fulfillment and purpose in renewing Shreveport’s social fabric, and in turn being renewed. No one is left out. All relationships find need of restoration and growth, which leads to people very much unlike each other, and in this case with deep historic rifts, leaning in to the discomfort and finding themselves changed by the encounter.

The Other Side Academy in Salt Lake City, while “tough love” in its approach, speaks in a language of mutual service. Co-founder Joseph Grenny only feels gratitude for how he’s being transformed, even as he watches these men and women find hope and a fresh life. Each person is invested in the success of the therapeutic community by sweat and by pledge, and to lose one is to experience a tear in the system helping to redeem your mistakes and transform your character.

Summer camp invites this all-in sense of belonging, as does a well-functioning family. The Twelve Step theory of addiction recovery is powerful in part because it’s a level playing field: Everyone comes as an addict, and everyone pursues the same sequence of confession, surrender, discipline, and recovery—even if the process looks different for each person.

The key is for a leader to act like every person matters and has a unique contribution to make. Does he or she treat the weakest and the lowest with the same dignity as those at the top? This example, in cooperation with a strong mission or telos, should inspire the all-in participation that changes human beings. This will get trickier as the workforce becomes less traditional and the broader culture continues to encourage a scatterplot of ever-shifting commitments, but those institutions that are able to compel full investment, ownership, and accountability will be those that leave the deepest mark.

Does the organization have a particular identity, a thick set of norms that gets passed on to its members? Does it have a unique quality that is recognizable in those it has shaped?


Don’t try to be everyman. Don’t pretend you’re a member 
of every community you visit. Don’t try to be citizens of some artificial 
globalized community. Go deeper into your own tradition. Call upon the 
geography of your own past. Be distinct and credible. People will come.
~ David Brooks


All families have their own way of doing things. Quirks. Traditions spoken and unspoken, norms that have developed through habit and choice that build a particular legacy.

College fraternities and sororities have something similar. So does the military. As do many summer camps, geographic regions, religious communities, and some companies. When fellow campers see each other again, they speak in a certain dialect—often reverting back to acronyms, phrases, and camp identities the way adults revert back to childhood patterns when visiting parents for the holiday.

The institutions that have this tend to be “thick” organizations—thick with history and custom, webs of relationships, and a cherished story that they tell and retell. Thick organizations leave an imprint. Meet a Davidson College alum, for instance, and he or she will likely be intellectually curious, broadminded, committed to several civic efforts in his or her community, and repelled by moral shortcuts (such as cheating). Meet a graduate of ­Kenyon College, and he or she will be comfortable amid diverse viewpoints and able to navigate conflict with grace. Meet a West Pointer, and you can expect to see fortitude, humility, leadership skills, and a grounded wisdom. Many Eagle Scouts anchor a core part of their identity in being an Eagle Scout—for life. It’s as much a private code as a public reputation.

By contrast, graduates of most big state schools are not as identifiable. They tend to find their most formative influence in a smaller sub-­experience of the college, such as their sorority or their sports team. This gets to a related principle: The smaller the size of a given community, the more likely it is to be thick with customs, stories, motivation, and accountability. It’s probably no accident that the Scouts, the military, many liberal arts classrooms, and business-school trainings structure their fundamental unit of action to hold between four and 20 participants.

But what does an institution’s level of particularity have to do with character? It’s not guaranteed that a distinct organization forms people in a good direction, merely that it forms them. But particularity is a clue, especially in a time tempted toward political correctness and being all things to all people, that an institution has a strong sense of self. It does not apologize for its customs, nor does it dilute its convictions. There’s something sticky about it that makes you want to belong. Its sharpness of definition compels meaningful commitment.

Outward Bound has a way of honing its young people to take risks and be more rugged, to respect nature’s force and learn survival skills with others. Most people who have gone through an Outward Bound experience have at once a flexible nature and a dependability, a quiet charisma and a problem-solving appetite. Cometa in Italy, through its emphasis on beauty and generosity without limit, has graduated a cascade of young people who now serve others through social entrepreneurship ventures that are as beautiful as they are practical, humane as they are committed to standards of excellence. Employers say, “Cometa students are different.” 

Thick institutions transcend our instrumental motivations—to get a degree or to earn a salary—to become instead part of our identities. The healthy ones tend to engage the whole person—head, hands, heart, and soul—in person, not online. They often have collective rituals, reciting or standing in formation or coming together at a frequent assembly. They have shared tasks, which often involve members closely watching one another. Thick organizations also tell and retell a cherished origin story about themselves, or about the larger tradition that animates them. Many incorporate the arts, especially songs, into daily life, and have a common ideal expressed in mottos and liturgies.

Traditionally, there have been particular professional codes, instilled through education, heritage, and an overt embrace of a moral ethos. “I’m not going to cheat because I’m a Davidson graduate,” for instance. Or, “I’m not going to drink to excess because I’m a doctor.” Ideals were integrated into identity.

Law, for instance, was a profession that thought of itself as stewarding a long tradition of justice, a tradition indispensable to preserving a sense of social unity. It relied on principles like confidentiality, respect for the rules, and avoidance of false statements or conflicts of interest. In the last 30 years, however, the profession has changed, emphasizing the short-range concerns and rights of clients over and above the stewardship of a longstanding moral tradition. The profession’s code has been diluted, either by a failure of transmission in the law schools or in the day-to-day practice of modern law. Lawyers no longer are required to pledge an oath to a set of standards beyond ethical technicalities that look more like compliance and job preservation than a deep moral affirmation.

Does the organization have a clear conception of the whole ­person—head, heart, and helping hand—and seek to develop it? Are employees and departments integrated across domains, serving constituents in complementary, mutually reinforcing ways?


Education is a holistic endeavor that involves the whole person, 
including our bodies, in a process of formation that aims our desires, 
primes our imagination, and orients us to the world—all before we 
ever start “thinking” about it.

~ James K. A. Smith


Character is a whole-person phenomenon. It does not get transmitted merely through cognition, nor only through the affections. It is crucially a function of the will and well-formed desires, shaped by many different experiences: family upbringing, school, sports, the arts, struggle, reading, dialogue, conflict, reconciliation, relationships, physical challenge, cross-cultural encounters. The character-building initiatives that weave these different strands into one integrated message have the most powerful effect.

Movements in health, education, workplace culture, economic development, and a variety of faith-based initiatives are catching on to this holistic understanding of human nature. You might say the country is seeing a “whole-person revolution” unfurl. Millennials talk about “bringing their whole selves to work.” Wharton Business professor Stewart ­Friedman has said, “Firms that fully embrace the needs and interests of the whole person will win today’s competition for the best talent.”

But how to move from awareness to implementation? How to shape one’s institution, or design a character-building initiative from scratch, to address the whole person?

At Wake Forest University, where educating “the whole person” is the mission, President Nathan Hatch has leavened each academic and administrative department with hires committed to seeing students not just as intellects, but as full moral agents capable of integrating the will, the heart, the head, and the helping hand. It begins with the application for admission, which asks questions like: “Choose an unsung historical figure who deserves the Hamilton treatment,” or “Hashtags trend worldwide. Give us a hashtag you wish were trending. Why?” These questions invite a form of personal disclosure that is alert to today’s world.

Wake Forest now has one of the most sought-after career-service models in the country. Integrating personal development with career development, students study chess and read psychology, philosophy, and history with an eye to discerning their vocation: what they should do and why, who they should be, and what or whom they should serve. They pair up with adult mentors from across the university—faculty, administrators, coaches, custodial staff—to explore the character tests in various career paths: what moral leadership might require in Silicon Valley versus a more traditional corporate job versus medicine versus social work.

Summer camps can also be wonderful examples of whole-person development. Incarnation Camp takes kids out of their normal environment and provides them with an opportunity, away from phones and pressure, to experience the sort of childhood that used to be common. Situated on 700 acres around a mile-long lake in Ivoryton, Connecticut, the campers live in tents, prepare their own meals, go on hiking, canoeing, and bike trips, and conquer their fears. Along with outdoor skills, kids learn to get along with people very unlike themselves. 

The era of metrics and assessment has often given schools an incentive to turn their students into proficient test-takers, but it has not prepared them to be moral leaders. The Great Hearts network in Arizona and Texas believes that the highest goal of education is to become good, intellectually and morally. With a curriculum built upon a classical liberal-arts tradition and extracurriculars that reinforce lessons in character, Great Hearts students practice arts, academics, and athletics with their moral purpose understood as the foundation for their knowledge and skills.


The Gifted Music School in Salt Lake City churns out lots of students who matriculate at Juilliard and Colburn, but its primary goal is to raise well-rounded citizens for the country. “We want to make kids capable of understanding values that are relevant to the survival of our society and our country,” says founder Eugene Watanabe. With the discipline required to master technical difficulty, the lessons in public grace and private grit, the honing of musical intuition and deep listening skills, a mentoring relationship with a tutor in the craft, and the unique dialogue with history that the study and performance of classical music invites, Watanabe’s view is that the arts impart a constellation of moral traits that can endure for life.

“I truly believe that when children make beautiful music together, in an orchestra, in chamber music, a notion of fundamental respect stays with them,” says Watanabe. “Whether they transition into politics, or economics, or business, or law, they carry that fundamental value and respect for others.”

Does the institution put relational health as the foundation for its success? Does the organization foster social trust? Does it have a strong sense of community?


In all my years of working with youth, I’ve never seen a 
program change a life. I’ve only seen relationships change lives.
~ Bill Milliken, founder of Communities in Schools


Character formation is inherently co-creative. Full human flourishing always comes about through communion, never isolation. Thus we are formed in the context of relationship—relationships with a loving authority figure, historical figures, other exemplars, fictional characters, those you work, befriend, and serve. While proving one’s character is itself a volitional act—the individual must choose to submit to be chiseled, must choose to do the right thing, even when it hurts—character is developed in light of relationships past, present, and aspirational future.

You see this affirmed in the three-part pattern described in the introduction. When people describe how their own character has been shaped, they always invoke (1) a relationship with an authority figure, (2) an experience of struggle, and (3) the experience of serving a context greater than self. The first touchstone is key: Love creates life, shapes life, and transforms us. We look to our mothers for cues from the earliest days. Our eyes seek the eyes of others to detect emotion, mood, affirmation, or lack thereof. We naturally learn from those we love and trust, be they mentors, coaches, teachers, or grandparents. Each of these relationships should press us onward and upward, modeling proper behavior and providing a pathway for accountability.

But we live in an era where many relationships have thinned in their power to correct and inspire. We are told to self-isolate in our moral judgments: “You do you” is the colloquial sermon for today’s young. Screens are replacing people as purveyors of wisdom and knowledge. Adults—particularly men—struggle to find and sustain friendships, while ­millennials crow for mentors. Fewer and fewer people grow up under the loving canopy of a whole and attentive family. The daily family dinner has been displaced by sports practices and extracurriculars, long working hours, and the distraction of technology. Social media deludes us into confidence that we understand other people, including their opinions. We have lost patience for an uncontrolled, open encounter, and we fear the messiness of two-way interactions between humans in real time. 

Community Renewal’s consistent testimonies of personal transformation grow out of its intentional relationship-building. The final core value of The Oaks Academy is that “relationships come first in all interactions.” The Positivity Project gets elementary- and middle-school kids familiar with their top five character strengths and weaknesses so that these students come to appreciate traits like kindness, curiosity, humility, self-control, and relate to one another more on grounds of character than their classroom smarts, what clothes they’re wearing, or how much their parents can or can’t afford.

More than ever, we need institutions to model and encourage healthy relationships. Positive relationships are key to social and economic improvement.

All Our Kids DC is a 501c3 started by husband-and-wife team David Simpson and Kathy Fletcher. After years of welcoming youth from challenging backgrounds into their home for a hot meal, a bed, and love, Simpson and Fletcher decided to formalize what they were doing so that more adults could mentor and resource their growing brood. This includes helping fund college tuition for the kids who seek it. Now AOK is a thriving, sprawling community where adults serve kids and kids transform adults. Every Thursday evening there’s a home-cooked meal. “No cell phones at the table,” says Fletcher. “Share yourself.” It’s become an unconventional family rooted entirely in relationships as the source of material improvement and character change. Some of the adults are now hosting kids in their own homes. Those in college keep in touch with AOK adults across the miles, psychologically strengthened to launch into self-sufficiency, supported by adults who believe in them.

The idea that positive relationships are key to social and economic improvement is gaining ground. More and more of the most effective social programs are speaking in a relational language. Nurse-Family Partnership helps teenage moms become good parents. Specially trained nurses visit young moms-to-be regularly for two and a half years, starting early in the pregnancy and continuing through the child’s second birthday. The nurses counsel the moms about health-promoting behaviors, offering advice on everything from child safety to developmental stages to ways of juggling work and motherhood. Paul Tough, acclaimed author of the bestseller How Children Succeed, says that because of NFP, we are seeing reduced incidences of child abuse, arrest, and welfare enrollment. In families where mothers scored especially low on measures of intelligence and mental health, children’s academic performance improved.

It sounds soft, and relationships are hard to measure, but if we don’t begin there, character loses its moral force.

Is the institution careful about the latest technological advance, embracing it insofar as it promotes healthy relationships and individual skill, and setting limits when it makes those objectives more difficult?


Technology is a useful servant but a dangerous master.
~ Christian Lous Lange


Technology has become an unavoidable thing in almost all our lives. It is at once a massively promising tool and one that’s a force with a logic and power all its own. How do we navigate a world of devices and nonstop distraction, unchaperoned and virtual access to any and everything, and ever-proliferating automation of both basic and complex human tasks?

When it comes to seeking the institutions today that are doing something special in the way of shaping a person’s will, mind, heart, and moral compass throughout life, the big elephant in the room is the screen. Our devices present a very real obstacle for all those well-intended efforts to form citizens who are wise, discerning, trustworthy, attentive, courageous, humble, honest, able to disagree without being disagreeable, patient, able to listen deeply, and who love well.

We talk often about what technology is doing to our brains, and there is growing research to deepen our concern. Beyond the brain, technology is also rewiring our habits, our impulses, our rhythms of rest, work, and play, our relationships and our networks of relationships, how we work, and how we engage a common life with others (or don’t). In short, the reality of “tech everywhere” touches most if not all of the spheres that shape and require character.

The institutions that choose to be discerning about technology are the ones that are likely thinking about character-building the right way. You have to be forceful about this stuff, even radical. You can’t just let the forces sweep over you and assume they bring progress. This is again an issue of moral agency, deploying it over and against technology’s steamroller, to preserve those spaces in life where deep beauty, goodness, and truth are shared.

All Our Kids DC doesn’t allow phones at the dinner table, a rule made to protect a space created to invite those of radically different backgrounds to attend fully to each other. Almost every institution featured in this book—Community Renewal, The Oaks Academy, The ­Other Side Academy, The Positivity Project, the historic Boy Scouts—puts thick boundary lines around technology.

Many Montessori Schools, known for their holistic, student-centered educational philosophy, have strict regulations on when technology is allowed and why. Montessori students use computers strictly as a curricular supplement, not as a substitute for books and materials. They view modest tech education as a practical necessity for skills needed in the workplace, such as typing, Excel, search engines, and the like. But beyond that, Montessori schools see technology offering diminishing returns to student development. Their belief is that technology is a useful platform for expressing human capacity that’s already been developed. It doesn’t help anyone learn the cello, or write a gripping short story, or solve conflict, or discern the proper course in a moral di  lemma. If you want an environment to be both formative and creative, technology tends to detract rather than enhance.

Writer and Praxis Partner Andy Crouch articulates a set of questions that every institution intent on character-building should ask before making a decision to embrace the latest technology. He frames them as a series of “technology is in its proper place when…” statements specific to families wrestling with the place of screens in the home, but with a few tweaks. These can apply to any formative institution:


  • Technology is in its proper place when it helps us bond with the real people we love. It's out of its proper place when we end up bonding with people at a distance, in an overly controlled and thus contrived and self-serving manner.
  • Technology is in its proper place when it starts great conversations. It's out of its proper place when it prevents us from talking with and listening to one another.
  • Technology is in its proper place when it helps us take care of the fragile bodies we inhabit. It's out of its proper place when it promises to help us escape the limits and vulnerabilities of those bodies altogether.
  • Technology is in its proper place when it helps us acquire skill and mastery of domains that are the glory of human culture (sports, music, the arts, cooking, writing, accounting, etc.). When we let technology replace the development of skill with passive consumption, something has gone wrong.
  • Technology is in its proper place when it helps us cultivate awe for the world we are part of and responsible for stewarding. It's out of its proper place when it keeps us from engaging the wild and wonderful natural world with all our senses.
  • Technology is in its proper place only when we use it with intention and care. Technology doesn't stay in its proper place on its own...[rather] it finds its way underfoot all over the house and all over our lives. If we aren't intentional and careful, we'll end up with a quite extraordinary mess.

These statements are deep, for they reveal an orientation toward what we as human beings are ultimately made to do and enjoy. They cause you to ask, “What is a home for, ideally? What is a family’s purpose, at its heart? How can a school encourage a child to seek the good and discover his or her hidden gifts? What is technology’s proper place in a particular company, sports team, artistic endeavor, rehab community, or neighborhood, and how can we keep it there?” The institutions that think hard about these questions, and act on them, are likely attuned to what great character formation requires. Perhaps we should brand such institutions as “Tech-Wise.”

Does the institution foster opportunities to relate to those unlike yourself? Are members consistently exposed to other worlds, trained in the arts of civility, deep listening, and cross-cultural agility?


Community is not uniformity…. Each one of us is different, 
one from the other. But all together we are like a symphony, an orchestra; all together we make up a beautiful bouquet of flowers. That means…that we must learn to love difference, to see it as a treasure and not as a threat. Community means the respect and love of difference…. If we let ourselves be attracted to those who flatter us or who are like us, who share our ideas, then we won’t grow. Growth will come as we come closer to people who are different from us and as we learn to welcome and listen, even to those who trigger off our pain.
~ Jean Vanier, founder of the L’Arche Communities


Guided encounters with the unexpected can lead to personal transformation, and an awakening to the opportunity for encounter everywhere. When truly working well, an institution that embraces diversity and attends to it properly cultivates lifelong, generative virtues in its members: civility, deep listening, humility, and cross-cultural agility. It produces people who are respectful of those who hold other opinions, who listen before speaking, who seek peace and compromise and not a warrior-like certainty that is dismissive of complexity and the possibility of being wrong. Our fragmented, distrustful world needs such people more than ever.

Washington University law professor John Inazu has a phrase he calls “confident pluralism.” He defines it as a temperament that gracefully accepts differences of background, identity, beliefs, and even values, and chooses to reach across the divide to work together toward a common end. Confident pluralists want to invest in shared projects with those who hold different views. They seek to build spaces where dialogue and persuasion are a way of life, where diversity is valued as a window on something more universal, and where vulnerability can be aired safely and lead toward deeper understanding.

The task of any character-building institution in the twenty-first century is to impart this civic virtue, for we need human bridges more than ever—people who are third-culture kids, border-stalkers, on the edge of the inside. Intentionally pluralistic institutions help people navigate changing times and deep difference without losing sight of who they are or where they come from. They help people discern the line between timeless truth and temporal expression, and to walk that line with grace and conviction.

The Oaks Academy embraces cultural and socioeconomic difference and attracts 50 percent low-income, 25 percent middle-income, and 25 percent higher-income students, with the racial and ethnic breakdown being 40 percent black, 40 percent white, and 20 percent biracial, Asian, or Hispanic. This human mosaic, while not without its rough edges, shines because The Oaks has a clear telos and an educational philosophy that puts the relationship between all teachers and all students first. Assignments like the capstone eighth grade essay trilogy on truth, beauty, and goodness help students consider how such transcendent ideals apply to each person’s unique life experience—aesthetic and moral differences, individual pain, and blessing. Because The Oaks has deliberately cultivated a climate that motivates kids to take hold of their own agency, their differences prepare them to be morally conscious leaders in society. This diversity is neither a divider nor a distraction.

Other programs form confident pluralists by encouraging bridge-building across lines of tribe and worldview. Waldorf schools, for instance, make an international immersion experience mandatory in middle or high school. The Kettering Foundation’s initiative ­Deliberative Dialogue trains college students in the art of civil discourse, hoping to penetrate the current climate of identity politics and withering free speech. Participants hold a substantive discussion around a specific issue by asking questions like, “What are we learning?” “How does this problem affect you and your family?” “What should we do? What would be the consequences?” “Who else do we need to solve the problem?”

Are there opportunities for growth and tests of character? Does the organization have a process by which such struggles are given meaning and direction?


Character cannot be developed in ease and quiet. Only through experience of trial and suffering can the soul be strengthened, vision cleared, ambition inspired, and success achieved. It is in the most trying times that our real character is shaped and revealed.
~ Helen Keller


While no parent wants his or her child to suffer, every good parent knows that there is no shortcut to cultivating character, and that it’s often forged most deeply in and through struggle. Persevering when the going gets tough, overcoming disappointment, accepting the truths that failure can teach, enduring pain, and learning to receive and grant forgiveness for the worst sins strengthen the sinew for wisdom and a generative life. Even if suffering is not automatically ennobling, growth is necessarily yoked to struggle.

When it comes to intentional character-forming initiatives, the best ones incorporate three things: (1) They allow for human struggle if not actively create opportunities for it; (2) They provide a structure for second chances, reflection, and accountability; and (3) They offer a pathway to growth, a chance to prove maturity with greater reservoirs of strength.

Struggle stretches you. It can deepen your empathy for others. It humbles and chastens you. It gives you a more accurate sense of your limitations. Struggle often reveals your true character: Are you selfish when everything you treasure seems threatened? Do you become volatile in times of crisis? Are you able to lead dependents when your world is crumbling? In what do you ultimately put your hope?

Outward Bound and the Boy Scouts have long pushed young people to shoot beyond their physical limits. Whether mountain biking through a dense thicket, bush-whacking with no end in sight, sleeping through dangerous thunderstorms, or climbing a steep rockface, the goal is to surmount daunting challenges. Kids who have been long-time Scouts, or have successfully completed an Outward Bound trip, report greater levels of confidence in themselves and in leading others, a healthy appreciation for the awesome power of the outdoors, a newfound sense for what really matters in life, and a quiet nobility that knows what it is to have overcome their greatest fears, their perceived physical or mental limitations, and to get along with difficult personalities when the circumstances demand teamwork. Struggle is central to both institutions’ mission.

Millions of young Americans are shaped by sports, perhaps more than by any other activity. And yet the youth sports culture has grown imbalanced. Youth sports programs often put intense pressure on children, emphasizing winning, and forcing them to perform in order to validate their parents. The Positive Coaching Alliance seeks to transform this culture. The primary formula is better athletes, better people. In the PCA method, coaches have their players (and team as a whole) focus on their effort and personal improvement, rather than simply on the results of the game. They help players recognize that mistakes are an inevitable and important part of the learning process, and that the key to success is the ability to rebound with fresh determination.

Is the organization one where members can trust the community and open up with honesty and a desire to be tutored in a better way? Is there a vehicle for grace and second chances? Is there a structure of mutual accountability?


Vulnerability is the birthplace of love, belonging, joy, courage, 
empathy, and creativity. It is the source of hope, empathy, accountability, and authenticity. If we want greater clarity in our purpose or deeper and more meaningful spiritual lives, vulnerability is the path.
~ Brené Brown

Accountability breeds responsibility.
~ Stephen Covey


Increasingly it seems that the programs considered “interventions”—where dramatic character transformation occurs—have a lot to teach our more gradual character-forming institutions (be they schools, sports teams, or adult learning communities). Some of this may be because the institutions in the business of radical transformation approach their mission with a no-nonsense rigor. Some of it is because those who have seen the ashes of their own choices tend to be the most humble before the hard work that real change demands. We all need a community to show up; the autonomy of life today makes it too tempting to skate. We also all need a community that is as “safe” for vulnerable honesty as it is challenging to our current selves. Where are these character wombs that hold shattered people and then rebirth them? Would we all not be healthier if we were a part of one safe yet rigorous community?

“200% Accountability” lies at the heart of The Other Side Academy’s success in moving people from moral kindergarteners to moral heroes. It’s peer-to-peer, which is typically the most effective form of accountability, and it’s ritualized through “games,” the biweekly group confrontation sessions. No ex-offender gets a pass—everyone is scrutinized, and everyone scrutinizes. It works because love is the motivating foundation, each person desiring to help the other improve his or her character and achieve true freedom.

Laity Lodge is an ecumenical retreat center in the Texan hill country born out of the depression of one man—Howard Butt Jr. Over the decades, CEOs, former U.S. presidents, writers, artists, and religious ­leaders have come to reflect on their vocations, their failures, and the concrete (and less concrete) nature of hope. While associated with an evangelical culture zealous to provide hope and certainty, Laity Lodge makes no such pretensions. Instead of encouraging a perfect facade, the Lodge invites ­honesty—warts and all. Its compassion and radical hospitality create a space to hold people in times of transition, grief, and searching. In all manner of sin and circumstance, the Lodge graciously allows people to get still and seek higher things. It is a place where people can be safely and truly known, thus opening the door to personal transformation.

Likewise, any addiction-recovery program based on the 12 Steps method (created by the founders of Alcoholics Anonymous) relies on this logic:

  1. Honesty: Recognizing the addiction and confessing it.
  2. Hope: Believing that success is possible—not through one's own ability, but through persistence and application.
  3. Faith: A statement of belief in a power greater than oneself to restore hope and sanity. 
  4. Courage: A scrupulous moral inventory of oneself. 
  5. Integrity: Owning up to one's evaluation of one's assets and shortcomings.
  6. Willingness: A decision to change one's character and behavior.
  7. Humility: Acknowledging one's own powerlessness to overcome the addiction alone.
  8. Discipline and Action: Removing barriers that can block forward sober growth.
  9. Forgiveness: Committing to making amends with others harmed.
  10. Acceptance: An ongoing process of owning and admitting one's mistakes and accepting oneself for being imperfect.
  11. Knowledge and Awareness: Making a conscious effort to do the right thing at every small and large moment, and to seek out one's broader purpose in life.
  12. Service and Gratitude: Seeking out and being available to help others in need.


What you see here is a tested structure for the routing out of a destructive behavioral pattern. People come to a 12 Steps program desperate, having reached the end of themselves, in need of help, and ­humble before the realization that they can’t free themselves alone. Church small groups have been inspired by the accountability model. Some of the more effective repositories for those experiencing mid-life or even ­quarter-life crises borrow from this sequence. When a community feels trustworthy, its members are able to be completely honest, which is the only way to get effective help.

Are there built-in processes for reflection, and excavation of one’s inner life and public fruits?


We do not learn from experience. We learn by reflecting on experience.
~ John Dewey

Ultimately evil is done not so much by evil people, but by 
good people who do not know themselves and who do not probe deeply.
~ Reinhold Niebuhr


We don’t live in a highly reflective society. Most of the time we’re rushing, seeking efficiency and results. But reflection is vital to our growth. When reflection is guided by a particularly deep listener, or a set of liturgies, it situates a person in his or her broader context—historical setting, present circumstances and relationships, future goals—such that he or she can gain perspective, see blind spots that need to be corrected, and discern the right course of action. Reflection is both a solitary discipline and a communal experience. Other people stir up the stories we tell, the stories we embrace, and the stories we reject. At the end of it all, fruitful reflection yields action, and change.

Open Sky Education manages a growing network of learning environments across the country. With concern for the widening achievement gap, focus among many education reformers has prioritized improving academic scores. Along the way, too many children have lost the opportunity to develop what many have historically considered a key component of education: character.

Open Sky‘s approach aims to make world-class academics, character formation, and faith-based educational choices accessible and affordable for all. Its Character Formation Project is a licensed program with an easy-to-teach framework, embeddable in everyday conversations, hiring practices, and the dinner table, too.

Early on, Open Sky noticed that the many schools that were attempting to weave in a character approach wound up doing behavioral modification instead of genuine virtue development. So it developed three core questions:


  1. Identity: Who am I? Reputation is who others think that we are. Character is who we really are.
  2. Purpose: Why am I?
  3. Performance: How do I live out who and why I am?


Students and teachers spend time throughout the school year reflecting on each of these as they grow, through experience, struggle, triumph, and grace. The beauty is that the questions are transportable: They can be “used” at the dinner table, in a religious context, the locker room, or with a piano teacher. They prompt conversation for both individual and communal understanding and improvement.

Houston Innovators is a vocational incubator for new companies. The year-long program helps budding social entrepreneurs focus on the guiding purpose and principles of their work, with intensive self-­examination. Houston Innovators provides a workspace, human capital, mentoring, training, coaching, and networking connections, and each month of gathering together over a two-day retreat involves reading in communion, reflective outpourings both alone and together, and documentation of progress. The hope is that tentative innovators become driven entrepreneurs, anchored in a deep place and moving to “new rhythms from the soul.” 

Students on college campuses today are expressing a deep hunger for wisdom, and finding little to satiate it in their classes or elsewhere. The Veritas Forum helps university communities “ask life’s hardest questions.” Students, chaplains, and professors plan and organize the events, featuring A-list speakers—such as psychologist Steven Pinker, Pulitzer Prize-­winning author Marilynne Robinson, and theologian N. T. Wright—who have thought deeply about how their work integrates with their worldview. Recent topics have included “The Closing of the Modern Mind” with Jonathan Haidt and Tim Keller, “Is There Something More to the Universe?” with Oxford mathematician John Lennox, and “What Do We ReallyKnow about Right and Wrong?” with J. Budzisewski. At this point, over 200 universities in North America and Europe have hosted 2,000 events and counting. Many students report that the Veritas Forum is one of the few, if not only, places on their college campuses where controversial questions of the highest magnitude get a free and open hearing.

The public square more broadly is increasingly void of moral content and curiosity, and there are few models of engagement where people of good will can present and debate topics that are marginalized or deemed too contentious. The Trinity Forum exists to “contribute to the transformation and renewal of society through the transformation and renewal of leaders.” Since its founding in 1991, the Trinity Forum has facilitated seminars, discussions, retreats, and lectures for thousands of leaders in North America, Europe, and Asia. These events feature profound reflection and candid conversation about life’s most important questions. Speakers including James Davison Hunter, Makoto Fujimura, and Francis Collins focus on topics such as the life and work of Dietrich Bonhoeffer, the complex connection between science and faith, and the dynamic relationship of politics and religion.

The Trinity Forum also produces a broad but focused body of classic and thoughtful writings designed to facilitate conversation and reflection around themes of character, leadership, freedom, civil society, progress, reform, philanthropy, and more.

“People won’t automatically imagine something—or have the imagination for something—until they see it,” says Trinity Forum president Cherie Harder. “We’re giving them something to see.”

Are there attentive and conscientious authority figures who serve as role models, coaches, and mentors? Does the leader set the character standard for the organization?


The heart cannot be taught in a classroom intellectually, to students mechanically taking notes…. Good, wise hearts are obtained through lifetimes of diligent effort to dig deeply within and heal lifetimes of scars…. You can’t teach it or email it or tweet it. It has to be discovered within the depths of one’s own heart when a person is finally ready to go looking for it, and not before.
The job of the wise person is to swallow the frustration and just go on setting an example of caring and digging and diligence in their own lives. What a wise person teaches is the smallest part of what they give. The totality of their life, of the way they go about it in the smallest details, is what gets transmitted.
Never forget that. The message is the person, perfected over lifetimes of effort that was set in motion by yet another wise person now hidden from the recipient by the dim mists of time. Life is much bigger than we think, cause and effect intertwined in a vast moral structure that keeps pushing us to do better, become better, even when we dwell in the most painful confused darkness.
~ Dave Jolly, veterinarian


Returning to our working definition of character, exemplars are critical. Let’s revisit it:

Character is a set of engraved dispositions to serve others and do good. This disposition is carved on multiple fronts and on multiple levels by:


  • Strong family attachments that teach what to love and how to love well.
  • Regular habits that teach small acts of self-control.
  • Teachers and role models who personify excellence and inspire emulation.
  • Professors and clergy who demonstrate what it means to be honest, courageous, and compassionate, and how to pursue these things intentionally.
  • Mentors and institutions that establish standards for and habits of good conduct.
  • Experiences of struggle, positions of responsibility, and the blessings and requirements of enduring commitments. The habits of character grow best in contexts that are orderly and predictable, with clear, humane feedback mechanisms, and an inspiring ideal in view.

Exemplars are vital to building an intuitive, full understanding of what it means to be a good person and to do good, what it means to lead, what it means to be a contributing citizen, a selfless mother, a dependable neighbor, an honorable athlete. We can read about the virtues, and at the end of the day we all have to face ourselves, but it’s moral exemplars that show us how to be, through a thousand instances of mannerism, action, personality, and choice.

The sector that understands this most profoundly is education. When you’re with children, and you’re a good teacher, you know that you’re being watched by dozens of impressionable eyes. You’re aware that how you behave is going to leave an imprint on still-moldable brains, bodies, and hearts.

But there are also sports, music lessons, the workplace, the family, and even the broader public square. The exemplary individuals in each of these spheres teach us by example, encourage us in conversation, guide, tutor, correct, and inspire. The best ones also instill a sense of responsibility to meet the standard they’ve set. We emulate those we love; we also hate disappointing them.

Some organizations set up a mentoring structure explicitly. Nurse-Family Partnership’s entire model is based on the relationship between a nurse and a first-time mom. New City Kids in Jersey City has instituted a three-layered approach. It hires 150 high-school students to be role models in the after-school program. The younger kids—many of whom lack good role models at home—see themselves in the high-school mentors and strive to assume their roles one day with good behavior. Each high-school student is also assigned an adult mentor to meet with on a regular basis. When big life decisions arise and crises hit, there is a trusted adult to call. The kids attend life-skills classes including money management, résumé crafting, and coaching on the college transition. Students visit companies and speak with employees about the nature of their work and how they got to where they are. New City conducts three performance reviews each year of the students’ individual progress, and the high schoolers can apply for leadership positions on staff.

Others have the cross-generational dynamic woven in to the very fabric of the community. Nyack College’s educational experience is enriched because grandmothers study alongside 19-year-olds. Ask today’s young people whom they admire most, and chances are they’ll mention a grandparent. This may be for reasons of distinctive character in the Greatest Generation, but it also could be the interesting nature of authority that one gap in a generational line grants. Whatever the explanation, organizations that foster relationships between old and young are doing something right.

Some organizations go out of their way to train the mentors. The ­Positive Coaching Alliance equips coaches to devote “teachable moments” to their players’ personal improvement and resilience.

While many young people clamor explicitly for mentors today, often the actual investment required seems to keep these same folks at bay. The Internet offers a quick fix for the quotidian questions one would normally ask a peer or authority figure. Technology generally has reduced people’s face-to-face engagement to emojis and words on a screen, without the inefficient yet far richer exchange that in-person encounters bring. The individualism that has permeated just about every formative institution in our society has weakened the appreciation for adult chaperones, adult authority, and adult attentiveness. The erosion of ­friendship—­particularly amongst busy adults—has also led people to feeling like they are accountable to no one (and cared about by no one). The organizations that fight all these tendencies are to be encouraged and strengthened.

Are members of the organization empowered to act, create, initiate? Are they encouraged to be responsible moral agents, not simply passive consumers?


Part of living consists of learning, personally and vicariously, what actions produce what consequences. When we govern ourselves by correct principles, we also govern our consequences. As men “act according to their wills,” there are consequences, good and bad. Part of maturing…is to realize this.
~ Neal A. Maxwell


Our culture has done a great job at forming the intellect. It’s done a terrible job at forming the will. So just what does equipping the will entail? Who is modeling the necessary conditions for moral agency to be claimed? How do we prepare people to make good judgments in a wide variety of circumstances?

Jeff and Laura Sandefer’s Acton Academy has pioneered an education model that empowers kids to teach themselves. Its goal is “to inspire each child and parent to find a calling that will change the world.” Acton motivates its students to see life as a Hero’s Journey, where someone with curiosity and character can use their innate gifts for good. Each child will:

  • Begin a Hero's Journey.
  • Learn to be a curious, independent lifelong learner.
  • Develop a deep respect for economic, political, and religious freedoms.
  • Cherish the arts, wonders of the physical world, and the mysteries of life on Earth.
  • Discover his or her most precious gifts and learn to use them to solve difficult problems.

Socratic Discussions and self-paced challenges equip children to be self-directed learners. Hands-on quests in science, entrepreneurship, and the arts prepare children for apprenticeships and real-world challenges. The Hero’s Journey, relational covenants, and real-world consequences use difficult decisions to form virtuous habits. As a result, Acton is guiding students who are uniquely self-motivated, primed for leadership, and creative, yet sensitive to the demands of a team.

Both established and emerging leaders increasingly say they cannot function without certain support systems, and without the daily work of deeper leadership development. Yet, leaders do not always have adequate language for what has aided their development and how they have become who they are. Groups like the Woodstock Arrupe Program, Acton MBA, Praxis Labs, Henry Crown Fellows, Gotham Fellows, and the Skoll Foundation offer incubators for leaders to spend time in discernment in a relaxed yet structured setting, and to slowly realize new ideas through a process of deep reading and reflection, dialogue, and some real-world experiments. The goal is to send participants back to their daily lives inspired and equipped with both practical wisdom and a sense of strengthened purpose.

Is there joy in the house? Are hospitality and unconditional welcome a key part of the institution’s DNA?


The joy of heaven will begin as soon as we 
attain the character of heaven, and do its duties.

~ Theodore Parker


It may sound like Oprah, but the presence of joy is almost always a sign that a community is doing something right. From ancient religious wisdom to contemporary education experts, history locates joy as the fruit of a well-ordered life. When you perceive this glow in a ­community—be it a school, a neighborhood, a synagogue, a salon, a company, a volunteer effort, even a prison—it should be a signal that most if not all of these 16 Questions are being answered with distinction.

Joy is difficult to define, but most of us know it when we see it. It is the fulfillment we get in surrendering ourselves to some noble cause or unconditional love. It is born in contexts where people feel united with those around them, when they find themselves serving a higher ideal, when they are giving themselves to something good, true, and beautiful. Joy is more textured than happiness; it comes through moral struggle, surrender, surprise moments of transcendence. Joy is the crown of a well-lived life. It satisfies the soul.

Long celebrated and cultivated in major religious traditions and non-Western cultural norms, joy is now making a comeback in modern social science, as well as in the work of those studying how human beings learn.

“You know that authentic, transforming learning is happening when you walk into a classroom and you get a palpable sense of joy,” says David Steiner, executive director of the Institute for Education Policy at Johns Hopkins School of Education. The Harvard Grant Study, one of the world’s longest surveys of adult life, has found that the people who were most satisfied in their relationships at age 50 were the healthiest at age 80. Their ability to withstand the toll of aging was directly related to the joy they had in the context of committed relationships—more important than career success, more important even than taking scrupulous care of their bodies.

At The Other Side Academy in Salt Lake City, people have seen and contributed to life’s underbelly. Some have stolen, some have murdered. They’ve all lied. They’ve all cheated. But here, in the context of peer-to-peer accountability and people who believe in unfurling their better angels, there is a palpable sense of delight as they learn to respect and trust others—and themselves.

Jean Vanier is a Canadian Catholic philosopher who founded the L’Arche communities that have reached over 8,000 handicapped and disabled people worldwide. L’Arche holds that everyone has needs and gifts, regardless of apparent capacity. Henri Nouwen, who lived at a L’Arche community for the last ten years of his life, experienced a joy there completely counter to the mainstream world’s understanding of value. He explained: “When we honestly ask ourselves which person in our lives means the most to us, we often find that it is those who, instead of giving advice, solutions, or cures, have chosen rather to share our pain and touch our wounds with a warm and tender hand.” 

Homeboy Industries in Los Angeles provides training and support to former gang members and other ex-offenders, allowing them to redirect their lives and become contributing members of the community. Each year over 10,000 come through its doors. They are welcomed into a community of mutual kinship, love, and a wide variety of services ranging from tattoo removal to anger management and parenting classes. Full-time employment is offered to more than 200 men and women at a time through an 18-month program that helps them re-identify who they are in their community.

“We choose to infuse hope in kids for whom hope is foreign,” ­Homeboy founder Father Greg Boyle says. “No kid is seeking something in a gang. They are all fleeing something.”

There is a transcendent association with true joy. Joy is often found in faith-based institutions, though not exclusively so. It graces people working and living in harmony and self-sacrifice. It is a mischievous function of the last becoming first, and the first becoming last.

Are there consistent testimonies of whole-person change in a positive direction?


Change is the essence of life; be willing to surrender 
what you are for what you could become.
~ Reinhold Niebuhr


Ultimately, character formation is about transformation. Sometimes it happens dramatically and overnight; other times it’s a more gradual process. Like joy, transformation is a sign of effectiveness, of these 16 Questions answered well.

The kinds of transformations to look for as a character-builder are: From selfish to selfless. From sullen to joyful. From passive to responsible. From insecure to other-centered. From engaged online to engaged offline. From proud to humble. From self-concerned to leading others.

Institutionally, there are often two ways to think about this: intervention programs ( The Other Side Academy, a 12 Steps program, Homeboy Industries, a three-day retreat), and long-term character incubators (the family, a school, a neighborhood, an artistic discipline). As a society, we’ve gotten better at the interventions while letting the permanent structures go.

The Other Side Academy speaks the language of transformation from sunup to sundown. It has a process for achieving dramatic results in each of its wounded and wounding individuals, and banks on it as the hope for each entering resident.

The Positivity Project deals in more gradual transformation. Through its strengths-finding tests, teachers come to realize that the brightest math student needn’t be the only student they attend to—that there are other qualities worth encouraging and applauding.

The 12 Steps program boasts dramatic, if gradual, change. Substance addiction is often so deep that it requires constant care and group support. Its common refrain returns again and again to our helplessness and need for grace, for others, for a second chance.

Gap-year programs with a moral bent transform young people from small in scope and mindset to empathetic citizens who can bridge divides, listen to foreign opinions, appreciate the complexities of poverty, and so on.

The National Advanced Academy of Teacher Education offers a two-year program to develop the nation’s top-tier educators for improved student and school performance. Through Socratic dialogue and case studies, NAATE attracts experienced teachers who have already been identified as high-performers and immerses them in an intense, residential program that links their daily practice to key theories and principles of education. Teachers gain tools to enhance their classroom practice, and hone leadership skills with peers and other adults outside the classroom. Graduates of the program walk away with a much deeper understanding of, zest for, and commitment to their educational vocation. They describe both the tight-knit peer community and the practice-based inquiry as being transformative to their professional and personal selves.

The key is to ask: Are people being transformed by this experience, these relationships, the embedded norms? Are they going from bad to good, good to great, passive to active, selfish to selfless?

When people depart from this formative institution, do they promote a similar culture in other contexts? Has the institution imparted a set of ideals that members want to live up to ever after?


Nothing that is worth doing can be achieved in our lifetime; therefore we must be saved by hope. Nothing which is true or beautiful or good makes complete sense in any immediate context of history; therefore we must be saved by faith. Nothing we do, however virtuous, can be accomplished alone; therefore we must be saved by love. No virtuous act is quite as virtuous from the standpoint of our friend or foe as it is from our standpoint. Therefore we must be saved by the final form of love which is forgiveness.
~ Reinhold Niebuhr


The ultimate sign of an outstanding institution is that those who have passed through it go on to embody and inspire similar values elsewhere. I will call this ripple-effect test “generativity.”

Nyack College in New York City is at once energetically Christian and yet urban and ethnically diverse. Most Protestant colleges in the country tend to draw from white evangelical families from the suburbs. Nyack’s downtown campus is made up of African Americans, Latinos, Koreans, Vietnamese, Chinese, Africans, and other immigrant students, most of whom hail from storefront churches in the city’s outer boroughs.

The first time I visited Nyack, I was struck by a palpable sense of joy, courage, and a radical hospitality. “Where love has a name” was the phrase that kept coming to mind. I asked the faculty what employers testified about Nyack graduates, who typically go on to work in the social sector, from nursing, to serving in homeless shelters, to counseling, to prison work. The faculty answered unanimously: “Employers tell us that our students create mini-Nyacks wherever they go.”

This was a powerful statement about institutional impact, and the ability students had gained to go out and foster similar conditions for others, even in places already set in their ways. It suggested that Nyack imparted a particular logic, a way of perceiving reality and relating to others, that students were able to share effectively in other contexts.

Williamson College for the Trades also does this. Students aspire to become “the Williamson Man” throughout their study and apprenticeship, learning values of integrity, self-sacrifice, concern for others, ­trustworthiness. They graduate and join construction companies, architectural firms, gardening squads, and plumbing units. Employer after employer testifies to the long-term influence of Williamson men—they lead, they model inspiring behavior, and they serve. An identity took root in their formative years, blossomed, and planted new seeds wherever they go. This is how cultures are made.

Generativity is the stage at which a person can make commitments to future generations, instead of focusing on self.

Psychologist Erik Erikson coined the term “generativity” to describe the stage of maturity in psycho-social development. In contrast to adolescence, when the personality is focused on self more than the needs of others, generativity is the stage at which one can make commitments even to future generations. This goes for institutions as well as individuals.

Case studies on organizations with socially generative practices find that these groups experience low turnover, low levels of internal conflict, high levels of motivation, participation, and trust, a strong sense of belonging, a culture of caring, promotion of personal development and spin-offs, a long-term timescale, and an orientation towards the needs of the surrounding community.


The Fabric of Character

A Wise Giver's Guide to Supporting Social and Moral Renewal

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