Reimagining Mentorship

The building blocks of society are its adult citizens. What kind of society do we want to build?

What is mentorship today?

Gangs initiate with criminal acts and violence. Members of organizations like Alcoholics Anonymous, with experience in sobriety, sponsor those who are newer to recovery. Bar mitzvah ceremonies convey manhood in a rite still recognized by every generation present, centuries after the first man taught another to read the Torah to the congregation.

As powerful as each of these models is, none of them is appropriate for all of the young people in the mainstream of our society. Our culture is egalitarian, diverse, competitive, and interdependent. And because it changes so quickly, our old ideas about mentoring may prevent us from taking seriously the need for mentorship.

Is it inevitable that when the culture is changing faster than ever, when we need mentorship of our young people like never before, we find ourselves grasping for meaning, lost without the rites of passage that used to delineate childhood from adulthood? Your first acid trip, or the first time you had sex,or got drunk, or went to Burning Man, or got a tattoo, or completed the highest level of a video game, might be a kind of milestone, but what was achieved, and was it recognizable to generations other than your own as a sign of your adult life beginning? Or was it just another experience that proved nothing about your capacity to do what is expected of you as a full member of society? Even useful milestones like high school graduation and getting your driver’s license are insufficient to create strong adults.

Mentorship must be as flexible and strong as the kind of adult, and society, it hopes to create. Video game scores and other meaningless milestones can’t be the foundation of initiation into adulthood, but neither can any other rites that have nothing to do with our current values.

Agents of change

It is a challenge to create a new system of mentorship, because we have lacked contemporary examples that are accessible and culturally appropriate to most people.

There are models in historical and contemporary modes of mentorship we can learn from, outside the grasp of capitalism. There are cultures and subcultures I believe we should feel free to borrow from—whatever might work with both our values and what we see as the challenges that await our youth. (It’s only stealing if you prevent others from using an idea, so why worry more about cultural appropriation than we do intellectual property rights?) Studying structures that have worked for others, we can then create a system that is formal enough to replicate, flexible enough for everyone to use, freely accessible to the young people who need it, and rewarding to everyone involved. But to do all of this, we will have to overcome ideas that have come to be associated with mentorship, that have made it seem unnecessary or outdated.

Some might expect that the mentorship of boys will reinforce old values that no longer serve men, or impose the double bind of old masculinity with new expectations. Under patriarchal systems, there are arguments for basing mentorship of men on the needs and desires of women. Joseph Campbell said that “Woman is life and man is the servant of life. The male’s job is to protect the women.” The heteronormative assumption that all men really want in the world is a wife and family, and that women want no part of public life, has in some cases only been updated to ask our archetype of the modern woman what she wants from men.

Today, being a man is more about being an adult than about distinguishing oneself from women. Our ideas of adulthood are no longer neatly bifurcated into male and female. Men and women are both encouraged to find their own public roles, as well as to create a family and support it in more or less equal and similar ways, with divisions of labor that are based on individual abilities and preferences rather than gender expectations.

Men are no more passive victims of change than women. We are all agents in the world, not objects for one another’s gratification, and we should raise our strong, free children to look for the same independent spirit in their partners. If our values include equality and freedom for women and men, then we must also make choices based on our individual strengths, not ready ourselves to receive marching orders or put on the double yoke. Mentorship assures boys that they do not need to simultaneously prepare to be both a stoic breadwinner and an emotionally intelligent, egalitarian partner.

We need mentorship today so that we will know, confidently, what it is we want to be teaching our kids. We need to raise the issue so we’ll ask ourselves the question, repeatedly, whatever our experience of child rearing or mentoring has been, what we want mentorship to be now and in the future. It’s not just up to parents to contribute to society through mentorship: all of us are adults, so we’re qualified both to ask, What do we require of the adult members of our society? and What can I give of myself to young people who need mentoring?

Motivation and relationship-building

We need to figure out what we want from our kids when they become adults, so that we can consider what to teach, and know how to teach it. Young people have to learn tolerance for discomfort: an ability to wait patiently, to pay attention instead of being its focus, to do unpleasant and necessary work, and to delay gratification. Because young people don’t yet know all of what they’ll need as adults, they need the meaningful connections to their peers and mentors, and shared rites of passage, as motivation.

Relationship building skills are arguably the most important that we can teach, and relationships occur on multiple axes. Mentors can begin by making meaningful connections with their mentees. Roger Durham, one of the men I interviewed for this article, has written about the importance of being vulnerable and fully present with young people. Ben Keeler, who has studied the power of mentorship for young men in building healthy relationships, told me that “the purpose of mentorship is to help young men find direction and motivation to pursue what they’re passionate about, finding purpose and healthy relationships.“ Mentors have the power to create safe spaces in which young people can do the work of learning about themselves and others without judgment. These are the building blocks for relationship skills: relating to ourselves and our friends, those who help us and those we help.

Real responsibility

The apprenticeships and religious rites that were commonly available to young men a few generations ago are no longer part of our mainstream ideas of adulthood rites of passage. Instead of teaching a trade while paying a subsistence wage to apprentices, there are entry-level jobs that pay subsistence, but offer no skills for advancement. Instead, these skills are sold separately in trade schools and technical institutes.

In “The Karate Kid,” Mr. Miyagi set out tasks for Daniel to complete, but it is Daniel’s error as a novice to presume they were pointless activities. Once he has progressed in his training, Daniel realizes that not only did he create something beautiful and useful through his work, but he also learned the skills he asked to receive training in, and that he could apply to his own goals.

We want our kids to be strong members of their communities, to not only find their niches in an interdependent society but to be heroes. To create kids who are altruistic—who want to connect with people who need help—is to make them confident that they are securely connected to others who will not let them fail, and who can help find the resources to help the ones they are reaching out to. Serving young people, answering their questions and directing their energy positively, demonstrates the power of service. Giving young people the tools they need, and genuine responsibility to act, for themselves and in service to others, is how to teach a service orientation.

Preserving and creating value

Our assumptions about the speed with which society changes might also include the belief that the generation that has preceded us has nothing of value to tell us. Technology has changed our world, but only on the surface: the people are still the same. Maturity and wisdom are different gifts from youth and energy; we need them all. There are skills for meeting change, and adults who have mastered these skills—the ability to be open, to learn, to be flexible, to accept not only changing technology but changing social norms and a diversity of people—have been successful because of them, and are needed to pass what they have learned down to the next generation.

The ability to take care of yourself and others is a gift. When we can connect with other people, this is another enduring source of happiness. Not teaching our kids how to be the kinds of adults that others will want to work with, be friends and partners with, doesn’t protect them from the rigors of responsibility: it isolates them from opportunities for pride and joy.

We have to do this for society, but also for our kids: each of us deserves the tools to find out who we are and where we fit in the world, and to get them when we’re at the right stage of development to use them.

Showing young people that they are precious—worth our time and attention to help them grow up right, worth their investment in practice and education—is one of the most valuable things any of us can do for someone, and the most likely to produce well-adjusted adults.

In business, we talk of “externalized factors,” meaning those that don’t appear on the accounting sheets. Guerrilla gardeners take advantage of wealth lying fallow in the form of neglected land. Mentorship is a way that we can create wealth in society with such externalized sources of value.

It’s been a cost of doing business, when mentorship has suffered as have the family and the community. Working for a living can be a grind: making things you don’t value, trading your health and peace for little pay and no security. You get a small fraction of the value you create for your employer, when you work for someone else. However, when you work to till the soil of your own community, you invest in your community. You create value through work that is personally rewarding.

We need to create a new form of mentorship that will allow each of us to do the meaningful, rewarding work of investing in the infrastructure of society.


Read more on Mentoring and Volunteering.

Image credit: slightly everything/Flickr

About Justin Cascio

Justin Cascio is a writer, trans man, and biome. His most recent publication is a short memoir, "Heartbreak and Detox," available on Kindle.
You can follow him on Twitter, Google, and Facebook.


  1. Great piece. Mentorship is so very important. I think it’s important between young boys and men and older men, and among girls and women as well. I also think it’s also important for young boys and girls to have mentors of the opposite sex so that they don’t just learn from their own gender, but the other gender as well.

  2. That is a beautiful call to action. There is no question about the critical influences good men can have in young male lives. The opposite is also true, when men don’t show up, chaos prevails. We see clear demonstrations of the need for men in boy’s lives on the news every night. Lost boys, most without men in their lives, gone violent or foolish in some tragic way. Without any form of positive or functional guidance in their lives it’s simply Goulding’s Lord of the Flies everywhere. It’s tempting to blame the boys, and in fact, our cultural answer is to imprison them in droves. But what we really have is an epidemic of under-male-nourished boys. It’s men’s work to fight that dis-ease.

    In the work with men and boys I’ve been doing for the last 10 years, I have yet to find a mentoring organization that didn’t have a long wait-list of boys who are hoping for a match with a man. But the men, except for a very few compared to the need, are not just not showing up. I don’t think we so much need a new form of mentoring in the world today, as men becoming willing to be involved with the young guys. I have an article on my website describing some of the many reasons men don’t step up in service to young males (

    What most men don’t realize is that thousands of years of men having to socialize testosterone fueled adolescent males has hardwired them for this work. If you put a collection of men and boys in a group doing just about any activity, all the right things happen naturally. Like I said, the trick is to get the men to show up.

    If you hear the call and can’t find a group of men and boys near you, you can go to the website (, put in your zip code, and you’ll get a list of mentoring groups and organizations near you that would love your involvement.

    You, as a man, are the book on manhood for a young male, and you can be sure the young guys are waiting for you to show up.

  3. Justin,

    Thanks for this insightful look at mentorship. You ask powerfully important questions, like “what kind of society do we want to build?”. Boys become men – at least chronilogically and biologically – just as a matter of course. But mentorship introduces a level of intention to the growing up process that allows us to answer your question.

    I’ve never thought of mentorship as a way to “create wealth” in society, but in a profound sense, that is certainly a potential outcome of positive mentorship.

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