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'Masterminds and Wingmen': Preparing your son for the pitfalls of a boy's world

In a changing world, proactive parenting can be the key to steering your child around the many impediments towards young adulthood. In "Masterminds and Wingmen," Rosalind Wiseman helps parents navigate the inevitable tests that they and their sons will face. Here's an excerpt.REDEMPTION AND RECONCILIATIONYou pick up the phone. You open the email. You say hello, expecting a brief, pleasant exchange

In a changing world, proactive parenting can be the key to steering your child around the many impediments towards young adulthood. In "Masterminds and Wingmen," Rosalind Wiseman helps parents navigate the inevitable tests that they and their sons will face. Here's an excerpt.


You pick up the phone. You open the email. You say hello, expecting a brief, pleasant exchange. The next moment you can feel your pulse beating, your stomach clenching, and your eyes closing as you try to process the information you’ve just been given. You have just found out that your son has done something really bad. Not just a little bit bad. Really bad.

Sometimes your son will mess up, and it can feel that life changes in an instant. Overnight you can feel that you and your son aren’t welcome in a place that was your home away from home just the day before. For your son, the life he had before seems to have been snatched away, and he has no idea how to get it back.

When your child gets in trouble that becomes public—that is, he’s done something bad that other people know about or that will be officially recorded in his school transcript—there are two reasons why he could be in this situation. One, he did something incredibly stupid but didn’t realize it at the time. Or two, he knew exactly what he was doing, and his cover-up failed. The latter includes the possibility that he has developed a pattern of “bad” behavior and isn’t getting how serious you or the school is about changing his behavior.

For him, the benefit of the first reason—of being ignorant until the ax comes down—is that he spends no time dreading getting caught. The drawback is that he’ll probably have at least one but probably several very unpleasant conversations with adults who’ll say, “What were you thinking?!!!!” (which isn’t really a question), and he’ll have no idea what to say except to miserably respond, “I don’t know,” fully comprehending how stupid he sounds.

When he knows full well that what he did was wrong, there’s no period of blissful ignorance. He’ll be such an anxious mess that his performance in all aspects of his life will suffer, he won’t sleep well, and the most innocent comment by anyone will throw him into a panic. It’s truly a horrible way to live. That’s a good thing. If he isn’t wracked with worry, that’s a way bigger problem because that would mean that the adults in his life have given him the message that he’s entitled to be above the law (either the law of the land or the law of his school or family).

Don’t Kill Him

Just like when you’ve found out about a smaller mistake your son made, even though this is bigger, it’s still a moment in time. Your son isn’t doomed to be a failure or a terrible person. All of the reasons you love him are still right there alongside whatever else made him do this thing you’re now dealing with. Just like you, his feelings could be so jumbled together that it’s hard for him to sort them all out: embarrassment, anger that he got caught, fury at someone else for somehow getting him involved or selling him out, shame, denial, and paranoia that everyone is talking behind his back or that this one mistake will forever damage his future. These are all understandable feelings to have.

Ignorant or not, the moment he finds out he’s in trouble he’s probably going to go into cover-his-butt mode. Specifically that means he has to figure out what you know and just as importantly what you don’t. Then he’s going to attempt damage control. That’s why, when you first speak with him, you should try to convey this point:

“The most important thing to remember for both of us is that the way we respond will determine if and when people regain their respect for you. If you refuse to take responsibility for your actions, if you blame other people, or if either of us make a point of telling other people how stupid the punishment is or minimize what you did, that won’t be any help. If you try to take revenge on the person you believe reported you, you’ll be acting like an immature, vindictive bully.”

If he does admit what he did and how it hurt people around him, he’ll regain the good reputation he once had or build a better reputation than he had before. Before I go any further, I’ll own up to an assumption here I’m making here, and it’s a big one. I’m referring here to mistakes your son might make that hurt other people. Obviously, there are other things that can get boys into trouble. For example, if he cheats on a test because he’s overwhelmed, he’s breaking a rule, but his feeling of desperation also needs to be addressed. If he gets caught violating a technology or alcohol or drug policy, he (and even you) may think the rules are stupid or unfairly applied, but he agreed to those rules by becoming a participating member of the community.[1] That means that if he violates those rules, he accepts the punishment and doesn’t try to get you to get him off. By the way, if a kid shows up to school high or drunk or carrying drugs or alcohol, he has bigger problems then getting suspended.

The Gray Area

Whether we like it or not, there are situations where the “right” answer isn’t going to cut it, where moral dilemmas can lead to serious consequences. It’s critical that our children know that we have a strong moral framework that guides how we parent. But it’s just as critical that we acknowledge to them that sometimes applying these morals is difficult. Are we sending mixed messages if we admit the gray areas? Are we being hypocritical? Because the reality is that the institutions our kids are a part of (school, athletic teams, our communities’ laws) are often governed by inflexible rules and policies.

'Masterminds and Wingmen'

Let’s take the most common example: teen drinking. Imagine that your fifteen-year-old son tells you his friends were drinking at a party. If you respond with the standard line “Drinking is illegal and dangerous,” you aren’t admitting the complexity of the situation. As a result, he’s going to think you can’t or won’t give him the information he needs. On the other hand, what can you say to him that doesn’t come across as endorsing teen drinking?

Ideally, as with so many situations, we have to start earlier than when our kids are actually faced with the situation. We need to have a clear conversation about drinking, such as:

Now that you’re thirteen (or look like a teen), you can get into situations where people are drinking and/or doing drugs. [If so:] We have people in our family who have addiction problems, so you’re going to need to be mindful about that as you get older. I also need you to know that if you do it and the police or the school get involved, I won’t be able to protect you from the consequences. I’ll support you, but I won’t bail you out.

The long-term approach is encouraging him to develop a passion for something—something that would be jeopardized by drinking or doing drugs. And that loss has to matter to him, not necessarily to you. For example, Elijah loves to play basketball. So when I talk to him about drinking, smoking, or taking drugs, it’s about how these things impair his athletic ability and compromise his team loyalty. (If his performance suffers or he gets kicked off the team, I want him to view it as letting down his teammates). Our children will make these decisions when we aren’t around. So if we want them doing the right thing, we have to explain the wrong choice in terms that truly matter to them.

As they get older, those concrete rules become the backdrop for the more complicated situations they get into. Let’s go back to the fifteen-year-old. I’d say to him, Thanks for telling me. I don’t want to assume anything, so can you tell me what bothers you the most about it?

What bothers most teens about their friends’ drinking is how their behavior changes when they’re drunk, like being fake, untrustworthy, and belligerent. It’s one of those times when teens realize that doing more “adult” things can make people act in unpredictable ways that they don’t like. That’s the critical conversation to have with your child because it allows him to step back and assess what he needs to do and in the process develop personal boundaries. And you can still remind him about consequences. As I said above, if he signs a no-drinking contract to participate in a school activity, he has promised to act according to the spirit and letter of that agreement or accept the consequences of breaking his word.

Cheating is another common problem that seems like there’s a simple “right” answer. But again, like drinking, the reality of cheating is more complicated. Our kids shouldn’t copy or use other people’s work and take credit for it. They shouldn’t use their phones to hide information that they can use during a test. But most kids I work with believe most kids cheat. They think most adults cheat and get rewarded for it.

Most of the cheating I’ve seen is motivated by one of three things: desperation, laziness, or a reasonable strategy to deal with a ton of busywork a teacher assigns that the child has no hope of finishing without splitting up the work with other students and then sharing their work. Those are completely different motivations, and they need to be responded to as such if you’re going to effectively reach your child.

One of the best ways I’ve found to talk to younger kids about cheating is about recess. Have they ever seen someone change the rules or refuse to follow the rules? Demand a do-over instead of accept a loss? What do they think about that? Does that person deserve the win if they win under these circumstances?

If your child is older and they like playing video games, I bet they’ve experienced someone hacking the game and giving themselves infinite powers, making it impossible for other players to have a chance of success. That’s the crux of the issue right there. Is it fair for some people to literally game the system in their favor? Is it fair for others to rig the system so they have an unfair advantage? That’s what we should be talking to our kids about.

Encouraging Him to Come Clean

When he gets home and you see him for the first time, leave him alone for a little while. Let him go to his room, listen to music, and have a chance to feel everything he’s been keeping inside. It can be excruciatingly uncomfortable to admit to himself, let alone anyone else, that he’s done something really wrong.

Remember that different situations require different responses. If your son has lied to you about a problem he’s struggling with (such as his performance in school) or because he’s worried you’ll reject him if he tells you the truth about something important to him, then tell him you’re sorry he felt like he couldn’t come to you earlier, thank him for coming to you now, and use the steps I outlined in the previous chapter to help him think through his situation. Above all, it’s critical to acknowledge your understanding of his motivation and clearly convey how much you respect him for coming forward.

If, however, he has done something that goes against your stated rules or values—such as doing something mean (or contributing to someone else being mean), being deceitful, or putting someone (including himself ) in harm’s way and then lying about it—your response should be focused on communicating that his actions are contrary to your values, his right to entertain himself or do whatever he wants is not more important than treating others with dignity, and you’ll hold him accountable for his actions. But that’s not all. Just as important is communicating to him that coming clean and taking responsibility for his lies is the course of action that will make you proud of him.

Do not underestimate how much boys want your respect or a clear path to regaining it when they have disappointed you. How you do that is a delicate balance of playing hardball and appealing to his aspiration, ultimately, to do right. Now it’s time to make amends. The faster he publicly holds himself accountable the faster he’ll feel better. This is what he needs to understand:

1.    He’s really sorry for what he did wrong.
2.    He recognizes what he did that was wrong and he’s not making excuses for it.
3.    He realizes that his future actions have to reflect his words now.

What If He Doesn’t Seem To Be Getting It?

Saying sorry isn’t enough. Getting an empty apology isn’t enough. Have him explain to you why he’s sorry. If you get a fake apology, use my suggestions in the “Friendly Fire” chapter to apologize on his behalf until he gets his act together. Jeff Lippman, the head of the middle school of the American School in Brazil, often asks these questions of students:

What is the difference between what you do and who you are? If you repeat certain types of disrespectful or dishonest actions, at what point do you become a disrespectful or dishonest person?

Lippman points out that “this kind of questioning is often very powerful with kids because they’re so intensely involved in their own identity involvement.” I agree because it gives the boy the power to define his destiny and what kind of man he wants to be.


The word “discipline” comes from the Latin word disciplina, meaning “instruction or knowledge.” The dictionary defines “discipline” as “to train someone to obey a code of behavior or rules.” The purpose of punishment should always be the greater goal of learning. Unfortunately, this is often not the case. When adults run off the rails and impose counterproductive discipline, it is because they’re angry, feel disrespected, or are imposing punishments according to a rulebook that doesn’t make sense for the child and the situation.

This is important because boys have a strong response to authority figures who discipline them fairly, even if they hate the punishment. People in positions of authority are important to boys. Boys accord an adult great respect if they believe in the person’s honor. They burn with resentment when they are under the control of an adult who abuses his or her authority and then take these experiences and often assume other adults will act the same way.

My general strategy in disciplining children (either my own or my students) is to frame my response in this way:

1.    Tell them exactly what they did that was a problem.
2.    Tell them why the specific actions they did are against what I believe in (as their mom or teacher).
3.    Tell them specifically what privilege will be taken away and for how long (which requires that you know the child well enough to know which privilege means the most to them).
4.    Give them a “way back,” i.e., a way to make amends that will make them and me proud.

Finally, if your son laughs or is disrespectful, tell him:

“You clearly don’t respect me as an authority figure, and I don’t want to have a relationship with my son where he doesn’t treat me with dignity. I’m working on what I need to do to deserve your respect. It’s your choice if you want to contribute to changing this relationship for the better, but the punishment /rules/expectations I have laid out still apply. If you choose to disregard them, then we have a different level of a problem. That’s not a threat. It’s just what I have to do to effectively address the situation.”

The Least and Most Effective Punishments According to Boys Themselves

I’ve asked boys to give me examples of punishments not only from their parents but from their schools.

The least effective punishment is grounding them plain and simple, without taking any sort of electronic device, such as laptop, computer, cell phone, iPod, etc., because they still have the basic social freedoms and can still have contact with their friends, but can’t go out and see them. In my opinion, it still gives kids the social freedoms they want, and they can still get by and not even feel remorse or understand what they did to get grounded was wrong in the first place.
—Stan, 16

The most pointless thing is when they ground you. When my mom sends me to my room, I don’t really care. I’m a musician, so I can always find something else to do. The most effective punishment for parents is when they take everything away from you. My mom once took my phone, my Internet, Xbox, guitars, pretty much everything. She did that so I would do this list of chores she had. It worked.
—Landon, 15

I got into huge trouble recently, and my parents grounded me for three months, but after a month they stopped. It’s like . . . I can’t trust them. Is that weird? But that’s what it feels like. Like I can’t trust them because they didn’t follow through.
—Tom, 17

The thing is that most parents don’t really talk about why they’re doing this stuff. It makes it seem that the parent likes punishing their kid. If parents just talked, it would be so much easier.
—Damion, 15

What’s the worst punishment—that is, the most effective punishment? Time and time again, boys say the same thing. The worst punishment is losing their parents’ respect and disappointing them and having their ability to communicate with their peers taken away.

No matter what, don’t hand down a punishment and then change your mind or fail to enforce it—unless you want to lose all credibility as his parent.

For any parent, it’s really hard to discipline effectively because embarrassment, anger, and anxiety can overwhelm calmer, more strategic thinking. Fundamentally, you probably feel really worried and confused about your son. It’s also possible that he has been giving you pretty obvious signs that things were running off the rails, but you didn’t see them. So when you do have to face the problem, you’re not only dealing with what’s happening right now but with all the factors that led up to it—like your own denial. You also could be angry that he isn’t representing the family well. This is not necessarily a superficial concern, since it might be masking your distress that he didn’t act according to your shared values.

Without excusing the really bad and ineffective things that parents can do, it’s important to recognize why this situation is so painful for them and for their son. In a nutshell, when a son gets into serious trouble, it can make his parents feel like they’ve been bad parents, make them worry about what people will think about their family, and make them worry that they don’t know him as well as they thought they did.

Making Public Amends

Here’s a sample letter your son can use as a starting point for writing his own letter to the school administrator but he has to make it his own to mean anything to the people he’s addressing.

I’m really sorry for [screwing up in a huge way]. I can imagine it’s hard for you to believe that I couldn’t figure out it was wrong before I did it, but for some reason that I don’t understand right now, I didn’t. I know the rules of the school, but I also know what the school stands for and what I did was against that. I know it’s not just about what I say but about what I do from now on. I’d like to take responsibility for my actions by apologizing to the class. I hope to gain your trust back one day, but I know it will take time.


Has He Ruined His Future?

It depends entirely on how everyone handles the situation. I’ve had countless conversations with school administrators about this issue. I promise you that, if you help your son take responsibility for his actions, teachers, administrators, and coaches will explain to college admissions offices what happened by noting the positive actions he took and what he learned after the event.

I know that, in the moment, it’s hard not to fight as hard as you can to minimize the public nature of the discipline. But as hard as it is, you can’t let your anxiety blind you to seeing the bigger picture. Maybe this was the wake-up call your son needed. Sometimes colleges will defer acceptance until a student has had a chance to prove that he’s learned from the experience, and sometimes colleges will withdraw an acceptance and this turns out to be a really good outcome for him. If that happens, it can feel like he’s failed. I promise you that he’s better off taking a step back, figuring out the best course of action for him right now, and try to be readmitted to the school once he’s had an opportunity to think and get himself together. Yes, I know this is easy to say when you’re not in the middle of all your friends talking about their children’s future plans, but if you and he don’t stop and figure out how he got into this situation, he’s doomed to repeat it, and each time the stakes get higher. I’m not referring to the college he gets into. I am talking about his emotional, physical, and spiritual well-being.

These experiences are hard, even excruciating, and can truly be among the most challenging moments of parenting. But one thing I know for certain. The moment your son decides to face what he did and make amends is the moment he begins to regain his sense of honor and hope for the future.

Excerpted from MASTERMINDS & WINGMEN by Rosalind Wiseman. Copyright © 2013 by Rosalind Wiseman. Excerpted by permission of Harmony Books, an imprint of the Crown Publishing Group, a division of Random House LLC, a Penguin Random House Company. All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.

[1] As much as we may hate to admit it, it is also important to acknowledge that the system is coercive—even though from an adult perspective that may not make sense. In order to participate in many activities, you must sign a pledge that controls other aspects of your life that are seemingly unrelated to that activity. It’s a difficult situation for a teen because it’s developmentally appropriate for him to explore new and possibly dangerous aspects of life but at the same time he’s being told he can participate in activities only if he gives up other things that he values and that he sees others do around him all the time.