Your Roadmap + 10 Tips: How To Raise A Boy Right (and Keep Your Teen Boy Emotionally Healthy)

We all want to raise our boys right.  “Right” is subjective, though; we might all have different ideas of what that means.  Here’s what it means to me (perhaps we have some common ground here):  I want my boys to be physically healthy.  I want to give my kids the resources to learn and to be resourceful and resilient.  I want to raise polite and respectful kids.  And I want them to be emotionally healthy.  To me, this means the ability to maintain healthy relationships and to feel and express the rainbow of emotions…to truly live a full and rich life. 

I worry about the emotional health of my boys.  They’re both growing up so fast (my oldest son is 14 and my youngest is 10).   I have so many questions as my teenager is racing toward adulthood.  How can I get a better understanding of what he’s going through so that I can best support him?  How can I ensure that he knows that we love and support him?  How can I encourage him to express his feelings and not hold them back?

I read a book called “Raising Cain:  Protecting the Emotional Life of Boys” by Dan Kindlon, Ph.D. and Michael Thompson, Ph.D.  In their introduction, the authors write, “We want to help people who love boys—their parents, teachers, and mentors—to see past the opaque surface of boys’ lives to their inner lives.  Their joy and their struggles.  We want you—our reader—to understand the ways boys suffer and what causes them emotional pain.  It is vital that parents and teachers not take boys at face value, even though they sometimes insist, furiously, that we do so.”  And I was hooked.

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If you’re a parent of an adolescent boy who would like a roadmap of how to raise your son to be emotionally healthy, consider this book your starting point.  

Let me tell you what I learned.

How Culture Teaches Us How To Raise A Boy To Be A Man

First, let’s examine how our culture shapes what it means to “be a man”.   This is important because our culture influences the way we interact with our sons, the way our boys interact with one another, and how they feel on the “inside”.  

In our society, boys are supposed to be strong and confident.  Because of this, we believe that boys aren’t emotional, sensitive, or needy.  Our boys learn that masculine emotions, such as anger and aggression are okay, while other emotions, (especially fear) are hidden and silenced.  They learn that stereotypical feminine traits, such as “tenderness, empathy, compassion and any show of emotional vulnerability” aren’t to be freely expressed. (1)

I remember picking up my oldest son from school when he was in the 4th grade.  It was his birthday—he had turned 8 that day.  I was so excited to hear about his special day, but it was obvious that he was upset.  I asked him to tell me what happened and what he was feeling, but all he could do was sit there, looking sad, and say “nothing’.  It took him a while to finally open up and tell me what had happened—his favorite teacher had gotten impatient with him about something that another student was to blame and raised her voice at him.  He was deeply hurt because he loved this teacher and her approval was important to him.  Yet, he was reluctant to express his sadness and hurt.  This is real life for a boy.  From an early age, they struggle to open up and talk about their feelings.  

Many boys don’t understand their feelings and have trouble expressing their emotions because society tells them that they are stoic, strong, and silent.  To cope with and downplay their emotions, boys use “shields of various forms to keep others away: irritability, sarcasm, nonchalance, stoicism, and others.” (2)  

“A boy lives in a narrowly defined world of developing masculinity in which everything he does or thinks is judged on the basis of the strength or weakness it represents; you are either strong and worthwhile, or weak and worthless.”

From:  "Raising Cain:  Protecting The Emotional Life of Boys"  (Introduction, p. xii)

At it’s simplest, boys must always appear strong and in control, and must never appear weak, emotional, or vulnerable.  As a result, boys learn to downplay, hide, or silence their fears, sadness, and vulnerability.  

But all of this doesn’t mean that a boy doesn’t experience strong feelings.  He does.  He just has trouble expressing them.

So how can we help our boys out of their emotional straightjacket?

1.  Recognize the cultural stereotypes that our boys are raised in and how this causes boys to shut down their societally unacceptable (“feminine”) emotions.  

2.  If you know something is troubling your son, don’t brush it off (even if he urges you to).   Spend the time and effort to find out what the issue is and what they’re feeling.

3.  Give him permission to experience and express the full spectrum of human emotions.  Allow him to be open about his feelings.

4.  Be respectful of his feelings.


How Harsh Discipline Can Backfire With Boys

There is a correlation between harsher discipline and children’s physical misbehavior (as opposed to talking back).  Because boys are generally more active and physical, they are on the receiving end of a more severe disciplinary style. (3).  This, coupled with the fact that we believe we have to “toughen up” our boys, cause us to use power, fear, and intimidation as disciplinary tactics.  Do these tactics work?

It might seem to work.  But the authors caution that success with this approach is short-term and has a greater likelihood of backfiring. (4)  The end result is that boys subjected to this type of discipline learn to make decisions based on external forces; what their parents or teachers expect. They don’t learn to use their internal compass as a guide. 

When our boys do something we don’t like, we react angrily because we’re upset.  But we’re also trying to teach them a lesson.  We are angry and therefore, don’t do it again, because what you did was dangerous, stupid, etc.  Remember, though, that to our kids, we are larger than life.  So when we react with intense anger, our boys are more likely to remember the emotional nuances of the moment:  how your face looked like when you were yelling, the power of your anger, where he was, and how he felt. (5)  And that’s not necessarily what we had intended; it isn’t the fear that we want them to remember, it’s the lesson.

The takeaway:  If you typically use anger and fear as disciplinary tactics, realize that your son will remember the fury far more than the reason you were upset in the first place.  Reflect upon your disciplinary style and make adjustments if they’re unduly harsh.

What can we do?

1.  Use consistent, clear and firm discipline.  

2.  Demonstrate compassion while disciplining.

3.  Model the desired behavior in your interactions with others.

4.  Engage your son in the discussion as opposed to reacting with anger. 

“Good discipline engages a child, encourages contact instead of isolation, draws him into the discussion instead of sending him away.  It involves the boy as consultant.”  

From:  "Raising Cain:  Protecting the Emotional Life of Boys" (6)


How Fathers Can Bond With Their Teenage Sons:  Improving Father-Son Relationships

4 Ways Fathers Can Bond With Their Teenage Son

It probably goes without saying that a father’s involvement in his son’s life is important.  In fact, the book cites research that the father’s role in child care was most influential in developing a boys’ emotional education and empathy. (7)

In early childhood, fathers will engage with their young sons in a much different way than mothers.  Fathers are usually more active, playful, and rougher than the mother.  Fathers rejoice!  Your active style of parenting has proven to be extremely important in building a strong father-son relationship.

However, when things don’t go to plan or if boys misbehave, fathers should be mindful of unrelenting criticism of their young son and shouldn’t withhold praise as punishment.  The authors state that doing so causes deep wounds that last well into adulthood. (8)

“In the early years, when they are rank beginners at so much, their father’s opinion of them carries enormous weight.” 

And, therefore:

“A boy wants a father who thinks he is fantastic—one who knows that he is still little and cannot do everything well but loves him anyway.” 

Both quotes from:  "Raising Cain:  Protecting The Emotional Life of Boys" (9)

In middle childhood, boys are watching and absorbing their fathers’ interactions with others, how he resolves conflict and conducts himself as a partner at home and at work.  Because our boys learn from observing, fathers should try to be the model of manhood they want their son to become.

Because his father’s approval is so important, a boy will seek his father’s advice.  Instead of only doling out advice or talking about his adult opinions, a father should consider and respect his son’s opinions and feelings as well.  If boys are made to feel like they don’t matter, they won’t share their feelings with their fathers.  Sadly, this is all too common.  Of all the close relationships in a boy’s life, research shows he is least likely to share his life with his father. (10) 

The takeaway here—start showing your adolescent son respect for his opinions as it may encourage him to share his life with you and bring you closer together.

To drive this point home, the authors outlined a study of 300 corporate male executives and managers.  They were asked about the single thing they would change about their childhood relationship with their fathers.  The most common response?  They wished they had been closer to their fathers growing up, and they wished their fathers had expressed more emotion and feelings. (11)

The takeaway:  a boy’s withdrawal in the teen years causes many fathers to believe their sons don’t want their love or attention. There is nothing further from the truth; boys still need and want their father’s attention, approval, and love.  

What can fathers do to strengthen their relationship with their teenage sons?

1.  Celebrate your son’s individual accomplishments.  Celebrate him for who he is, not how he measures up to others.  Don’t push him to compete in something for you.  Tell him that he’s fabulous just as he is. 

“More fathers need to communicate more often to their all-too-flawed sons the simple message that they are loved and valued.” 

From:  "Raising Cain:  Protecting the Emotional Life of Boys" (12)

2.  As your son gets older, ask for his opinion, and listen to what he has to say.  Try not to judge his teenage boy feelings and opinions through your adult lens.  Validate his opinions instead.   If all you do is voice your own opinions, he’ll feel like he doesn’t matter and he’ll be less likely to share his life with you.

3.  Model emotionally healthy male friendships.  Encourage your son to have friends, maintain close friendships, and model positive conflict resolution in your own relationships.

4.  Do ordinary, everyday things together.  Go for regular haircuts and create a ritual out of weekly trips to the Farmer’s Market.  Do some gardening together.  Give the dog a bath and clean out the fish tank.  Play H-O-R-S-E.  These can be the building blocks for a strong father-son relationship that can survive the ups and downs of growing up.

5.  Recognize that a strong father-son relationship probably will look wildly different from a strong mother-son relationship.  


Improving Teenage Boys' Relationship With Their Mothers:  Don't Mistake Distance for Rejection

How to Improve the Mother-Teenage Son Relationship Infographic

In early childhood, being a mom to a boy is pretty simple and straightforward.  We comfort them, read to them and cuddle with them.  We do their laundry, dress them, pack their lunches and see them off to school.  But it gets more complicated they grow up.  They seem to not need us as much—which makes it tough to figure out where we fit into their lives.  

As moms, we have to remember that boys are different.  Keep this in mind when you think about how you communicate with your son.  Realize and accept that communication with your son is very different from your conversations and interactions with your BFFs or your mom.Here’s what happens:  as a boy gets older, “he will still look to his mother for love and acceptance, but he will distance himself from her when he feels the need for autonomy or to assert his “boyness” (13).

This behavior is confusing to moms.  Some mothers believe that their son’s distance and desire for independence mean they don’t need or want love and nurturing.  They take it as rejection.  This is a mistake.  In fact, “A boy never loses his need to be understood and loved by his mother.” (14) 

Despite his distance, your son still wants and needs the nurturing touch and expressions of love from his mother. (15)  Don’t stop trying to create physical closeness with your adolescent son.  Just realize that the physical expression of caring and nurturing will look a lot different for a teen boy as opposed to when they were little.  As moms, our job is to figure out what that is.

What can mothers do to strengthen their relationship with their teenage sons?

1.  Accept the high energy levels and physicality of boys.  Give your son safe places to express it.

2.  At each milestone in the boy’s life (such as toddlerhood, entering Kindergarten, hitting puberty, and then graduating from high school and leaving home), a mother must adjust her parenting style, in order for her son to feel that she has confidence in his ability to handle new experiences.  Let him stand on his own as he experiences new things. Don’t try to insulate him from all failure.  

3.  Provide him with emotional support by simply listening and sharing his emotions.  Express confidence in him, and support him as he solves his problems.

4.  Determine how and when physical closeness is appropriate for your son.  Remember that he still wants and needs the physical closeness but may never say anything about it.

5.  Try to view the world through your son’s lens and not your own. 

When we see a mother and son in a synchronous relationship, we see a mother willing to look upon child rearing as a practice—and willing to try to view the world through her son’s eyes in order to understand his needs.” 

From:  "Raising Cain:  Protecting the Emotional Life of Boys" (16) 

6.  Support your son’s friendships and accept the fact that they will look very different from your female relationships. 

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We love our boys.  They’re smart and funny, active and physical.  And they’re capable of experiencing mighty feelings and emotions.  Let’s help them grow and develop academically, physically, and emotionally.

Here’s what they need from us to develop and protect their emotional health:

1.  Teach your son to understand and recognize the emotions inside himself and others.   Talk about your own emotions.  Help him to develop empathy and compassion by caring for pets, children, the elderly or disabled.

2.  Teach boys that there are many ways to be a man.  Celebrate the differences.  Let him know there are so many ways for him to be a man--not just the strong, unflinching, stoic, superhero male stereotype.

3.  Listen without judgment to your son’s opinions and feelings.  Don't discount his opinions.  Honor his feelings. 

4.  Consult and problem solve with him.  Don't simply dictate what you think the solution to his problem is.

5.  Communicate with him in a “boy” way.  Be direct and specific.  Don’t be disappointed with brief responses.

6.  Use firm, clear, and compassionate discipline which allows him to build character.   This helps him develop his inner conscience to guide him in his decision making.

7.  Recognize that while boys pull away due to their need for independence, they still need an emotional connection with you.  Don’t mistake their withdrawal for lack of caring or rejection.

8.  Be patient.  It may take some time to draw a boy out and to persuade him that it’s safe to be emotionally transparent.

9.  Create a safe and protected space where there is no judgment and no pressure; a space or place where our boys are given permission to express all of their emotions.

10.  Create your safe space by using a familiar ritual.  This could be commuting to school and practices and games, riding bikes around the neighborhood, hiking, going grocery shopping, playing basketball, or working in the yard.  Find something familiar and make it your own. 

10 Tips :  How to Raise a Boy Right Infographic

I’ll leave you with one final quote from the authors:

“Our boys are going to grow up to be many sizes, to possess many skills, and to do a wide variety of things.  We must not disregard their many offerings; we must not make them feel that they do not measure up, that we disdain their contributions.  We have to ask a lot of them, morally and spiritually, and we have to support them in their efforts to please us.  And if they try to please us, we must communicate to them that they are not a disappointment to us.  The only thing that will make growing up psychologically safe for our sons is for them to know that we value them and that we love them, and that we have every confidence that they will grow naturally into good men.” 

From:  "Raising Cain:  Protecting the Emotional Life of Boys" (17)


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Until the next time....aloha.



Kindlon, Dan, Ph.D. and Thompson, Michael Ph.D. Raising Cain: Protecting the Emotional Life of Boys.  New York:  Ballantine Books.  1999:  (1) p. 79, (2) p. 154, (3) p. 55, (4) p. 62, (5) p. 64, (6) p. 70, (7) p. 100, (8) p. 112, (9) p. 103, (10) p. 106, (11) p. 100, (12) p. 112, (13) (14) p. 117, (15) p. 129-130, (16) p. 138, (17) p. 258