Letter to a Teenage Boy

Last year, one of my best friends shared her concerns about her teenage son. I had known Alex (not his real name) since he was born and we had always had a great relationship, so I wrote him a letter. With my friend’s permission and encouragement, I am reprinting that letter here in the hope that other parents will share it with their sons.

The teenage boys of today will play a big role in shaping all of our tomorrows. May they come to know the value of love, compassion and empathy sooner than the generations of men that came before them.

Dear Alex,

When you answered the phone the last time I called, I heard a deeper voice than what I was accustomed to. When your mom later confirmed that your voice had recently changed, my thoughts flashed back to my teenage years . . . and I found myself cringing. At fourteen, I was incredibly naïve; to make matters worse, I didn’t have a clue that I didn’t have a clue. Thankfully, you are much more mature and wiser than I was at your age.

As I reminisced, I found myself wishing that an adult friend of our family had taken it upon himself to pull me aside all those years ago and give me a heads up on what to expect from life and how to handle myself as I approached adulthood. If you would be so kind as to indulge me for a few minutes, I’d like to share with you what I wish someone had shared with me at fourteen. Even though you have been blessed with great parents who I’m sure have already told you all of this, sometimes it’s helpful to hear the same thing from someone outside your family.

Do you know why I was so naïve and unaware as a teenager, Alex? It’s because I was so loved and cared for and because the worst thing that ever happened to me was, well . . . I can’t really think of anything bad I was forced to deal with. I had a pretty easy life and that was the problem: a privileged life can come at a steep cost. Kids who have to deal with great adversity at a young age tend to grow up more quickly; as a result, they are better equipped to make mature decisions and contribute value to the world.

Life has not dealt you any cruel blows either. So, like I did, I imagine you’re taking it for granted that you have parents who love and cherish you and take care of your every need. I urge you to reflect on all your many blessings from time to time, Alex, and what you might be like today if those blessings had been taken from you in your formative years. If you do, I believe that you will feel a deep sense of gratitude and a strong desire to express that gratitude in any number of ways.

Based on how I acted when I was your age, Alex, I’d guess that your focus is pretty much all about you right now. Yes, I am sure you are thoughtful and considerate and capable of acting unselfishly and compassionately. I was, too. Even so, I had taken up residence on Planet Me and was so self-absorbed that I pretty much tuned out the needs of everyone else.

Alex, you’re better than that. I’m confident that you will learn at a much younger age than I did that there is a difference between being self-centered and being centered in yourself. Here’s a tip to help you get there faster—post these five words where you will see them every day: “It’s not always about me.” The sooner you realize the wisdom in those words, the more rewarding your life will be and the greater the impact you will have on the world.

Life is all about balance, Alex. Yes, take time for yourself and experience all the pleasures that life has to offer you as you come of age. At the same time, however, you will enrich your life by making a conscious effort to be even more kind and generous of spirit than you already are.

How do you live more consciously? As author Eckhart Tolle advised, start by watching your thoughts as if they were someone else’s. When you can step back like this and become a conscious witness to your own life, you begin living with much greater awareness.

By learning to live more consciously, you may be able to avoid the malady that has afflicted pretty much every teenage boy who ever lived: knowitallitis. I was a prime example. By the time I finished high school, I was certain that I knew virtually everything I needed to know to succeed in life. I could not have been more deluded if I was convinced I had wings and could fly.

Don’t just take my word for it: ask any man past the age of forty if he thought he knew it all as a teenager only to find out that he knew virtually nothing. Every man you ask will laugh and tell you that this is so. You may protest that you are the exception to this rule. Guess what? There are no exceptions.

I tell you this not to make you feel unsure of yourself, Alex. Quite the contrary. I hope that it humbles you and heightens your awareness that even though you are a very special young man, you have much to learn from those who have come before you.

Too many people do not learn the value of humility until life forces them to their knees at some point. Do not think that this will not happen to you, Alex. It will. But if you develop a sense of humility now, you will be better prepared for life’s difficult moments.

Many young men think that humility is a sign of weakness, when in fact the opposite is true. As author Ken Blanchard noted, humility does not mean you think less of yourself, it means you think of yourself less. All truly great men know the value of humility, Alex. The less often you think only about yourself, the more meaning and purpose you find in life and the greater your desire to interact with others in deeper, more meaningful ways.

Speaking of interacting with others, I’d like to take a few moments to talk about girls, a subject I imagine you’re pretty interested in by now. Since the dawn of time, men have complained that they don’t understand what women want from men. The answer actually is simple: women want to be cherished; they want to know that your desire for them is coming from your heart, not from your head or from your hormones. I can assure you of this, Alex: the more you honor a girl’s feelings, needs and desires by tuning into her and listening to her as if your world depended on it, the stronger your relationship will be and the more enjoyment you will get from it.

I’m now going to say something that sounds pretty stupid, Alex, but here goes: girls are people, too. Obvious, yes, but I know what’s it like to look at a girl’s body and forget that there’s a human being inside of it; every guy, especially teenage boys, knows that feeling. Even though you can’t control that feeling, how you choose to act on it is entirely under your control. Fortunately, I believe you have the strength of character to treat girls like you would like your own sister to be treated: with respect, empathy and kindness at all times. Allow me to repeat those last three words: at all times.

Let me take that one step further. The measure of a man is how he treats others, especially those who are not as smart, skilled or good-looking as he is. In your case, Alex, that means the vast majority of people you encounter. Remind yourself frequently that each person is a unique, beloved child of God, no matter what their outward appearance may suggest. In practical terms, that means making a conscious effort to treat every person you meet like you would like others to treat your brother (who is mentally challenged). My wish for you is that you live your life so that when people are asked to describe you in one word, the word they choose will be “kind.”

Alex, even when you were very young, I could tell that there was greatness within you. The world is now opening up to you and soon it will be yours for the taking, for you are handsome and talented and strong.

But trust me on this: the years fly by faster than you can imagine. Long before we are ready for it, looks fade, bodies age and athletic prowess diminishes. Ah, but here is the good news: love grows.

Therein lies the secret, Alex: life is about the quality of your relationships. Ultimately, it does not matter how fast you can run, how far you can throw a ball or how big your muscles are. All that matters is how much love is in your heart and how much of that love you share with others. The sooner you begin living that truth the more amazing your life will be.

Alex, I believe in you and in what you are capable of becoming. It is fitting that I write this on Christmas Day because you are truly a gift to the world.

With love,


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8 Responses to “Letter to a Teenage Boy”

  1. Global Patriot Says:

    An amazing message Phil, and one that even adults can learn from, as we all have a tendency to fall into a “it’s about me” frame of mind. Treating those around us with love and respect sounds like the most basic act of being human, yet we all too often lose sight of its profound meaning, and the sooner we learn (and embody) that message, the better!

  2. Phil Bolsta Says:

    RIght you are, Global Patriot! No matter how much we know, we all need reminders of the value of love and kindness.

  3. Julia Rogers Hamrick Says:

    Beautiful! And right on.

  4. Phil Bolsta Says:

    Thank you, Julia. If it helps even one family, it will be worth the effort.

  5. lou Says:

    What a beautiful letter as well as your soul. Thanks for sharing.

  6. Phil Bolsta Says:

    It’s my pleasure, Lou. Thank you.

  7. Patricia - Spiritual Journey Of A Lightworker Says:

    This should be required reading for all teenagers everywhere. Love and respect are very important to all relationships. Thanks for sharing this beautiful letter. As a teenage girl, I too was naive, not because I was protected but because I was abused. I didn’t know what healthy or normal families were like. I was naive because I was isolated from others by a father that was afraid of losing control so he was a dictator.

  8. Phil Bolsta Says:

    I’m so sorry to hear of your painful teenage years, Patricia. I know that so many others, especially women, share your experience, and that’s heartbreaking. Congratulations on transcending your pain and choosing to live a loving, positive life.

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