A Dad’s Message to His Son About Fear and Failure on Graduation Day


Love Hard. Be Kind. Do Much. Don’t Be Afraid To Fail.

To My Incredible Son — Tomorrow you are graduating from high school and preparing to move on to What’s Next. It is a surreal moment for me, both as a parent and as a man. In watching you over these last 18 years, I have seen clearly that you have accomplished so much: as a young man, as an actor, and as a human being. Your efforts and grades reflect your unwavering dedication to achievement, and your wanting the best out of life. You have internalized and demonstrated critical lessons in discipline, planning, focus, and tenacity. You are on your way.

I watched you go to school this morning—your last day as a high school student—and my mind was flooded with memories. It’s cliché, but it wasn’t so long ago that we were building forts in the living room, or waking your mother and sister (WAY too early in the morning) by banging metal bowls with chopsticks on the kitchen floor, or running top speed through Disneyland so we could get on Space Mountain before anyone else. As you grew, our time together remained as fun and playful as always, yet it shifted slightly — transitioning into working with you on your homework, discussing your thoughts on a book you (or I) were reading, acting with you on stage… and then… watching you perform from the audience. With tomorrow’s ceremony, I will again be in the audience, while you will be stepping into the Limelight of Your Life… and with that comes me being relegated to being that audience member in a slightly permanent fashion — watching from a distance as you perform, and forever supportive with my attendance, my attention, and my perceptual ticket stub.

You are taking the reins in various aspects of your life, and I can’t help but smile. And as you wind your way down The Path and into the next evolution of You, I would like to pass on a few key things that might assist you on your journey. These are lessons that I have both learned and am still learning. Don’t be fooled by my (or anyone’s) age; learning never stops, and I certainly don’t have it all figured out. And as you discover new truths, please be sure to share them with me… as my fervent hope has always been that the Student surpasses the Teacher.

THE DEFINITION OF MONEY. You are gaining perspective on what is needed financially in this world. I implore you to remember that money isn’t what you think it is. Contrary to popular belief, money doesn’t allow the accumulation of things; that perception is flawed. Things purchased with money, while cool/comfortable, don’t matter in the long-term as those things can be lost, stolen, broken, or taken away. What money enables is freedom and flexibility, both for you and for those around you.

FEAR AND FAILURE. Don’t be afraid of failure. Fear will paralyze you and control you. Those who are afraid to fail are also afraid to succeed. To accomplish anything, you must risk losing in order to capture what you want. My wish for you: Please risk failure. It is our struggles that not only define us, but also cause our growth. Remember: You will win some, and you will learn some… and either way you are loved for just being you.

WANT AND NEED. Sure, you’re going to need a paycheck; creditors can be annoying that way.  But don’t lose sight of what you WANT from life… not only what you NEED. As you get older, you will regret so few decisions that you made… and instead will experience profound remorse about the decisions that you *didn’t* make and the opportunities you *didn’t* pursue. Don’t live a life of What If; instead, take chances.

LOVE HARD. You can’t control what the other person does or says… you can only control you. If you love them; love them completely. Don’t hold back out of fear. If you do, you will never know what might have happened. Sure, it might not work out… but don’t let that be because you were ruled by fear.

BE KIND. You will never know what another person’s experience has been. As such, please keep empathy and compassion at the top of your outward persona.

DO MUCH. Learn, grow, experience, change, shift, adjust, and then change again. Do as much as you can and experience all you are able. Life is not measured by how fast you arrive at the end — because NONE of us are going to make it out of this alive.  Life is about the journey… the experience… the accumulation of what you know, what you did, what you learned, and what you thought about through it all.

GIVE. Be giving with your time, your knowledge, your money, your effort, your love, and yourself. You are a gift to the world, and you should share.

ALWAYS DREAM. There are times to be a Realist… but not at the expense of passion. Dream BIG… and chase what you want. Don’t allow anyone to tell you that your dreams are too big.

DON’T GROW UP. At some points in your life, being an adult will be necessary and hard decisions will need to be made. However, being an adult doesn’t mean that you are forced to grow up. Be a kid; life is immensely more fun that way.

BE BRAVE. As a man, you will face challenging times; it happens to all of us. What defines you is how you respond to that adversity. It’s normal to be scared… just don’t stop moving forward.

BE YOU. Don’t allow anyone to define who you are. You are an incredible, vibrant, resourceful, amazing, talented, tenacious, outstanding, courageous young man. As you get exposed to new things/learnings/lessons, your perspective will shift… but YOU do the shifting. Don’t hand over the definition of You to anyone else. YOU choose who you are, what you stand for, and what you believe.

In closing, you need to know this: I am exceptionally proud of you. My pride is not a selfish pride… but is instead a pride of observation. As a father, I have tried to show you and guide you… but ultimately YOU have—and will—decide your OWN path. Your character is built on all the right things, as you are unyielding in your honor, your loyalty, and your desire. You have listened. You have internalized. You are DOING IT! 

Give ’em Hell, Drew! You have just begun. I am so excited to see what you have in store for the world!

I love you.


Originally appeared on Charles Orlando’s Facebook page. Reprinted with permission.

About Charles J Orlando

Charles J. Orlando is a bestselling author, and relationship and interpersonal relations expert. Referred to as "The Malcolm Gladwell of Relationships" by the media—and "Carrie Bradshaw-meets-Hitch" by his readers—Charles has built a 1,600,000+ person fanbase on Facebook—completely by word-of-mouth—where he offers free, street-smart love advice to men and women around the world. Charles is an active member of Mensa ("the High IQ Society"), is a contributing writer to a variety of online and print publications, and is regularly tapped by the media for his relationship and marriage expertise, including Self, Men's Health, Shape, and The Reporter.


  1. edward fyada says:

    good step but follow up is required

  2. Shariah Jafar says:

    Thanks Charles for the awesome letter. I am glad there are men like you who are also helping raise men of quality in today’s world. And yes, also attractive to other women of quality he might want to seek as well 🙂

  3. Bradley Kirkland says:

    Charles, what a beautiful note to your son. As a father of a daughter a little older, this is the kind of person I’d like her to find. You to not have it here, specifically, but I would just add Be Respectful – of other views, etc., but especially other people, more especially even, his mate (male or female). You’ve obviously taught self-respect, so respecting others is something that would come natural to him. 🙂

    BTW … did you ever read/see ‘Free to be You and Me”? You give much the same advice/insight.


    PS: CONGRATS Drew! It is a big, incredible day for you. RELISH it …

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