Open Letter to my Son


I wrote the first version of this letter when you were five years old. As you approach your 13th birthday and edge closer and closer to high school, I can’t help but think you’re growing up too fast. While life has certainly challenged us in ways none of us could have ever imagined over the last few years, I have no doubt that you will succeed in anything you choose to do in life.

As a father, there’s something special about having a son. Of course I love your sisters as much as you, but it’s different. They are my princesses. You, on the other hand, are my son. And there’s something intrinsic and almost primal about having a son. It’s hard to explain, but maybe someday, if you are lucky enough to have your own family, you too will feel the same way.

While it is certainly true that we share many of the same likes and hobbies and you always loved to do “dude things” as a kid, what’s so powerful about our relationship is the fact that I have been given an amazing opportunity for a do-over of sorts. Of course the path you take in life will be your own – much of which I’m sure I will not agree – but it does afford me the opportunity to guide, teach, support, and show you that there are no true shortcuts worth taking in life.

When you were little, you wanted to be just like me. But you’re not, and I love that.

So as you venture down this unknown path of life, there are a few things that I’d like you to remember as you get older and experience the jubilation of a Red Sox win over the Yankees (tonight!), the pride of getting into that college, or the gut wrenching torture of that first breakup. Maybe, just maybe, this will help keep you grounded and navigate the meandering and often uncertain roads of life.

So for what it’s worth, remember:

  1. I am not perfect and the day you come to realize that, don’t feel guilty for being disappointed.
  2. Your sisters are and will be your two best friends for the rest of your life. They will stand up for you, help you, and provide you an endless array of potential girlfriends. So stop hitting them.
  3. You once wore your sisters’ underwear on your head. I have pictures so don’t push your luck when I tell you to be home by 10 or they might find their way to your Facebook wall.
  4. Always be yourself and ignore those that don’t respect that.
  5. Call your mother. And go golfing with your dad now and then.
  6. Don’t lie – it won’t get you what you want in the long run. The truth is hard to swallow but people will respect you for always being honest even if they don’t like it.
  7. Take risks, get in over your head, ask that girl out, and be spontaneous. Repeat.
  8. Travel and learn about different cultures, customs, and beliefs. Be tolerant of others. You are not always right.
  9. If you fail, learn from it and fail enthusiastically. Just as you would in success, extract everything you can out of your failures. Never stop learning.
  10. Rescue a dog. Or two. They will return the favor.
  11. PLAN but deviate often.
  12. Say, “I love you.” And don’t settle for anything less in return.
  13. If you get in trouble, know that I will always be there to dust you off, prop you up, and stand by your side. We all make mistakes but it’s what we learn from them that makes all the difference.
  14. Be assertive. Be heard. Be present. Contribute. What you have to say is important.
  15. Stand tall and be confident in love and business. It will take you far.
  16. Learn to play guitar because there’s nothing better around a campfire. And because your dad always wanted to so he needs to live vicariously through you.
  17. Know that when I yelled at you when you were a kid, I’m sorry. There were just those times when I couldn’t keep it together anymore (see #1).
  18. Every day that I dropped you off at school and you were instantly off running with your first best friend, I dreaded the day when you didn’t need me anymore.
  19. Hugs can cure almost anything. Or at the very least, they can’t hurt.
  20. From the day you were born, I couldn’t wait for the day that I could take you to Fenway Park.
  21. You might be my best friend but that’s not my job. My job will always be to help you avoid the mistakes I made, embrace the things you love, and when you fail or lose your way, help you get back on track.
  22. Above all, see #1.


PS: Don’t forget to take out the garbage.