With a consistent commute to my office at Health Data Vision, I find myself with more time for personal development and reflection than I’ve ever had. One of my favorite podcasts - the Top, concludes with the same question posed to every person ‘What advice would you give your 20 year old self’? I decided to take the question in a different direction. Why not write a letter now that I can give to my son, Brayden when he turns 20 in 2023.


Brayden, I am incredibly proud of you today. You have turned into a fine young man who has contributed positively to your classmates,
teammates, and the community you live in.  As you embark upon the next chapter your life, I would like to leave you with a few thoughts.  Life is short, full of wonderful opportunities, and it’s up to you as to what you do when these present themselves.

So Big B, I hope you will consider these thoughts from dad.  Hold on to this letter and refer to it over time.  Even if these suggestions seem like nonsense, don’t discard my letter and commit to revisit it from time to time.

  1. Stay in learning mode. While it is easy to say “I’m done after having been in school for 16+ years."  Don’t do Jay Blog - Letter to Son FINAL.png
     it!  Never stop learning.  The world is moving at a faster and faster pace, you’ll need to reinvent yourself at least 2-3 times during your work life.

    • Take up a new sport / hobby. Hey it’s not too late for you to learn hockey. Ok maybe that ship sailed. But think about what else you can throw yourself into.
    • Always have a book that you are reading - never never say I don’t have time for reading.  Try different books. It’s okay to give up on a book if it isn’t working for you.
    • Talk to interesting people. Don’t bury yourself in technology. Pick your head up, engage.
  2. Live below your means.  I know you and I have always loved calling out our favorite cars. And no one knows them better than you.  But don’t get hooked on material things and overspending.  Living below your means will create options for you during your life. This one will make sense with time.
  3. NYC or SF choose one.  One of these great American cities must be part of your port of call.  Better yet. Consider a stint in cities like London, Munich, or Shanghai. *This one could get edited out by your mom.
  4. Be Generous.  Give generously of yourself to others.  Create this ‘muscle’ early in life.  You’ll be surprised how it makes you feel, see the world differently, and how it will help you better define your value set.
  5. Always have a Coach. You have been fortunate to have great sports coaches through your life.  Think about it: an MLB All-Star, Tom House and his team at NPA West, and Coach E for the Rockstars.  Always maintain a coach in your area of focus. Whether it’s baseball or business. The best always have a coach.

I know you are going to have a wonderful life.  You have a tremendous heart and soul.  Just promise me to read this note once a year.

Love, your dad

About The Author

Jay is the President and CEO of Health Data Vision, Inc. He is a seasoned software and services executive with over 25 years of experience in various leadership capacities, including his most recent position as Chief Revenue Officer at Guidance Software. Jay holds his MBA from NYU’s Stern School of Business along with a bachelor’s degree in economics from Connecticut College.