Waterford: Return to My High School

Hanging with dear friend and mentor, Todd Winters at Waterford


When was the last time you walked the hallways of your high school?

I swear those classrooms were bigger, doorways taller, and common spaces intimidatingly more judgmental.

It was 25 years ago that I was last able to grace the very classrooms I once sat in, eyes peering out the window, wishing I could be somewhere else, while struggling to make it through another day of focus and study.

I attended a private school called Waterford, tuition as great as some universities, and it was a major sacrifice to my parents financially to give me the gift of such education.  I still have no idea how they could afford to send my siblings and I there.

It was in these halls where fast friendships were forged, crushes and hopes of romance were dashed, and my aspirations to star in the NBA changed in the blink of an eye upon being discovered by a music teacher who heard me singing in the hall and set my feet on the correct life path.

A few weeks ago, Waterford called and asked me to help out with their annual day of giving, where I would take over their Instagram for a day and ask for donations from Alumni to give back.



It was such an honor to be asked to do this.

I had full reign of the school, to faculty who didn’t know me, and then the ones who were still there, what a thrill to relive such memories.

It is a most sobering experience to come face to face with former teachers, who at the time were old and so very adult to us kids, and now seeing your hair is more gray than theirs, while these forever young teachers have stayed the same!

There were many laughs, many fun selfie videos made, multiple laugh out loud moments.

I actually held back the tears when thinking of stories I shared in my book you may have read, such as:

  • The meeting of my lifetime best friend, Quinn Dietlein, the first person to truly take me under his wing, be my basketball buddy, and find out I could sing.  No one encouraged or believed in me more.  We are still dear friends to this day.
  • The very spot where I gave my high school crush a drawing I had worked all summer on, to which she casually tossed it aside and I immediately understood why the word crush actually leads to being crushed.
  • The locations where I made the basketball team, did my first Michael Jackson standing ovation performance, and gave my weekly student body presidential speeches.

Walking down memory lane can bring up feelings of joy and equally sorrow.

Reflection can help us see how far we’ve come, and face the reckoning of what we still haven’t done.

The Promise I made as a kid upon graduation from Waterford was to do all I could to share my talents with the world that were discovered there.

I feel I’ve kept that Promise, and continue to strive to do so.

It’s very validating to feel your alma mater recognizes you’ve kept that Promise and brought the school some semblance of pride.

At the same time, I left the school the other day making a new Promise:

I Promise to Keep Pushing To Make Waterford Proud

Enjoy this video of my visit there, and comment below if and how you’ve given back to your high school, college, or education past, to Keep The Promise and make them proud.



~ Jason Hewlett

Husband, Father, Writer, Mentor, Hiker

  • Speaker Hall of Fame * Award-Winning Entertainer * Promise Legacy Project Coach
  • World’s Only Keynote Speaker utilizing entertainment, musical impressions, and comedy to Create Legendary Leadership through the Power of Commitment
  • Author of “The Promise To The One”





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2 thoughts on “Waterford: Return to My High School”

  1. I had forgotten that Waterford was the name of your high school. It is also the name of the county where my grandmother came from in Ireland!
    And, of course, that wonderful music teacher whose name I have forgotten at the moment. (IT is 0 degrees in Mn at the moment.)

    You are giving back from the gifts you received there.
    Many Christmas blessings,

    1. It’s a great name: WATERFORD. My teacher you are referring to, and thank you for remembering, is Mrs. Rosalind Hall. What a blessing she has been to me. Thank you for your always kind and encouraging words! Merry Christmas my friend.

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