round eyeglasses on white paper beside daisies
Photo by Towfiqu barbhuiya on

By Colleen O’Boyle, assistant head of school for academic affairs

November 16, 2022

Dear Country Day, 

As a child, my paternal grandfather would often visit from New York City and stay at our family home for several weeks. I recall eagerly awaiting his arrival, sitting outside, scanning the cars as they passed by until inevitably, my father would arrive with my Pop in the passenger seat. As the old wagon came to a stop, he would roll down the window and extend his arm, giving a big wave. I could see his paperboy hat adorned with a plaid pattern nested comfortably on his head, casting a shadow over his sharp nose, distinct floppy ears, and warm yet crooked smile. My brothers and I would run toward him, where he waited with open arms. My father would head to the back of the wagon and pick up my grandpa’s items that always accompanied him: his suitcase, a notebook and pencil, and a satchel that carried his travel chess board. 

An immigrant from the west coast of Ireland, my Pop had very little education growing up in County Mayo, Crossmolina, Lough Conn, a farming community. Upon his arrival to the U.S. in 1926 through Ellis Island, he arrived with little on his body but a pad of paper and a series of pencils. I later learned just how powerful and meaningful the pencil and paper were to him.

I can’t recall the exact age when my Pop began to teach me how to play chess, but I do remember a long talk during one of our games. It was a particularly brutal game in which every move I made resulted in his block or a capture. Peering up at him with mercy in my eyes, he asked me, “When was the last time you wrote a handwritten note?” Confused and convinced that this question was a tactic to get me off my game, I ignored him and made my move. He quickly placed his hand directly over mine, sliding the piece back to its original spot, and asked again. Annoyed by this, I shared with him that I had no recollection and wanted to continue with the game. He pulled the board over to the side of the wobbly card table so that we sat squarely across from each other. 

He smiled at me and reached into his tweed jacket pocket, pulling out a small pad and pencil. He quietly jotted down three sentences, starting with “Dear Colleen…,” tearing the sheet out of the notebook. He shared that a handwritten note is extremely powerful and capable of engaging with another person more deeply than any other form of communication. This is how he first connected with my grandmother, Bridget Agnes, who also came from the west coast of Ireland but of a different background.

Bridget, as my Pop would share, was quite sharp, and for a poor boy with a third-grade education to court an educated woman, he needed to communicate from the heart and mind. Prior to marrying her, he would write her notes, run down the block in the South Bronx, and leave them on her stoop. She would write a reply and courier it back to his stoop. This continued for several months until Bridget finally accepted my Pop’s invitation for a walk. Over the arc of their marriage, my Pop would write notes and drop them in mailboxes all over Manhattan so that my grandmother could open the Post and sift through bills to find a letter from her husband. 

He lifted his index finger and allowed me to read his note. It read, “Dear Colleen, When you love or care for someone, take the time to write them a note. When you have hurt or need to apologize to someone, take the time to write them a note. When you are curious and wish to learn or wish to share your mind with someone, take the time to write them a note.” I’ve never forgotten that piece of advice. Over the years, I’ve sat down with pen to paper and written to those I love or care deeply about or to those with whom I enjoyed a conversation by writing them a handwritten note.  

In the last note that I wrote to my Pop, I asked him why he never let me win one game of chess, to which he replied in writing: because he was the better player, and that was that. I cherish this note and the many notes that my father and mother wrote to one another, the notes that my husband and I have written, the notes that my childhood best friend and I have exchanged over the years, and the notes from the many students who have inspired me. 

And so, I leave you with this, my dear Country Day: I challenge you in the next month or so, to sit down with pen to paper and write someone a handwritten note. My guess is that you will receive a note back and/or a gracious smile or gratitude in return. 


Colleen O’Boyle Jones

Colleen O'Boyle
Colleen O’Boyle

Assistant Head of School for Academic Affairs

Colleen A. O’Boyle believes it is not enough to prepare students for high school and college, rather she has a deep responsibility to prepare students for a life of leadership and innovation. This process begins early when we position young minds to become active in their own decision-making with the help and guidance of trusted adults.

What to do if Your Child Doesn’t Want to go to School
Reflection On Past Teaching

Share post:

Leave a Reply