Nancy Cremins | A Letter To My Son On the First Day of School

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Yesterday I received an e-mail from Nancy Cremins, a Boston-based start-up and employment attorney, mine actually (yes, she's excellent, sharing that she has been overwhelmed by the prospect of sending her oldest child off to kindergarten.  I immediately asked her to share her experience — ah, parenting.

I can’t believe it.  Here you go off to Kindergarten.  Mostly, I try to stick to wit and/or wisdom when I write, but the wave of sentimentality I am experiencing about this event requires a slightly softer approach in this letter on this day.

The first day of Kindergarten feels different than all the days I dropped you off at daycare or your time in preschool.  Kindergarten marks the real beginning of your journey to becoming who you are, independent of me and your dad. It also signifies the end of your time as my baby.  I'm not sure I am ready for that yet, but it comes anyway. So on this day I worry more, I hope more, and I share my dreams for your future, which will continue to arrive faster than I am prepared for.


I worry that you will not like school, that it will be too hard, or too easy, or too something.  I hope that you will try hard, that you will stick to your lessons, and that you will ask for help when you need it.  I dream that learning will bring you joy and the pride that comes when you master new things, like learning to read and eventually, I hope, to write your own stories and adventures.

I worry that your teachers won't understand or appreciate your boisterous energy and that you won't be able to contain it. I hope that you and your teachers find a way to harness that energy and put it to good use.  I dream that we will be able to do better than putting kids in boxes or slapping labels on them because they act a “certain” way.

I worry that you will be picked on, or worse, pick on other kids.  I hope that we have taught you enough to be resilient to teasing, to be kind to others, and to be brave enough to defend those who need help.  I dream of a time when we are all compassionate and caring with the feelings of others and bullying is a thing of the past.

I worry that in school you will absorb the assumptions that certain things are “boy” things and certain things are “girl” things and that will limit your view of the world and yourself. I hope that your dad and I have been and continue to be examples of the fact that there are very few things in this world that are limited by your gender.  I dream of a time when gender roles are less restrictive for boys and girls and that you and your sister can like, do, or be anything.

I worry that school will change the open way that you communicate with the world.  I hope that you will learn to temper that openness just enough so that you won’t be hurt too often or too deeply.  I dream that the world will become a place where we value openness more and it is OK to wear your heart on your sleeve for all to see.

I worry that as you grow, you will grow away from me.  I hope that we will learn new ways to talk, to connect, and to share our experiences.  I dream that you will grow into an adult that I actually like spending time with, and that we will be friends.

Finally, a parental prayer:  May you dare to be completely yourself, to learn with enthusiasm, to question things, to fail with grace, to succeed with humility, to be brave, to love learning, to make good friends, to be happy, and to always know that no matter what, I will be there for you on every step of your journey of growing up, even when you won't hold my hand anymore or want me to drop you off 2 blocks from your friend's house because I “embarass” you.

Best wishes on this day.

With love,


What do you want to say to your children as they leave for the first day of kindergarten, middle school, high school, college, work?

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