A Letter to Winchester Parents on Christmas

January 6, 2012

This is a letter I published in my hometown newspaper on Christmas day 2009.

Although it’s not a direct story of my life, it represents a lot of what I’ve gone through and the feelings I’ve had growing up.

There is a follow up article: Please Believe In Me

Dear Mom and Dad,

It’s been a few years since I graduated college and as Christmas approaches I want to share a few reflections I’ve had this year. First, I want to tell you how lucky I feel. I never really appreciated what I had until I saw that many people weren’t as lucky to have parents and a community that truly cared about not just me, but every kid growing up in Winchester. From the youth soccer leagues to helping me apply for college, you’ve been consistently going above and beyond what is expected and it has made all the difference. Now that I’m through college and out on my own, I can’t help but notice that my life has changed.

Leaving college was a little like reaching the end of a moving walkway, everything up to that point had felt very structured and the decisions I had to make were easy. At the end of that walkway it was a little scary. The stark contrast between a set track and complete autonomy was intimidating, and at first, I wanted to get back on another walkway.

In high school I played sports and studied hard so I could become well rounded and get into a good college, but after college things were different. The standard logic that I learned growing up told me to go to grad school, but there was nothing more in particular I wanted to learn at that time after 15 years of school.

I tried the big company job but corporate environment and working long hours left me feeling very unfulfilled and without anything at the end of the day but a paycheck. After spending a few years at my corporate job, I’m again looking for another moving walkway, but it’s not what I truly want. It seems like whenever I discuss the possibility of quitting my job with you, I get an uneasy reaction. I understand that you, as my parents are looking out for my safety and security but what about my sanity? At times it feels like I would let you down if I didn’t “have a plan” or make a certain amount of money a year. In a way, I even feel like I’d be letting down the town of Winchester, since what I grew up with was the expectation that I should be in a safe, traditional career path by now. When I expressed these concerns to you the last time I was home you supported my decision to quit my job and asked “so what do you WANT to do?”

I didn’t have a good answer and to be honest, I still don’t know. I want to make you happy and show that I have a plan to be successful, but sometimes I don’t even know what “success” is anymore. Is it making a lot of money? Is it getting married and putting kids through college? When I was young people always told me to follow my dreams but that doesn’t seem to be in line with what is expected of me.

A few years ago, I ran into a friend from high school who graduated a few years before me. We talked about all the things I’ve been thinking and he gave me some advice. One thing I really admire about this guy is the fact that he seems to know exactly what he wants, and even though it’s a bit non-traditional (by Winchester standards), he is fully committed and living his dream. I asked him how I could find the kind of happiness he had and his answer surprised me.

He said I needed permission to fail. He said that if I tried to satisfy two things at once, I wouldn’t be able to satisfy either one. As I thought about what he said I realized that while part of me wants to follow my dreams and live out my passions, the other part of me wants to play it safe and show my family that I’m “on the right track”. Although I’ve certainly tried, it’s become clear to me that I can’t have both.

Since then I’ve been trying to find some clear direction in my life, but I still feel caught up in trying to please too many people.  I want to make a plan an seek your approval but it seems like a catch 22, I can’t free myself to find what I want until I have your unconditional approval and support.

This Christmas, I’d like a new iPod, and of course some home cooking that I miss so much, but more than any other gift, I’d like you to give me the permission to fail, it’s what I need the most. Look me in the eyes and tell me I have all the skills I need to do amazing things and that you will support me 100%, no matter what I choose to do. Reassure me that life is about the journey, not the destination and that although I may not find what I’m looking for right away, the important thing is that I begin down the path, alone, but knowing you are behind me.

Above all, I want you to know that I love you. I want you to know that if I really go for my passion it won’t be easy for either of us, since it will might involve some uncertainty and maybe empty bank accounts for a little while. I admire you and love you for taking on this challenge with me. It’s a path I must take, and although some say I could break free and do it without you, the truth is I don’t want to.  I’d rather hear it from you.

Merry Christmas,
Your Son


Get new thought-provoking essays that question the status-quo
(and question questioning the status-quo).