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On Disappointment

Tuesday January 27, 2015

I ran out of the main building, and burst into tears as I reached the stairwell of my dorm.  I sat there crying, afraid someone would find me, and hoping that someone would find me and ask me what was wrong. No one ever did find me and I swallowed my disappointment.  I was too embarrassed to tell anyone. 


I had found out that I had not gotten a part in my friend’s dance recital and all my friends had gotten parts.  I was in tenth grade at the Hotchkiss School in Lakeville, Connecticut.  Now that I have a thirteen year old, memories from my adolescence are coming back to me and that is the one that sticks in my mind the most.  I think it was in that moment that I unconsciously decided to go long and hard in academics.  I was good at academics.  I got good grades, which stoked my ego.  But I stopped trying to do anything risky, anything that would involve disappointment or failure.


Thirty years later, I volunteered to do the scenery for my daughter’s second grade class play.  By this time, I had gone to law school, gotten married, practiced law at a big city law firm, had four children, and was working part-time as a trusts and estates lawyer.  As I sat there mixing paints and creating perspective, I realized I had not tried to create anything in art since I was very little and I was feeling so happy.  The pleasure I took in the painting led to volunteering as one of the costume coordinators for the Middle School production of Pirates of Penzance.  I sewed costumes, learned to use a glue gun, and while I did all that I could, I wasn’t focused on the outcome, but took intense personal pride in that I had done it.  I had a vision and it came to life.


This fall I took my first adult ballet class.  I had quit ballet when I was twelve because I had reached the highest level at my ballet school, and I was expected to audition for the ballet school of the Teatro Colón Buenos Aires, Argentina.  I “knew” I would probably not make it, and I knew that trying and being told I wasn’t good enough would hurt, so I quit.  It didn’t occur to me to work really, really hard, or to ask for extra coaching, and to go for it.  So I gave up something that I loved, that I had done my whole life, because I was afraid.  Now every time I take class I am still a bit afraid.  I sometimes dread going out to center because my performance is so far away from my aspirations that it almost hurts, but I have kept doing it.  I strive for my own personal excellence and beauty, and revel in small victories, like learning to hold my arms a bit more gracefully, or to point my toe just a little harder.


This summer we stayed at a house in England, and the family motto was inscribed in the mantelpiece. “Work hard, expect nothing, and celebrate.” It is natural to focus on outcome, especially in the community we live in, but if there is one thing I would like to do as a parent, it would be to encourage, support, and coach my children to keep doing what they love, to keep risking disappointment, regardless of how "good" they are.  I know that when I stopped taking risks, I may have been escaping the feelings of disappointment, but I also cut myself off from feeling joy.  I have quit my law firm job, and have several new ventures, but all of them involve risk and putting myself out there and am so much more joyful for it. Along the way, I have had my disappointments, my speed bumps and setbacks, in fact, many more disappointments than successes or victories, but I am not going back to living afraid.  Like the Grinch, it feels like my heart has grown three sizes bigger and that is the best part of all. 


About the Author


Caroline Pillsbury Oliver is married to Drew Oliver, and is the mother of four children.  Caroline and her family live in Greenwich, Connecticut. Caroline works as a volunteer for Greenwich Country Day School, Ballet des Amériques, Manhattan Christian Academy and is an Independent Consultant with Arbonne International, Inc. 

Caroline is a graduate of the Hotchkiss School in Lakeville, Connecticut, Brown University and Columbia Law School. Caroline grew up living abroad as the daughter of an American Foreign Service Officer, and was born in Lubumbashi, Democratic Republic of the Congo. 


0 Holbrook 02-10-2015 02:15
Caroline - I LOVE honest and inspiring...So wonderful that you're pursuing your passions and getting such joy from that pursuit!
0 Caroline Oliver 02-11-2015 16:48
Dear Holbrook,
Thank you for your response and thank you for visiting preppydom!
0 Victoria 02-14-2015 23:03
You go girl!! This is such an important lesson to learn at any age. I'm so proud of you for taking on new challenges! :)
0 Caroline Oliver 02-18-2015 16:35
Dear Victoria,

Thank you for your support and for visiting preppydom!

0 Fendell 02-26-2015 19:22
Dearest Caroline, This is the heart of Caroline, my sister, I've always known, creative dedicated and determined and always able to self challenge. . I am not surprised yet I am so delighted that the creative part is coming back out so beautifully now and it will serve you in great stead in this new phase of your life. The shadow of disappointment is just that, a shadow of a memory. There is always a chance to revisit the shadow and reinvent the outcome!
I really feel this is your strongest piece yet and this resonates on a very wide scale. As Julia Cameron from the Artist's Way says "Doing it "wrong" is what we are trying to avoid, and so we often avoid doing it at all.""When we have the courage to dream with passion and precision, the Universe responds."
My love and respect go out to you!
0 Carole Alexis 03-22-2015 13:26
Dear Caroline,

To Be or not to Be? is not a question for you for Caroline... :)

Thank you for sharing your heart and soul ! this is very inspiring ! and the first expression that burst out when reading such is a huge " you go girl!!" but let's make it "you are... woman!!"

Carole Alexis

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