What We Learn from Shel Silverstein

I chose the title for this blog “Where The Sidewalk Starts” for a few reasons. One being I like metaphors and new beginnings. The other was I love Shel Silverstein. I have all his “children’s” poetry books and have saved them from donation many times. I say “children’s” because I could read these poems every ten years, and they would still be relatable and resonate with me in different ways. His words surpass the children’s generation.

Recently, a co-worker discovered my love for Shel and handed me a biography.


He, too, loved Shel and thought I might be interested in the knowing more about his life and works. Little did I know that I knew nothing about this incredible man. Here’s what he taught me in about 226 pages.

  • Life is too short to be doing just one thing for the whole duration. Not only did Shel write poetry, but he loved drawing and composing. Cartoonist, singer, writer, playwright…when Shel felt his creativity on one outlet was waning, he would move on to the next. One of my favorite quotes from the book: “I’d like to be happy with one thing, it would save a lot of energy. I’d like to be happy with one woman. It would be easier and give me more time to work and time to relax. But I don’t find that one town or one woman, or one job or one career makes me happy. What makes me happy is changing all the time.”
  • Don’t dwell on the past. When Shel decided to move on to another outlet, he would commit to it and did not look back. After The Giving Tree was published, he moved on to the next project and did not give its success another thought. Awards would come knocking at his door for it, and he would shoo them away so he could focus on his present task. His friends always referenced him as a forward mover.
  • Owning a houseboat would be awesome. For a while, Shel escaped to a houseboat community and lived on the water. Granted, he would come down with seasickness on occasion, but his boat was filled with books and his work. Not really a life lesson, but I would love to experience that for a year or so.
  • If an opportunity sounds half exciting or crazy, do it. One of the things that shocked me the most about Shel’s life was how diverse his work was. He was a cartoonist for Playboy and best friends with Hugh Hefner. His songs were unique and off-beat, but he wrote one of Johnny Cash’s famous songs “A Boy Named Sue.” You could fill up a whole page of his collaborations with famous artists and other authors. If he ever had a resume, which I doubt he would ever need, it would probably be all over the creative spectrum. Rarely did he allow an opportunity pass him by. He says, ” You can go crazy with some of the wonderful stuff there is in life.”
  • Be spontaneous, but remember where your heart rests. Shel lived all over the world, and when he decided he wanted to move, he would jump on a plane and leave. Although this lifestyle made it quite difficult for many to keep in contact with him, his mother and a few loyal friends always knew his whereabouts. If anyone he deeply cared about needed anything, he would never hesitate to drop everything and come to them.

His biography shared plenty more interesting and strange happenings in Shel’s life; these points were just a few that resonated with me. I recommend it to anyone who loves this man’s work or who enjoys reading biographies about peculiar individuals.

Read a great biography? Let me know about it!


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