5 Valuable Life Lessons From Shel Silverstein in His Poems

On September 25th, we are wishing Shel Silverstein a happy birthday! Let’s celebrate him by reflecting on some important life lessons he wrote about.

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Shel Silverstein is well-known as a poet, writer, songwriter, cartoonist, and playwright. Also, a fun surprising fact many don’t know is he is also a two-time Grammy winner. Silverstein is truly a man of many talents, especially for his one-of-a-kind poems and cartoon drawings for children’s literature. And that is why today, we are celebrating Shel Silverstein’s birthday!

Growing up, Shel Silverstein’s books were a huge part of my reading. All of his most popular books such as The Giving Tree, Where the Sidewalk Ends, A Light in the Attic, and Falling Up made up most of my childhood. Of course, his works were read for fun as a child but rereading them now when I’m older makes me realize how many valuable life lessons he wrote about in his writings.


Lesson One: Always Be Creative


Shel Silverstein uses a lot of creativity in his writings and perhaps that is to inspire his readers to do the same. He reminds us to use our imagination in “Magic” because we can be anything and do anything if we set our minds to it. It is not something found, but something we make and do ourselves. Creativity is meant to be fun and it gets you to think outside the box just like in his poem, “Ourchestra.” They don’t have any instruments, so they think outside the box and use their bodies such as their bellies and hands to become the instruments in an orchestra. His writings remind us to always be creative.

Lesson Two: Stay True to Yourself


An important lesson, especially for children readers, is to stay true to yourself. It’s more meaning when you are older, so it’s a nice reminder to have from Silverstein’s writings. Growing up, you will repeatedly hear opinions from others or feel pressure to live up to certain expectations.

And this includes the little voice inside our heads too because who knows us better than ourselves? We are the ones who will know what is best for us so sometimes we should listen to the voice inside of us. Poems like “The Voice” and “Listen to the Mustn’ts” tell us to stay true to ourselves and follow the dreams we want, not what is expected of us. In “Listen to the Mustn’ts,” Silverstein teaches us that “Anything can happen, child, ANYTHING can be.” It’s such a meaningful statement about remembering that we can make anything happen as long as we listen and trust ourselves rather than others.

Lesson Three: It’s Okay to Not Be Okay


Another key life lesson Shel Silverstein writes about is how it’s okay to not be okay. Oftentimes, we feel the need to hide it under a façade.  His poem, “Underface,” reveals how we hide under a mask that we don’t show anyone. Then we pretend that everything is fine. It’s a face that isn’t always smiling and happy nor is it a face that is always so sure and certain all the time.

Silverstein reassures readers how that same face is “a whole lot more like me.” Sometimes it’s difficult to not only express our feelings and emotions but also to understand them as well. Therefore, it is definitely nice to be reminded that it’s okay to not be okay because we don’t always have to be so put together all the time. It’s all part of what makes us who we are.

Lesson Four: Be Unique and Embrace Individuality


A life lesson we should always be reminded about is to be unique and embrace our individuality. In “Masks,” they couldn’t find anyone blue like them because they hid it. It’s important to learn that not everyone is the same and we shouldn’t spend time hiding what makes us different from others.

In The Missing Piece, the incomplete circle spends time trying to find their missing piece to be a perfect circle. In the end, it doesn’t need the missing piece. It’s perfect just how it is. The line, “I am my own piece” is a reminder that we are all our own person. His stories encourage readers to just be themselves. Embrace individuality without letting others influence how you perceive yourself.

Lesson Five: Don’t Let Growing Up Keep You From Having Fun


Let’s be honest, growing up is hard. Life often has us doing things that make it difficult such as working and studying more which keeps us away from doing things we enjoy. I’m sure as children, our perception of adults are serious people who rarely have fun. But now as grown-ups, it’s more like adulting has us doing things that make us seem serious.

Silverstein’s poems remind us it’s necessary to slow down and enjoy life’s moments by doing things we love. We shouldn’t let things stop us from having fun. His poem, “Put Something In,” reminds us never to take ourselves too seriously. Don’t be afraid to just be silly because silly is what makes the world fun to live in. 


Of course, many of these writings overlap in life lessons and there are other life lessons in his works too. The unique style of Shel Silverstein’s works is the simplicity of his writing. They read very easily but can be understood at a deeper level. There is never just one meaning, instead, the meaning has layers. Multiple interpretations are possible despite how simple it is.

Just as Shel Silverstein’s poem, “Invitation,” reads, “If you are a dreamer, come in” because readers of all ages are invited to read his poems and they will always resonate with them. That is why we celebrate his birthday and look back on how valuable and meaningful his writings are. 

To read more about Shel Silverstein and his impact on children’s literature, check out more Bookstr articles about him here.