What I Learned From Playboy Magazine’s Cartoonist

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Sometimes inspiration comes from the most unexpected places.

I was reading the biography of author, poet, and cartoonist Shel Silverstein today and learned several lessons that apply to anyone striving to be more than just average.

Besides being the first cartoonist for Playboy Magazine, who is Shel Silverstein anyway?

Silverstein was multi-talented but he did not discover his talents in the traditional ways. In fact, you could say that he was a rebel, through and through.

Silverstein recorded over 15 albums of his own and is responsible for the lyrics of several 70’s bands and singers such as Dr. Hook, Johnny Cash, Loretta Lynn, Waylon Jennings, Gordon Lightfoot and others.

He wrote most of the Dr. Hook songs, including “The Cover of ‘Rolling Stone'”.
But he refused to be confined to just one genre of music.

Silverstein wrote “A Boy Named Sue” which was Johnny Cash’s biggest hit. Johnny Cash also performed another of Silverstein’s songs – “25 Minutes to Go”, which is about a man on death row with each line counting down his life and bringing the listener a minute closer to the execution.

In spite of all this success you still may not have heard of Shel Silverstein.

I learned of him in the most unlikely way. I first discovered Shel Silverstein through my 6 year old’s books of poetry.

Oddly enough, even though he was the first cartoonist for Playboy magazine and wrote several hit songs, Silverstein is best known for his collection of children’s books, if you can believe it.

As I read about him I began to realize that his comments contained lessons that any of us could apply to our life’s journey.

Here are some of those observations:

During an interview, Silverstein told Publishers Weekly:
“When I was a kid—12 to 14, around there—I would much rather have been a good baseball player or a hit with the girls, but I couldn’t play ball. I couldn’t dance. Luckily, the girls didn’t want me. Not much I could do about that. So I started to draw and to write.

By the time I got to where I was attracting girls, I was already into my work, and it was more important to me.

Not that I wouldn’t rather make love, but the work has become a habit.”

He said, “…I was already into my work, and it was more important to me.”

I found it interesting that once he had found his life’s calling, he just wasn’t very concerned about all the other things anymore because his work had become a habit.

To be successful, you have to love your work more than anything else.

It sounds so easy doesn’t it? It is easy.


Most people will never do the work necessary to be successful.

Lesson Learned: Do the work that you’re called to do and everything else will come to you – girls, money, fame.

Silverstein was drafted into the U.S. Army in 1953. During his time in the military, he kept working on his drawings. Soon his cartoons were published in Pacific Stars and Stripes, a military magazine. His first book was published in 1955. It was a compilation of his military cartoons. That book put him on the map but didn’t give him huge success.

He later said his time in college was a waste and that his time would have been better spent traveling around the world meeting people. Notice, this is a famous author who says that even back in the 50’s college was a waste of time.

How many of you have been plucked from your environment and forced to go somewhere you really didn’t want to go?

Heck, most of us have every advantage available to us and still can’t find motivation to just do whatever it is we’re supposed to do.

We have just enough to keep us comfortable – and mediocre.

Even those among us with the least resources are better off than the majority in other countries AND WE DON’T EVEN RECOGNIZE IT.

Sure, you might have a reason to despair if you were in a third world country.

Well, maybe.

Many of those people still find a way to success, in spite of being born in a place with limitations.

Lesson: Even if life doesn’t go the way you plan, find a way to keep pursuing your dreams.

After leaving the military, Silverstein began submitting cartoons to magazines while also selling hot dogs at Chicago ballparks. He continued to pursue his dreams even while taking on menial jobs to support himself. Eventually he got a position creating all the drawings for Playboy magazine.

Lesson Learned: Even if it takes doing a menial job, do not give up on your dreams. Continue working toward making them come true.

When asked whether he had been surprised by the astronomical sales of The Giving Tree, (link to Amazon) one of the most successful children’s books ever written, Silverstein was emphatic. “No, what I do is good,” he said. “I wouldn’t let it out if I didn’t think it was.”

Lesson Learned: In whatever you do, always provide excellence. Everything you produce should be the best you can produce – only quality material.

You can look online and find his cartoons and music, but I’d like to focus on some of Silverstein’s poetry here.

The Best Of Shel Silverstein
The Best Of Shel Silverstein

His poems and stories are very poignant and speak to the soul in ways that we can all appreciate. They serve as guideposts on how to live life to the fullest and how to overcome the challenges that come with life.

Here are a few of those guideposts as illustrated by his poems:

Guidepost 1:

“Listen to the mustn’ts, child.
Listen to the don’ts.
Listen to the shouldn’ts,
the impossibles, the won’ts.
Listen to the never haves,
then listen close to me…
Anything can happen, child.
Anything can be.”

The lead up to that last line says to listen to all of the naysayers in the world, then take what they say and throw it all away and, instead, “…listen close to me…”

Sometimes it doesn’t seem like you can create anything you want, especially when the world around you is telling you that it can’t happen, or that you shouldn’t do it. Ignoring the naysayers can be tough because they usually come in the form of friends, family, or significant others.

But learning to ignore their remarks and still pursue your passion is the difference in being one of those “never haves” or an “anything can happen” type person.

Guidepost 2:

“Just ’cause somethin’ ain’t been done
Don’t mean it can’t be did.”

You don’t have to wait for a precedent to do the things you want to do.

Sometimes you’ll dream up something that doesn’t yet exist. That doesn’t meant it can’t exist, it just means no one has created it yet.

The same was true of the four-minute mile. The four-minute mile is the act of completing the mile run (1,760 yards, or 1,609.344 metres) in less than four minutes. It was said to be humanly impossible.

Everyone thought it couldn’t be done, until Roger Bannister broke that barrier in 1954. Bannister’s record lasted only 46 days. After everyone saw it was possible, more and more people suddenly were able to run the mile in under 4 minutes.

You can be that person who does it first and show others that they can do it too.

Guidepost 3:

“Sandra’s seen a leprechaun,
Eddie touched a troll,
Laurie danced with witches once,
Charlie found some goblins gold.
Donald heard a mermaid sing,
Susy spied an elf,
But all the magic I have known
I’ve had to make myself.”

The earlier parts of the poem discuss others magic, or, as I read it, luck.

Life is magical – you are the magician, but if you don’t perform your tricks, life won’t perform them for you.

It is your responsibility to make your own luck.

Each of us has a “magical” talent – something you can do better than anyone.

Find your magical ability and be sure to put it to use each day.

Guidepost 4:

“How many slams in an old screen door? Depends how loud you shut it.
How many slices in a loaf of bread? Depends how thin you cut it.
How much good inside a day? Depends how good you live ’em.
How much love inside a friend? Depends how much you give ’em.”

You get out of life whatever you put into it. Each topic discussed in the poem reinforces this point. Let’s focus on “how much good inside a day”.

There aren’t really good days or bad days; a day is neutral. It’s what you do with a day that makes it good or bad.

“How much good can I pack into a day” should be the real question.

You may want to write a list of things you think would make up a good day, and then try to live up to that list each day. This creates a checklist that you can refer to throughout the day to make sure you’re on track for another great day.

Gid rid of the habit of referring to good days and bad days, and treat them all equally, since good can be had out of each one.

The main points you need to understand from this article;

Do the work. Nothing else is as important. Everything else is secondary.

Once you become a master at your chosen profession everything else will be available to you – so focus on your work.

Do the work and everything else will take care of itself.

If you are too distracted by trying to acquire a girlfriend or keeping up with the Joneses (or whatever), you’ll never fulfill your passions.

Even if life doesn’t go the way you plan, find a way to keep pursuing your dreams.

In whatever you do, always provide excellence. Everything you produce should be the best you can produce – only quality material.

Ignore what others say and pursue your passions.

When you have a good idea, even if someone else has thought of it already, get busy developing it. You could be the one everyone looks back to as the visionary.

Make your own luck. There’s a quote that says “Luck is what happens when preparation meets opportunity”. Get busy pursuing your passions and it’s amazing how lucky you’ll be in life.

Make the best of each day. We’re only given so many and how they turn out is by and large your choice.

I’ll end with another poem by Shel Silverstein:

“All The Woulda-Coulda-Shouldas
Layin’ In The Sun,
Talkin’ ‘Bout The Things
They Woulda-Coulda-Shoulda Done…
But All Those Woulda-Coulda-Shouldas
All Ran Away And Hid
From One Little Did.”

Don’t just talk about your plans. Get busy carrying them out.

What plans are you putting into motion?  Tell me about them in the comments.



One Response

  1. […] Instead, find your one thing — something you’re really good at and enjoy — something that also benefits others — and then get to work doing that “job” to the best of your ability.  If you can find that one thing you’re good at, your job will be enjoyable most of the time and wil… […]

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