How Shel Silverstein liberates single moms everywhere

silverstein the voice


Last night my kids and I read — for the zillionth time — from Shel Silverstein’s Where the Sidewalk Ends. I’ve loved Silverstein’s poems since I was a kid, and I now appreciate so much what a great artist he was. “Backwards Bill,” about a doofy dude who does everything wrong is my favorite. It manages to be ridiculous (“Backward Bill he rides like the wind, Don’t know where he’s going but sees where he’s been.”), tragic (“And he’s got a wife named Backward Lil, ‘She’s my own true hate,’ says Backward Bill.”) and tenderly evokes empathy for the poor dolt, leaving us with the brilliant wordplay of:

Backward Bill wears his hat on his toes
And puts on his underwear over his clothes.
And come every payday he pays his boss,
And rides off a-smilin’ a-carryin’ his hoss.

After the kids went to bed I googled Silverstein to learn more. Turns out that he had a long, varied career as a songwriter and performer with the 70s outlaw rock band, Dr. Hook and the Medicine Show, and cartoonist of record for Hugh Hefner for 40 years. Much of his content was raunchy tales of sex and drugs.

Yes indeed. The man who makes parents around the world weep like babies with The Giving Tree, evokes children’s giggles (“Sarah Cynthia Sylvia Stout [would not take the garbage out]”) and squirms, with warnings about the sharp-toothed snail who lives in your nose and chomps off little picky fingers, also penned songs “Masochistic Baby,” and “I Love My Right Hand” for an album called Sloppy Seconds. Cartoons for Playboy spanned topics from orgies, weed, and cynical commentary on marriage.

This is so liberating! Silverstein did whatever the fuck he wanted to do, created whatever he wanted to create, paid no attention to any marketers or moralists may have tried to box him into a single brand, a single medium, target just one demographic. Though he may be remembered mainly for children’s literature, it seems he had a pretty awesome time writing songs about rolling the perfect joint and documenting sex parties for Playboy. Because that suited him. And we’re all richer for it.

This applies to single motherhood. No one tells you that if you are the sole provider for kids, it is A-OK to quit a safe, high-paying job and go follow your creative and professional passion. No one tells you it is really great if you chose to have a hot bath instead of playing Legos, or buy yourself expensive chocolate and not share any with the kids. There is no broad paradigm in which it is celebrated when women prioritize being really awesome mothers AND fulfilled lovers.

SO I’M TELLING YOU: You can do whatever you want! We are all blazing new paths of feminism and family here. WE, SINGLE MOMS, ARE MAKING THE RULES. The rules include being passionate and real and making the world a whole lot better for it. Go forward!


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Emma Johnson

Emma Johnson is a veteran money journalist, noted blogger, bestselling author and an host of the award-winning podcast, Like a Mother with Emma Johnson. A former Associated Press Financial Wire reporter and MSN Money columnist, Emma has written for the New York Times, Wall Street Journal, Forbes, Glamour,, U.S. News, Parenting, USA Today and others. Her #1 bestseller, The Kickass Single Mom (Penguin), was named to the New York Post’s ‘Must Read” list.

Emma regularly comments on issues of modern families, gender equality, divorce, sex and motherhood for outlets like CNN, Headline News, New York Times, Wall Street Journal, Fox & Friends, CNBC, NPR, TIME, MONEY, O, The Oprah Magazine and The Doctors. She was named Parents magazine’s “Best of the Web,” “Top 15 Personal Finance Podcasts” by U.S. News, and a “Most Eligible New Yorker” by New York Observer.

A popular speaker, Emma presented at the United Nations Summit for Gender Equality. Read more about Emma here.

11 thoughts on “How Shel Silverstein liberates single moms everywhere

  1. I’ve always loved Shel Silverstein – I still have my original copies of The Giving Tree and Where The Sidewalk Ends (and now a part of my son’s book collection) … and reading this, now I love him even more!! Thanks for sharing this Emma, and for always reminding us that we single moms ROCK!!

  2. Great timing to get this today (thank you!) as some sudden changes in my business have me questioning if it’s the right path, only problem is that I have no idea which direction to turn. With a 4 year old, debt and an unreliable baby daddy, I feel like my options are limited. I think of a great idea and then say, oh yea, I can’t do that because I care for my daughter 80% of the time.

    Trying to be open to something new and get outside the box of my life!

  3. Just in time….. Cant thank you enough. This was a great read and as a single mom of 3 trying to find her way…. This was spot on. I just caught myself an hour ago lying about having a massage and claiming i went to the grocery store instead…why? I have no idea why. Perhaps because i should have helped in my kids class on my day off, or spent that hour cleaning the house…..or that im selfish for spending money on a massage…. These are things i struggle with daily. The guilt. So thank over and over for the un-sugar coated eye opener. I love it.

    1. Really interesting note .. yeah, why do we do that to ourselves?!?? I decided I’ll go on one field trip per year with each of my kids and say no to the rest. Outsource housecleaning without guilt. Go for it!

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