Shopping Cart

Taking Risks and Getting Away With It

The plan was simple. The target was unwitting. The execution was flawless.

I stole a shopping cart in broad daylight and got away with it. This is both a confession and a blueprint. How often do you get to conspire with a low-level thief?

Spying the unattended, Shop-Rite cart resting haphazardly against a parking block, I knew it was time to make my move. Enlisting the aid of a driver (my wife) turned out to be paramount because the snatch and flee would have been far more difficult on my own.

Slowly, my wife backed our Jeep Patriot into position. Casually, I approached the cart as if to use it for a shopping trip, as if I were saving it from relative obscurity. Mightily, I lifted the cart into the trunk, the seats of which had already been folded down to maximize my time. Finally, I slammed the trunk shut, returned to the passenger seat, and gave my getaway driver a sly smile. We had done it. We had become the most pathetic Bonnie and Clyde knockoff ever, and it felt so good.


Cormac McCarthy’s brilliant, Pulitzer Prize winning novel, The Road, is one of my favorite novels of all time, and its inclusion in my senior English class marked a shift in my career. Set against the backdrop of an unnamed apocalypse, the story follows two characters, named only the Man and the Boy, a father and son trying to “make it south” to survive. The bleakness of the landscape is matched only by the dearth of dialogue, marked by McCarthy’s refusal to use punctuation, and the lack of material possessions at the duo’s disposal. Essentially, they have a lone item.

A shopping cart.

Though I taught the novel to seniors, I knew they would struggle. McCarthy’s style is best described as functionally simple–as I mentioned he considers most punctuation a waste of time–but philosophically complex. After all, the end of the world tends to bring about some pretty heavy issues.

I wanted my students to experience the novel, not just read it, so I had to bring the novel’s desolation to them in a way that made sense. I couldn’t do that without the shopping cart, so I decided to risk my own freedom, and that of my accomplice, to do just that.

When the cart first appeared in my classroom, kids were understandably abuzz. Promising to explain more later, I deflected questions about why it was in my room and, more importantly, how I got it.

“I borrowed it,” was my preferred euphemism.

Finally, I shared the tale of the cart’s heist and its purpose in my room. My kids would consider their impending graduation as their “adolescent apocalypse” and contribute at least one item to the shopping cart with which they were not willing to part in the new world. Then, they had to present on that item to the class and field questions about its inclusion.  It worked like a charm.


So many teachers and leaders are skilled thieves. They know where to look to find great ideas, they recognize that in order to grow they have to beg, borrow, and steal, and they risk their own egos to bring their content to life.

Moreover, the word “risk” has risen to the top of the education cliche leaderboard, but it earned such status for a reason. There’s a distinct difference between telling our students about our content and showing it to them. Without risk, the latter is nearly impossible. SImilarly, as leaders, we constantly challenge our teachers to take risks, but how often do we model such risk? How often do we show our teachers that we are willing to fail forward as leaders?

Whether you’re stealing a shopping cart, presenting at an Edcamp for the first time, or pushing publish on your first-ever blog post, you are in complete control of the risk you are taking and need to be prepared to accept the reaction such risk brings.

After all, sometimes all it takes to level up is commiting a minor misdemeanor.

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