Land Your Dream Job
Careers that help you move from intention to action

Ask A Stupid Question!

A stack of papers with question marks on them.

Ever hear the expression, “no question is a stupid question”? You may have heard it from a teacher encouraging you and your classmates to voice your inquiries. Asking questions has its role in learning- by thinking more deeply about the subject you are studying, you can understand it better. It also helps the person to whom you asked the question get a better idea of the way your mind works and your learning style.

In honor of Ask a Stupid Question Day, typically celebrated on September 29th (or the last school day of September) each year, I challenge you to get curious and ask a question or two of your own. This fun holiday was launched in the 1980s by teachers who wanted to prompt students to ask more questions in the classroom. If you can recall being in elementary school, feeling nervous about asking a question and fearing that your question would be laughed at, this day gives you license to jump in and celebrate. In fact, I invite you to have fun with this and ask the most ridiculous, obscure questions you can possibly dream up!

You can ask questions like, “Why don’t penguins’ feet freeze?” or “What if water went through umbrellas?” I dared to ask the interwebs that last question and I learned that the purpose of the umbrella was originally to protect people from the sun, not the rain (e.g. the predecessor to the umbrella: the parasol). It was only in the mid-1700s that it became popular for use as protection from rain. Mission accomplished---I asked what I could have viewed as a “stupid” question, and instead of feeling stupid, I learned something.

There are many different types of questions you can ask, but I will be focusing on two: informational questions or “ponderables” and requests to strangers.


Ponderables are questions such as “have you ever wondered... “ that may have you thinking for quite a time without actually discovering a conclusive answer. In some cases, you just have to take action and experiment. For other ponderables, surveying others might help guide you towards a good hypothesis, or the answer itself.

While listening to the High Talkers episode of one of my favorite podcasts, Betty in the Sky with a Suitcase, Betty wonders why flight attendants’ voices go up when asking passengers, “Can I get you a drink?” This is not dictated in any training manual, yet most attendants, by Betty’s observations, seem to do it! So she starts to ask why.

This might not be a question you or I would think of asking, but it relates to Betty’s work and helped her understand the subconscious goings-on that might be creating this phenomenon among her and her co-workers. She suggests that they do it so that they will give passengers the impression that they are in a good mood and ready to serve.

What are some questions about your own life and work that you would like to ask? This is a great way to stretch your creative muscles and discover a-ha! moments. Imagine the feeling that the first person who asked, “Why are sewer covers round?” might have had.

Making requests (“Rejection Therapy”)

While asking informational questions such as, “How do I become an alchemist?” or “What do I do with my great-great-grandmother’s button collection?” might come to mind, there are other types you may want to try, ones in which you are making an actual “ask”...for things that seem ridiculous.

Imagine asking questions like, “Will you let me borrow your hamster?” or “Can I paint your portrait while you flip burgers on a golf course?” These can produce strange stares, require more input and action from person you are asking, and be challenging and fear-inducing, because the risk of someone saying “no” is far greater. However, they can also make requests like, “Would you review my resume?” seem more run-of-the-mill and doable.

When intentionally making these types of requests for the purpose of taking the fear out of rejection, it is referred to as rejection therapy. While reflecting on Ask a Stupid Question Day, the practice came to mind. Jia Jang, an entrepreneur, author, and TedX speaker settled into 100 days of putting himself into situations in which he could potentially face rejection. His goals were to become desensitized “from the pain of rejection” and “overcome (his) fear."

Jang’s plan was to make requests of people---namely strangers---that might seem outlandish, entitled, or bizarre. Some of these requests, which you can view in the 100 days of rejection archives, included Ask Strangers for Compliments, Be a Greeter at Starbucks, and Dance with a Dancing Santa. His experiments taught him that rejection and the fear associated with it (that same fear you might have when asking a “stupid” question) won’t necessarily be as pain-inducing as we might envision, and that people are a lot kinder than we would expect. After his 100 days, Jang embraced his breakthrough, writing a book and launching a course that guides other people to try out rejection therapy. In essence, he created an opportunity for himself by taking on this challenge.

Ask a Stupid Question Day is a great one to launch your own rejection therapy mission. At the very least, start asking questions that truly make you and those around you ponder.

By Victoria Crispo

Explore Jobs on Idealist