The Educator Chalenge: Can You Solve These 20 Educational Riddles?

I love how riddles challenge the status quo and they stretch us to think differently. They can be frustrating, even addicting. Yet, the moment that we find the reason, connections, or contexts necessary to figure one out, there is this mini or major experience of what feels like personal victory. We might even pump our fists or raise our arms in celebration. As such, I decided to put together a little challenge for the willing educator (or others interested in education). Each riddle relates to education in some way. If you are familiar with the themes in my writing, then you have an advantage, but this is doable for anyone willing to invest the time and effort. Feel free to post your guesses or answers in the comment section, noting the number of the riddle that you think you have solved. Enjoy!

  1. You see me best when people fail. You can fix me. You can grow me.  You can change me if you know me. HINT: This one was inspired by the name of a celebrated book that continues to gain traction in thinking about how people learn.
  2. Sometimes I’m welcome. Sometimes I’m not. I encourage. I discourage. I direct. I reflect. And when I’m used well, I can even help perfect. HINT: This is an essential ingredient of learning.
  3. I can fill your mind while emptying your pockets. I can open doors. Many claim I give you profits. The public sign says, “Ignoring Me Can Be Your Doom” even though some do so on their way to the boardroom. HINT: Abraham Lincoln would probably guess this one in an instant.
  4. I’m used to rank eggs, beef, bonds, boys and girls; and people prize me like I’m made of pearls. HINT: Do you really need a hint for this one?
  5. I’m hot or cold and made of paper, and some insist that I can help you climb a skyscraper. HINT: This one is closely connected to #3.
  6. I’m the road you take to the town of better, but staying on me is no guarantee. How you travel and what you think will determine the time and length. HINT: Every expert did this for years.
  7. I tell kids where to be over 16,000 times before I finally set them free. HINT: I wrote an article on this one in the past, so you can probably find the answer by searching for the title…but you don’t need that, do you?
  8. I will not tell, but I’ll help you see. My query is part of your discovery. HINT: This one goes back to before 399 BC.
  9. I light fires. I irrigate deserts. The better I am, the less I’m needed. The less I’m needed, the more of a difference I have made. HINT: Note every one these will agree with the content in this riddle.
  10. I’ll all about deep and doing. I’ll serve you best if you’re focused and pursuing. And while some will claim that I’m a progressivist design, I’m really part of an ancient bloodline. HINT: Ask Buck if you need some help.
  11. At my best, I’m a trinity of integrating, deliberating, and other-centered concentrating. HINT: Ask Robert Sigmon.
  12. I was first invented to count a doughboy’s smarts. Then I became a defining part of the largest factory in human history. HINT: This is a test.
  13. I was the innovative tool that ended the one room school, and shifted a peer-to-peer structure to a place of homogeneity and lecture. HINT: This was uncommon in the US before the 1850s.
  14. I’m a central part of the K-12 and higher education system. Yet, I was built on the flawed notion that a man running for 50 minutes & another man walking for 50 minutes will cover the same distance. HINT: I’m named after the man whose work helped fund public libraries around the United States.
  15. From tennis to gorillas and warfare, I’ve seen over 20,000 sunsets and created billions of dollars. Now some want to use me to solve world problems & shape the next young scholars. HINT: This isn’t an education term, but it is finding its way into education more every year.
  16. I go all the way back to Alexandar the Great, but I started to go down with an 1852 mandate. Yet, in the New World I’m now 3% and I’m on the ascent. HINT: Ironically, this describes the education of Horace Mann.
  17. I’m a child. I’m a symbol. I’m largely unrestricted and incredibly nimble. I can help people see who you are to some degree, although that is not me. HINT: Some hate the boy scout comparison but I still find it useful.
  18. I’m an agent on a mission. I set why and when and how. I’m a pupil with a thousand teachers. HINT: Knowles, Boles, and Gibbons each wrote a book on this.
  19. Manage me to keep on learning. The more you know going in, the less I’m hurting. Seeing or hearing two at once can make me grow and make you a dunce. HINT: John Sweller is my father.
  20. Too often people think we’re twins, but that is just not true. He is small, while I am grand. He is contained while I will constantly expand. But if you think we’re both the same, you mind risks becoming both tame and lame. HINT: The Kettering Foundation has a great video by Dr. Edmund Gordon that speaks to these two words.

A New Teacher and the League of Extraordinary Game Masters

Craig Swanson taught sixth-grade science, but he thought of himself as more of a game master. As he liked to describe it, he got paid to blow things up, design games, set up fun experiment, and watch kids learn. He prided himself on not being your ordinary teacher.


When Craig went to middle school years before, he hated school. Science was his least favorite class because a bully kicked his chair and back almost every day while the teacher droned on at the front of the class, displaying what seemed like an eternal series of text-filled PowerPoint slides. Everything was focused on getting ready for the next quiz or test. As Craig described it, there was no wonder and no room for curiosity.

Love & Hate

Craig loved science. He just hated science class. He received his first chemistry set for Christmas at age ten and proceeded to beg for every possible science kit, educational game or gadget for all subsequent birthday and holiday. The contrast between what he experienced in middle school science class and what he loved about science at home set the path for his future. While sitting in the back of a middle school science class, trying his best to stay awake, Craig made the decision that he would grow up to be a completely different type of science teacher. He was going to be fun, engaging, wacky, even a little weird. He dreamt of growing his hair out to look like one of those old Einstein photos where it looks like he just stuck his finger in a light socket.

The Birth of a Game Master

Fast forward ten years and Craig was a recent college graduate and a first-year middle school science teacher with mad scientists flair. Every day he made it a personal mission to tap into the curiosity of his students, to invite them into the wonders of the natural world and the joys of game-based, quest-based, experiential and curiosity-driven learning. Students arrived in class with some sort of challenge or clue on the board. The necessary materials were set out, often with props and decorations tied to the theme for the day. Every day in this class culminated with some sort of interesting science experiment, quest or game followed by a group debriefing about what they experienced and learned from it.


Craig’s class could not be more different than what he experienced as a kid. Nobody sat in his class bored. In fact, students hardly ever even sat in desks. They were on the floor, outdoors, or gathered in a huddle around some sort of puzzle or experiment. They were thinking, moving, collaborating, laughing, problem-solving, experiment, and theorizing.

A Typical Day

This was not just some special event. It was a normal day in his classroom. He approached each day with the energy, passion, and attention to detail that you might expect of a wedding planner. Each detail mattered. Every student mattered. Each game, experiment or simulation was design was carefully prepared, and you could see the pride and playful smirk on Craig’s face as he watched students walk into class and get drawn into the activities for the day. Some days it was a single class challenge. At other times, the challenge or experiment extended over days or even a week.

The Gift

One morning Craig arrived early to get his class set up for a new challenge. He turned on the classroom lights and saw a large red box sitting on the floor in the middle of the room with a message next to it. “Are you ready for a challenge, Mr. Swanson? Read the riddle on the back and let the games begin!” The box had three padlocks on it.

Craig grinned in delight. His students shifted from game players to game makers. For the next forty-five minutes, Craig struggled from riddle to riddle, taking him outside, back into the classroom, then outside again. Each riddle led to the next, and each challenge tied into this wonderfully creative story. In the story, Craig was an undercover spy disguised as a middle school science teacher, and he only had an hour to solve the riddles and save the planet.

He figured out the final clue and removed the last lock from the box, saved the world and a raised his arms in victory. He opened it to find a box full of thank you letters from his students. Each one, of course, required to a cipher to decode. Looking at the clock, he had 30 minutes before the first class started that day, so he set the box aside for some evening fun and finished preparations for the day.


As students arrived one-by-one, they each entered the room with a look of clever pride, excited to see the teacher’s reaction. Craig pretended like it was just an ordinary day, but once everybody was there, he gathered them in a circle on the floor. He told them the story of his morning adventure, the strange box that he found in the room and the series of clever riddles that clearly took a deep knowledge of science to create. After thanking them for providing him with such a wonderful gift, he shifted the conversation back to the students.

Making Game Makers

Craig loved do debrief learning experiences with the students and this situation was no different. He asked them about the process of designing the game. He asked about what worked well and what was challenging for them. He asked about how they collaborated in the design. Then he invited them to consider what they learned through the process of designing such a “learning experience.”

The students were excited to tell their stories. It turns out that this design took them almost two weeks of researching, planning, meeting, and experimenting. They tested the riddles on one another, gathered feedback, and revised. They even reached out to a couple of professional game designers to get input on their project. Craig listened with astonishment. He knew they were an engaged and curiosity group, but had no idea that they were capable of such work.

The League

He wondered what would happen if he invited the students to more consistently join in the design of the games, experiments, and adventures in the class. He shared this musing with the class, and a group of more than half of the students volunteered to join what they decided to call The League of Extraordinary Game Masters. Each day after school, this group met to plan and map out games and experiments for the rest of the class. They learned to align the experiences with mandated standards. They learned how to embed assessments, various ways to check for student understanding of key ideas. They learned about how to design rich learning experiences that engaged and also truly helped students learn. Along the way, they also learned about science while discovering important lessons about how to learn.

Craig loved surprising students with daily challenges, immersive games, and engaging experiments. Yet, it didn’t take long for him to see the incredible power of inviting students to be designers of their own experiences. As the semester continued, a growing number of students volunteered to join The League of Extraordinaryry Game Masters. By the end of the year, the students designed and managed almost every game and experiment, and student learning was as strong as ever.

Politicraft: A Game to Nurture Active & Engaged Citizens

There are many games that teach kids about civics, but what about games that actually help young people develop the competence, confidence, sense of agency, and a growing awareness for tangible strategies to be civically engaged? That is the mission of the partnership that resulted in the design and launch of Politicraft, a narrative-based card game that gives us a glimpse into the power and possibility of using games for deep and meaningful learning around civics. The initial pilot is over and it is now open to interested educators who want to purchase and use it this fall.

Over the past six months, I’ve been steeped in texts and research about game-based learning, testing out different types of games, and experimenting with my own rudimentary games. Along the way, I had an idea for a game to help future teachers, and I settled on the concept of a card game. As such, I started searching the web and came across the web site for Politicraft. Intrigued, I reached out the the developers and they were kind enough to spend an hour with me, explaining a bit about the history and vision of this exciting project. As such, I had a great conversation with Rachel and Kevin Lyle who work with I-IMPACT, along with Lucien Vattel, founder of GameDesk.

When you are designing a game to teach civics in a new and impactful way, where do you start? For this team, they turned to the National Council for Social Studies, more specifically Mary Ellen Daneels, a NCSS board member who is well-known for her immersive civics simulations at Community High School in West Chicago. In Mary Ellen’s class, students get out of the school and into the community. They learn by doing and through direct experience. While this is ideal, the team wanted to design a game that drew from Mary Ellen’s deep well of knowledge and expertise, providing a simulated experience that might not send students directly into the community, but has promise to do the next best thing. As the group explained to me, “Civic mindedness is not something you are born with. The knowledge, skills and dispositions of effective civic engagement must be acquired and practiced in a safe environment.  That is the purpose of PolitiCraft.  PolitiCraft embraces the best practices in civic education to prepare students for college, career and civic life.”

There are many games that teach how to do civics, but the designers of Politicraft went a whole new direction. They wanted to show students what it might look like to be actively involved in their community, providing ideas for how to be active, civilly engaged different-makers. To get at this, they eventually settled on a narrative card game where students pick an issue at the beginning of the game…something they care about. Then they work through the game to take civic action to solve this issue. They are engaged in a personal passion project while learning different ways to get involved in their community. Within the game, they might take actions to build a website, attend a rally, get elected, become a media mogul, and much more.

In this digital age, why a card game? The team explained that they originally started with the idea of some sort of digital game. Perhaps they will return to that idea at some point in the future. However, Lucien and his team suggested starting with this narrative card game idea and, after getting feedback from people, they quickly discovered that it worked and resonated with both teachers and students. As one teacher explained to them, “I love that it is a card game because I don’t have to deal with all the digital tech that I don’t have in my classroom.”

Lucien and the team at GameDesk had a key role in this project, and I was inspired to hear his larger vision for their organization. Originally funded by the Bill and Melinda Gates Foundation, Lucien explained that he is driven to show that experiential learning engaged with other people can be one of the more profound ways of learning. “Some think of schools as places of career and college readiness. I think they have potential to be incubators for the designers of the future of the planet…equipping people to be self-driven, self-aware, creative, and thinking outside the box.” This extends to many crisis areas in society. Imagine engaging and equipping students to tackle the health crisis, socio-emotional crises, and political crises. “What can we do to create great opportunities for kids to think strategically and experimentally about the structures in our society?”

That spirit is certainly what animates Politicraft. Students are introduced to a massive social system in which they are largely not engaged. Yet, within the context of the game, students are placed inside of the systems. They discuss, in an empowered way, how they would tell their story in the system and effect positive change. This is a game that is about nurturing agency in learners. In 45-50 minutes (although it can run longer if the kids are really leaning into their narratives), students play through a series of rounds, play different roles, engage in civil action and discourse, reflect, articulate, grapple with and use relevant terms, and understand those terms in a context that resembles the real world.

As they’ve piloted this game with students, Rachel and Kevin explained it this way. “You watch kids and they are engaging in a way unlike reading a book or listening to a lecture.” The pilot also showed that the engagement seemed to increase the second time that students played the game, giving even more attention to the nuances and context. As Rachel explained, “We see kids thinking about what matters to them, and that passion this brings to the game is powerful.”

Ultimately, this game is about agency. Students make decisions. In Lucien’s words, “students are creating thought forms in their minds that they have not had. Instead of seeing it as something removed from them. There is a door open in their mind that was not opened before because they have partaken with their voices and minds.”

Amid debates and conversations about the affordances, limitations, power, pitfalls, and potential of games in education, Politicraft is definitely a model that warrants closer attention.

The EduRiddle Challenge: A Multi-Modal Game for Educators

The EduRiddle Challange is a 4 phase, 20 level game about contemporary issues in schooling and education. Phase 1 starts with a series of simple riddles about schooling and education. The answer to each is the password to the next level. While you will experience riddles throughout the game, they are just a part of the challenge, as you will see if you make it to phases 2-4.

Anyone can play. There are two simple ways to join the fun. If you have a Twitter account, you can follow @bdean1000, find one of my Tweets that announces the game and provides instructions, retweet it, and wait. Within 24 hours you will receive a direct message with a link and password to get started. The other option is at the bottom of this article. Fill out the form and you will receive an email within 24 hours providing you with the starting link and password. New participants are welcome to join the game until it is closed (a currently undisclosed date in the future).

Why the EduRiddle Challenge? There are three reasons.

The first reason is a secret. You might just have to participate in some of my games over the upcoming year(s) to discover it.

The second is because I made a decision over the last year to start investing more time into the research of game-based learning, game design and gamification. I love to experiment, even with rudimentary designs, as a means of learning. One of my three words for 2016 is “design” and I had games in mind when I chose that word. I have lots of ideas scribbled in my idea book and drafts of potential future blog posts (many of which never go public), and I’m looking forward to bringing some of these ideas to life. I plan to experiment with web-based games, augmented reality, apps, simulations, project-based games, card games, multi-modal riddles and scavenger hunts, and much more. Along the way, I expect to learn a ton and maybe even have a little fun.

The third reason is because games and gamification are both integral aspects of the future of education. Their growth, impact, and potential is undeniable. While there are plenty of debates about the best or ethical uses of game-based learning and educational gamification, it seems to me that those of us in education really only have two choices. The first is to get involved; learn about them, join in a rich and robust conversation about the possibilities, applications, affordances and limitations; then strive to create, use and/or promote them in positive ways. The second is to stand on the sidelines and ignore them or lament their existence, which will likely do nothing to slow their growth. This is essentially the decision that I had to make in the 1990s with the role of the digital world in education. Will I join in helping to shape its use, or will I watch and complain? By getting involved, I’ve made plenty of mistakes, but I’ve also had incredible opportunities to help shape where we go and how we think about the intersection of education and digital culture. I happen to think that the role of games and gamification, combined with the digital revolution, will greatly expand the ways in which we learn throughout life; and I have every intention of being actively involved with that.

So, why not join in by experimenting with the EduChallenge1?

You are a form submission away from joining the fun.