I sometimes joke that guessing is my superpower. Usually, this is after my wife has asked me a random question on a subject I know very little about. I think for a moment and make a guess. We look up the answer, only to learn that I was nearly spot on.
But, like all real-life superpowers, my guessing ability is actually a skill.
Let me tell you two stories from my time as a student that illustrate this point.
Story #1
Sophomore year of high school, I was in Honors World History. Late in the year, we were studying 18th and 19th century European history. Some of the material got covered during lectures, but most of it was in the textbook: several chapters that I did not read. The test was 80 multiple-choice questions, all drawn from past AP exams (so they were difficult).
As I worked through the first several questions, I realized that I really should have done the reading. I knew very little of the material, maybe 25% of it. Even making educated guesses on the other 75%, I would still fail the exam.
But I didn’t do that. In fact, I got the only A out of the three sections of Honors World History. How?
I knew from past experience that exams often contain the very information they’re testing. For example, a Spanish test might contain fill-in-the-blank grammar and vocabulary questions followed by a reading passage. Usually, the reading passage contains examples of the grammar and the vocabulary that you can use as a guide for the earlier sections. Is that the right conjugation? Does that word have an accent? Odds are, the answer you seek is somewhere else on the test.
On this particular exam, the verbiage of multiple-choice questions was lengthy, often giving a lot of historical facts as a setup to the questions themselves. The answer to question #7 might be hiding in the setup to question #45. So I blasted through the exam, reading all of the questions but answering only what I was sure of, all the while trying desperately to learn from the exam itself. On my second pass-through, I knew a lot more. I could confidently answer more questions and confidently eliminate more answer choices. By my third pass-through, I had acquired so much actual knowledge that my educated guesses were genuinely educated. I used every second of the allotted time. It was a sweaty, stressful affair, but it worked.
90 students took that exam, but the only one who got an A was the one who was determined to treat guessing as a skill rather than as a lottery.
Story #2
Four years later, I still hadn’t figured out how to be a good student, but I had been honing my guessing skills at each opportunity. I had gone far beyond the basic technique of process-of-elimination. I had learned to think like the test-writer. I had learned to spot “trap” answers. I had learned when to trust my gut and when to doubt it.
I was taking Social Psychology, an interesting class I enjoyed attending. However, I didn’t take notes in class, and I hadn’t done any of the assigned readings. Admittedly, I was planning to do the readings because this was college, after all. But I was a terrible procrastinator, and I was certain the exam was on Thursday, so I planned to do the readings on Wednesday.
So I was quite surprised when I walked into class on Tuesday, and the professor began handing out the exams. Gulp.
I was familiar with the material, but I didn’t truly know it. The test consisted of 15 multiple-choice questions, four short-answer questions where a paragraph response was expected, and a 5-paragraph essay question. While I could certainly guess on the multiple choice section, the rest of the exam required me to actually explain what I knew … and I didn’t know much.
Nonetheless, I did what I’d always done and gave it my best shot. I went back and forth between the sections, trying to learn as much from the test as possible, but it wasn’t like the history exam from my first story. So I was forced to make far more genuine guesses. On two of the four short-answer questions, I grabbed an appropriate-sounding vocab word from the multiple-choice section (a guess) and then boldly explained its definition (a guess) and how it answered the question (also a guess). For the essay, I had to interpret the prompt (a guess because it contained unfamiliar vocab), commit to a thesis (which would only make sense if the first guess was right), and defend it with facts and theory (mostly guesses). I said logical things that were related to what I remembered from lectures, but I was never confident in my responses.
The next week, the teacher held our exams at the front of the classroom. Before handing them back, he admonished us for our poor performance. He was disappointed in us. We needed to study more.
Yikes.
Well, here it is. I probably failed. Fingers crossed for a C.
He placed my test on my desk upside-down. Tentatively, I turned it over, fearing the worst. And I could not believe what I saw. I flipped through the sections, seeking confirmation. Surely there he’d made a mistake. But no, it had really happened.
My score?
100%
All of my guesses had been correct.
I’m a Good Example of a Bad Example
Now, let’s be clear. I’m not suggesting that the choices I made as a student were wise. I was a terrible student who got good grades despite my bad habits.
Guessing should never be your primary game plan.
But it is a skill you should keep in your back pocket. And it is a skill worth cultivating whenever you’re forced to. It allows you to perform better than you should, given what you know. And it’s valuable in many situations in life, not just exams.
Guessing is a Life Skill
So much of life is uncertain. We constantly have to make choices with incomplete information, from big choices like which career to go into or which investments to make, to little choices like which route will have the least traffic or what clothing to pack for a vacation.
The information age has fooled us into thinking we can know everything, but we can’t. And constantly worrying about what we don’t know and wishing we could have all of the facts or predict the future is a major source of anxiety. So we have to practice embracing uncertainty.
Guessing is Most of What Your Brain Does
You probably don’t realize it, but your brain is actually guessing all of the time. It’s a prediction machine, always trying to figure out what it’s going to need.1
You’re hiking and about to step on a root. Your conscious mind is admiring the forest, but part of your brain is guessing what it will feel like to step on that root and how to adjust your weight to maintain balance.
Your boss comes up to your desk and gives you an extra project. You’re thinking about how you’ll fit this into your already-busy schedule. Meanwhile, you feel anxious because your brain is running a prediction about whether or not you’ll have the resources to meet this challenge, and it’s guessing that you won’t.
When you’re hungry, it’s not because you need food right now; it’s because your brain is predicting that your body will need food soon.
When you get a raise and feel happy, it’s not because you’re already enjoying that extra money; it’s because your brain is predicting that the extra resources will make your life easier or more fun.
So guessing is natural, but that doesn’t mean we’ll be naturally good at it. Like all skills, it gets better with practice.
Elements of the Skill of Guessing
I can’t tell you how to pick winning lottery numbers. There’s no skill in that. But I can tell you what it takes to hone your ability to make educated guesses.
Everyone knows about process of elimination, but most people make the mistake of doing it in their head. Physically cross out the answers you’re sure are wrong because it lightens your cognitive load.
Guessing is largely an exercise in logic, so honing your logical thinking skills will improve your guessing ability. A lot of guessing comes down to analyzing the options and applying what little knowledge you do have in a carefully logical way.
You have to be comfortable guessing, which means you have to learn to be comfortable being wrong. And even though you might be wrong, you have to commit. When I wrote my social psychology essay, I didn’t hedge; I wrote it as though I were confident everything I was saying was true. Emotionally, this is tough. It’s hard to fully commit to a decision when you’re worried about being wrong. It takes practice.
Luckily, the modern world has created a wonderful way to develop all of these skills in a low-stakes, high-fun environment. I’m referring, of course, to table-top strategy games.
Playing games like Harmonies, Wingspan, or Terraforming Mars is a delightful way to build up these intellectual and emotional abilities.
So go play, and with practice, you can claim guessing as your own superpower.
1Barrett, Lisa Feldman. How Emotions Are Made: The Secret Life of the Brain―How We Create Emotions Through Brain, Body, and Culture. Mariner Books, 2018.

Chris Loper has been working as a tutor and academic coach since 2014, racking up over 13,000 hours of experience supporting students.
Along with Greg Smith, Chris is the co-creator of Parenting for Academic Success, a series of classes that create empowered parents, confident students, and harmonious families.
Chris writes the popular self-improvement blog Becoming Better, where he also offers habit coaching, helping busy adults with habit formation and productivity.
Chris’s most recent endeavor combines his academic and habit-formation expertise to help students thrive in college. Visit SmartCollegeHabits.com to learn more.
In 2021, he published a humorous memoir titled Wood Floats and Other Brilliant Observations, a book that blends crazy stories with practical life lessons.
He lives in Issaquah, WA, where he is the owner of South Cove Tutoring.







