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How to Teach What You Love,

While Making Good Money

and Changing Lives:

A Comprehensive Guide to Online Tutoring and Teaching

So, You Want To Be A Tutor!

So, You Want To Be A Tutor!

Tutoring—especially the independent, online variety of it—is a wonderful job for many reasons:

  • You make a tangible, positive difference in students’ lives


  • You set your own hours and schedule


  • You can tutor from anywhere in the world, such as Bali or Crete or Taiwan


  • Whether this is side gig or main gig, you develop a skillset of teaching and speaking that probably supports your life mission in some way


In this guide I will share the most helpful methods, tips and tricks I’ve learned in my time of professional online tutoring. Learning these tips will help you to launch yourself like a rocket ship heading straight for warp speed (i.e. great success, freedom, abundance etc.).


A word of caution: You have your own style, your own path, your own way of being and moving. This guide is a record what has worked well for me—not a prescription for you to follow. I suggest trying things out, seeing what works, heeding the age-old advice:


“Take what resonates and leave the rest.”

Who Am I? Why You Should Trust Me

Who Am I?

I've been doing this for a while. After tutoring independently for many years, I joined a medium-sided, high-end tutoring company. Due to happy clients and helping students to achieve big score increases, I was promoted. After three years there, it became clear that my personal growth (and my ability to serve my students to the utmost) would be best facilitated by working independently, so I left the job and have been tutoring and teaching on an independent, freelance basis ever since.

A number of folks have asked me for tips about getting started as an online tutor. So, as an outgrowth of that, I’m putting together everything I’ve learned that has served me best as a tutor, as well as what a new online teacher or tutor would need to know, into this one, comprehensive guide.

While this guide is geared especially toward independent, online, one-on-one tutoring and teaching, much of it applies to in-person and group/classroom settings. I suggest referring to the menu to find what’s most helpful to you.

This guide is evolving; I’m always working on my own craft. I’d love to hear from you with questions, comments, or what’s worked well for you.

My intention: to benefit all students and teachers. May all teachers teach well.

TL; DR: I have experience; I do my job well; I care. Therefore you can trust me 😉





Below are two options (“recipes”) that cover the essentials of what you need to tutor online:

a teaching platform, a payment system, a means of communication, and marketing.



  • Zoom (teaching platform)


  • payment method(s) of your choice (e.g. PayPal, Venmo etc.)


  • payment record service of your choice


  • email service of your choice (communication)


  • social media platform of your choice (marketing/communication)


  • optional: a personal website where you describe your services


Yes, it’s that simple! ClassForThat integrates all of the key ingredients: an online teaching platform, course descriptions, payment system, communication, and marketing. I found that switching from 'Option 1' to 'Option 2' nicely streamlined my life as a tutor. Of course it's up to you.

Benefits of ClassForThat

Benefits of ClassForThat

  • free marketing — Yes, the Holy Grail of freelancing! Listing your offerings on the website is free, and connects you with a large and growing market of students.


  • a fully integrated platform that simplifies your life see “option 1” vs. “option 2” above. Speaking from personal experience, switching from option 1 to option 2 streamlines all the logistical and technical aspects of tutoring, allowing you to maximize your time and focus solely on teaching.


  • a referral system that benefits all parties — as a teacher you gain a percentage commission for simply bringing other teachers and students into the fold. From the student’s point of view, inputting your referral code gives them the benefit of paying lower rates for your classes (if you choose to offer lower rates—it’s all customizable).

full disclosure: I know the founders of ClassForThat personally. They did not ask me to write this guide, and it is my genuine opinion that ClassForThat is the best platform out there (fully integrated, user-friendly, holistically useful), for teachers and students alike.

For more information about how ClassForThat works, and to sign up:


If you do join ClassForThat, please input my referral code: Will1


Inputting my referral code costs you nothing, and benefits me! How nice of you! 😊

(You also get lower rates on my classes)


  • a laptop with a reasonably large touchscreen


  • a writing stylus — I find that having a touchscreen and writing stylus (in combination with a whiteboard app/feature), while not 100% necessary, noticably improves my teaching ability (e.g. writing out the steps of a math question, annotating a reading passage, etc.).


  • a mouse


  • a reliable internet connection


  • optional: a passport (link to digital nomad top 10 cities)



  • Khan Academy — The go-to resource for so many subjects. For individual students, I suggest creating a “class of one” so that you can assign and review lessons and practice modules.


  • College Board — For SAT and Advanced Placement resources. Khan Academy also has excellent SAT resources.


  • — For ACT-specific resources, of course.


  • NoRedInk — Like Khan Academy, but specifically for English and writing. Not all of the content is free, but a good portion of it is. It has some grammar topics that Khan does not.


  • Your friendly neighborhood search engine — Witness the democratization of education! Searching things like “free ______ practice test” or “free ________ practice” typically yields good results without much digging.

Do I need a textbook

"Do I need a textbook?"

It depends. If it seems like a specific textbook will benefit the student, I recommend that the client purchase one and I also buy one for myself, including the price in what the client pays.

On the other hand, oftentimes a textbook is not at all needed, due to the treasure trove of high-quality, easily accessible online resources (see above).



Being a magnet is a big idea that can revolutionize your whole life. For the purposes of applying it to attracting clients, I suggest working with these principles:


  • Do your best work. Do everything in your power (short of being a doormat) to give your clients excellent service, and have confidence in the quality of your work. Because of course…


  • Word-of-mouth is best. Being a magnet means you shine so brightly upon everyone you meet that, quite naturally, word spreads of your good work, and folks come your way. In fact you might shine so brightly that…


  • Social media is not necessary. If you’re a social media person, by all means, go for it. But if, like me, you enjoy relative solitude, that’s the main point of being a magnet: you don’t have to overextend yourself to get clients. On that note…


  • Effortless marketing is best marketing. Besides word-of-mouth, again I mention ClassForThat as an easy way of connecting with folks who want your services. Another method of effortless marketing is paying someone to do marketing for you.

The point is that YOU are in charge of this whole thing you’re creating — so why not make it easy for yourself? Give your best gift by cutting out everything that doesn’t jibe.

not chasing clients

"If I'm not chasing clients, how am I supposed to build a client base?"

Now I’m going to say the opposite of what I said above. When you’re getting started, the fastest way to pick up much business is probably to reach out to everyone you know. Think of it as a cosmic shout that shakes the universe: craft a punchy announcement, and spread the message through every means you have:




Maybe don’t use that many exclamation points. But you get the idea.


Another tried and true method is to offer free or donation-based services, gather testimonials, and proceed from there, focusing on serving folks well. It’s written in the stars:


Serve others well, and the Universe shall serve you.



This is a question you’re advised to reflect upon right from the start. What’s your passionate intention behind getting into this business—to make money? To have more freedom in your work? To teach what you know and love to interested students? To make a positive change?

Regardless of the specifics of it, taking time to connect with your intention—to feel the fire behind it—is something that will fuel your whole journey. You might ask (with any endeavor you’re considering starting), “Is my passion for this sustainable?”

If your motivation is purely self-centered, chances are it’s toward the “unsustainable” end of the spectrum. Connecting with your heartfelt intention (e.g., writing or speaking about it) is a good way to cultivate sustainable joy, joyful sustainability.



what does school teach children.jpg

Disclaimer: The above meme represents only one, limited, strongly stated viewpoint. I don’t endorse it; neither do I oppose it.

Reflecting on my own education, I’m terribly grateful for the teachers who cared so much—who taught with contagious passion, who took the time and effort to make sure we students were learning, enjoying ourselves, becoming halfway decent human beings. Great teachers make all the difference, teaching with contagious passion.

Institutionalized education robs students of that very passion insofar as it overplays its rigid aspects: compulsory courses, rote repetition, the endless drive to gauge, quantify, separate and sort students. Remember being forced to study history in school, when you didn’t care about history? Or if not history, there was likely some other subject that simply didn’t light your fire, but that someone in power decided ought to be studied by all young ones.

I’m not here to trigger the age-old debates over standardized testing, government mandates, etc. etc.. I only wish to point out: in comparison to the typical school environment, individualized online education offers both student and teacher a powerful degree of freedom, a degree of personalization that allows for deeper, more engaged, more meaningful learning. There’s no red tape; there’s nothing preventing us from teaching to what truly excites the student and will also serve the student practically. This is a beautiful facet of online, personalized tutoring and teaching.

If this section rubs you the wrong way, please disregard it. Now I’ll step off my soapbox and get back to the good stuff 🙂

owl advice 3.png


This section is the real JUICE of this guide: tried and true strategies for effective teaching. I recommend trying them out and seeing what fits in with your own personal style. You’ll build a toolbox of practices: such a practical toolbox will help you to meet every student and every moment with the best approach.


Note: These methods are equally well-suited whether you’re teaching virtually or in-person. Though they’re phrased toward one-on-one teaching, they are also adaptable and useful for larger classes.



In Greek tradition, Socrates’ beautiful gift to the world was to expose the foolishness of those around him.* He did so by asking folks question after question, revealing their assumptions, their blind spots. Realizing how little you actually know is a gift in itself, and it’s also a precursor to deep learning: as the saying goes, “If you’re confused, you’re learning.” On the other hand, if you think you already know, there’s no space for learning.

As a teacher, following in Socrates’ footsteps will serve you terribly well. If you’re asking questions, the student is actively engaged, and literally teaching himself. The key is to ask questions that are not too difficult, but not too easy, so that the student is constantly hovering around that sweet spot of “healthy challenge,” where learning occurs.

If you master this technique, you can actually teach things you don’t know about! Not that I recommend this, but it can work in a pinch 😉 

There are certain questions I ask time and time again in my tutoring practice, centering questions that evoke learning see below for examples.


*As Socrates is said to have said, “I know that I do not know.” Being aware of your own ignorance as a teacher is key… As I apply the Socratic method I’m ever amazed at how students find methods and ways of thinking that I’d never before considered.



When your student is in over their head (for example, trying a math question that is beyond their ability), the best move is usually to take a step back before stepping forward.

Practically, this means to break it down, make it simpler, reduce the question to its most basic building blocks. Focus on the basic lessons one-by-one, and then build back up to the more complicated question.

For example, if a student is “stuck” on a math problem involving multiplying fractions, I might come up with a simpler example question, only involving multiplication. Next, I might ask a simple question about fractions. Once they have a handle on all the parts of the question (first multiplying, and then fractions), we return to the original question they were stuck on (multiplying fractions).

We work with a core learning process:

starting with the fundamental building blocks,

learning consciously at first, practicing the basic patterns,

internalizing and distilling those patterns over time,

building more complex knowings on top of those.



This is the power of “monkey see, monkey do.” (Not that your student is a monkey.) “I do, we do, you do” is a basic, three-step process that will serve you well in many scenarios when teaching a new lesson.

1. “I do” — The student observes as you demonstrate how to do something, for example a math question, step by step.


2. “We do” — Working with a fresh question of the same type, you and the student solve it collaboratively.

3. “You do” — Starting a third question of the same type, the student solves it on their own, with minimal help from you.  

“You do” is the most important part of this process, because it’s when the student is most fully engaged. Therefore a good teacher minimizes time spent on “I do” and “we do.” Most commonly, the way I achieve this is by staying in the “You do” zone, but asking the student a simpler question that builds toward the more complicated question we’re currently working on (see above "Make It Simpler").



You must let the student fail. Benefits of failure:

  1. The student learns resilience and self-confidence

  2. Failure simulates the real-life scenario when the teacher will not be present to baby the student

  3. Failure exposes the exact step(s) of the process where the student is making a mistake, and gives them a chance to correct it


Number 3 is most important. Time spent watching a student fail is almost always worth it, because afterward, asking them questions like, “Where did you make a mistake?” and prompting them go back and self-correct is a wonderful way of inviting precise and meaningful self-teaching.

Let the student fail all the way! If they make 3 mistakes on a single question, that's 3 lessons they're about to learn.

This is called “Failing Your Way to Success.”



Usually in our first meeting, I take 5-10 minutes to go over basic learning styles (see below) with the student, giving them a chance to self-identify which one they favor. This informs how I teach the student. Of course, learning differences such as dyslexia or Attention Deficit Disorder are also helpful to ask about and work with. Usually the student already has a lot of self-awareness, so oftentimes, all you need to do as the teacher is ask the student what kind of teaching works best for them.

It’s also quite helpful to have a sense of your student’s interests, passions, hobbies—for the sake of connecting with them as people, and also in order to connect the subject matter with what the student loves.

An example: I love working with student-athletes because they often already have a slew of effective habits of preparation, mental focus, performance under pressure etc., that are easily applied to academic life. It doesn’t really matter how much you know about their sport—just ask!


For example:

“What do you do to get focused and ready for a big game? What do you do to help channel the nervous energy (excitement)?” 

“How do you refocus yourself when you realize you’re feeling scattered?”

Things like how to reach peak performance and how to perform under pressure become all the more important if the student is prepping for a big one-time test.



The “basic three” (four if you include "Reading/Writing") of learning styles, which I usually briefly overview in the first meeting, are Visual, Audio, and Kinesthetic. While it’s helpful to identify the student’s preference, it’s also a good idea to emphasize that usually the best way to learn is to engage all learning styles simultaneously as much as possible.

While most students are visually and auditorily engaged most of the time, kinesthetic learning (“body learning”) is often neglected, especially in the context of the student sitting at a desk, in a classroom or in front of a computer. In this context, kinesthetic learning means: USE YOUR PENCIL! Yes, moving the hand is a form of body learning. Encourage the student to take notes, make study guides for themselves, draw diagrams, and to annotate readings (margin notes, underlining, circling, etc.).

Also note: there are many learning styles to engage, depending on who you ask. Simply being aware of this multitude is a step toward broadening your modality of teaching into the plane of holistic engagement.



Given such a multitude of learning styles and ways of knowing, you will find value as a tutor in opening up the way students consciously choose their method of problem-solving.

What I notice about some students is this: having filled in bubble sheet after bubble sheet, completing standardized-this after quantified-that, they’ve boxed themselves into a limited, linear application of their intelligence—they mainly use straightforward logic to solve everything front-to-back, step-by-step. This approach is often effective. Other times it falls flat.

An example: it’s possible to be so linearly focused on a math question that you end up with an answer like 5 ¼ (five and one-fourth). But let’s say the question is asking the maximum number of people that can fit in a certain elevator. Including that one-fourth person in your answer is both incorrect, unreasonable, and a little gross! It’s possible to be so zeroed in on logic that we miss the bigger picture of common sense. And you know what they say about common sense—it’s not so common.

Another piece of advice that often comes up: “Trust your ear.” This applies especially on SAT/ACT and other English tests wherein, the student may or may not know the particular grammar rule that applies to a certain situation, but, reading through the answer choices, they can “hear” the correct way of phrasing. For example if I say to you “Those boys is wild,” you might instinctively want to correct me, “Those boys are wild,” regardless of whether or not you can explain to me that the plurality of a verb should match its subject. Some things we know deeply, nonverbally, from long ago. Therefore, trusting the intuitive (arising from the subconscious) sense of what “sounds” or “feels” right might be all your conscious mind has to go on.

A final extension of this topic: “Go with your gut” and “Trust your heart” can apply to standardized tests too. The body has such knowledge if only pay attention. A direct example regarding heart intelligence is when the SAT asks emotion-centered, relationship-centered questions in the Literature passage of the Reading section.



Metacognition is a beautiful ability you have as a human being. Not only are you aware; you can bring awareness to your awareness. You can think about how you think; you can tinker with your thinking processes. Your mind can be like a microscope, zooming in and expanding upon the tiniest of details, or like a telescope, zooming out and out and out to see the bigger picture. I like to frame metacognition within a conversation about practicing mindfulness as it relates to learning: consciously directing your awareness in ways that are conducive to learning.

Sometimes it’s as simple as asking, “What serves me best at this moment: to engage with the details, or to back up and look at the bigger picture before diving in?” An example: many math questions can be solved in multiple ways—some quick and easy, others time-consuming and difficult. Many students don’t take the time to ask themselves, “What’s the easiest way of solving this question?” This saves time and effort.

Another aspect of metacognition is perspective swapping. If you’re studying a book, get into the writer’s point of view. If you’re studying tai chi, soak in the master’s mindset. If you’re preparing for a test, think like a test writer. On a multiple-choice test, learning to recognize the common traps set by the test-writers can make eliminating incorrect answers a breeze. In this case, you can ask questions like, “What do you think the test-writers were thinking when they came up with these incorrect answer choices?” The test writers are always trying to trick you, I warn the students. But when you see those tricks for what they are, the tricks turn into helpful hints, guiding you to the correct path.

Applying meta-awareness to timed tests or other timed situations: Mind the clock. One undesirable extreme is to anxiously and over-frequently check how much time is left, actually wasting time in doing so. On the other hand, having no awareness of time is not the solution either. A good middle path is to take a couple of intentional “check-points” to see how much time is left, adjusting pace if needed. As a central part of the tutoring process, doing plenty of timed practice smoothes out the wrinkles and develops an intuitive sense of timing.

In basketball practice, Coach always used to say, “Practice how you play.” No matter what you’re preparing for, the best practice is to simulate the real-life conditions as much as possible. This means giving full or near-full effort, doing timed practice if you’re prepping for a timed event, even going through the same pre-event rituals and preparations that you will go through before the real thing.

“Switching gears” between modes of intelligence: You have so many minds, and many of them have something helpful to say about how to gracefully move through any given situation. You may find it useful to name and discuss certain ‘minds’ with the student: the “logical mind,” the “practical (common sense) mind,” the intuitive mind, (“Trust your ear,” “go with your gut,” the gut mind), the heart mind, other kinds of minds.



Especially when you’re new getting started in a new subject area, it’s a good idea to over-prepare your lessons. This means making sure you know the material well, planning questions and other ways of inviting student engagement. For example if I’m going to teach an hour-long session, I might prepare what seems like 90 minutes of material. This gives you flexibility of what to teach during the session itself, and also builds out your conceptual framework of the given topic.

As time goes on and you build mastery of the material, you’re likely to shift away from concrete planning, toward more in-the-moment adaptation. For example, during an SAT tutoring session, we usually start by going over some of the homework. If I see that the student missed two or more questions of a specific type (say, math questions dealing with exponents), I might take that opportunity to dive deeper into exponents—posing questions to the student, going through the process of solving them, solidifying the student’s understanding of that particular topic. This in-the-moment adaptation might take up half of our planned time that day, but it’s worth it because we’re capitalizing on a momentary opportunity to address a key area that is ripe for improvement.

So, there is always a balance of preparing vs. adapting. I like to create a word-processing document for each student, containing a working outline of where we’re headed, major goals and content areas to work on. This way you have the freedom to explore fruitful tangents, with the security of a solid plan to return to once the tangent runs its course.



Anxiety and depression affect so, so many people. It’s true—you’re not a licensed therapist. Yet, as a tutor, it is becoming of you to start a conversation about anxiety and emotional well-being. Much can be said about how to address anxiety. Usually there is no one simple solution, but you can help more than you think, even by only briefly addressing it (though sometimes spending more time here is the key to unlocking everything else). Touching base with the student’s parents might be part of the solution.

One quick exercise: allow yourself to bring to mind the last time you felt very anxious. What did that anxiety feel like, physically, in your body? Did your heart rate increase? Did you feel a burst of jittery energy? Did you feel the urge to take action?

Now, bring to mind a time when you felt very excited for an upcoming, positive event. Ask yourself the same questions as above. Between anxiety and excitement, what similarities do you notice? Differences?

This is not to minimize the reality of anxiety, or to say the solution is as simple as re-labeling it as excitement. But, re-labeling (or un-labeling) emotions is a powerful act. Many excellent test-takers and others who succeed in high-pressure situations feel a similar physical response as those who suffer from anxiety. One difference is that the folks who cope well are more likely to treat “anxiety” as “excitement,” e.g. by employing positive self-talk, for example “This is my body telling me that I care about this situation. My body is energizing me, and I am channeling this energy into constructive action.”

If a student suffers from test anxiety, I usually give a homework assignment early on of writing about test anxiety.

As the saying goes, “The man who is puking has trouble helping the one with diarrhea.”  Caring for your own emotional well-being is a fundamental aspect of helping students with theirs. Personally, I’ve found great benefit in a consistent meditation practice.



As much as we love to fracture and compartmentalize our lives, the reality is that everything affects everything. Taking interest in your student’s overall well-being is not only the compassionate thing to do, but also a wise choice in terms of helping them perform well at whatever you’re teaching them.

Practically, being an undercover life coach means checking in about life’s basics: is the student getting enough sleep? Eating well? Often stressed, with barely any downtime or “me time”? How are the student’s study habits? What about time management and planning in general? These are all areas to ask about. Especially if the student seems imbalanced or lacking in a particular area, don’t hesitate to spend time outlining the appropriate strategies (for example, if the student is in the habit of taking sloppy notes or no notes at all, you might outline particular strategies of note-taking and assign homework based around note-taking).

Holistic tutoring also reaches into down-to-earth practices of emotional well-being and clear thought. I spend at least a nugget of time with every student suggesting academic applications of mindfulness, positive thinking, visualization, and affirmations. If the student expresses enthusiasm about a particular method, we’ll explore it further and keep it as an “ongoing” homework assignment.

Outwardly, you’re a tutor; behind the scenes you’re tutor/life coach/mentor/caring human being. Another coach-type thing to touch upon in one of your initial sessions is goal-setting. While it’s reasonable enough to set goals that are realistic, I find that what gets the most kick is to challenge the student’s idea of what is “realistic” in the first place. Seek to undermine any and all limiting beliefs a student has about how well they can perform. For example, if a student wishy-washily tells me their goal on the SAT is a 1400 or 1500, I’ll probably say, “Why not shoot for a perfect score?” If we want to perform anywhere near our greatest potential, we’ve got to open ourselves to risk, to vulnerability, to the possibility of falling short.

Truly, I recommend questioning limiting beliefs whenever you hear them, be they heard from your student’s mouth or your own, or within your inner mental chatter. A topic where many students carry limiting beliefs is Math. How many of us, from a young age, internalized the idea that we’re lousy at math, and then fulfilled that false prophesy by performing below our true potential? To reframe limiting beliefs in a healthy way, I suggest that a student phrases more neutral- or positive-leaning beliefs, using language that is both believable and in line with a growth mindset, for example: “In the past I have not excelled at math, but I’m getting better with practice.” Something like that—but it’s more powerful if you prompt the student to word it herself. In the context of learning, the least burdensome kinds of beliefs are ones that align with a growth mindset.

What limiting beliefs do you hold about your ability as a tutor or teacher? How might you reframe them?



If your work is one-on-one, you ought to keep your student thoroughly engaged at least 99% of the time. Humor is an excellent tool for this. In a group setting, humor and relatability are all the more important.

If the session starts to lull or stiffen, why not throw in a quick joke? Or, why not ask a random question about the student’s life, like, “How’s the baseball team doing?”

Have fun! Play! If you’re not enjoying yourself, chances are the student isn’t either.

I once showed up to teach an English class in Taiwan, and the owner of the school said he forgot to prepare the day’s lesson, so he told me to talk about anything. I decided the topic of that class would be “Jokes.” I told every joke I know, and the students told jokes too, for example, “Taiwan is the P.R.C.: People’s Republic of Canada.” That one got a huge laugh. Besides being one of the most joyful classes I’ve taught, and a wonderful cultural exchange (jokes are so odd, even before they cross cultural lines), the students really brightened and engaged in a way I’d never before seen. One of the usually quietest students told of his dream to travel the world and minister to the poor. Humor opens hearts and minds.



It must be said: on the other side of goofiness and “I’m the cool, funny-guy-teacher” lies sternness, seriousness, disciplinarian power.

I admit this is somewhat of a weak point for me. I’m lacking advice. My strategy sometimes in the past has been to shout louder and louder, giving the students no choice but to hear me.

I will say, making agreements works well. This is especially pertaining to homework, e.g., “If I assign you only about an hour of homework per week, will you commit to completing it every week?” I like to let the student know that they have the right to speak up if anything we’re doing seems irrelevant or useless, and that the other side of that coin is that it’s their responsibility to commit to the process. They’re only going to get out of it as much effort and care as they put into it. I find that students appreciate the sense of purposeful responsibility that comes with making intentional agreements.


(i.e. LOVE)


Holding your students in unconditional positive regard means seeing them in their best light. It means you care. You want students to learn whatever the topic is you’re teaching them, and you also want them to be happy, healthy, fulfilled and successful human beings. You might express unconditional positive regard through small-but-significant actions, like sending a note of encouragement before exam day, or expressing appreciation to the student’s family.

Another aspect of unconditional positive regard is to really meet the student where they’re at: don’t assume they already know something that they “should have already learned.” Practice patience. As much as it will benefit the student to do so, don’t hesitate to go back to basics, starting from the ground up and making questions simpler.

If you notice a sense of judgment or frustration arising (e.g. “We’ve gone over this three times already—why don’t they know it?”), simply recognize it, take a breath, and let it go. Practice unconditional positive regard for yourself too—you’re doing your best 😉



We’re students of life from the first breath to the last; why not embrace it? Be a student of your craft; be a student of the unknown.

Speaking practically, being a student of your craft means learning it well and continuing to study, to expand, to follow your curiosity, your longing. It means studying thoroughly what you teach, but also keeping a student’s mindset’ even as you teach: keeping your authority as a teacher, while joining students in their discovery. Every iota of personal expansion will shine through into your teaching; will enliven it, will make it new.

You are a master, right now: you are a constellation of understandings, of life experiences, that no one else has ever had and no one else ever will have. Own your mastery and embody it — while remaining the unknowing, eternally humble student.



The more freedom you grant the student to be just as they are, the more you can see how brightly they shine.


The more you see your student in their best light, the greater your capacity to reflect back to them their brightness.

If you are mirroring back to your student how bright, capable and intelligent they already inherently are, you’re doing something well.



This section provides key examples of questions that I find myself asking students time and time again. Some of these questions are ways of engaging in the Socratic method (breaking things down, deconstructing the student's underlying thought processes); other questions are more constructive (e.g. progressing toward a solution, naming specific strategies).


“What is the question asking?” (“What’s the central question here?”)

This simple question is key because it counters the common mistake of skipping ahead, diving into deep waters and confusing ourselves before we even give ourselves a chance to identify the simple core of the task at hand.


“What’s the first step? … What’s the next step?”

This accords with the K.I.S.S. maxim, “Keep It Simple, Sweetheart.” I have seen so many students miss questions not because they don’t know the material, but because they skip steps and make silly mistakes.


“What’s your approach here?” (…sometimes followed by) “Is there an easier way?”

Inviting students to describe their method of problem-solving is an example of practical and powerful metacognition. A similar metacognitive act is to “zoom out” and take a moment to ponder if there is an easier approach. This one can save a lot of time and trouble, for example on a math question where there’s one very easy, straightforward way to solve it, a few ways that are difficult and time-consuming, and infinite ways of getting it wrong. (Infinite “opportunities for learning,” we might say.)


(when we are correcting a missed question) “What made you originally answer _______?”

This question encourages the student to identify and correct specific errors in their thought process, so that they’ll have a chance to avoid making the same mistake next time. “Silly mistakes” account usually for a large portion of missed questions. For addressing silly mistakes, the usual prescription is to emphasize basics such as taking good notes on questions (underlining, circling etc.), especially noting what the question is really asking at its core.

Typically, I end of focusing a large portion of our sessions to correcting missed questions and other kinds of errors. It’s up to you to balance this out with positive feedback and encouragement (see below, “What did you do well?”), and also to gauge what best serves the student today and in every moment: Does this moment call for positive encouragement, or constructive, kindhearted criticism?

Every once in a while, especially for a boost of confidence before a big test, I’ll shift the focus to reviewing easier questions, questions that the student already answered correctly. Here I’ll ask questions like, “What did you do well here, that you can carry with you going into the test?”



“What did you do well on that question?” or “I like how you ____________” (naming the specific method/process that the student did well, concretizing it in their mind so that they can apply it next time)

               This is a positive spin-off of the question below. You could ask it when a student aces a question, or you could just as well ask it when you just spent 10 minutes on a math question that they ended up missing. Of course it’s helpful to unpack and correct errors, but asking the student what went well is a good way of breathing fresh air and encouragement into the session, especially if the energy is ebbing or if the student seems discouraged.

(after completing a question/problem/task) “What’s the takeaway?” or “What’s the lesson to remember from this one?”


This must be my number one, most frequently asked question. If you feel like a broken record based on how often you ask this question, you’re probably doing okay. “What’s the takeaway?” is the perfect combination of question-asking, metacognition and allowing students to teach themselves: an open-ended prompt that allows the student to review what they just learned, distilling the practical lesson that can be carried forward and applied to similar future situations.

If you start to feel like a robot asking these useful questions time and time again, I encourage you (encourage myself) to stay sharp, stay present, and mix things up when they start to feel stale. In fact I would recommend forgetting everything you've read in this guide, in favor of orienting toward what best serves the student, right now.

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illustrations by @biskyoot

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