Teaching Children to Fail Well

a cartoon cat golfing, but swinging and missing

So much of what we do as parents, coaches, and educators is focused on helping kids succeed. Ace the test. Make the team. Pass the class. Win the game. Get into college.

In my work with students, I teach them how to get the right answers, study effectively, and be productive, all so they can be successful students.

Every summer, I co-teach a class called “Parenting for Academic Success,” showing parents how to better support their kids at home.

Success, success, success. That’s the goal.

But what if that’s the wrong place to focus?

Perhaps, what we actually need to do is teach children how to fail.

The True Challenge of Education

Vice Admiral James Stockdale was a fighter pilot who got shot down during the Vietnam War. He spent nearly eight years as a prisoner in North Vietnam. During his time as a POW, he saw many of his fellow prisoners give up and die because they were psychologically unable to handle the long, painful ordeal. But, as the ranking officer among the prisoners, he led many others through those tough years, helping them rise to the challenge and survive.1

Stockdale became famous for the leadership and Stoic resolve he displayed in that POW camp. He learned the hard way how important it is to be able to handle whatever difficulties life throws at you. So when I heard his thoughts about what parents and educators should focus on, I paid close attention:

“The challenge of education is not to prepare people for success but to prepare them for failure.”2

Preparing Children for Failure

Success is great, but you can’t count on life being an unbroken string of successes. There will be problems. You will make mistakes. You will fail.

And failing hurts. It almost always catches us off-guard. And then, because we’re unprepared, we don’t handle the failure well.

A toddler crying on the ground after falling on his knee.

We get frustrated with the world and with ourselves. We feel wronged. We feel ashamed. And we take the wrong lessons from failure:

  • Failing means I’m not smart enough, strong enough, or talented enough, and I’ll never be good enough.
  • Failing means I should just give up.
  • Failing means I’m a failure.

These thoughts are symptomatic of a fixed mindset. And they’re as unhelpful as they are wrong. Children need to learn to reject this line of thinking. And they need adults to show them how.

Responding to Failure Well

Better, growth-minded responses to failure include thoughts like these:

  • Failing means I need to use different strategies, seek out resources, and ask for help.
  • Failing means I need to keep practicing and try again.
  • Failing at something doesn’t make me a failure. Failure is an event, not an identity.

It is critical that children learn how to respond to failure in this way. Without this mindset, they will avoid challenges in order to avoid risking failure. Or, if they do risk something challenging and fail, they’ll give up and never try again. Without this mindset, they cannot learn and grow.

The Necessity of Failure

“Learn to fail or fail to learn.” –Tal Ben-Shahar3

To learn anything, you have to start as a beginner. And the fastest way to move past being a beginner is to make mistakes and learn from them. Human nature has primed us to learn from failures precisely because they’re painful.

When a child runs around without watching where their feet are going, trips, and skins their knees, their brain eagerly learns how to avoid this mistake in the future. When you’re learning to ride a bike, and you crash, your brain becomes convinced that it needs to learn how to balance.

Both of these examples show the necessity of risk. You can’t truly learn to ride a bike with the training wheels on. You have to go for it before you’re ready.

a boy taking a jump on his bicycle

Learning most any academic subject requires risks as well. You try reading aloud, even though you don’t know all the words. You attempt math problems, even when you’re unsure of the right steps. You speak up in Spanish class, even when you might mispronounce things. You go for it, fail a little, and learn.

For these reasons, it is essential that parents and educators teach children to fail well.


As usual, leading by example is one of the most powerful strategies available.

Don’t try to present a façade of perfection. Be open about your own mistakes and failures and what you’re doing to learn from them. Show your kids that a bad day can be good data. Show them how to take risks in spite of your fear of failure. And show them how to fail well through the way you live.

Don’t Rescue

Although children can learn a bit about how to handle failure well by watching others, there’s no substitute for learning through living.

So don’t rescue your kids from failures, unless they’re life-threatening. Let them try things on their own, stumble and fall, and practice dusting themselves off. And failing well is a practice. It’s best to start small, with the minor failures of a typical childhood, slowly building up the mental calluses that will prepare you to handle the larger and larger setbacks that come with age.

Of course you want to protect your children from failure, but someday – sooner than you’d like – you won’t be able to anymore. As your children turn into teenagers and adults, they will experience painful failures. And if they don’t have any practice because you’ve always rescued them, these higher-consequence failures will be devastating.

So start letting them fail now, so they can learn to fail well.


2 Stockdale, James. Thoughts of a Philosophical Fighter Pilot. Hoover Institution Press, 1995.


Why Confusing Things Are Hard to Remember

A student confused while doing homework

Imagine you’re asked to memorize the Gettysburg Address. This would be moderately challenging, but ultimately doable.

Now imagine you’re asked to memorize a speech of equal length in Russian (or some other language you don’t know). Yikes. This would be tremendously difficult, borderline impossible.

Why is the second task so much harder?

The answer has to do with the fact that the human brain is very skilled at forgetting. And no, I’m not being snarky. Forgetting is a genuinely important thing for your brain to do.

Forgetting is Good

So much of what we see and hear each day is useless. You don’t need to remember all the little sounds you heard coming through your window today. You don’t need to remember all the license plate numbers on all the cars you walked by in the grocery store parking lot. Your brain does you a huge favor by deleting everything that seems unimportant.

“More than 99 percent of experience is fleeting, here and gone. The brain holds on to only what’s relevant, useful, or interesting – or may be so in the future.” –Benedict Carey1


Sometimes your brain forgets information because you’re not using it. This is the “use it or lose it” principle of memory. The things you learn but never practice are quickly forgotten.

But most of the “forgetting” your brain does is more immediate than that. It’s a form of filtering. Your brain sorts out all the information coming in, tossing aside everything that’s obviously irrelevant. This helps us focus on what matters.

In How We Learn, Benedict Carey writes, “Forgetting, remember, is not only a passive process of decay but also an active one, of filtering. It works to block distracting information, to clear away useless clutter.”1

A lego man sweeping up a mess

And your brain is unlikely to recognize something as useful if it doesn’t make sense.

Why Confusing Things Are Hard to Remember

The first step in learning anything is called encoding: the process through which information is taken in and understood.2 Notice the key word there: understood. If the information that’s coming in doesn’t make sense, there’s little hope of storing it in your brain.

If you’re at a café, and you overhear someone’s conversation, it might grab your attention. If it was an interesting conversation, you might remember some of it later. But if the conversation were in Russian (or some other language you don’t know) you won’t remember what was said because you never understood it in the first place. It will also be less likely to grab your attention. It will seem more like background noise.

That’s what makes memorizing a speech in a foreign language so difficult. Our brains hear confusing information the same way they hear utter nonsense. Since we don’t understand it, our brains treat it like background noise or the babbling of a baby – something we’re aware of but don’t need to retain.

Now, the point of this isn’t to explain why it’s hard to memorize a speech in Russian. That’s not the kind of learning task students get asked to do. The point is to explain why it’s so much harder to remember school material that’s confusing.

Disconnected Information

We’re most easily confused by information that’s disconnected from things we already know. If I start telling you about the competing factions within the Jacobins during the Reign of Terror, you’ll be completely lost unless you already know a lot about the French Revolution. Lack of context makes things confusing.

A confused student feeling frustrated while studying

Teachers, of course, try to avoid presenting information in this way. They logically connect one idea to the next as they build up a concept or tell a story. They work through the curriculum in a natural progression:

  • Simplifying expressions is followed by solving equations, which is followed by solving inequalities.
  • A study of eukaryotic cell parts is followed by the function of DNA, which is followed by protein synthesis.
  • Industrialization is followed by imperialism, which is followed by World War One.

Unsurprisingly, students get confused when they fall behind. If you fail to learn a foundational concept, the concepts that build on it won’t make sense. If you haven’t kept up with the curriculum, you’ll lack the necessary context. And if you’re confused, you’ll have a hard time remembering what’s being taught.

Getting Caught Up

The ideal thing, of course, is to never fall behind. But the ideal thing rarely happens, so students should expect to need catchup work. This can range from patching holes in your math knowledge to reviewing old Spanish vocabulary to watching Crash Course videos to get caught up in science or history.

Whatever knowledge you’re missing, go learn it. The sooner you get caught up, the better. You don’t want things to get so confusing and hard to learn that you slip into a downward spiral of avoidance.

Too Many Details

Another reason information is sometimes confusing is that there are too many details. Topics like the French Revolution and cellular respiration are so riddled with minute details that it’s incredibly easy to get overwhelmed. And as soon as the material stops making sense, it stops being memorable, which is bad news if you’re taking a test on it.

A teacher at a very busy chalkboard that has too many details

This is why you should start with the summary when reading history and biology. Building familiarity with the content before trying to absorb the details helps you retain those details. Get the overview down first, and the rest will be less confusing and therefore more memorable.

Analogies Help

Confusing things are often best understood through analogies:

  • DNA transcription is like making a photocopy of a recipe (a gene), which you then take to the kitchen (a ribosome) to cook the recipe (a protein).
  • Noble gases are like snooty royalty: they’ve got everything they need (a full set of valence electrons) and don’t want to interact with anyone else (they’re inert).
  • Good studying is like learning to ride a bike. (It involves failure and repetition, and thereby forms a lasting memory.)

Analogies take unfamiliar things and connect them to things we already understand. This not only helps us make sense of them but also makes them more memorable.

The Solution is Mechanical

As with nearly all difficult problems, the challenge of remembering confusing academic content calls on us to remember the wisdom of Steven Pressfield:

“The problem is not you.

The problem is the problem.

It’s hard because it’s hard.

The solution is mechanical.

Work the problem.”3

You’re not struggling to retain what your teachers are presenting because you’re not smart enough. There’s nothing wrong with you. The content is just genuinely difficult to understand, and you need to employ strategies to make it easier to comprehend. When you do that, you’ll find that you’re perfectly capable of remembering what you’re studying.

1 Carey, Benedict. How We Learn: The Surprising Truth About When, Where, and Why it Happens. Random House, 2014.

2 “How Memory Works.” The Derek Bok Center for Teaching and Learning. Harvard University.

3 Pressfield, Steven. Do The Work!: Overcome Resistance and get out of your own way. Do You Zoom, Inc. 2011.

Navigating Financial Aid Offers From Colleges

I’m pleased to introduce a special guest author, Sharron Starling. Sharron is a college admissions professional for Cornish College of the Arts, so she has inside knowledge about the process of applying for college and what happens after you get accepted.

In this quick article, Sharron is going to give you a crash course on navigating the financial aid offers you get from colleges: comparing costs, figuring out what you’ll be expected to pay, negotiating better offers, and coming up with payment plans.

And if you’re looking for more information or personalized support, send us an email to schedule a session with Sharron.


Greg Smith

A highway road sign with several options, all of which point to learning.

Congratulations! Your student now has several offers of admission to college!

What’s next?

Besides visiting and comparing wants/needs between programs, the other main concern is financial: How much will it cost, and what is reasonable for your family?

So, how do you compare college costs and navigate financial aid offers?

Step 1: Compare the offers side-by-side.

Build a spreadsheet, so you can see everything in one place. I suggest putting college names across the top, starting in column #2, and the following in column #1, starting in row #2:

  • Tuition + Fees
  • Room + Board
  • Total Cost Without Aid
  • Merit-Based Aid Offered
  • Need-Based Aid Offered
  • Total Aid Offered
  • Adjusted Total Cost (Cost Without Aid – Aid Offered)

Step 2: Know your numbers.

If you have completed the Free Application for Federal Student Aid (FAFSA), you have an Expected Family Contribution (EFC).

This factors heavily into where schools start with their aid offers and how much they can/will offer.

In addition, figure out what is financially feasible for your family.

Step 3: Negotiate.

With your own numbers and that spreadsheet in hand, you’re in a good position to ask for a better offer.

And yes, it is possible to negotiate the offer, especially if you are comparing private institutions with other private institutions.

Whom should you contact? The Director of Admission or the assigned Admission Counselor is a great place to start.

Step 4: Decide how to pay the balance.

Most colleges will offer some type of payment plan over 9 -10 months, possibly even 12 months.

There are also loans that parents can borrow on behalf of their students. The Parent PLUS loan can be a great way to invest in college if the cash flow for a payment plan is tight.

Outside scholarship searching is always an option. Schools aren’t the only ones offering money to help pay for college. While fairly time intensive, it can be an ongoing project for a student throughout their college years. Funds earned from outside scholarships can be added to each semester, as they are secured.

Also, in divorce situations, each parent can participate with a loan or payment plan of their own.

Want personalized guidance?

Sharron Starling has recently joined the NWES crew, and she is here to help!

Want to explore this in more depth?

Want help preparing to negotiate?

Want to discuss complicated situations, such as combining payment plans, PLUS loans, and part-time work?

Send us an email to set up a session with Sharron:

About the Author

Sharron Starling oversees and directs all aspects of the admission process for Cornish College of the Arts. A dedicated admission professional with over thirty years of experience, Starling is a frequent presenter in the PNW, has served the region on the PNACAC Executive Board, and is a current elected member of the National Portfolio Day Association Board. She has served as an ex-officio member of the Board for the Washington Association of Art Educators and is the City Representative for the NACAC Seattle Performing and Visual Arts College Fair.

In her role at Cornish, she also serves as the site host for the annual Seattle National Portfolio Day. Presentations at national conferences include HECA, IECA, and NACAC.

She is the parent of two classically trained ballet dancers who have taken that early training into the professions of Lighting Design and Stage Management. A long-time supporter of Billings Middle School and Spruce Street School, she currently serves on the Board of Trustees for Spruce Street School.