In a video I posted last week, I committed what sometimes feels like the cardinal sin of social media — I dared to mispronounce a word.

Horrifying, right? Or rather, I assume that’s what the Internet thinks about mispronouncing words because, as usual, doing so immediately produced an enormous flurry of comments:

How does a Duke professor not know how to say that?

You teach at Duke and you can’t pronounce a basic word?

Isn’t this guy supposed to be smart?

And pronunciation issues aren’t the only screwups that generate this kind of shock. The same genre of comment shows up every time I make any minor mistake. My audio might be hard to hear, I’ll have a typo in a caption, or an image will be a little too shaky, and I’ll get similar criticisms. Apparently, in addition to being an expert rhetorician who pronounces everything flawlessly, I’m also supposed to be a professional-level audio engineer, copy editor, and videographer.

To be clear, I don’t mind people noticing and pointing out when I screw up. After all, anyone who posts on the Internet as much as I do has to have thick skin. Plus, criticism is a great way to improve.

Instead, the reason these comments always catch my attention is because of the strange, backwards assumption they carry with them. They all seem to agree that “professor” means “smart,” and that smartness must be some universal state of being where you’re an expert at everything. But that’s not what knowledge actually looks like. In fact, real knowledge requires accepting enormous amounts of failure.

Subscribe now

The Misconception Around Expertise

I understand why so many commenters are appalled to see a professor making mistakes. School trains us to believe the “smartest” people in the world get straight-A’s. Therefore, “smart people” are the ones who know all the right answers on their tests across all the various disciplines — math, chemistry, language arts, history, and so on. But what nobody ever tells us when we’re in school is that this kind of school-coded smartness — the straight-A, good-at-every-subject kind — is the reversee of what expertise actually looks like. While school rewards being broadly, evenly capable across every discipline at once, the deepest and most valuable kinds of knowledge are built by doing the exact opposite.

In my case, my “expertise” (whatever it amounts to) exists almost entirely because I’ve spent an absurd number of hours directing my attention toward a very specific, very narrow slice of the world. However, all that focus hasn’t been free. Every hour I’ve spent going deep on my subject was an hour I didn’t spend on chemistry, or car repair, or personal finance, or geography, or how to pronounce whatever word I just butchered in front of the internet. This means my expertise didn’t magically accumulate on top of everything else I could have learned. It came instead of it.

The result, as I often like to remind my students, is that their professors are experts in whatever we research and teach, and we’re functionally idiots on every other subject.

The quip is usually good for a laugh, but it’s also true. By pouring so much time, energy, and attention almost exclusively into one deep, narrow column, any “expert” you ever meet is someone with a large amount of very specific knowledge alongside a much larger amount of ignorance, blindspots, and, in some cases, mispronunciations.

The Cost of Getting Good at Something

The reason I’m sharing my intellectual shortcomings with you is because, if you want to get good at something — anything — you’re going to have to make a similar sacrifice. And it’s a tricky sacrifice to make because it goes against everything we learn about “smartness” in school.

Most of us walk around believing we should want to know as much as possible about everything. As a result, we arrange our areas of incompetence into a nice to-do list of deficiencies we’ll eventually get around to fixing. And by doing that, we imagine some future version of ourselves as a “successful person” who is broadly and evenly capable of not screwing up no matter what the task. But that person doesn’t exist.

Instead, getting good at anything has a price. It’s the price of knowing how to do other things.

And getting truly good at one thing… that’s the most expensive kind of knowledge there is. It means you’ll have to sacrifice being good at almost everything else.

Yes… that’s the trade. You simply can’t be exceptional at something and have no areas of glaring incompetence. The incompetence isn’t a bug you failed to patch. Incompetence is proof of your focus and dedication.

What Did You Trade For?

Learning to appreciate the ways in which knowledge and incompetence are two sides of the same process is a liberating opportunity, so let’s take it.

Make a quick list of the things you feel like an idiot about. Include the stuff you assume a capable adult should have figured out by now even if you somehow never did. Be specific, and be honest… nobody is seeing this list but you.

Are you bad with money? Maybe you can’t cook? Hopeless with directions? Whatever your shortcomings, write them down.

Now, parallel to the list you just created, I want you to write down things you consider yourself to be good at. These are most likely things you’ve spent years doing, whether anyone pays you for them or not.

Next, once you have your parallel lists, I want you to look closely at the two of them side by side while asking this question: How much of the first list is simply the cost I had to pay in order to develop the second list?

To be fair, for some of your shortcomings, the answer will be “none.” It’s OK to be genuinely bad at things, or to have just been uninterested in learning them. However, if you were honest and thoughtful during this exercise, I suspect you’ll notice how many of the things you’re ashamed of not knowing or not being good at are balanced out with the things you’re proud of knowing and are highly skilled at.

That’s the knowledge-incompetence tradeoff in-action. If you grew up being on the competitive cheer team or the lacrosse team or took all AP classes, it means you didn’t have time to get good at sewing or gardening or cooking. In other words, the hours to get good at something had to come from somewhere. And the things you’re not good at… that’s where the hours came from.

By the way, you don’t have to do anything with this information. For example, you’re not obligated to suddenly feel great about being bad at dealing with car issues. But the next time one of your shortcomings makes you feel like a failure, take a moment to remember why that shortcoming exists. You’re not experiencing a failure. You’re experiencing the natural result of operating inside the same 24 hour day as everyone else and having to make decisions about where/how to spend your time.

This week was orientation for Duke’s incoming students. As a result, campus has been full of freshmen doing… well… the things freshmen do, including lots of welcome events and programs.

I’ve been to a handful of the activities, which is always a fun opportunity to hear what the newest crop of students are complaining about. Lots of stuff changes from year to year, but some topics are consistent. And one of the most consistent complaints I encounter is freshmen wondering why they have to take so many required classes.

Why do I have to take a writing class when I’m here for engineering?

What does an art course have to do with being pre-med?

I’m a musician… when am I ever going to need to know math?

By the way, this isn’t a Duke-specific gripe. Most schools have some base level of curricular requirements, and liberal arts colleges are basically built around making students take classes they wouldn’t have picked.

Why? Because, as I reminded every student I heard complaining about curriculum requirements, those classes might be the most important ones they ever take.

Yes, I realize how patronizing it sounds, and yes, I remember being 18, hearing adults say things like that, and finding them insufferable. But I repeat the message anyway since it happens to be the story of my life.

The Class I Didn’t Choose

The 18-year-old version of me went to college expecting to come out as a doctor. I was pre-med, taking freshman organic chemistry, and already looking for an internship in the hospital. However, thanks to a curriculum requirement I definitely resented at the time, I got stuck in an English class I didn’t care about.

A decade later, I left college with a PhD in English, which I guess means the class wasn’t as bad as I’d originally thought. It also technically means I did come out as a doctor, but not the kind my mom could brag about to her friends at dinner parties. (Sorry, Mom!)

Over the years, I’ve told that story to lots of freshmen. I usually frame it as a cheerful little lesson about keeping an open mind. But, when I told it this year, I found myself thinking about it from a slightly different angle. I’m starting to wonder if the important part of the story isn’t about the value of keeping an open mind. After all, I didn’t have an open mind when I got forced into that English class. In fact, I remember being annoyed for at least half the semester.

Instead, the important part of the story is that I never would have chosen the English class on my own. The only reason I wound up taking the class was because the choice got taken away from me. As a result, my entire career — everything I do, the way I think, and the person I became — exists because a system I resented overrode my preferences and forced me to do something I’d have certainly avoided if I’d had any choice.

While that outcome leads to all sorts of cliches about the value of leaving your comfort zone and being willing to try new things, I wonder if the more important lesson is a lesson about the value of having forcing mechanisms in our lives.

When the Scaffolding Comes Down

For all the grumbling that goes on around college campuses from students being “forced” to take required classes, that forcing mechanism is enormously important. The required classes (and distribution requirements and prerequisites and core curriculums) are all designed to override an eighteen-year-old’s instinct to only do what already appeals to them. And, as a whole, the system works beautifully. It helps huge numbers of people find their callings, their fields, and their life’s directions among things they’d almost certainly not have otherwise discovered.

In fact, I’d go so far as to guess that lots of you reading this are, in ways you perhaps don’t even recognize, the byproduct of an educational system that made decisions for you. But once we finished school, most of our “forced discovery” scaffolding vanished.

Is that a problem we should be more worried about?

From what I can tell, adult life has almost no equivalent to “required classes.” Nobody makes you take a course in something random at thirty-four, and nobody hands you a schedule with some unfamiliar thing wedged into the middle of it that you have to attend for four months.

Instead, adulthood is basically the exact opposite. When you’re an adult, you finally get to arrange your life entirely around what you already know you like. You pick the job in the field you already chose, you pursue the hobbies you’re already good at, you hang out with the people who already share your interests, and you eat at the restaurants you already know you enjoy.

In other words, the vast majority of choices adults make point them toward doing familiar and comfortable things. But doesn’t school teach us the importance of not allowing that? And what does it mean that adulthood is, in a sense, the systematic elimination of exactly the mechanism that leads to so much chance discovery?

I honestly don’t know.

As I sit here trying to write the part of this essay where I’d usually share some critical lesson or definitive proclamation, I’m realizing I don’t have one. Instead, I find myself questioning a lot of the choices in my life and wondering what other things I might have discovered a passion for if only someone had made me try them

Something to Sit With…

Instead of an exercise this week, I feel like the best thing I can do is offer a few questions worth wondering about. None of these have right answers. Just ask them and see where the answers take you…

• How many of my favorite preferences and experiences in life are a result of things that were forced on me?

• When was the last time something forced me into an experience I wouldn’t have chosen on my own? How long ago was that?

• How much of my current life is arranged around things I already know and am familiar with?

• Do I have any forcing mechanisms in my life that are causing me to try things I otherwise wouldn’t have done?

• What might be the impacts — good and bad — of living a life where I choose almost everything?

Notice how none of these questions require you to take any sort of action. That’s actually part of the point. I’m not sure if any of this is worth “fixing,” but it seems like something worth thinking about.

This week, I have to confess to doing something I’ve never done before. It’s a little embarrassing to admit this so publicly to so many people… but… well… we’re all friends here, right?

Here it goes… and please don’t judge me…

I made a recipe I saw on TikTok.

I know. I know. I’m a grown man with a job, two children, and a professional skepticism about everything I see on the internet. But somehow I got convinced to make a dessert by a shirtless stranger with the abs of a Renaissance sculpture.

The recipe was for something called two-ingredient watermelon sorbet… basically just a watermelon and some lime juice. It looked delicious and seemed healthy, so the next time I was at the store, I grabbed a watermelon and a handful of limes.

The Video’s Promise

In the video, the glistening adonis sliced the watermelon open in roughly two seconds. Then he scooped out the flesh, laid the chunks in a tidy single layer across a wire baking rack, and slid them into the freezer.

A second later he pulled out a shelf of perfect little ruby ice cubes, tipped them into his food processor — the same food processor I own, which felt like fate — and pressed the button. Within seconds, the machine whirred its way toward a lush, uniform, softly whipped pink cream. He squeezed in some lime juice, gave it one more satisfying pulse, then scooped the contents into a hollowed-out watermelon rind. The result looked like the kind of soft-serve spiral you’d expect from someone who’d been working at Dairy Queen for twenty years.

Naturally, at the end of the video, he scooped a spoonful into his mouth, closed his eyes, and told me: Mmmmmmm… delicious.

My Flawed Recreation

After sitting on my counter for so long I began to worry it had gone bad. I finally cut into the watermelon a couple nights ago, mostly out of guilt over the eight dollars I’d spent.

My first hint the process wasn’t going to go very well began as soon as I started scooping the insides. Before I’d even scraped out half the flesh, watermelon juice was dribbling off the edge of the counter and onto the floor.

Even freezing the watermelon wasn’t easy. In the video, the guy had spread his watermelon out in an aesthetically pleasing single layer on a wire rack, but I challenge you to find a suburban house with two young kids that has room for a flat rack of watermelon in its freezer. Instead, I crammed the chunks into a Ziplock bag, wedged it into a corner between a package of peas and a box of chicken nuggets, and spent the next 15 minutes scrubbing my counters and mopping my floors.

A couple nights later, excited for sorbet, I removed my watermelon from the freezer only to discover it had frozen into a single solid brick. As a result, in order to fit pieces into the food processor, I had to physically chisel them apart. Then I pressed the button and got… essentially nothing. The blades chopped the bottom layer, but everything above stayed frozen.

Basically, the next 15 minutes turned into a repeated cycle of stabbing the frozen chunks of watermelon with a spatula to break them apart, shoving them down, pulsing, and repeating. But slowly, and after again flooding my counter and floor with watermelon juice, it finally began emulsifying into the pinkish-red cream I’d seen. Sure, by the time I was done, there were still some solid red chunks. But it was close enough.

I squeezed in a little lime juice, gave it a final mix, and tasted it.

It was actually delicious. Certainly not the best dessert I’ve ever had, but it tasted like a decent watermelon sorbet and, with only two ingredients, I presume it was genuinely healthy. I certainly ate a lot of it, so I hope it was healthy. Regardless, technically, the recipe worked, which means the effort was a success, right?

So why am I sitting here telling you about all this while feeling like a huge failure?

The Parts That Get Edited Out

The entire time I was hacking at that watermelon brick or mopping my floor, I kept thinking about the guy in the video, and how effortless he’d made it look. Why did I think any of it was real?

I literally make social media videos for a living. I know, with absolutel professional certainty, exactly how that watermelon video got made. I know his watermelon was just as hard to cut, his food processor was just as ineffective as mine, and he made the same mess. He probably even swore the same swear words.

I also know his flawless final swirl took a dozen attempts to get right, and that holding up a half-watermelon full of sorbet for the camera is a heavy, awkward, arm-trembling challenge. And yet, none of that knowledge is protecting me at all. I completely understand the illusion, but I still feel like a failure for not being able to match it. So what’s going on here?

The issue is the editing. He hid the mess — the twenty minutes of stabbing an ice brick with a spatula — and focused only on the success. And even though, intellectually, I know that’s what happened, by not seeing it, the part of me that’s insecure and self-conscious still has room to believe he didn’t actually have to deal with the hard stuff.

And I bring this up because I’m pretty sure the same thing happens with a lot more than TikTok recipes. We see colleagues who make their jobs look easy, or parents who seem to be raising quiet, respectful angels instead of teenagers, or the classmate who never appears to study but aces every test.

We all know none of that’s real. But because their struggles are edited away from our view, we’re left with just enough doubt in our minds to imagine we’re doing something wrong.

Unfortunately, I’m not sure there’s actually a solution for any of this. Heck, I’m literally a “scholar of social media”... I professionally study the stuff, and I still feel like a failure while watching other people edit away their struggles.

So maybe the goal isn’t to stop feeling like a failure when you compare yourself to other people. At the very least, if I can’t manage to do it, I’m not going to pretend you should. Instead, maybe the goal is to simply keep reminding ourselves that everything we see is edited. And even though it’s going to make us feel like insecure, self-conscious failures, that feeling is measuring the mess rather than the result.

After all, my sorbet may have been a time-consuming mess to make. But it was still delicious. Which means the sorbet wasn’t the failure. The failure was believing I could do it without soaking my counter in watermelon juice.

Seeing the Edits

Since this issue is about the struggles that get edited out of what we see from other people’s lives, here’s a helpful skill to get better at recognizing those edits.

Instead of taking the polished versions we always see at face value, I want you to spend some time deliberately reconstructing the messes that had to exist for various things happening around you.

For example, the next time someone shows off a new outfit, you might spend a few moments imagining all the driving, and going in and out of stores, and trying stuff on that was required for it. Maybe even with a bored tween walking behind you constantly saying, “Can we go home yet?” (Yes, that’s coming from a voice of experience…)

Here are some questions you might ask:

• What would this have actually required someone to do, make, or obtain in order to accomplish it? Walk through the real steps, including the boring, hard, and unglamorous ones.

• Where are the cuts? What part of the process would be the most tedious or embarrassing, and therefore the first thing anyone would edit out of a story about it?

• How many attempts am I not seeing? The single, shareable result you’re seeing usually sits on top of a pile of failed ones you’ll never watch.

• If I had told my own version of this story, what would I have edited out, and would my final version seem just as effortless as theirs?

• Am I comparing my whole process to their whole process, or to the two seconds of it they chose to show me?

Getting good at this type of analysis is going to help you switch from seeing effortless people everywhere to seeing edited people. And while that won’t stop you from comparing yourself (and feeling bad), it’ll at least help you learn to separate processes and outcomes.

If you’re reading these words, it means I finally did it… I finally managed to move this newsletter over to Substack. Hooray! Success!

Except the success I’m celebrating is the direct result of a long series of failures. Funny how that works, huh?

The truth is I started planning this move roughly six months ago. And it was probably always going to be a six month project, but the original deadline I’d set for myself was the end of Duke’s spring break, which was mid-March.

In other words, in my mind this triumphant announcement is showing up roughly five months later than I’d planned.

And those five months weren’t 150 days of me just “not getting to it.” They were a series of starts and stops, second thoughts, and struggles with deliverability. Then there was the actual transfer, which I’d estimated would take an afternoon. After all, how long could it take to copy and paste a few articles from one platform to another?

Spoiler alert: It took a lot longer than an afternoon.

The 20% That Ate Everything

The first thing I’d forgotten is that I’ve been writing this newsletter for over a year, meaning “a few articles” was actually closer to sixty. The second thing I’d forgotten is that the phrase “copy and paste” sounds effortless until you’re actually doing it and remembering how every text editor ever built handles formatting slightly differently. Each weird indentation and random extra spacing took an extra 10-15 seconds to fix, which probably doesn’t sound terrible until you realize there were, conservatively, a thousand of them.

And to be clear, I’m not telling you all this because I want you to marvel at all the time and effort I put into making this email possible. Instead, I’m admitting to a wonderfully human form of miscalculation that takes the shape of Pareto’s Principle.

For those unfamiliar, Pareto’s Principle is often referred to as “the 80-20 rule.” It’s the observation that 80% of the value comes from 20% of the work. However, when it appears in these types of “underestimating the work” failures, it manifests itself as roughly 80% of your time getting consumed by roughly 20% of the work.

In my case, when I imagined the project of moving my newsletter to a new platform, I imagined the big, obvious tasks like copy/pasting articles. But I completely failed to account for the enormous, invisible longtail of tiny edge cases that never show up in our mental estimates but end up devouring the majority of our time.

Simply put, us humans are fantastic at predicting the big stuff, but we’re comically and catastrophically bad at recognizing all the little details. And the result is most of us are terrible at setting proper expectations.

When “Failure” Is Just a Bad Estimate

Obviously none of you care about the step-by-step logistics of transferring newsletter platforms. Instead, the reason I’m walking you through my technical misadventures is to share how often, in the middle of my five-month ordeal of missing deadlines and screwing up things that should have been simple, I caught myself feeling like I was failing.

It’s a kind of failure I’m certain all of you reading this can relate to. It’s a failure to meet expectations we set for ourselves, which is a particularly miserable kind of failure because most of us are our own worst critics.

Luckily, it’s also a very solvable kind of failure because failing to meet our own expectations is almost entirely self-manufactured. After all, expectations happen to be some of the very few parts of life we can actually control. Sure, you can’t control how long something really takes, or how many hidden edge cases will appear, but you have enormous control over the expectations you set for yourself, which means you have enormous control of how much failure you’re preparing yourself to experience.

Most people never even try to set those expectations carefully. They just grab an optimistic number based on whatever limited knowledge they have, commit to it, and then spend the entire project feeling badly about their shortcomings.

However, while getting better at the up-front guesses isn’t necessarily easy, and it won’t make your plans more accurate, it is possible. And getting better at setting proper expectations at the beginning of something will eliminate entire categories of failure, in reality, were never actually failures in the first place until you created them for yourself.

Expectation (Re)Setting

Since this issue is about the difference between an actual failure and a poorly set expectation, let’s use it as an opportunity to practice getting better at setting those expectations.

To be clear, I’m not asking you to get more accurate or more pessimistic. Instead, the next time you’re about to start a decent-sized project, I just want you to pause for a few moments at the beginning and deliberately recalibrate your expectations before you begin.

Here are a few questions that can help:

• What’s a pessimistic estimate for how long this will take or how hard it will be, and how does that compare to what I’ve imagined?

• Where’s the hidden 20% in this project? What are the small, boring, forgettable edge cases that are easy-to-overlook but, when combined, will take significant time to manage?

• Is my estimate based on the visible task, or the whole task, including the tiny issues and challenges that are easy to overlook?

• If this ends up taking twice as long as I think, what would have to go wrong, and how likely is that to happen?

• What does “going exactly as it should” for this project realistically look like, and am I measuring against reality or my initial fantasy?

Admittedly, these are going to be hard questions to ask yourself. When we set our minds toward something, we usually want to get to work as quickly as possible, and pausing to recalibrate expectations will feel like a big (and pointless) stall. But if you can convince yourself to do it, you’ll stop feeling like a failure when things go exactly the way they were supposed to.

A NOTE FROM DR. DININ: As promised in my email last week, welcome to the new newsletter. Swanky, huh? More importantly, it’s going to help me deliver more of what you’ve been asking for, starting with a full archive of the entire first year+ worth of posts. Read the current issue below, then grab yourself a cup of coffee, curl up in your favorite chair, and enjoy finally being able to catch up on what you’ve missed.

Also, if you think Learning to Fail would be valuable to someone you know, please help spread the word by sending this to a friend. Or even an enemy. I’m honestly not that picky.

Share

Earlier this week I flew to Mississippi to speak with a group of high school teachers. (Shout out to my new friends at Puckett High School… go Wolves!) As always with these trips, I found myself driving a rental car. But don’t worry… I didn’t run into any deer this time. I did, however, spring for the insurance.

While I don’t particularly enjoy driving strange vehicles in strange cities, one small benefit is that I drive a sixteen-year-old car at home, so a rental is my periodic opportunity to tinker with whatever new features have become standard.

While some new features make me feel like a caveman encountering fire for the first time (hello, blind spot detection!), on this trip, nothing really jumped out at me. However, I did notice an interesting bit of unexpected functionality while sitting at a red light. Apparently I waited a beat too long after the car ahead of me started moving, which triggered a soft chime. I glanced down at the dashboard, where a little message appeared:

“Leading vehicle is driving on.”

I paused for a moment, trying to understand what I was looking at, but then it clicked. It was a feature built for a very modern kind of failure where drivers are regularly sitting at traffic lights, staring at their phones, and oblivious to the lights turning green. In other words, it’s a feature built for all of us, because we’ve all, at some point, been that person.

After experiencing the feature, I found myself debating its merits. On one hand, it’s a smart feature because it’s surely preventing lots of crazy road rage incidents. On the other hand, it’s a problematic feature that seems to encourage using phones while driving. In both cases, the chime reveals something wonderfully deep about how humans actually deal with our failures.

The Thing We’re Bad At

If we’re being honest with ourselves, we all have to admit that humans are strangely OK with sabotaging our futures in exchange for things we want right now. By that I mean we tend to reach for the immediacy of comfort and satisfaction while ignoring long-term consequences that’ll almost certainly become a problem for some future version of ourselves who, frankly, we don’t seem to like very much.

A perfect miniature of this phenomenon is using our phones at traffic lights. Every single person who has ever glanced at their phone at a red light knew, in the abstract, it was a bad idea. After all, most of us know someone whose life has been touched in some horrible way from an accident caused by distracted driving. And yet we do it anyway because, in the moment, the pull of I’ll just check this one thing real quick reliably overwhelms the distant, statistical knowledge that doing it enough times is how the odds eventually catch up with us.

The obvious solution to the problem is, of course, to simply put the phone down and not look at it while operating two tons of machinery. It’s not a complicated solution, and it would work perfectly.

But we don’t do that. Instead, we keep looking at our phones while telling ourselves, “This one time is fine.”

More importantly, our preference for instant gratification at the expense of future consequences goes well beyond phones and traffic lights. It impacts nearly every failure we try to correct in our lives… how we eat, how we spend, how we manage our time, how we treat the people closest to us, and so much more. We know we don’t want to be unhealthy or broke or distracted, but we’re rarely willing to make the necessary sacrifices. Which means “just stop doing the bad thing” — usually the most obvious and most effective solution — is the solution we’re the worst at actually executing.

The Thing We’re Good At

Even though humans are bad at stopping self-destructive behavior for the sake of immediate gratification, the gentle chiming I experienced in my rental car points to something we’re genuinely good at. Since we can’t convince people to stop looking at their phones in cars, some engineers somewhere accepted that failure as a fixed feature of human nature and asked a different question. They must have wondered: “Given that people are going to keep looking at their phones while driving, how do we build something that helps make it less bad?” Their answer was a little sensor and a soft chime. Sure, it doesn’t fix the underlying problem since people are still looking at their phones while behind the wheel. But it adapts to the problem, and in doing so, it makes the problem meaningfully less bad.

This, it turns out, is the thing humans are actually excellent at. Even though we’re terrible at stopping our failures, we’re fantastic at inventing clever infrastructure that lets us fail more safely. We couldn’t make people stop looking at their phones, so we made a chime. We couldn’t make ourselves less distracted in general, so we built screen-time reports and grayscale settings and apps whose entire job is to lock us out of other apps. We’re not good at losing weight, so we invented drugs to curb our appetites. And so on. Every one of those “innovations” is simultaneously an admission of defeat and a small victory.

To be clear, I’m not arguing any of this is good (or bad). I’m just pointing it out. And the reason I’m pointing it out is because so many of us interpret our failures like they’re these grand character flaws we’ll need to correct if we want any sort of success in the world. But, in general, fixing our failures isn’t something humans are particularly good at. Instead, focus on getting better at the skill humans already have a knack for, which is adapting.

In other words, the next time you run into one of your own stubborn failures — and you certainly will — resist the urge to fix it. Heck… you’ve probably already tried (and probably more than once). So try asking the same question the engineers behind the chime in my rental car asked: assuming I’m going to keep doing this, what would help? The solution you come up with won’t be perfect, but it’ll almost certainly be a lot better for you… and maybe even some of the people around you.

Building Your Own Chime

Since this whole issue is about adapting to failures instead of fixing them, here’s a short exercise. Pick one stubborn failure in your life. It’s probably one you’ve tried to fix before, promised yourself you’d stop, or otherwise attempted to rectify multiple times. But instead of gearing up to fight it again, I want you to try asking the same kinds of questions the engineers who built my rental car asked:

• Have I actually tried to fix this before? How many times, and how’d that go?

• Am I resisting the goal, or am I just resisting the sacrifice that “fixing it” would require?

• If I assume I’m going to keep doing this, what would make it less costly to me and/or the people around me?

• Instead of trying to be someone who never slips, what’s a small system, constraint, or piece of infrastructure I could create that catches me when I slip and makes that mistake less problematic?

• Who else is affected when I fail at this, and would implementing this adaptation protect them, even if it can’t cure me?

Also, just to clarify, this exercise isn’t about giving up on improving yourself. We’re just trying to be honest about what can actually help. After all, consistent partial improvement is better than a permanent cycle of trial and failure.

Last week my family and I were in Iceland. By chance, the trip overlapped with my birthday, which was a coincidence rather than a plan, but it meant I had some unusual choices for how to spend it. I ultimately settled on whale watching, mostly because, like eating beignets in New Orleans, whale watching in Iceland seems to be one of those things you’re contractually obligated to do.

Unfortunately, we didn’t see any whales.

However, we did get to see the North Atlantic in a decently foul mood. For two hours, we stood on the deck of a small boat as the wind worked its way through every layer we’d optimistically described as “warm enough.” My youngest lost feeling in her face somewhere around the forty-minute mark. I didn’t last much longer. And I’m still not sure I can feel all my fingers. By the time we finally shuffled back onto the dock, we looked less like a family on vacation and more like four windswept popsicles.

As we walked away from the boat, my oldest daughter said, “Well, that was a complete waste. Sorry we ruined your birthday.”

An Early Verdict

When I was her age, I would have said exactly the same sentence. Honestly, ten years ago I probably still would have. We went to see whales, and we didn’t see whales. As a result, the outing failed and the day was… not entirely ruined, but certainly diminished.

However, thanks to a decade of thinking and teaching about failure, I’m finally learning how to slow down my temptation to rush judgment, particularly when that judgment is negative. So instead of immediately agreeing with my daughter, like I might have not too long ago, I asked her why she thought we’d ruined my birthday.

“Because we didn’t see any whales,” she rightfully replied.

“Okay,” I said. “But think about what would happen if we had seen whales. We’d have been excited for about ten minutes. We’d have taken some blurry photos of a fin. And then, honestly? In two years none of us would remember it. It would just be one more nice thing that happened on a trip.”

She didn’t look convinced, which is fair, because she was still cold. So I kept going. “But this? This is something we’re going to talk about forever. Every single birthday from now on, somebody’s going to bring up whale watching. When you’re older and you bring someone you’re dating home for Thanksgiving, this is a story we’ll tell them. When you have kids of your own, they’re going to hear about that one birthday of Grandpa’s where the family nearly froze to death looking at an empty ocean. So is that a waste? Or did we just make something incredibly special?”

My daughter thought about it for a second and then chirped back, “That’s kind of annoying.” Which I’m choosing to interpret as agreement.

What We Were Actually Watching For

The excursion was sold to us as whale watching. But what we actually spent two hours doing was something closer to fail watching — standing on a deck together, scanning an empty sea, slowly and collectively realizing that the thing we came for wasn’t going to happen. But, oddly enough, that shared experience of not seeing whales is going to be much more valuable than seeing them could have ever been.

Successes have a way of getting consumed. You get the thing, you enjoy it, you file it away, and then it quickly dissolves into the general pleasantness of a life that went basically fine.

In contrast, failures get retold. They become stories, and stories are a form experiences take when they want to survive. Nobody at Thanksgiving has ever said, “Remember that vacation where everything went according to plan?” The stories that get passed around a table for thirty years are almost always about the flight that got cancelled, the wedding where something went horribly wrong, or the trip where absolutely nothing worked. The failures are what we’re still holding onto, long after the successes have evaporated.

Which means my daughter wasn’t wrong about the facts. She was wrong about the timing. She rendered her verdict — “complete waste” — at the precise moment she had the least possible information about what that experience would eventually be worth. She was grading the day using the only measure available on the dock, which was the one we’d brought with us: did we see whales? But, in the years to come, that’s not going to be the measure that matters.

To be fair, I should be careful here, because there’s a lazy version of this idea that I don’t believe at all. I’m not suggesting every failure secretly becomes a gift, or that things always work out, or that a bad day is really a good day wearing a disguise. Plenty of failures are just losses, and they stay losses, and no amount of retelling redeems them. So that’s not my argument.

The point I’m trying to make is smaller and, I think, more useful: you almost never know what an experience is worth at the moment you’re having it.

We assign value instantly and confidently, using whatever criterion we happened to walk in with, and then we treat that snap judgment as settled fact. But experiences keep accruing meaning long after they end. As a result, some of the best things in your life will turn out to be things you were furious about at the time. To be clear, it won’t be all of them… but enough that assigning an instant verdict to anything (and especially the bad stuff) is usually premature.

Go Fail Watching

Here’s an exercise I’ve found weirdly clarifying every time I’ve done it, and it costs nothing but ten quiet minutes.

Go back through your life and find a failure that’s old enough to have finished happening. In other words, nothing from last month, or probably even last year. You’re looking for something with real distance on it.

A job that fell apart

A relationship that ended badly.

A trip, a project, or a plan that went sideways enough that you remember exactly how it felt at the time.

Pick a moment where you can still recall the verdict you gave at the time when you were certain you knew exactly what it meant. Then look at where it sits in your life now.

I’m not asking you to force a happy ending onto it. Plenty of your failures won’t have happy endings, and pretending otherwise is how this exercise turns into a greeting card. Instead, I just want you to be thoughtful about what actually became of it. Is it a story you tell now? Does it still sting the same way, or has the sting changed shape? Did anything come from it that you couldn’t have predicted while you were inside it? Do you know things about yourself because of it that you’d have had no other way of learning? And, most usefully: is your assessment of it today the same one you delivered back then, with total confidence, when you had very little information?

Whenever I do this activity, I find at least one experience where my current view is so far from my original verdict that it’s hard to believe both opinions came from the same person. And that’s really the whole point of the exercise. You’re not trying to convince yourself that old wounds were secretly blessings. You’re just collecting evidence, from your own life, about how time reliably changes the way things look. And that’s a genuinely useful insight to have on hand the next time you’re standing on a dock, face frozen, absolutely certain you’ve just wasted an afternoon.

Last week, I took my family to a baseball game at our local minor league park. For the first couple of innings, my seven-year-old was perfectly content, mostly because she was eating snacks. By the third inning, she’d started fidgeting. By the fourth, she was draped over her seat, singing quietly to herself. And by the fifth, she’d entered a state of full existential despair, sighing up at the sky like a tiny philosopher confronting the fundamental meaninglessness of it all.

Naturally, I asked her what was wrong. Why wasn’t she having fun? Why didn’t she want to watch the game? And she gave me an answer that, in retrospect, should have been obvious, but somehow caught me completely off guard.

“I don’t understand what’s going on.”

The Thing I Couldn’t Explain

Of course she didn’t understand. She’s seven, and nobody had ever actually explained baseball to her. She was staring at a field where grown adults periodically threw a ball, swung a stick, and ran around in a seemingly random pattern while thousands of strangers cheered at moments that, to her, had no discernible logic. Why on earth would that be fun? It would be like being taken to a three-hour opera in a language you don’t speak and being asked to enjoy the plot.

Obviously I decided I would fix the problem by explaining the rules of baseball. Once I did, she’d understand the game, and then — in my imagination, at least — she’d fall in love with it and we’d have a lovely father-daughter evening.

I began to explain: “Okay, so there’s a team that’s hitting, and a team that’s fielding. The hitting team is trying to score runs by getting all the way around those four bases.” Fine so far. But then the rules started branching. “The fielding team is trying to get the hitting team out, which they can do by catching the ball in the air, or tagging the runner, or sometimes just by stepping on the base while holding the ball — except that only works in certain situations, depending on whether the runner’s forced to run, which depends on who else is already on base…” I watched her eyes glaze further with every added clause. There were balls and strikes and fouls and innings, each one requiring three more concepts just to explain the first, and about ninety seconds in, I realized I had no idea how to make any of this make sense to a person starting from zero.

And it wasn’t for lack of understanding on my part. I’ve understood baseball for as long as I can remember, which, it turns out, was exactly the problem. I don’t actually remember learning baseball. It simply seeped into me over an entire childhood of backyard catches and little league games and summer afternoons on the couch until it felt as natural and obvious as breathing. And so, sitting there next to my miserable kid, I discovered I had no way to hand her the thing she was missing because the thing she was missing was never something anyone handed to me.

Eventually, I gave up trying to explain the rules. My daughter wasn’t interested. She was busy being bored, I was getting frustrated, and we left in the seventh inning without her falling in love with baseball. In fact, as far as I can tell, she likes it exactly as much now as she did before, which is to say, not at all.

The Curse of Already Knowing

Psychologists actually have a name for part of what happened to me that night. They call it the “curse of knowledge.” It’s the cognitive bias where, once you understand something well, you lose the ability to remember what it felt like not to understand it.

Interestingly enough, it’s also one of the reasons experts often make terrible teachers. The thing they’re explaining feels so obvious that they skip the very steps beginners actually need.

But the more I’ve thought about that baseball game, the more convinced I’ve become that the curse of knowledge creates a second problem that’s even more damaging.

It doesn’t just make us bad at teaching. It makes us impatient with beginners.

Once we’ve forgotten how confusing something used to feel, we start treating confusion as evidence someone isn’t trying hard enough. We wonder why new employees ask “obvious” questions. We roll our eyes when a colleague struggles with software we’ve been using for years. Or we get frustrated when our kids don’t immediately grasp something that seems completely intuitive and leave in the middle of the seventh inning.

Simply put, the better we know something, the more we feel like learning should look smooth. You study, you understand, you move on. If you’re confused, you’re behind. If something feels difficult, you’re missing something everyone else already knows.

But that’s almost never how learning actually works. Real learning is awkward and full of half-formed explanations where every answer somehow creates three new questions. It’s sitting in the stands of a baseball game wondering why everyone around you seems to understand something that feels completely arbitrary.

And if we’re honest, adulthood feels like that far more often than we’d like to admit.

Starting a business feels like that.

Parenthood feels like that.

Leadership feels like that.

Marriage feels like that.

Every meaningful part of life eventually asks us to become beginners again.

Which means the real challenge isn’t learning baseball… or business, or parenting, or leadership. The real challenge is remembering what it felt like to sit in the stands, completely confused, while everyone else seemed to understand the game.

If we can hold onto that feeling — both for ourselves and for the people learning beside us — we’ll probably become better teachers, better leaders, and, perhaps most importantly, kinder and more patient human beings.

When You’re the One in the Stands…

The next time you find yourself lost while everyone around you seems fluent in something, here are some questions you might try asking yourself:

• Is this confusion a sign I can’t do this, or just a sign I’m in the early innings of learning it?

• Am I comparing my beginning to other people’s middle — measuring my first game against their hundredth?

• Did the fluent people around me actually learn this instantly, or have they just forgotten how long it took?

• What would change if I treated this awkward, half-formed stage as a normal part of learning rather than proof I don’t belong?

• Am I about to walk out in the seventh inning of something that was always going to take longer than one game to understand?

Confusion isn’t evidence you’re failing. It’s usually just evidence you’ve started learning something complicated.

When You’re the One Who Already Knows…

Being an expert trying to help a beginner can be frustrating. And simply reminding ourselves to have patience isn’t usually as effective as we’d all like it to be. Instead, when you feel that flash of impatience with someone who “should” get it by now, try asking:

• Do I actually remember what it was like to not understand this, or has that feeling become invisible due to my own expertise?

• Is this person struggling because they aren’t trying, or because they’re simply earlier on a path I can’t remember?

• What are the “obvious” steps I’m skipping because they stopped feeling like steps to me a long time ago?

• Am I treating their confusion as a character flaw when it’s really just missing information?

The kindest thing you can do for a beginner is remember you were once one, too. Who was patient with you in those early moments of learning, and could you be more like them?

Before heading home from California this summer, my family and I visited Sequoia National Park. It’s home to the giant sequoias, which are the largest trees on the entire planet, including the General Sherman Tree, which is generally regarded as the biggest tree (and living thing) on Earth by volume.

By the way, describing the size of that tree is tricky. Photos don’t do it justice. The thing is roughly 275 feet tall, wider at its base than most rooms in your house, and somewhere in the neighborhood of 2,200 years old, which means it was already a substantial tree when the Roman Empire was getting started. For context, my kids were impressed, and they’re hard to impress.

But the most interesting fact I learned on that trip wasn’t about the size of the trees. It was about fire.

Naturally, when most of us think “fire,” we also think “burning wood.” As a result, early conservationists decided they needed to protect the giant sequoias from forest fires. And so, for the better part of a century, conservationists suppressed every fire that threatened the sequoia groves on the seemingly sensible theory that fire was the enemy and the trees needed to be shielded from it.

Except they were almost exactly backwards in their thinking.

The Trees That Were Built for Fire

What the conservationists eventually discovered, and what our park guide explained to us as my children slowly lost interest, was that giant sequoias don’t just tolerate fire. They depend on it. In fact, they can’t reproduce without it.

A sequoia’s cones are sealed shut with resin, and they can stay sealed for up to twenty years, holding their seeds in reserve. What opens them is heat, which means when a fire moves through the grove, the heat melts the resin, the cones finally open, and they release their seeds. And oh-by-the-way, thanks to millions of years of evolution, those seeds happen to thrive in the exact conditions fire creates. Because fire doesn’t just burn wood. It also clears away the thick layer of accumulated debris on the forest floor, exposing the bare mineral soil that sequoia seeds need in order to germinate. Plus, fire burns away the competing vegetation that would otherwise crowd out and shade the young seedlings.

That’s right… fire doesn’t kill sequoias. Fire is a partner sequoias evolved alongside and can’t live without. Even their famous, absurdly thick trunks have bark that can be as much as two feet deep. That bark evolved specifically so adult trees can survive the very fire their own offspring require to be born, meaning the whole organism is built around fire.

You can probably already see where all this is going. Turns out, a century of well-intentioned protection actually devastated the forest.

What We Protect People From

When I first heard about what was happening with those trees and the mistake around preventing forest fires, I immediately began thinking of my children. After all, as a parent, don’t I do the exact same thing? How much of my life is devoted to stopping the bad stuff from happening to them?

And, of course, it’s not just a parent thing. I suspect most of us are constantly making the same mistake with the people we love and, just as importantly, with ourselves.

We look at the people we care about, we recognize how precious and irreplaceable they are, and we conclude that the most loving thing we can do is shield them from the destructive stuff. The failures. The rejections. The hard, painful, seemingly damaging experiences that we’d do almost anything to spare them from. Not only does it feel correct. It feels obviously correct in exactly the way protecting rare trees from fire felt obviously correct.

But humans, like sequoias, didn’t evolve in a world without fire. We have been dealing with hardship, loss, failure, and struggle for as long as there have been humans, and it seems worth at least considering the possibility that we, too, are built for it. Some of what makes a person grow tall and wise and resilient isn’t the absence of difficult experiences but the presence of them.

People who are never allowed to fail don’t become invincible. They become the sequoia grove full of magnificent old trees and no new growth. They’re fine on the surface, but they can’t develop the things that only difficulty can produce. The seeds stay sealed in their cones, waiting for a heat that never comes.

So the next time you’re thinking about protecting someone — or yourself — from something difficult just because you don’t want them to experience pain, take a moment to remember the General Sherman Tree. The Sherman Tree has been alive for over two thousand years and has survived, by some estimates, thousands of fires. It didn’t grow to be the largest living thing on the planet despite all that fire. It grew that way, at least in part, because of it.

It turns out, the trees we tried hardest to protect were the ones we very nearly loved into barrenness.

Before You Reach for the Fire Extinguisher

Since this issue is about the instinct to protect both ourselves and the people we love from difficulty, here are a few questions worth holding onto for the next time you feel that instinct rising:

• Am I protecting this person from genuine harm, or from the kind of difficulty that might actually help them grow?

• Is this a fire that will simply burn things down, or one that clears the ground for something new? (They’re not always easy to tell apart, but the question is worth asking before acting.)

• When I think back on my own growth, how much of it came from the comfortable stretches, and how much came from the hard ones?

• Am I confusing “keeping someone safe” with “keeping someone from developing”?

• What am I sealing up and protecting that might actually need some heat to open?

To be clear, I don’t mean you should be throwing the people you love into the flames, or seeking out hardship for its own sake. This story and set of exercises are just meant as a reminder about the importance of pausing and reflecting before you rush to prevent every difficult thing. Sometimes, the difficult thing is also the valuable thing.

This weekend, America turns 250, which means all my American readers will be grilling burgers, setting off fireworks, and celebrating the familiar story we’ve all absorbed since elementary school about how, on July 4th, 1776, a nation was born.

It’s a wonderful story (assuming you’re not British). But it’s also not quite what happened…

For starters, the vote for independence didn’t happen on the Fourth. It happened on July 2nd. In fact, the 2nd seemed so much more important than the 4th that John Adams wrote to his wife predicting July 2nd would be celebrated by future generations with parades and fireworks forever. Whoops!

What actually happened on July 4th was Congress formally adopted the text of the Declaration. And the document most of us picture everyone solemnly signing on the 4th mostly got signed on August 2nd — nearly a month later. Plus, there was no email back then, so the news took weeks to travel, and the “birth” of the nation was something most people found out about well after it had supposedly occurred.

And that’s just the paperwork!

The actual fighting started more than a year earlier, at Lexington and Concord in April of 1775. Then the war wouldn’t formally end until the Treaty of Paris in September of 1783, meaning if you asked a British official when America was “born,” you’d likely get an answer seven years later than the one on our calendars. Plus, the Constitution, which is the framework governing the current version of the country, wasn’t drafted until 1787, eleven years after the birthday we’re celebrating. Then there was another entire war with the British from 1812 to 1815, during which the White House was burned to the ground. And when we fast forward another 50 years after that, we land in the middle of a country trying to tear itself in half.

In that context, was America really “born” in 1776?

The Story We Can Only Tell Afterward

To be clear, I’m not suggesting we cancel the Fourth of July. After all, it’s hard enough these days getting everyone to agree it’s worth celebrating a very simplistic version of America’s founding story. Imagine trying to rally a nation around a “gradual and contested emergence of American sovereignty over roughly two decades of war and argument.”

Instead, I’m adding this context to the story of American independence because it’s a reminder of how judging things too early can lead people to assume things are failures when they’re not.

The only reason we associate July 4th, 1776 with the triumphant birth of an enduring nation is because we’re doing it from 2026 after knowing the experiment worked. The war was won, the Constitution held, and the union came back together, which means the American story is being written by people who already know how those things ended.

But nobody actually living through those moments knew the endings. Picture standing in the colonies in 1776, watching a ragtag collection of farmers declare war on the most powerful empire on earth. That doesn’t look like the birth of a great nation. It looks like a reckless gamble that’ll probably get a lot of people killed for nothing.

Picture James Madison in 1814 watching the capital burn. Picture Abraham Lincoln in 1861 watching neighbors killing each other by the tens of thousands.

In other words, if you had visited America at almost any point in its first century and asked whether the country was a success or a failure, the person you asked might very reasonably have answered: failure. It was an unstable, violent, half-formed thing that seemed as likely to collapse as to endure.

That person wouldn’t have been stupid or wrong to think so. He’d simply have been doing the only thing any of us can do from inside an unfinished story, which is to guess at the ending based on a middle that didn’t look so great.

You’re Living in the Middle

On this July 4th, I want you to remember where you are in your story. Are you at the end yet? And, if not, why are you judging yourself like you know the outcome

We’re constantly rendering verdicts on our own lives, and we’re usually doing it from the middle. As a result, when a few things go wrong — we shut down a business, we end a relationship, we get rejected for an opportunity — our minds instantly declare ourselves “failures.” But are we failures? Or are we just grading an unfinished story?

“Success” and “failure” are narrative judgments, and narratives require endings. But life isn’t nearly as neat as the stories we tell, which means the real question isn’t whether you’ve failed. It’s whether you’ve simply mistaken the middle of your story for the end of it.

Reading Your Own Middle

Since this issue is about the danger of judging an unfinished story, here are a few questions I’d encourage you to sit with during the holiday weekend (hopefully between bites of hamburger):

• What in my life am I currently calling a “failure” — and do I actually have the ending yet, or am I judging from the middle?

• If this were the messy middle of a story that eventually turned out well, what might this chapter turn out to have been for?

• Where am I mistaking “unresolved” for “failed”? Those are very different things, and only one of them is a verdict.

• What would I tell someone I loved if they were standing in exactly this moment, convinced it was the end of theiry story?

• Looking back, what past chapter of my life did I once judge as a failure that turned out to be a middle, and what does that teach me about the one I’m in now?

  ---

At various times over the past few weeks, for a handful of unrelated reasons, I’ve found myself buried in contracts. There was an insurance thing, some employment paperwork, a couple of speaking agreements, and so on. None of it was particularly dramatic, but it did mean I spent an unusual amount of time reading the kind of dense, clause-heavy language most of us skim past on our way to the signature line. And somewhere around the third or fourth document, I noticed something I’d never really thought about before:

Isn’t it strange how contracts are almost entirely about failure?

The next time you’re handed a contract, read it closely and you’ll quickly notice how the bulk of the language isn’t describing the wonderful thing two parties are excited to do together. It’s meticulously cataloging everything that could go wrong. What happens if one side doesn’t deliver? What happens if the money doesn’t arrive? What happens if the project collapses, the relationship sours, the timeline slips, or one party simply walks away?

A contract is, in essence, an exhaustive map of failure. It’s every pothole, every wrong turn, and every way the whole thing might fall apart, written down and agreed upon in advance.

Isn’t that strange?

Here are two parties, presumably entering a relationship because they’re optimistic about what they’re hoping to accomplish together, and the document formalizing that relationship is fixated almost entirely on all the ways it could end badly. What does it say about us that so many of our most important relationships — with our employers, our partners, our insurers, even our phone carriers — are built on a foundation that expects failure? More importantly, what does it say about failure itself

The Thing Contracts Actually Do

I suppose the easiest way to interpret the natural pessimism of contracts is as reflections of distrust. We write everything down because we don’t trust the other party, and the more elaborate the contract, the deeper the suspicion.

But the more I sit with that interpretation, the more I find myself wondering if it’s exactly backwards. Rather than viewing contracts as expressions of distrust, what if a contract is the thing that lets you proceed without trust?

For example, I have no personal relationship with my insurance company. They don’t have one with me. We have no reason, on a human level, to trust each other with anything that matters to us, and yet we can enter into a serious, high-stakes, long-term relationship — a relationship involving real money, real risk, and real consequences — precisely because the contract has already worked out what happens if things go wrong. In other words, the failure planning of the contract isn’t the pessimism that undermines the relationship. It’s the foundation that makes the relationship possible in the first place.

Nobody would ever buy a car, accept a job, board a plane, or insure a house if every party first had to be genuinely certain that nothing would ever fail. That certainty doesn’t exist and never will. What lets us act despite uncertainty — act boldly, ambitiously, and with real commitment — is that we’ve taken the catastrophic version of failure off the table by signing a contract. Rather than hiding from the failure, we’ve made it known, survivable, and pre-handled. And once the worst-case scenario is safely accounted for, both parties are suddenly free to pour their actual energy into making the thing succeed.

In a way, it’s kind of beautiful. A contract is two parties agreeing, in advance and in good faith, to treat each other fairly even on the worst day of their relationship. It’s a promise about how you’ll behave when things fall apart, made at the precise moment when everyone’s still hopeful and nobody’s angry yet.

That’s not cynicism. It’s actually something closer to… tenderness?

We Have It Backwards

Now compare the situations where we sign contracts versus the situations where we don’t. In our actual lives — in the relationships and ambitions that matter most — we tend to do the exact opposite of signing contracts. We refuse to plan for failure at all. We treat any serious consideration of “what if this doesn’t work” as a kind of betrayal, and we presume that naming the ways something might fail is the same as inviting it to fail and admitting we don’t really believe in the thing we’re supposedly committed to.

But the more I think about it, the more I’m seeing how that refusal to consider failure doesn’t really protect us. If anything, it makes the whole enterprise more fragile. When failure does arrive — and some version of it always does — there’s no structure waiting to absorb it and no agreed-upon understanding of what happens next. What’s left are two people forced to improvise their way through the worst day of the relationship with nothing to hold onto except whatever painful emotions are surely floating around. And how does that help anyone?

I suppose it doesn’t. As much as I hate to admit this, I suppose the contract-writers have it right, and the rest of us have it backwards. The people most able to commit boldly aren’t the ones who’ve convinced themselves nothing will go wrong. They’re the ones who’ve already made peace with how things might break. That’s not disloyalty. It’s the thing that lets you chase hope without being paralyzed by everything you can’t control.

In other words, a contract isn’t what you write because you expect to fail. It’s actually the thing that lets you act as if you won’t.

Writing Your Own Clauses

So here’s a small, slightly strange exercise I’ve been thinking about ever since I climbed out of my pile of paperwork… just trust me on this one, OK?

Pick one important thing in your life that’s never had a contract — and never will. It could be a friendship, a marriage, a creative project you care about, or a goal you’ve been chasing for a while. It can be related to anything, just make sure it’s something that matters enough that the thought of it failing is genuinely unpleasant.

Now, instead of doing what we normally do — which is to look away from that unpleasant thought as quickly as possible — try doing what a contract would do. Sit down and actually write a few clauses for it. Obviously, it doesn’t need to be real legal language. Instead, focus on producing honest answers to the questions a contract would force you to answer if anyone had bothered to draft one:

• What does it actually look like if this fails? Name the real version, not the vague dread. Vague dread is paralyzing precisely because it stays vague. But a named failure is just a problem, and problems can be planned for.

• What would we — or I — do if that happened? This clause does most of the important, challenging work when it’s not nearly as hard to do. Knowing, in advance, that there’s some plan for the worst day tends to drain that day of an enormous amount of its terror.

• What am I promising to do even if things go badly? Contracts are, at heart, promises about behavior on the worst day. How do you want to treat the other person — or yourself — if this thing falls apart? Deciding now, while everyone’s still hopeful, is a lot easier than deciding in the wreckage.

As you do this exercise, you’ll hopefully notice that the act of writing the clauses doesn’t make failure feel more likely. It actually makes failure feel more survivable. And even though our instincts tend to confuse those two things, they’re very different.

By the way, with this exercise, I’m not suggesting you actually draft a contract for your marriage and hand it to your spouse over dinner. (Please don’t. I take no responsibility for how that conversation goes.) I’m suggesting that the thinking behind a contract — the willingness to look directly at how something might break — is a tool we’ve quarantined to lawyers and insurance companies when it might be one of the more useful things we could bring into the parts of our lives that actually matter.

For those of you who’ve been reading regularly (Thanks! You’re the best!), you’ll probably remember how last week I shared the very dramatic, very stressful story of a deer launching itself into my rental car somewhere in the mountains between Tahoe and Yosemite. Since that was definitely the most cinematic failure I’ve experienced in a while, this week, I feel like moving toward the opposite end of the spectrum because I think the contrast is actually worth something.

This week’s failure has no injured wildlife, no sheriff, no murder-motel, and no kindly stranger named Eddie. This week’s failure is just a medical bill that I can’t figure out how to pay.

Here’s the situation. Apparently we owe a small co-pay for one of our daughters. Duke Health, my healthcare provider, called my wife about it, and, rather than reading her credit card number to a stranger on the phone who may or may not have actually been from Duke Health, did the very responsible thing and said she’d just hop online and pay it through the portal, the way she always has. So she logged in, navigated over to our daughter’s account, found the bill, went to pay it… and then discovered she’s no longer able to because she isn’t listed as the “guarantor” on the insurance.

I’m the guarantor. Our health insurance runs through my employment, which means I’m the one the system recognizes as financially responsible.

Fine. No problem. I’ll just log in and pay it myself. Except our daughters’ medical records are connected to my wife’s account, not mine. So my wife can see the bill but isn’t allowed to pay it. And I’m allowed to pay it, but I don’t have any way to see it. The bill exists in a kind of administrative purgatory, fully visible to the one person who can’t act on it and fully payable by the one person who can’t find it. As of this writing, it remains gloriously, stupidly unpaid. And it’s not because we’re unwilling or can’t afford it. It’s simply because the system has constructed a small, perfect maze with no exit.

Somebody, Somewhere, Ticked a Box

What I love about this failure — and I do, in a way, love it — is there’s no villain or evil mastermind. Nobody at Duke Health woke up one morning intending to make it impossible for me to give them money. Instead, what almost certainly happened is that somewhere an administrator or a software vendor or a committee made a perfectly reasonable-sounding decision. It just didn’t account for a weird edge-case they had no real reason to imagine.

And I’m sharing this story because it’s a great example of what failure actually is. It’s bureaucratic. It’s the accumulated downstream consequence of a thousand individually reasonable choices, made by people who couldn’t possibly have anticipated how their small decisions would interact with everyone else’s small decisions.

It’s the least dramatic failure imaginable. And yet, it has something important in common with the poor deer that collided with my rental car last week.

The Hidden Thing the Deer and the Bill Share

My family’s collision with that deer was random. There’s no lesson in it, or cause we could have addressed. An animal made a decision at a moment we couldn’t have predicted, and our day was upended. Pure circumstance.

The medical bill is also random. The particular collision of rules that’s trapped us isn’t aimed at us. We happened to be the family whose arrangement of employment, insurance, and parental record-keeping fell into a weird crack in the policy. One different decision a decade ago, and the bill gets paid in thirty seconds. We didn’t earn this failure any more than we earned the deer.

More importantly, this extends way beyond deer and medical bills. Most failures are like this. Even the ones that look causal — the ones that seem to clearly imply you did something wrong — are filled with chance and randomness.

For example, maybe you gave a presentation last week, your boss tore into it, and you spent the rest of the day convinced your work was bad. But what if your boss stubbed his toe on the way into the room, or got a worrying text from his doctor, or simply didn’t sleep well. Maybe the thing you’ve been carrying as evidence of your own inadequacy was, in reality, a stubbed toe you never saw. You’ll never know, and that uncertainty is precisely the point.

We have a deep habit of reading our failures as judgments on our competence, our worth, our intelligence, and our ability. But a failure is rarely a verdict. It’s just data generated by a tangle of circumstances, most of which had nothing to do with you.

The deer wasn’t a referendum on my driving. The bill isn’t a referendum on my responsibility as a parent. And your bad meeting was, quite possibly, a referendum on someone else’s toe.

Failure isn’t a grade the universe assigns you. It’s information about what happened — circumstance, chance, and sometimes just bureaucracy, all of which look an awful lot like judgment until you remember to ask: What else was going on, and how much of it was completely beyond your control?

By the way, the bill is still unpaid. If anyone at Duke Health is reading this, I’d genuinely love to give you your money. I’m just not bureaucratically permitted to unless you’d like to help.

In the Moment…

A helpful reframing for those moments where failure feels possible.

When something goes wrong and you feel that familiar pull to read it as a verdict on your competence, your worth, your judgment, etc., I want you to pause. The story you tell yourself in the first few minutes after something happens is usually the least accurate one you’ll ever have access to, but, unfortunately, the most powerful one. So try asking some of the following questions in order to disrupt it:

• How much of what just happened was actually within my control, and how much was circumstance I’ll never fully see?

• What else might have been going on for the other people in this situation that I’d have no way of knowing about?

• Am I treating this as information about what happened, or as a judgment about who I am?

• If a friend described this exact situation to me, would I read it as their failure, or as bad luck?

• What’s the most boring, least dramatic explanation for this, and is it possibly the true one?

To be clear, the goal with these questions isn’t to dodge responsibility for the failures that are genuinely yours. Instead, the goal is to stop automatically assigning yourself the full blame for results that had plenty of other inputs.

The Debrief…

Reflecting on our experiences is where the most important learning happens.

After some time has passed and the sting of whatever failure you experienced has faded, it’s worth going back and separating what you actually controlled from what you merely absorbed. That separation is where the real learning hides. Try asking:

• Looking back, what part of this was genuinely mine to own, and what part was circumstance I happened to be standing in front of?

• What judgment did I assign myself in the moment that, with distance, looks less deserved than it felt?

• Where have I been carrying a past failure as evidence about myself when it was probably just chance?

• If this was mostly circumstance, what’s the actual lesson?

• What would change about how I move through the world if I genuinely believed most failure is data rather than a grade?

Again, our goal here isn’t to avoid responsibility for whatever bad thing happened. We just want to make sure you’re only feeling responsible for the parts that are actually yours.

This week, after finishing a month of teaching in California for the Duke in Silicon Valley program, my family flew out to meet me. We spent a few days visiting friends in Lake Tahoe before driving down to Yosemite.

If you’ve ever made that drive, you’ve seen how crazy the roads are, including a seemingly endless string of narrow, winding mountain switchbacks that demand your full attention and reward it with views that almost make the white-knuckle steering worth it.

All was going well enough until I rounded the 500th or 600th corner. Without warning, a deer came leaping down the hillside and launched itself directly onto the hood of my car.

Boom!

I’ll spare you most of the details, partly because they’re unpleasant and partly because they’re not really the point.

The short version is simply that, by almost any measure, I had a catastrophically bad day. The car — a rental — was totaled. Plus, I was in the middle of nowhere with two young children. An injured buck was writhing in the road and I had to call the local sheriff to “dispatch” it. (Yes, I sent my already-traumatized daughters far down the road for that part.) We had to spend the night in a motel that had a distinctly “was someone once murdered here?” atmosphere. I wasted hours on the phone with insurance and the rental company. I waited two hours for a tow truck, spent another two hours riding in that truck to Sacramento to pick up a replacement car, and then I drove two more hours back to my family along the very same roads that had just tried to kill me, except this time I got to do it in the dark. Yay!

So, yes… a tough day. But the thing I can’t stop thinking about isn’t the deer…

The People Who Stopped

This all happened on the edge of a small town in the middle of the California mountains. People immediately began stopping. Within five minutes of the crash, something like half a dozen strangers were helping me drag the deer out of the road, waiting with me until the sheriff arrived, giving me water, checking on my kids, and just generally trying to do whatever they could to make a crappy situation slightly less awful.

None of these people knew me. None of them owed me anything. They surely had places to be and things to do. Yet every single one of them treated my disaster as if it were, at least for a moment, their problem, too.

And then there was Eddie.

Eddie was on his way home from a church meeting when he stopped, and Eddie simply would not leave. After everyone else had drifted off (including the Sheriff), and after the immediate crisis had passed, I was still standing on the shoulder of a dangerous mountain road trying to arrange a tow. And Eddie was still there, too, patiently taking in the scenery and smiling kindly at me each time I glanced his way.

I kept assuring him I was fine, that he should get on with his day, and that I had it handled. In reply, he would gently insist that he wasn’t going anywhere until my family was settled.

Eddie helped us get to the hotel. When my phone couldn’t find a decent signal, he even offered to drive me to his own house so I could use his internet. He was, without exaggeration, one of the kindest human beings I’ve ever encountered. And in that particular moment, kindness was precisely the thing I needed most.

I’ve thought about Eddie a lot in the days since. And even though I realize he didn’t do anything enormous — he didn’t exactly pull anyone from a burning building — his refusal to let a stranger struggle alone on the side of a road is a kind of heroism we don’t talk about nearly enough.

The Story We’re Told vs. The One I Lived

I think the reason I can’t stop thinking about Eddie is because of how he completely contradicts the current narrative online and in the press for the way we’re supposed to view the world. If you spend any time watching the news or scrolling through social media — and most of us spend far too much — you come away with a very particular picture of humanity. It’s a picture in which everyone is furious, nobody can agree on anything, strangers are threats, and our whole society is fraying at the seams. The story we’re constantly told is that people, fundamentally, are out for themselves and the world is getting colder and meaner by the day.

I understand why that story dominates. Conflict is louder than kindness, and outrage always spreads faster than decency. A screaming argument gets ten thousand shares while a guy patiently waiting on the side of a road to help a stranded family gets seen by exactly one person — me.

In other words, the algorithm has no idea Eddie exists, and it never will. Which means the version of humanity we absorb through our screens is systematically, structurally biased toward the worst of us, and almost entirely blind to the best.

But my actual experience, on the actual worst day of my recent memory, told a completely different story. When I was genuinely stranded and genuinely in need, the people around me — without exception — were generous, decent, and kind.

And even though I want to make myself the hero of this story — the husband and father who overcame a terrible string of failures — the biggest failure I experienced that day was the failure of a system that constantly tries to convince us the world is an angry, hate-filled mess. The stories we consume had convinced me to expect callousness and indifference. What I got instead was a parade of people who stopped what they were doing to make sure my kids were okay.

I think that gap matters. Because if we’re not careful, the false story starts to feel true. We begin to move through the world a little more guarded, a little more suspicious, and a little quicker to assume the worst about the stranger in front of us. In doing so, we slowly become less like the Eddies and more like the hateful, divided, partisan people our media tells us we’re supposed to be.

The truth, as best I can tell from standing on the side of a mountain road next to a totaled car, is that most people are kind. Most people will stop. Most people, when they see someone struggling, feel the pull to help.

And the very best of them don’t just stop. They stay. They’re the Eddies, and I suspect this world has far more of them than the news would ever lead you to believe. We could all do a better job of noticing them. And, when the moment comes, we could all do a better job of being like them.

Some Thoughts on Becoming an Eddie

If I’m going to tell you “the world needs more Eddies,” I feel like I should spend a little time offering ways of actually doing that.

The easiest suggestion would be simply telling everyone to “be kind.” And sure, it’s true, but it’s also useless because nobody finishes a newsletter and decides to start being cruel. We already know we’re supposed to be kind. That’s not the hard part.

So instead of offering worthless platitudes, I’ve spent the past few days trying to understand what actually distinguished Eddie. Surprisingly, very little has anything to do with the things he did. What makes Eddies so exceptional, and what we should be studying, is his disposition.

Here’s what that includes:

• Eddies quietly place someone else’s wellbeing above their own convenience. This is the whole thing, really, and everything else is downstream of it. Eddie had a day to get on with, a home to return to, his own life waiting for him. But he set all of it aside. Just as importantly, he didn’t do it dramatically, or with any sense of sacrifice. He simply acted as though my family’s situation had become more important than his schedule for a while. That reordering, done without resentment or fanfare, is the essence of it. Most kindness lives or dies on whether we’re willing to be a little inconvenienced, and the Eddies of the world have somehow made peace with the inconvenience before it even arrives.

• Eddies don’t need to be useful to be present. This is the part that surprised me most. Eddie didn’t fix my car or have any insight about insurance or tow trucks. In practical terms he solved none of my problems. This was surprising to me because, personally, I often hang back from helping when I feel like I don’t know what to do. But maybe that’s wrong. Maybe kindness doesn’t require competence. After all, Eddie wasn’t useful in any practical way. He was just there, fully and without distraction. That might not seem immediately valuable, but, ultimately, his presence was worth more than any practical skill anyone offered me that day. Being an Eddie has almost nothing to do with having answers.

• Eddies see past “I’m fine.” I spent most of that morning insisting I was okay and that Eddie should go enjoy the rest of his day. He gently declined to believe me, which created a satisfying kind of attentiveness. Rather than accept the easy answer that would have let him off the hook, he was focused on reading what I actually needed, which is difficult. After all, “I’m fine” is very often what people say precisely when they aren’t, and the Eddies of the world seem to know this instinctively. They pay attention to the person in front of them more than to the script that would release them.

• Eddies don’t keep score. Eddie will almost certainly never know he ended up in a newsletter read by thousands of people, or that I think about him often, or that he was the best part of one of the worst days I’ve had in years. He helped with no expectation of being thanked, recognized, or repaid, and he drove off later that afternoon with no idea how much he’d mattered. That’s the impressive thing about genuine goodness: most of it goes permanently unacknowledged, and the people capable of it are entirely fine with that. They aren’t being kind in order to get something back. They’re being kind because kindness is how people are supposed to be.

  ---

If you were anywhere near the internet last Thursday night, you probably saw the video of Blue Origin’s big new rocket erupting into a fireball on the launchpad at Cape Canaveral. Thankfully nobody was hurt, but the rocket was gone, the launchpad got wrecked, and the missions the rocket was intended to support are going to be significantly delayed. Simply put, the entire thing was a very spectacular and very expensive failure.

I watched the clip a few times, the way you do. And then I made the mistake of scrolling into the comments, where everyone had already landed on the same three words people always land on when a rocket blows up: space is hard.

To be fair, that’s true. Space is genuinely and almost absurdly hard. But the more I think about that phrase, the more it bugs me. Sure, “space is hard” sounds like wisdom. It’s humble, knowing, and properly respectful of how difficult the work is. Yet, if you actually look at how the phrase operates, it isn’t doing what we think it’s doing. In fact, it’s doing almost the opposite.

A Cliché That Stops the Questions

The problem with “space is hard” is that it’s a category-level explanation for an instance-level event. In this case, the rocket didn’t explode because space, as a general category of human endeavor, is difficult. It exploded for a specific reason. Some particular system during a particular test failed, and the interesting question isn’t whether space is hard. We know space is hard. The interesting question is what, precisely, went wrong.

I bring this up because the people who are actually responsible for the failure aren’t the ones saying “space is hard.” Bezos (owner of Blue Origin, in case you didn’t know) said it was too early to know the root cause, but that his team is already working to find it. That’s not a man reaching for a comforting generality, which is a good reminder that clichés usually point in the opposite direction of the real work.

“Space is hard” doesn’t explain anything. What it does is give us permission to stop thinking about it. It allows observers like us to take a specific failure with specific, learnable causes and dissolve it into a general truth about a category. The moment we’ve done that, we’ve excused ourselves from the harder and more useful work of figuring out what actually happened.

In other words, the phrase feels like the conclusion of an inquiry, when it’s actually a way of never starting one. Which, in Blue Origin’s case, is fine for people who aren’t building rockets. But the problem goes beyond rocket launches.

The Clichés We Use on Ourselves

I expect most of you reading this — myself included — turn to the phrase “space is hard” when we hear about what happened to Blue Origin because we’re not in a position to take any other type of action. The problem, however, is when similar phrases show up during the many types of non-rocket-related failures we actually encounter in our lives.

Dating is hard.

Starting a business is hard.

Losing weight is hard.

Parenting is hard.

Every one of those statements is true. And every one of them is almost completely useless as an explanation for why a specific thing went wrong for you on a specific Tuesday.

For example, when a date goes badly, sighing and saying “dating is hard” lets you avoid asking what actually went wrong during dinner.

When your business stalls, saying “startups are hard” lets you skip the uncomfortable questions about your own shortcomings as an entrepreneur.

When you get on the scale and you’ve gotten heavier, saying “losing weight is hard” becomes the crutch that lets you justify eating another pint of Ben & Jerry’s.

In other words, clichés tend to arrive at exactly the moment you’d otherwise have to look closely at something difficult, and they offer a tempting exit. They let you feel like you’ve processed the failure when really you’ve just categorized it and walked away.

The people who get good at solving genuinely hard problems don’t do that. They refuse to let “it’s hard” be the end of the sentence. For them, “space is hard” is where the inquiry begins, not where it ends.

So when something blows up in your life — and it will, because the best things in life are always hard — you’ll be tempted to say the equivalent of “space is hard” and move on.

Resist that temptation. Instead, start trying to figure out what specifically went wrong so you can fix the problem and take the next major step forward.

In the Moment…

A helpful reframing for those moments where failure feels possible.

When something goes wrong and you feel the urge to explain it with a general truth — this is just hard, this never works out, that’s how these things go — pause before you let that explanation settle and try asking yourself one of the following questions instead:

• Am I explaining what specifically happened, or just filing it under a category?

• What’s the actual, particular cause here? Or am I just assuming I know it?

• Is this the explanation helping me understand the failure or helping me avoid thinking about it?

• What would I have to admit or examine if “it’s just hard” weren’t available to me?

By asking yourself these kinds of questions, you’ll be better able to notice the moment when “it’s hard” is becoming an excuse to avoid the hard thing rather than a step toward fixing it.

The Debrief…

Reflecting on our experiences is where the most important learning happens.

After getting some distance from a big failure — especially the kind you were tempted to wave away as just the cost of doing something difficult — go back and ask:

• What was the specific cause, as best I can reconstruct it, beyond “it was hard”?

• Where did I reach for a general explanation to avoid a more uncomfortable specific one?

• What did this failure actually have to teach me, and did I collect it or skip it?

• If this exact thing happened again, would I know why, and would I know what to do differently?

• What’s the difference between the failures I’ve genuinely learned from and the ones I just categorized and moved past?

Remember, you already paid the price for the failure. Don’t walk away without learning the lesson it was trying to teach you.

Last week, the Faculty of Arts and Sciences at Harvard University voted — by a pretty wide margin — to cap the number of A grades in undergraduate courses at 20 percent per class. They did it as a way of managing grade inflation, which has become a big problem at universities around the United States. Simply put, an A doesn’t mean much anymore, and this policy is meant to address that.

As you’d probably expect, the change is getting mixed reactions. Some people think it’s a long-overdue correction, while others think it’s going to create a more anxious and cutthroat student culture. And, to be fair, both sides have reasonable points.

But I keep getting stuck on something everybody in the debate seems to be overlooking…

If Harvard — or anyone, really — actually believed grades were a meaningful measure of learning, the solution to grade inflation would be obvious: Make the courses harder to master. After all, if we raise the bar for what earns an A, then the grade would reflect genuine achievement, and the distribution would sort itself out naturally.

Problem solved!

But that’s not what Harvard did. Instead, they capped the number of A’s that can exist in a class regardless of how well the students in it actually perform. And this tells us the policy isn’t really about learning at all. It’s about managing a signal. Harvard wants to make sure the grade distribution looks a certain way so employers and graduate schools can better use it as a sorting tool.

In other words, Harvard’s faculty just voted to “fix” grades by making them less connected to individual performance, not more. And I think that’s worth discussing because it underscores everything I keep trying to explain in Learning to Fail about the strange relationship all of us develop with grades as a result of spending so many years in school.

The System Measuring Itself

The news out of Harvard is a great reminder that grades aren’t a precise instrument for measuring what any individual student knows or can do. Instead, grades are a tool for managing a very large, complicated, and imperfect system.

Consider, for example, that twenty years ago, A’s accounted for roughly a quarter of all Harvard grades. By last year, that number had climbed above 60 percent. What does that tell us about Harvard students? Did they suddenly get dramatically smarter? Or maybe the faculty got dramatically more effective at teaching?

Obviously, neither of those things are true. What changed was the incentive structure for students, for professors, and for everyone operating inside a system where grades carry enormous downstream consequences and nobody particularly benefits from giving a bad one.

That drift happened slowly, invisibly, and through thousands of individual decisions that each made sense in context and collectively produced something obviously problematic. The system drifted away from measuring learning and toward measuring something more like performance within the system, which is a different thing entirely. And the solution the faculty landed on is, in its own way, further evidence of the same dynamic. Rather than reconnecting grades to learning, they’re recalibrating the distribution so the signal works again as a sorting mechanism.

To be clear, I don’t mean any of this in a cynical or malicious way. It’s just what happens when a bureaucratic system tries to serve millions of people across decades. The tools they deploy drift from their original purposes, and eventually the institution has to make adjustments. That’s not just normal… it’s healthy! But it should also tell you everything you need to know about what grades actually measure and how seriously any of us should take them in terms of being a meaningful representation of someone’s actual capabilities.

What Grades Never Measure

After teaching for nearly two decades, I’ve had students who were genuinely brilliant and original thinkers, but they struggled enormously with grades. I’ve also had students who were exceptionally skilled at getting good grades but who I’d hesitate to confidently call knowledgeable about anything hireable or valuable.

None of this means grades are worthless. But it does mean grades don’t reflect what most people think.

Overwhelmingly, people assume grades equate to things like intelligence, potential, and worth. But none of that is true, and Harvard’s new policy proves it.

If a school like Harvard can simply limit the number A’s, they’re telling us grades aren’t actually a system for accurately measuring people. They’re a system for helping institutions manage large numbers of students. As a result, they measure the pressures and incentives of the institutions.

And I’m telling you this because, if you made it this far, there’s a good chance you (or someone you know) struggles with that reality. You equate getting bad grades with being a failure.

Those aren’t the same things.

If you’ve ever lost sleep over a GPA, or let a rejection letter convince you you weren’t smart enough, or internalized a grade as evidence of something flawed about yourself, take a closer look at that Harvard vote. The people at one of the most prestigious “givers of grades” in the world just admitted grades are a bureaucratic instrument that were never really about students in the first place.

And while that doesn’t mean grades are worthless, it does prove they’re not the objective measure of human potential we were raised to believe.

In the Moment…

A helpful reframing for those moments where failure feels possible.

You don’t have to be a Harvard student to let the lessons of the Harvard vote impact your response to critical assessments.

The next time a grade, a score, or someone else’s evaluation of your performance lands harder than you’d like, try asking a few questions before you let it settle into something permanent:

• What is this actually measuring, and what was it designed to measure?

• Who built this system, and what problem where they trying to solve when they built it?

• What does performing well here actually require — and how much of that overlaps with what I care about getting good at?

• Is this a verdict on me, or is it feedback about my fit with a particular set of rules?

• What would someone who knows me well say this result says about me?

The goal isn’t to dismiss every evaluation that stings. Some feedback is genuinely useful. It’s just worth knowing the difference between a measure and a mirror.

The Debrief…

Reflecting on our experiences is where the most important learning happens.

After you’ve had some distance from an experience where you were evaluated — and especially one where the result didn’t reflect how you felt about your own performance — try asking:

• What did I actually learn here, separate from what the grade or score said?

• Where did my performance within the system diverge from my actual understanding, and why?

• What was I optimizing for, and was that the right thing to be optimizing for?

• What would I have done differently if nobody was going to evaluate the outcome?

• What does this experience tell me about the system I’m operating in, versus what it tells me about myself?

Systems need to measure something. But you don’t have to let someone else’s measurement be the last word on what you’re capable of.

In case you didn’t hear, last Sunday, two Navy jets collided mid-air during an air show in Idaho. The planes came down in a fireball, but, luckily, all four crew members ejected safely. While one was treated for minor injuries, everyone went home, which, considering what the footage looked like, feels about as close to miraculous as anyone can hope to get.

As I read the news coverage, I found myself doing what I always do when something dramatic happens… against my better judgment, I opened the comments. And the comments were exactly what you’d expect. Two planes worth of expensive military hardware just fell out of the sky in front of a crowd of spectators, which is not a subtle event, and the internet had… lots of opinions.

What a waste! Taxpayer money, gone! These pilots will never fly again! Air shows are reckless! We should stop doing this entirely!

While I’m as prone to a gut reaction as the next Internet commenter, I also happen to be a bit of an #AvGeek (i.e. someone who enjoys learning about the aviation industry), and the more comments I read, the more I found myself thinking about the gap between how the internet was responding to this event and how the people actually responsible for understanding it were going to respond to it.

That gap is worth paying attention to…

The Difference Between Reacting and Investigating

When something goes wrong in aviation, there’s a formal process for figuring out why. Investigators collect data, interview crew, examine wreckage, reconstruct timelines, and work through hypotheses systematically before drawing conclusions. It’s a slow, methodical process, and one of its foundational principles is that your first instinct about what happened is probably incomplete, possibly wrong, and almost certainly too simple.

Simply put, the aviation world has learned, through hard experience, that complex accidents almost never have simple causes.

For example, in a case like this, what looks like pilot error could easily turn out to involve equipment, communication, environmental factors, procedural gaps, or some combination of all of them. In other cases, what looks like negligence sometimes reveals a systemic flaw that nobody had noticed because nothing had gone wrong yet.

My point is, the natural rush to assign blame frequently points at the wrong thing and obscures the right one.

Knowing this, investigators don’t rush. Instead, they do the uncomfortable, patient work of actually figuring out what really happened.

The Most Expensive Lessons Are the Ones Worth Learning

The other thing that struck me about the comment section was the reaction to the cost. Two military jets are, of course, an enormous amount of money. But assuming expensive jets shouldn’t continue flying in air shows misses something important about how complex, high-stakes industries actually get better over time.

From what I was able to find, deaths during airshows over the past three-ish decades have declined by over 66% (it’s now around one per year).

That’s still not perfect, but it’s a dramatic improvement, and it didn’t happen because aviation professionals responded to accidents by calling for fewer flights. It happened because they treated every accident — every expensive, painful, embarrassing accident — as a source of information they didn’t have before.

Even though losses like what happened last Sunday are real, the lessons are real, too. And the willingness to extract the lessons rather than simply absorbing the losses is a significant part of why the aviation industry, as a whole, is orders of magnitude safer than it used to be.

And that approach to failure doesn’t have to be unique to aviation. We can use it in our own lives, too.

Sure, failures are expensive. They’re also usually embarrassing, and they’re occasionally spectacular enough to end up on the internet with thousands of people yelling about them. But, if you’re willing to do the work, they’re some of the most reliable sources of information available precisely because they reveal things that normal operations keep hidden.

In the Moment…

A helpful reframing for those moments where failure feels possible.

When something goes wrong — at work, in a relationship, in a project you’ve invested in — the first few minutes produce a lot of feeling and not a lot of clarity. Before you act on the initial reaction, try asking:

• What do I actually know right now, versus what am I assuming?

• Is my instinct about what happened pointing at the cause, or just the most visible thing?

• Am I trying to understand this, or am I trying to decide who’s to blame?

• What would I need to know before I could draw a conclusion worth trusting?

• If I wait before responding, what might I see that I’d miss if I react immediately?

Remember, you’re going to react. Your goal is to notice how your initial reaction will always arrive quicker than the full set of information, and you want to practice slowing yourself down enough to get more details.

The Debrief…

Reflecting on our experiences is where the most important learning happens.

Once you’ve had some distance from a failure, that’s when the real work begins. Try asking:

• What do I now know that I didn’t know when it was happening?

• What did my initial instinct get right, and what did it miss?

• What was the actual cause and how did that compare to the first explanation?

• What would have stayed hidden if this failure hadn’t happened?

• What did this cost me versus what did it teach me that I couldn’t have learned any other way?

• What’s different about the way I’ll approach this next time?

Remember that the most expensive lessons have a way of also being the most durable ones, but only if you do the work to actually learn them.

I was at a birthday party for a family friend when someone pulled me aside. She told me, not unkindly but quite firmly, that, as someone with a large online audience, I had a responsibility to speak out about one of the various armed conflicts happening around the world right now. By staying quiet, she argued, I was failing the people caught in the middle of it.

I didn’t say much in response. Partly because a birthday party isn’t really the right venue for that conversation, and partly because I wanted to sit with it before I reacted. But I’ve been thinking about the moment ever since and trying to figure out what kind of failure it might be.

The Seduction of Certainty

Like most people, when I encounter news about a major geopolitical conflict, I immediately form an opinion. It feels almost involuntary. Within seconds of reading something or watching something, I find myself thinking I know which side is right, what should be done, and what responsible people ought to say about it.

But if I slow down long enough, I quickly realize my opinion is almost entirely a reflection of the last thing I read or watched. And if I read a different article or watch a different video that makes a counter argument, what had originally seemed like the “obvious” answer looks less convincing. And, when this happens enough times, I start to realize that most of my opinions about “what’s going on in the world” are simply borrowed from whoever was speaking to me most recently.

By the way, this isn’t a character flaw or something that’s unique to me. It’s how most of us engage with complex, distant events. We understand them through other people’s framings. We absorb their perspectives, we feel the moral certainty that comes with having a view, and we mistake that certainty for understanding.

But any sense of understanding is absurd. At least, it is for these kinds of large, complex, global events. For example, the armed conflict I was being chastised for not speaking about has a history stretching back a long time. It’s a history that specialists spend entire careers studying and still frequently disagree about. So what makes me think my opinion should have any meaningful validity?

The Failure Hidden Inside Conviction

The reason I wanted to share this story is because I wonder if the tension I’ve been feeling around “speaking up” is a tension other people have been grappling with, too. After all, confident wrongness isn’t a neutral act. When we share opinions that are poorly informed, we’re not just parroting what other people want us to believe. We’re helping spread those beliefs in ways that are likely serving agendas we can’t even begin to fully understand.

And again, this isn’t just about global conflicts or the pressure to weigh in publicly on serious events. We do a version of this constantly, at much smaller scales. We form judgments about colleagues after one bad interaction. We decide what a piece of legislation will do based on a headline. We constantly take positions on important arguments after thinking about them for forty-five seconds, and we never question whether that’s really enough.

But conviction is a dangerous feeling. What I’d rather practice — and what I think is genuinely more useful — is curiosity. While conviction asks “Which side is right?” curiosity asks “What would I need to understand to actually have an informed view of this?” And doesn’t that seem like the more responsible approach to big, complex issues?

Conviction performs certainty, but curiosity admits what it doesn’t know. And admitting what you don’t know is, in my experience, one of the most undervalued things a person can do in a world that constantly rewards the appearance of having answers.

In the Moment…

A helpful reframing for those moments where failure feels possible.

The next time you feel strong conviction rising about something — a news story, a conflict, an argument you’re in — before you say it out loud or act on it, try sitting with a few questions:

- Where did this opinion actually come from, and when did I form it?

- How much of this is the last thing I read or watched, rather than something I’ve actually worked through?

- What would I need to know to feel genuinely confident here — and do I know it?

- Am I trying to understand this, or am I trying to feel certain about it?

- What’s the thing that would most complicate my position, and have I gone looking for it?

While I realize this pause might feel like paralysis, it’s much more about noticing the difference between having simply arrived at a feeling of certainty versus having actually thought something through.

The Debrief…

Reflecting on our experiences is where the most important learning happens.

After you’ve held a strong opinion long enough to see what it led you toward, it’s worth asking:

- How did that view hold up, and what made it stronger or weaker over time?

- Where was I borrowing someone else’s certainty without realizing it?

- Did expressing this opinion help anyone think more clearly, or did it mostly just feel good to say?

- Where was I defending the position instead of interrogating it?

- What would genuine curiosity about this have looked like, and what might I have found?

The discomfort of sitting with a question is almost always better than the comfort of a wrong answer.

Last week, I went to my daughter’s 4th grade science fair. And, yes, it was basically exactly what a TV-show version of an elementary school science fair would look like. There was a room full of tri-fold poster boards, a bunch of 10-year-olds standing proudly next to their experiments, and a group of parents wandering around trying to look engaged while asking very polite questions. Honestly, the only thing missing was the paper mache volcano (which I’ll definitely be making my daughter do next year).

Overall, the experiments were… great… in the way 4th grade experiments are great. Nobody was curing cancer or redefining physics. Instead, I was looking at lots of projects about baking, pickling, dissolving, and growing things. What happens if you add more baking powder to cookies? Which vegetable pickles the fastest? That sort of thing.

But what really stood out to me wasn’t the experiments. It was the questions.

Every parent, myself included, was doing the same thing. Walking up to a table, smiling, and asking something along the lines of, “Oh, that’s interesting… what do you think would happen if you tried this instead?” or “Why do you think that turned out the way it did?”

They were perfectly reasonable questions, but, as I was making my way around the room, I found myself thinking: If I’m going to do this… shouldn’t I ask a question that actually matters?

The Question I Learned in Writing Class

The question I ultimately chose is a question I’ve been relying on since I learned it my freshman year of college in, of all places, my Writing 101 class. Every time the professor gave us feedback on our essays, no matter how well-written they were, she would always get frustrated and force us to answer:

“So what?”

At the time, it felt almost dismissive. You’d spend hours working on something, trying to make a point, organizing your thoughts, crafting your argument… and her response would be, essentially, okay… but why does this matter? However, over time, I realized she wasn’t asking that question to minimize our work. She was asking to help us understand why our work actually mattered.

She was teaching us how it’s not enough to notice something, or analyze something, or even explain something. None of that creates value on its own. The value comes from connecting our work to things that actually matter in the world.

Without that connection, you’re not really communicating anything meaningful. You’re just… saying things.

That idea stuck with me. And, apparently, it followed me into a 4th grade science fair.

The Question That Changes Everything

Instead of asking the usual, superficial questions to all my daughter’s classmates, I started asking a different one. After each student explained their experiment, I’d say something like, “That’s really interesting… so how are you going to take what you learned and use it in the world going forward?”

The responses were exactly what you’d expect from a bunch of fourth graders. In other words, mostly blank stares, nervous laughs, and some very creative attempts to answer a question they clearly had not been asked before.

My daughter, for what it’s worth, wasn’t thrilled.

“Daddyyyyyy… stoooooop…”

And, to be fair, that’s probably the correct response when your father decides to turn a 4th grade science fair into a philosophical exercise. But, awkward as it was, I couldn’t help thinking this is exactly the kind of question we should all get more comfortable asking.

For those kids, the experiment itself didn’t really matter…

And, for the freshman year version of me, the essay didn’t matter…

For my current students, the grade doesn’t matter…

At your job, how your boss responds to your presentation, whether the customers make a purchase, and even if you got passed over for a promotion after your annual review… none of it matters.

Or rather, none of that matters on its own.

What matters is what you do with those things. What do you learn from them? How are you going to apply them? How are they going to change the way you think, act, or move forward?

And I’m sharing this story of my daughter’s science fair because it’s a great reminder that the “So what?” is the thing we all tend to skip. We do the work, we have the experience, something good or bad happens, and then we move on without ever asking the one question that actually creates value: So what?

And it’s not our fault we don’t ask. It’s what we were taught… all the way back in elementary school. We were taught to focus on the “what,” but rarely do we get reminded to think about the “why?”

Just remember, “why?” is much more important than “what?” The “why?” is how you turn everything in life — the successes and the failures — from things that happen to you into things that help you create meaningful value.

In the Moment…

A helpful reframing for those moments where failure feels possible.

When something happens — especially something frustrating, confusing, or disappointing — you’ll naturally find yourself getting stuck reacting to the surface-level outcome.

When that happens, try asking:

• What actually happened here, beyond my initial reaction?

• What part of this is within my control, and what isn’t?

• What is this experience trying to teach me, even if it’s not obvious yet?

• If I look past whether this was “good” or “bad,” what’s actually useful here?

• What assumptions did I make that might not be true?

• If I had to go through this again, what would I pay more attention to?

• Where is the opportunity in this moment, even if it’s small?

These questions won’t change what happened, but they’ll change what you take from it, which is going to ultimately be more valuable..

The Debrief…

Reflecting on our experiences is where the most important learning happens.

After you’ve had some distance from an experience — good or bad — that’s usually the best time to go back and interrogate the outcomes more directly.

Try asking:

• So what did I actually learn from this?

• What, if anything, will I do differently going forward?

• How did this experience change the way I think about things?

• What patterns am I starting to notice in how I respond to situations like this?

• Where did I grow, even if the outcome wasn’t what I wanted?

• What part of this experience still feels unresolved, and why?

• How can I turn this into something useful, rather than something I just move past?

Remember that experiences, on their own, don’t create value. Value comes from reflection. And the simplest way to start reflecting is to ask two words we often avoid: “So what?”

The school year is ending here at Duke, which means it’s time for students to start getting upset with me for not giving them the grades they wanted.

The first of those complaints arrived within minutes of releasing grades. I posted them around midnight on Monday, and by 12:05 I already had an email. It was from a student who wrote to tell me she didn’t feel like her grade reflected how much she learned.

As I read her message, I honestly felt like I understood what she meant. Not necessarily about the grade itself — I still stand by how I evaluated her work — but about her broader point. The entire semester she’d been a smart, thoughtful contributor during class who improved over time. Unfortunately, her grade didn’t reflect that growth because she’d submitted a bunch of late assignments. As a result, I had to penalize her with a lower grade than some other students who likely “learned less” but had followed the rules.

And isn’t that weird? After all, school is supposed to be about learning. So why was the student who learned more being penalized with a lower grade?

The easy answer is to simply say, “grades suck.” And while that’s certainly true in lots of situations, in this particular case, I wonder if the actual issue isn’t grades at all. The real problem is misaligned incentives masquerading as failure.

When the System Rewards the Wrong Thing

Misaligned incentives show up everywhere. School is just one of the easiest places to see them. For most of the semester, we tell students that learning is the goal. But at the end, we translate everything into a single letter that carries major consequences. Naturally, students start treating the letter as though it’s more important than what it represents, and they start optimizing for grades.

Of course they do! It’s very clearly what the system is encouraging.

Similar things happen in companies, where employees are told to focus on long-term impact, but they get rewarded for short-term metrics. And at hospitals, where Doctors are told to prioritize patient care, but measured on efficiency. Even as a parent I find myself telling my kids I want them to be more independent, but then I intervene the moment something goes wrong.

In each case, the behavior that follows isn’t irrational. It’s perfectly aligned with the incentives. And this is where things get confusing because when misaligned incentives show up in our lives, they often feel like personal failures. They feel like you didn’t do enough… or perform well enough… or that you somehow missed the mark.

In those moments, what you’re experiencing aren’t failures of effort or ability (even though that’s how they seem). These are failures of alignment. You’re trying to care about one thing while being evaluated on another.

And the tension creates a kind of frustration that’s hard to explain, because, from the outside, everything looks like it’s working the way it’s supposed to. And yet, something still feels off.

Seeing the System for What It Is

To be clear, when these kinds of misalignment issues happen, I don’t mean to suggest the system is entirely wrong or that it needs to be torn down. Grades have their benefits. So do performance reviews, allowances, and any other types of evaluations and incentive systems encouraging certain types of behaviors. They provide structure, accountability, and a way to make decisions at scale.

But complex systems always have limits. Simply put, they can’t be everything to everyone all of the time. It’s just not possible. So rather than trying to fix the limitations, the best thing you can do is recognize them.

Once you see how a system is rewarding something specific — and that it might not perfectly align with what you personally value — you gain a powerful piece of separation from it. And while that separation doesn’t magically make the problematic rewards go away… grades will still matter, productivity matters, and so on… it’ll change how much meaning you attach to them. You’ll start to appreciate that the outcome only says something about how you performed within a particular system, but it doesn’t say everything about who you are or what you’re capable of.

More importantly, understanding the incentives of a system is what allows you to make more intentional decisions about how you behave inside of it. And that intentionality is what gives you the power.

In the Moment…

A helpful reframing for those moments where failure feels possible.

The next time you find yourself frustrated by an outcome that doesn’t seem to match the effort you put in, don’t automatically assume you failed. Instead, I want you to try asking yourself some of the following questions:

• What is this system actually rewarding?

• Am I optimizing for what I care about, or what’s being measured?

• Where are the incentives pushing my behavior, even subtly?

• If I continue on this path, what will I get better at... and is that what I want?

• What part of this outcome is within my control, and what part is driven by the structure of the system?

• If I were designing this system myself, what would I want it to reward?

• How can I engage with this system effectively without losing sight of what actually matters to me?

These questions won’t change the system, but they will change how you see it, which is the first step toward deciding how much power it should have over you.

The Debrief…

Reflecting on our experiences is where the most important learning happens.

After you’ve had some distance from one of these moments where the incentives don’t seem to match the purpose, you may get some additional value by reflecting on some of the following questions.

• Where did I feel tension between what I valued and what was being rewarded?

• How did I respond to that tension?

• Did I change my behavior to fit the system, or did I hold onto what mattered to me?

• What did I learn about how this system actually works?

• Where might I have more agency than I initially realized?

• If I encounter a similar situation again, what would I do differently?

• How can I better align my actions with my values, even within imperfect systems?

Remember, you don’t have to “fix” every “failure.” Sometimes you just need to understand them. And once you understand a system with misaligned incentives, you’re in a much better position to decide how you want to move forward without feeling so frustrated by it.

Last week at Duke, the school hosted an event called “Blue Devil Days.” It’s when the university invites all the admitted high schoolers to campus while they’re figuring out which college to attend.

Because these students are struggling with a tricky decision, and because more than a few of them recognize me as “that Duke professor from social media who likes giving unsolicited advice,” when they’ve seen me around campus, they’ve been stopping me to ask: “How do I know which school to choose?”

While I obviously have my biases about the best university, I try not to let that bias control my response. Instead, I’ve been taking the opportunity to help them see what kind of question they’re really asking.

Specifically, whether they realize it or not, the challenge they’re facing isn’t a “how do I choose the right college” issue. It’s more of a “life” issue that we all face at various points in time. And the decisions never get easier unless we learn to approach them the right way.

The Life You Didn’t Choose

I remember facing a similar type of choice back when I was deciding where to go for my PhD, I was wavering between SMU in Dallas and the University of Maryland, and even though I ultimately chose Maryland, I occasionally find myself wondering about the version of my life that might have come from going to Texas.

When I think about that version, it doesn’t feel like a worse life. It just feels like a different one.

Different city…

Different colleagues…

Different opportunities…

When I follow that thread far enough, I start imagining a world with a different wife, different kids… basically… different everything. In other words, the entire foundation of my life that currently exists basically wouldn’t have happened because of one decision.

No wonder these types of life-altering choices we all encounter from time to time can feel so stressful. They’re clearly bigger than “normal” choices.

I like to think of these bigger decisions as “fork in the road” moments. They’re the decisions where the stakes feel high, the options feel meaningful, and — most importantly — you feel like your future hinges on picking correctly. A fork in the road moment is basically choosing between two completely different worlds.

The Illusion of a “Right” Path

Every time I spoke with students about their college choices this past week, I tried helping them see how they were framing the decision the wrong way. They kept imagining they were supposed to be choosing the “right” school, but that’s not how fork in the road moments work. The options in front of you aren’t competing versions of the same life. They’re entirely different lives. And, as we all know, lives aren’t simply “good” or “bad.” They’re infinitely complex.

As a result, when we frame the biggest choices in life as “Which option is right?” we’re pretending the future is something we can predict and optimize as if there’s a version of our life already waiting for us at the end of each path, and our job is simply to pick the one that’s going to get us there.

But that’s not how life works. Our futures don’t exist yet. They’re waiting to be built, which means the biggest choices we make also create the most responsibility.

This increased responsibility is the part that makes fork in the road moments so important to understand properly. Once you realize a “right” answer doesn’t exist, you avoid thinking one option is going to result in “success” and the other will end in “failure.” Instead, you gain ownership over the outcome.

A fork in the road decision sets a direction, but you shape the outcome based on the effort you put in, the relationships you build, the opportunities you choose to pursue, and every other choice that follows… big and small.

In other words, the future you’re trying so hard to predict isn’t waiting for you at the end of the path. It’s something you’re going to create along the way. And while knowing all of that won’t necessarily make these types of difficult decisions feel less important, making them will hopefully feel less stressful because you’ll know the outcome isn’t predetermined. You can finally stop searching for a perfect answer and start focusing on what you’re going to do once you’ve made the choice.

In the Moment…

A helpful reframing for those moments where failure feels possible.

The next time you find yourself confronting a fork in the road moment, step number one is to stop asking yourself, “Which option is right?” That question makes the decision feel like a lottery ticket, which is creating lots of the stress. The best way to avoid this stress is by reframing the choice, which you can do by asking yourself some of the following questions:

• Which path am I most curious to explore?

• Which set of tradeoffs am I more willing to accept?

• Which environment feels like it will challenge me in a way I want to grow?

• If there’s no perfect answer, which choice feels most worth committing to?

• Which option feels more aligned with the kind of person I want to become?

• Where do I feel a sense of energy or pull, even if I can’t fully explain why?

• If both options were going to be hard in different ways, which kind of “hard” would I rather take on?

• Which path would I regret not exploring, even if it doesn’t work out?

• Where am I most likely to take action instead of waiting for things to happen?

• Which option gives me more opportunities to create something, rather than just consume what’s given?

These questions won’t remove the uncertainty. But don’t worry… that’s not the goal. The goal is to shift your focus away from trying to predict the future and toward choosing a direction you’re willing to invest in.

The Debrief…

Reflecting on our experiences is where the most important learning happens.

Once you’ve made a difficult, complex, fork in the road kind of choice and lived with it for a bit, the questions will naturally start to change. Obviously, you can’t reset the decision. But you also don’t need to. After all, at that point, the decision itself matters a lot less than what you’re doing with it. So instead of asking whether you picked the “right” path, try asking:

• What have I done so far to make this the right choice?

• Where have I been fully engaged, and where have I been holding back?

• What opportunities have I taken advantage of... and which ones have I ignored?

• Have I been building this path, or quietly second-guessing it?

• What has surprised me about this experience so far?

• What parts of this decision have been better than I expected? Worse?

• Where have I been waiting for things to happen instead of creating them?

• What relationships, habits, or routines am I building that will shape where this path leads?

• If I fully committed to this path starting today, what would I do differently?

• What would it look like to take more ownership over the outcome from here?

Remember, these questions aren’t about judging whether you made a good or bad decision. The decision was made, you can’t change it, and you can never know how the other choice(s) would have worked out.

Instead, now that you’re here, it’s time to recognize you’ve chosen a direction, so it’s time to focus on the outcome. That outcome is going to be shaped by your actions, so focus all of your attention and energy on those.

In general, I try to avoid having any opinions about my students’ love lives. However, because college campuses are basically the original version of Love Island, relationship drama occasionally finds its way into conversations I’m having with students, which is exactly what happened earlier this week when a couple of my students began complaining about their girlfriends.

Specifically, they were frustrated because their girlfriends didn’t think they were spending enough time with them.

Mind you, these weren’t students with lots of free time. They were student athletes, which meant early morning workouts, practices, games, team obligations, travel, and — somewhere in between all of that — trying to also be full-time college students. From their perspective, they were working their tails off just to keep everything afloat, and they didn’t have lots of extra time to give even if they wanted to.

Obviously, their girlfriends didn’t feel that way. From the perspective of their girlfriends, my students simply weren’t prioritizing them.

The Work No One Sees

Again, I try to avoid weighing in on student love lives, so I didn’t say anything directly to them. But, in my head, I found myself thinking about how their problem was basically the same issue that manifests from time to time in every relationship… romantic or otherwise. That issue is perspective.

In fact, I’m fairly convinced the vast majority of arguments and disagreements between people aren’t really about the surface-level disagreements at all. They’re about the gap between what one person experiences and what the other person can see.

For example, as I mentioned in a previous newsletter, I recently had to get a new roof put on my house. If you’ve ever had that done, you know replacing a roof creates lots of debris in the attic. So one morning, before heading to campus, I decided to clean it up.

I figured it would take maybe 20 or 30 minutes.

It did not.

It turned into a much bigger project, and, before I knew it, I’d spent over two hours crawling around the attic, cleaning up the aftermath of the roof replacement. By the time I finished, I was running late, so I rushed to get ready and hurried out the door.

Fast forward to later that evening, and the dishwasher hadn’t been emptied.

My wife was understandably annoyed. Couldn’t I have taken a few minutes to empty it before leaving that morning?

And just as quickly, I felt myself getting annoyed in return. It wasn’t like I was sitting on the couch drinking beer and watching sports. I had spent hours doing something that needed to get done. The dishwasher wasn’t ignored out of laziness — it was simply lower on the priority list that morning.

Not that she saw any of that. From her perspective, the dishwasher was still full, which meant, just like my students and their girlfriends, we weren’t actually arguing about the dishwasher. We were operating from completely different contexts.

What We Don’t See

I’m sharing these stories because they reflect one of the most common but quietest forms of failure. In both cases, even though nobody actually failed, we perceive failure and feel failure because we mistake what we can see for what’s actually true.

We see the unemptied dishwasher. We see the lack of time spent together. We see the outcomes. But we don’t see the effort, the tradeoffs, the invisible decisions that led to those outcomes. And because we don’t see those things, we fill in the gaps with our own assumptions.

“She didn’t care enough to do it.”

“He didn’t prioritize me.”

“They could have done more.”

Those stories feel real because they’re based on the only information we have access to. But they’re also incomplete. And the trickiest part is that this isn’t just something other people do to us. It’s something we do to them, too. Just like my wife couldn’t see the two hours I spent in the attic, I couldn’t see whatever context she was operating from when she noticed the dishwasher. And just like my students’ girlfriends couldn’t feel the exhaustion of a busy student athlete’s schedule, my students couldn’t fully understand what it felt like to be on the receiving end of that limited time.

Simply put, we’re all making judgments from inside our own experiences and then reacting as if we have the full picture.

We don’t.

Learning to fail, in this case, isn’t about proving you’re right or convincing someone else they’re wrong. It’s about recognizing you’re both working with incomplete information.

And sometimes the most productive move isn’t to explain yourself more clearly. It’s to get curious. To ask what you might be missing. To invite the other person to share what you can’t see. To acknowledge that there’s probably more going on than what’s immediately in front of you.

Because more often than we’d like to admit, the issue isn’t that someone doesn’t care. It’s that we’re all trying to understand each other from inside our own heads. And that’s a much harder problem than an unemptied dishwasher.

Seeing What You Can’t See

For this week’s failure challenge, I’d like you to revisit a recent moment where you felt frustrated with someone… a partner, a coworker, a friend, or even a stranger. But instead of replaying what happened and fixating on why they were wrong — which is our natural response — I want you to focus on a different question:

What might I not be seeing?

What effort might have gone into their side that you didn’t witness? What constraints might they have been dealing with? What tradeoffs might they have been making that never showed up in your version of the story?

To be clear, you don’t have to excuse their behavior or agree with their decisions. That’s not the goal. The goal is simply to recognize that your version of the situation is incomplete.

Also, if it feels appropriate — and this is where things might get a little uncomfortable — try asking them about it.

Remember, you’re not trying to challenge them or prove a point. You’re just trying to genuinely understand.

After all, learning to fail isn’t about getting better at being right. It’s about getting better at noticing how “right” and “wrong” aren’t nearly as obvious as we like to imagine.