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Learning to Fail · May 7, 2026

When the System Isn’t Properly Aligned

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Aaron Dinin · Learning to Fail

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.

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.

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.

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.

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.

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