Anti-Boring Doesn’t Mean What You Think It Does

At a recent Anti-Boring Certified Coach’s Hangout, one of our coaches admitted something a little shyly:

“I never tell my students I’m an Anti-Boring Coach.”

It wasn’t that she was embarrassed about the work or unsure of the methods. She’s deeply committed to this work as an academic and executive function coach, and she genuinely loves the Anti-Boring Toolkit.

It’s just that she had this small fear that a teenager would look her straight in the eye and say something like, “Weird. Because you’re kind of boring.”

First of all, ouch. I wanted to give this coach a big ol’ hug. She is sooooo not boring.

But also — this is exactly the kind of misunderstanding the phrase “Anti-Boring” can invite, and I want to take a moment to clear this up.

We have a new summer cohort of tutors, coaches, and teachers coming in to learn the Anti-Boring Toolkit after all, and I’d really love for them to feel confident calling themselves “Anti-Boring.”

So here’s the deal:

I didn’t coin the term to suggest that educators need to be endlessly entertaining, charismatic performers in front of students. Quite the opposite.

It’s not about the coach being the source of “non-boringness” in the room. Instead, it’s about students learning how to stop boring their own brains when they learn.

That distinction matters.

And it also points back to where the original Anti-Boring shenanigans began.

Where the name came from

Early in my coaching career, when I was trying to convince students that coaching could actually help them, I used to say, with complete sincerity:

“Work with me! I can make school fun for you.”

Oh, the side-eye I got.

Students looked at me like I had just said something wildly naive—or maybe even a little insulting.

How—how—can school be fun?!

I meant it honestly. But what teenager, especially one who has struggled in school, is going to believe that promise?

And they were right not to.

Let’s face it: schools as they currently exist are not built for the human brain.

Not even for neurotypical brains.

Much less for brains with learning differences.

And certainly not for students carrying identities that schools have historically marginalized—whether because of race, gender, sexuality, disability, culture, or class.

For many young people, school is not a place where they get to feel relaxed, understood, energized, or free to learn in ways that actually work for them.

So when some enthusiastic coach shows up promising to make it fun?

That side-eye is earned.

I respected that. Or maybe I was just trying to stop getting side-eyed by teenagers. Either way, I started experimenting with different language, that eventually morphed into:

“I can’t make school fun for you. But I can help you stop boring your own brain.”

That landed differently.

That students could work with.

And that is where “Anti-Boring” came from.

Not as a promise of entertainment, but as a promise of agency.

Not: I will make this fun for you. But: I will help you build what you need to make this work for yourself.

But wait…there’s more!

That was the origin story 15 years ago. But the more I’ve thought about it, the more I’ve realized that “anti-boring” is one of those ideas that keeps getting more interesting the longer you sit with it.

And recently it occurred to me: we have an origin story for the word, but we don’t really have a working definition for what it means in all its increasingly nuanced glory.

As I’ve been trying to write one, I’ve noticed there are several layers embedded in the phrase that keep revealing themselves the more I look at them.

So what follows is my thinking-in-progress about what it truly means to be “anti-boring” and committed to “anti-boring learning.”

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1. Attention with intention

At its core, anti-boring is attention with intention.

It’s the student learning to bring their attention to their work on purpose — not waiting for focus to magically appear, not hoping motivation shows up first, but actively directing attention in a way that feels chosen.

And it’s the coach doing the same thing in real time: paying attention to the student with intention, noticing what’s landing, what’s not, and what might be ready next.

It works in both directions at once — which is part of why this feels less like a technique and more like a way of being.

2. Genuine enthusiasm for brain-based study skills and executive function strategies

Anti-boring also has a very specific kind of energy to it: real curiosity about how learning actually works.

Not surface-level engagement tricks, but genuine interest in things like the study cycle, retrieval practice, habit formation, and executive function strategies — and the moment a student realizes these aren’t just abstract ideas, but tools they can actually use.

This is not performance. It’s nerdy, grounded enthusiasm for how brains learn. And students can feel the difference immediately.

3. Rooted in the belief that boredom is a rational response to compliance-based learning

At the next level, anti-boring rests on a particular interpretation of boredom.

Boredom isn’t a character flaw. It’s not laziness or lack of effort.

It’s a rational response to systems that ask many students to learn in ways that don’t match how they actually think, process, or engage.

So when a student disengages, the question shifts from “what’s wrong with this student?” to “what’s not fitting here?”

That small shift changes everything about how we respond.

4. Back to the beginning: helping students stop boring their own brains

And underneath all of it is the simplest version of the idea:

We are trying to help students stop boring their own brains.

Not by making everything entertaining or constantly engaging, but by giving students enough awareness, language, and tools to notice what actually helps them learn — and to act on it.

This is the shift I see over and over again: from “school is boring” to “I’m starting to understand how I can work with my own brain.”

And that shift is the point.

One story that brings it all together

Anti-Boring Certified coach Jessica Mintz had been working with a freshman student-athlete with ADHD for months.

He was juggling a lot, often overwhelmed, usually focused on whatever felt most urgent in the moment. Their sessions had a rhythm: habit tracking, immediate demands, triage. Whenever Jessica tried to introduce one of our anti-boring mini-lectures—bite-sized lessons about how the brain learns—he would shut it down.

Not yet.

Jessica offered. He said no.

Jessica offered again. He said no again.

Jessica, apparently, has both the patience of a saint and the persistence of a golden retriever.

So she kept offering.

Then one session, something shifted. He said yes.

She pulled out the Study Cycle—one of our Anti-boring mini-lectures on how retrieval practice actually works in real studying—and as they worked through it, something clicked. He realized he had never actually been using retrieval practice. Which suddenly explained…a lot. Including the repeated test struggles.

That insight didn’t stay contained.

He started to request Jessica’s feedback on his essays. Revising more deeply. Staying with assignments longer than he ever had before.

His dad later texted to say he had spent two hours after school revising on his own. Without prompting. Without pressure. Just because he wanted to improve.

We’re still not over it.

And what I love about this story is that it actually contains all four layers of “anti-boring at once.

• “Attention with intention” shows up in how Jessica stayed with him over time—never forcing, but never disappearing either.

• “Nerdy enthusiasm for the brain” shows up in the moment the concept finally lands and becomes usable.

• “Boredom as a rational response to compliance culture” shows up in how his earlier resistance is never treated as a flaw—just a signal that the timing wasn’t right yet.

• And the final shift is exactly what this work is about: a student starting to learn “how to not bore his own brain.”

Anti-boring. In every sense of the word.

Why I’m so proud of these coaches

I feel a deep kind of pride when I look at coaches like Jessica—and like the coach from the top of this story who felt shy calling herself “Anti-Boring.”

Both of these educators are true Anti-Boring Coaches. And I don’t just mean that as a credential. I mean it in the sense that they are actually living this work in real rooms, with real students, in real time.

And what stands out is not performance.

They are not trying to be the most engaging person in the room.

They are building the conditions where a student can re-enter engagement with themselves.

That’s the shift.

Not performance. Not personality. Not energy management.

Something more durable than that.

A way of being that makes it more likely a student will think: “Okay…maybe I can try this.”

And over time, that’s what starts to move students from “meh” to “motivated.”

Speaking of which…

Want to be anti-boring too?

If you’re an academic coach or executive function coach, and something about this feels familiar—or like a missing piece you’ve been circling—you’re not far off.

This is exactly what we’ll be unpacking together in our upcoming free webinar, From Meh to Motivated.

We’ll walk through five coaching moves that aren’t really “moves” at all—they’re ways of being that shift students from stuck to starting.

And maybe the bigger question underneath all of this is still the one we’ve been discussing:

If “anti-boring” is really a way of being rather than a technique…what part of that feels most alive or most challenging for you right now?

If you’d like, I’d genuinely love to hear what lands for you.

And if you’re curious to see how this comes alive in real coaching practice, you’re warmly invited to join us. Sign up for free here!