The Hardest Thing to Unlearn Is the Habit That Still Works

The Hardest Thing to Unlearn Is the Habit That Still Works

The habits that are easiest to break are the ones that are clearly failing you. If your approach stops producing results, there’s motivation built in. Something has to change or the problem doesn’t get solved. But the hardest habits to question, the ones that have the deepest roots, are the ones that are still working. Because when a habit is producing results, you’ve built your identity around it, and changing the habit feels like changing yourself. And you know, most people don’t actually want to change themselves. They want the results to be different while staying exactly the same.

I have a story about this that I’ve been sitting with for a long time. When I was in school, I doodled constantly. I was drawing during lectures, during reading, during almost everything that required me to sit still and pay attention. And my teachers hated this. They saw it as distraction, as me not taking things seriously, as some kind of behavioral problem that needed to be corrected. One teacher in particular was very clear about it, told me I needed to stop, that I was being disrespectful to the class by not paying full attention. And I remember being maybe sixteen and thinking, okay, I’ll try to stop, because the adult has authority and they’re telling me this is wrong.

But here’s what I didn’t understand then and what took me years to learn. The doodling wasn’t the problem. It was the solution. I have ADHD (diagnosed much later, and I’m 64 now, so we’re talking about a pretty significant delay in understanding). When I was sitting in class trying to just listen, my brain was scattered. There was too much input and not enough place for it to go. But when I was doodling, the motor task gave my brain something to do with the restless energy, and suddenly I could actually pay attention. The doodling was the thing that made attention possible. The teacher’s advice to stop doodling was telling me to remove the thing that made the whole system work.

I didn’t follow that advice, which turned out to be the right call, but for years I felt guilty about it. I thought I was getting away with something, breaking the rules in a way that happened to work out. It wasn’t until much later that I realized I wasn’t breaking the rules. I was following the rules of how my own brain actually works, not how it was supposed to work according to someone else’s understanding.

And this became one of the central things I’m always watching for in my teaching. Because every student has some version of this. Every student has some habit or approach that the system is telling them is wrong or insufficient, and yet it’s the only thing that actually allows them to do the work at all. But the students with the most resistance to changing their process are often the ones who are getting the best results with their current process. They’ve built an identity around being the kind of person who executes technically perfectly, or who works super fast, or who has beautiful intuition, or whatever the successful habit is. And then you’re asking them to try a different approach, and what that feels like is not “try a new tool,” it feels like “stop being good at what you’re good at.” It feels like you’re asking them to become worse at the thing they’ve built their entire relationship to their own competence around.

I saw this over and over in the classroom. A student would be producing technically excellent work, and I would point out that the work was shallow, that it was technically correct but creatively empty, and the student would look at me like I was asking them to fail. Because in their experience, technical excellence and creative depth were supposed to be aligned. If you did the work correctly, you were done. But that’s not actually how creativity works. Technical competence and creative depth are different skills, and often they’re in tension with each other. The habits that get you to technical excellence can actually be the same habits that keep you from creative growth.

So I would ask them to try a different process. Maybe instead of starting with the most refined version of their idea, start with the messiest version, let it be ugly and unfinished and wrong, and see what lives in that version. Or maybe instead of trusting their intuition about what looks good, trust the constraints of the exercise more than they trust themselves, see what happens if they follow the rules exactly before they break them. And the resistance would be palpable. Because I was asking them to temporarily become bad at what they were good at, in service of finding out if they could be good at something else.

Some of them did it. The ones who did almost always found something they didn’t know they were missing. They’d come back and say, okay, I understand now. The approach I was using was protecting me from making certain kinds of mistakes, but it was also protecting me from taking certain kinds of risks. And once I understood that, I could make an actual choice about when to use the protecting habit and when to step outside of it. That’s different from being told to stop doing something that works.

I’m dealing with this right now in my own work on a project to help serve my students better. I have habits built up over decades of teaching and designing, and some of them are working really well. I can design something quickly and it’ll be functional and people will use it. But I’m at a point in this work where that speed and that functionality aren’t actually the bottleneck anymore. The bottleneck is depth. It’s understanding the problem at a level that lets me see something no one else is seeing. And my fast, functional approach is actually keeping me from sitting with the mess and the contradiction and the uncertainty long enough to find that depth. So I’m having to deliberately slow myself down, deliberately make things worse before they can get better, deliberately step away from the habits that made me successful before.

It’s genuinely uncomfortable. Because success becomes a kind of identity armor. You know how to do this thing and it works, so you’re good at this thing, so you are a person who is good at this thing, and changing that feels like becoming a different person. But that’s exactly where growth lives. It lives in the space where you’re no longer executing your habits perfectly because you’re too busy learning something new.

The teachers who tried to take the doodling away from me, they didn’t understand that the problem wasn’t the doodling. The problem was a system that assumed everyone’s brain works the same way, and everyone’s creative process requires the same conditions. They were trying to fix a student who wasn’t broken. They were just working differently than the model assumed. It took me decades to not feel bad about that. And I don’t want my students to spend decades feeling bad about being different from the model.

The question I’m sitting with is this: what habit are you currently defending because it’s working well enough, when actually it might be the exact thing that’s keeping you from growing in a direction you want to go?