There’s a particular kind of discomfort that comes from doing something you believe is wrong, on purpose, because someone you’ve never met wrote in a book that it’s actually right.
That was my experience for about three months after I started restructuring my practice sessions based on what I’d learned from “Art of Practice” and from observing naturals. Every single change I made triggered the same internal response: this can’t be right.
But it was right. And the gap between how it felt and what it produced taught me something fundamental about learning: your instincts about practice are almost perfectly calibrated to point you in the wrong direction.
The First Wrong Move: Starting Cold
The first counterintuitive change I implemented was starting every practice session with the technique I was worst at. No warm-up beyond the minimum needed to get my hands loose. No comfortable moves to build momentum. Just immediate, cold engagement with the thing I couldn’t do.
The first time I tried this, I sat down at the desk in my hotel room, picked up my deck, and went straight to a technique that had been giving me trouble for weeks. No preamble. No gradual build. Just the technique, right now, with stiff fingers and a brain that hadn’t yet settled into “practice mode.”
It was terrible. My first several attempts were worse than they’d been the previous day. My hands weren’t warmed up. My focus wasn’t sharp. I felt like I was sabotaging myself.
But here’s what I noticed after about ten minutes: my focus had sharpened dramatically. The challenge of the material itself had woken my brain up in a way that comfortable warm-up material never did. I was fully engaged not because I’d gradually ramped up, but because the difficulty demanded it immediately.
By the end of that first session, something had shifted. The technique I’d been struggling with showed a tiny but unmistakable improvement. Not because I’d had some epiphany about the mechanics. Because I’d given it twenty minutes of my sharpest attention instead of twenty minutes of my most depleted attention.
I kept doing it. For the first two weeks, every session started with the same uncomfortable jolt. But by the third week, I started looking forward to it. There was something oddly energizing about confronting your weakest point head-on, first thing. It was like cold-water swimming — the initial shock was brutal, but the clarity afterwards was remarkable.
The Second Wrong Move: Stopping Early
This one was harder to accept than starting cold, because it directly contradicted my consulting-forged work ethic.
In consulting, you don’t stop working because you feel tired. You stop working when the work is done. If you have two more hours of analysis to finish, you do two more hours. Fatigue is just a feeling. You push through it.
I’d transferred this mentality directly to my practice. If I’d blocked out two hours for practice, I practiced for two hours. Stopping after forty-five minutes because my concentration was fading felt like weakness.
“Art of Practice” told me the opposite: stopping when you hit the low-value energy phase isn’t weakness. It’s intelligence. Because those last sixty minutes of unfocused practice aren’t just unproductive — they can actively reinforce bad habits. When you practice with depleted focus, you’re training your hands to do imprecise versions of precise movements. You’re paving neural pathways to the wrong destination.
The first time I stopped a session after forty minutes because I felt my focus fading, I sat on the edge of my hotel bed feeling guilty. My brain kept saying: “You’ve only been at this for forty minutes. That’s not even an hour. Are you really going to quit?”
But I’d committed to trying the counterintuitive approach. So I stopped.
The next day, something remarkable happened. When I sat down to practice, I felt eager. Not dutiful, not disciplined — eager. Because the previous session hadn’t drained me. It had been intense and short and I’d ended it while I was still engaged, which meant my last memory of practice was focused intensity, not grinding exhaustion.
Over the following weeks, my practice sessions shortened from two hours to roughly fifty to sixty minutes. My progress accelerated. The math didn’t make sense until I realized: fifty minutes of focused practice contains more productive repetitions than two hours of progressively unfocused practice. I was doing less but achieving more.
The Third Wrong Move: Moving On Too Soon
This was the counterintuitive move that took the longest to trust.
I had a technique I’d been working on for about three weeks. I’d gotten it to roughly eighty-five to ninety percent consistency. Most of the time it worked. Sometimes it didn’t. My instinct was to keep grinding until it was perfect. One hundred percent. Reliable every single time.
“Art of Practice” said: move on. At ninety percent, the technique is almost comfortable. The adaptation signal — the stress that forces your brain to improve — has weakened to almost nothing. You could spend another three weeks grinding that last ten percent, or you could spend those three weeks on something harder and let the last ten percent resolve itself when you return.
This went against everything I believed about learning. You don’t build on an incomplete foundation. You don’t move to calculus before you’ve mastered algebra. You don’t advance before you’re ready.
But I tried it. I left the technique at ninety percent and moved to something significantly harder — a technique that was perhaps ten to fifteen percent beyond my current skill level. Something that made me fail more often than I succeeded.
The first week was psychologically brutal. I was failing at the new technique while simultaneously worrying that I was losing the old one. Every instinct told me to go back and shore up the foundation before attempting the next level.
I forced myself to stay the course.
After two weeks on the harder technique, I went back to the original one on a whim. I just wanted to check if I’d lost it. If the ninety percent had deteriorated to eighty or seventy.
It was at ninety-five percent. Without having practiced it once in two weeks, it had improved.
The book had explained why this happens — adapting to the higher level strengthens everything below it, like how training to lift forty kilograms doesn’t weaken your ability to lift thirty — but experiencing it firsthand was something else entirely. The rational explanation didn’t diminish the feeling that I’d witnessed something that shouldn’t be possible.
The Consulting Client Who Understood
I remember sitting with a client once — a tech company that was agonizing over whether to launch a new product before their existing one was “perfect.” They’d been polishing and refining and fixing edge cases for months. The product was at maybe ninety percent of where they wanted it to be. They could feel perfection just around the corner.
My advice: launch the existing product at ninety percent and redirect your engineering team to the next one.
“But it’s not ready,” the product manager said.
“It’s ninety percent ready. The last ten percent will take as long as the first ninety. Your competitors aren’t waiting for your perfection. Launch, learn from the market, and start building what’s next.”
They didn’t like it. It felt reckless. It felt like putting an unfinished product into the world.
They did it anyway. And the market feedback they got from launching the ninety-percent product was more valuable than any amount of internal polishing would have been. Meanwhile, the work on the next product made the engineering team better, and they went back and fixed the remaining issues on the first product with a level of skill they wouldn’t have had if they’d just kept grinding on it.
The parallel to practice was exact. Move on at ninety percent. Work on harder things. Come back and find that the easier thing has improved on its own. It’s the same principle whether you’re building software or building card skills.
The Accumulation of Wrong
Each of these counterintuitive moves was uncomfortable on its own. Together, they transformed my practice sessions into something that felt fundamentally alien.
My old sessions: long warm-up, comfortable material first, gradual difficulty increase, push through fatigue, don’t move on until perfection.
My new sessions: minimal warm-up, hardest material first, decreasing difficulty as energy fades, stop when focus drops, move on at ninety percent.
The two approaches were exact mirror images. And sitting with the new approach felt like wearing someone else’s clothes. Nothing fit quite right. Everything was slightly off. Every instinct nagged at me to go back to the old way.
What kept me going was the data. My own data. I was keeping a practice journal — a habit from consulting where you never implement a change without measuring the result — and the numbers were unambiguous. Progress on my weakest techniques had accelerated. The time to reach ninety percent on new techniques had shortened. My overall consistency across all techniques had improved.
The approach felt wrong. The results said otherwise.
Why This Matters Beyond Practice
I’ve come to believe that the counterintuitive gap — the space between what feels right and what works — exists in almost every domain of human performance.
In business, the intuitive strategies often fail while the counterintuitive ones succeed. In investing, the crowd is usually wrong at the extremes. In relationships, the instinct to control often backfires while the willingness to let go often strengthens.
Practice is just one theater where this dynamic plays out. But it’s a particularly clear one because the feedback loop is tight. You change your approach, you measure the results, you see the difference within weeks. In business or investing, the feedback loop can take years. In practice, it takes days.
This tight feedback loop is what finally convinced me that the counterintuitive approach wasn’t just theory. It was empirically better. Measurably better. Better in ways that my practice journal documented session by session.
The moves looked wrong. The moves felt wrong. The moves worked.
And once you’ve experienced that — once you’ve seen firsthand that your instincts about practice are reliably pointing in the wrong direction — something shifts in how you approach everything else. You start asking, “Is this the right move, or is it just the move that feels right?” And you learn that those are two very different questions.
The counterintuitive path doesn’t get comfortable. Even months in, every session started with a moment of resistance, a voice saying “this isn’t right.” But I’d learned to hear that voice as a signal. If it feels wrong, I might be on the right track. If it feels comfortable, I should probably worry.
That reframe — discomfort as signal, comfort as warning — became one of the most valuable things I took from this entire journey.