I invite you to upgrade to a paid subscription. Paid subscribers have told me they have appreciated my thoughts & ideas in the past & would like to see more of them in the future. In addition, paid subscribers form their own community of folks investing in improving software design—theirs, their colleagues, & their profession. We’re all trying lots of new things these days. Even avoiding trying new tools has become its own skill. So, new is the new black. I’m also working with a variety of people. When I think about their approaches to situations they don’t understand, & when I think back on the best people I’ve ever worked with, common patterns emerge. There are better & worse ways to not understand. One of the things I love about consulting is how much I have to learn with each client. I didn’t know pizza shops did essentially all their business in 2 hours a day. I didn’t know that repositioning empty shipping containers is a big investment. I didn’t know printers call the ink colors “blue” & “red” even though they are officially cyan & magenta. Although I’m excited by vistas of ignorance, I’ve noticed that not everyone is. Some folks freeze. Or loop. Or lash out. So, for all you explorers of the not-yet-understood, here is how I’ve seen the most effective explorers approach The New. Thank you to sponsor Augment Code for bringing you this post. Augment has been busy making the genies more useful. They just released a model picker with support for GPT-5 and Claude Sonnet 4. Build with either (or both) while also leveraging Augment’s context engine. They’ve recently dropped a slew of other features (including a CLI in preview). Sign up today to start building with the AI Agent designed for professional developers and see where your augmented coding adventures take you. Don’t Understand, Making ProgressThis is my default state. I’m learning a new language, or a new programming paradigm, or a new approach to visualization. I don’t have that comforting sense that I know what’s going to happen next & I know what I’m going to do about it. I can’t explain the current situation to someone new. When I was a kid (early 70s) my dad would bring home books on computing. I would read them cover to cover, not “understanding” anything but still fascinated. I can probably dredge up details of the Burroughs 6700 instruction set if absolutely necessary. I still do that when I don’t understand. Read something. Don’t understand. Fine. That makes enough sense. Keep going. Show me another example. Another. This seems to be equivalent to that. Are they? Much of this phase looks like play. Your curiosity clues you into the pieces you’re almost ready to learn. Wait a minute, why is this any different than that? Could we rephrase this another way. Let’s try that again, but with a twist? Thinkie Naive Solution is my frequent friend. Why is this any more complicated than X (where X is something I do understand)? Either I have spotted simplicity or (more often) I have spotted complexity I need to learn about. The key to wading smoothly through Don’t Understand, Making Progress is gentle impatience. Okay, I got that, or I got enough of that to get enough of the next thing. Next. The best explorers just keep marching (until they don’t, which we’ll get to in a minute). Don’t Understand, Totally LostSometimes I pass from making progress to being totally lost. They look the same superficially. I’m doing a thing, then doing the next thing, then the next. The difference is that nothing is getting easier, nothing is looking familiar. I can keep going but it isn’t going to help. When I’m totally lost all I can do is step away. I need to trust that all those experiences are in the old noggin rattling around, connections are being made, maybe some day I’ll be able to come back to this. I use exercise, art, poker, naps, & talking to friends to help me reset. Some clear signs I’ve passed to Totally Lost:
If I notice any of these, it’s time to reset. About To UnderstandRemember I said that explorers keep marching until they don’t? There is a moment, an exciting, delicate moment, when all those bits & bobs are about to coalesce into a coherent picture. It’s like the explorer has been tracking big game, running to catch up, when suddenly the prey is in sight in the distance. Rather than continue gobbling new experiences, the best explorers slow to a saunter when they are about to understand, chew each thought before swallowing. This liminal moment is the payoff for me, the feeling of trembling anticipation. You can’t rush being about to understand. First you have to do the foundational work of the previous phases. Then your brain is going to latch on, the puzzle pieces are going to fall into place, exactly when they are ready, not when I am ready. Continue pushing, but gently. Sometimes I lose my nerve when I am about to understand. What if I can’t learn this? What if this is beyond me? What if all this excitement is setting me up for disappointment? I can descend into thoughtless busy work to distract myself from my fears. I can give up & switch gears. The thing is that moment of revelation wants to be born. It will bother me until I give it space. Better to acknowledge my fears & return to the work. Eureka!Once I finally understand (what a joyous feeling!) the work isn’t done. Now I need to integrate the understand into the rest of my thinking. I need to teach others what I’ve just discovered. Some useful Eureka exercises:
The real juice in an idea comes with community. Once I understand, the sooner I bring community into the picture the better. ConclusionThe hypothesis here is that not only can we learn new ideas (aka growth mindset) we can also get good at learning new ideas. The above is my first cut at reflecting on how I learn best & how those I’ve worked with who learn effectively learn best. On reviewing the above, it strikes me that the consistent key is self-awareness.
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