witter’s main constraint is encouraging concision. It’s hard to dwell on word choice when you have so little space to work with. Twitter’s conversational tone also helps here—I can just write like I talk, and any fancy words would seem out of place. And of course, I can’t tweak fonts and margins, which cuts off a distraction vector.

each idea has to be wrapped in a little atomic package. I find this helpful for figuring out the boundaries between my thoughts and clarifying the discrete units of an argument.

a thread is linear! No indenting allowed. This forces a brisk straightline through the argument, instead of getting mired in the fine points of the sub-sub-sub-arguments of the first idea.

I think Twitter is useless for persuading a skeptical reader; there’s simply not space for providing enough detail and context.

I prefer to use Twitter as a way to workshop ideas with sympathetic parties who already have enough context to share my excitement about the ideas.

Overall, it seems that we want constraints that help keep us on track with fluid thought, but don’t rule out too many interesting possibilities. Considering both of these criteria together is a subtle balancing act, and I don’t see easy answers.

low barrier to finishing. On Twitter, a single sentence is a completely acceptable unit of publication. Anything beyond that is sort of a bonus. In contrast, most of my blog posts go unpublished because I fear they’re not complete, or not good enough in some dimension. These unpublished drafts are obviously far more complete than a single tweet, but because they’re on a blog, they don’t feel “done,” and it’s hard to overcome the fear of sharing.

This seems like a crucial part of sketching tools: when you make a sketch, it should be understood that your idea is immature, and feel safe to share it in that state. There’s a time and a place for polished, deeply thorough artifacts… and it’s not Twitter! Everyone knows you just did a quick sketch.

I believe that quantity leads to quality. The students who make more pots in ceramics class improve faster than the students who obsess over making a single perfect pot. A tool with a built-in low barrier to finishing makes it easier to overcome the fear, do more work, and share it at an earlier stage.

For me, Twitter does an oddly good job at simulating the thrilling creative energy of a whiteboarding session. People pop in and out of the conversation offering insights; trees and sub-trees form riffing off of earlier points.

I’m curious to think more about the constraints/freedoms afforded by different kinds of creative tools, and whether we could get more clever with those constraints to enable new kinds of sketching. I’m especially curious about kinds of sketching which are only possible thanks to computers, and couldn’t have been done with paper and pen.

Imagine, for example, that you were thinking of starting Netflix back when it was founded in 1997. How would content providers, distribution channels, and competitors respond? How soon would technology develop to open a hidden door and let you distribute online instead of by mail? Or consider Dropbox in 2007. Dozens of cloud storage companies had been started before. What mistakes had they made? How would incumbents like Amazon and Google respond? How would new platforms like mobile affect you?

When you’re starting out, it’s impossible to completely map out the idea maze. But there are some places you can look for help: History. If your idea has been tried before (and almost all good ideas have), you should figure out what the previous attempts did right and wrong. A lot of this knowledge exists only in the brains of practitioners, which is one of many reasons why “stealth mode” is a bad idea. The benefits of learning about the maze generally far outweigh the risks of having your idea stolen. Analogy. You can also build the maze by analogy to similar businesses. If you are building a “peer economy” company it can be useful to look at what Airbnb did right. If you are building a marketplace you should understand eBay’s beginnings. Etc.

Your best thinking is when you are fully engaged in the stuff in front of you, connecting it to other stuff—and finding your unique perspective amongst it all.

Meaningful additions to the world rest on novel connections among pre-existing concepts, objects and situations, not self-indulgent originality for its own sake. What we glorify as flashes of brilliance are usually astute observations about the world, improved by critical thinking and critique. And observations often begin from a question.

because many of us have been rewarded and praised for having right answers and clever ideas, in school as well as in professional life, the questioning and critiquing part of design can get very uncomfortable.

A quick and effective fix is to stop brainstorming ideas with your team, and start brainstorming questions instead. Getting together and listing every question you can think of about a problem, a process, or a situation is uncomfortable at first, and then in very short order enhances collaboration, decreases risk and puts you on the path to being a learning organization.