Chasing Ideas

Sometimes I have a whole aquarium of unfinished thoughts and half-baked ideas in my head. They tend to stay that way if I don’t do something about it. I can remember such an idea after years of not thinking about it, and it’s still half-baked. The only way I’ve found to develop it into a fully-baked idea or discover if it’s a dud (and finally discard it) is, you guessed it, writing about it.

Dump It on Paper (or Screen)

I suspect the same might be true for anything creative, like drawing or building something. I’ve experienced a similar trend while programming. I would have a fuzzy idea about what I want to code, but it wouldn’t develop further until I started coding.

It seems important to start creating without many assumptions about what the end product will be. I’ll probably discover most of it along the way and discard a lot of what I began with.

Sometimes I can write the whole thing in one sitting, and sometimes I need a few weeks to develop my thinking. Sleep seems to be a big part of it. I always wake up with a fresh perspective. Next time I need to solve a problem, I’ll think about it really hard and go take a nap.

Chasing Your Reading

Robin Hanson from Overcoming Bias writes about chasing your books and information:

Hunting has two main modes: searching and chasing. With searching you look for something to chase. With chasing, in contrast, you have a focus of attention that drives your actions. You may find something else worth chasing along the way, and then switch your focus to a new chase, but you’ll still maintain a focus.


So if you read to be intellectually productive, rather than just to fill your time, consider reading while chasing something, anything.

When I’m chasing, I’m constantly critical about what I read, looking up references and skipping to more relevant sections of a book or article. Always questioning whether what I’m reading is relevant to my quest or question, whether the author has something new/interesting to say.

Also, readers who chase have mental hooks in place, prepared to hang the knowledge they find in a specific place. I retain more info and integrate it better into my thinking. Readers who search are less likely to remember the points and lessons unless something really surprises them.

This morsel of wisdom felt like a church bell that rang “Truth!” in my head. I would often choose a book that everyone recommends, a niche classic that seemed interesting, but I wasn’t looking, wasn’t chasing for anything specific. Often I wouldn’t even finish those books. (It should go without saying that I’m talking about non-fiction here.)

Chasing Writing

I finally started implementing the chasing process with ideas in writing, after reading Paul Graham’s excellent essay on writing essays (hehe). Whenever a question is bothering me or I want to explore an idea, I would just start writing. But that’s only the beginning. Paul said:

Questions aren’t enough. An essay has to come up with answers. They don’t always, of course. Sometimes you start with a promising question and get nowhere. But those you don’t publish. Those are like experiments that get inconclusive results. An essay you publish ought to tell the reader something he didn’t already know.

Sometimes I have too many thoughts about a specific idea bouncing around inside my skull. It’s impossible to type coherent text in an orderly fashion, so I do a brain dump in the form of a 10-minute round of freewriting. I will give up mid-sentence if I can’t finish a thought. If I can’t translate my thoughts into language well, I will paraphrase and come back to it later.

Most of it would be garbage, but at least it would be out of the way. The few useful and interesting thought caterpillars get to go in the main text and become butterflies of meaning and insight.

The first draft is always messy. Sometimes my thinking process just reaches a dead-end and I have to go back and try a different route like Paul said:

Sometimes, like a river, one runs up against a wall. Then I do the same thing the river does: backtrack. At one point in this essay I found that after following a certain thread I ran out of ideas. I had to go back seven paragraphs and start over in another direction.

This can be frustrating at times. But even in a maze, dead ends improve my understanding of the whole and paint a clearer picture. Now I know where not to go anymore. Twists and turns are interesting. They captivate both creator and consumer. With time I learned to separate signal from noise and cut out something that won’t captivate my audience. Here’s Paul again on being interesting:

Err on the side of the river. An essay is not a reference work. […] I’d much rather read an essay that went off in an unexpected but interesting direction than one that plodded dutifully along a prescribed course.


So what’s interesting? For me, interesting means surprise. Interfaces, as Geoffrey James has said, should follow the principle of least astonishment. A button that looks like it will make a machine stop should make it stop, not speed up. Essays should do the opposite. Essays should aim for maximum surprise.

When to Chase an Idea?

The answer to this question is one of those unfinished thoughts I have that need to be explored. I have a feeling mindfulness plays a big part. You have to be tuned to certain signals from your mind. Some signals are so strong you can’t miss them, they roar inside your head, practically demanding attention. But it may take practice to become aware of the weaker ones that float just below the threshold of detection.

If you notice a ping from your awareness that says: “This is strange. There might be an idea here worth exploring.”, ask yourself the following questions:

Why did this experience stand out to you, personally?

Pay attention to things that elicit an emotional response from you. If something frustrates or angers you, makes you sad, compassionate or hopeful, it might be a pattern you should explore. Especially if you have to question taboos, the status quo, or “the way things have always worked around here”.

Was there something that surprised you?

There’s a huge chance that it will surprise other people as well. If this is something you’ve put a lot of thought in, it would definitely surprise people who don’t think about it often.

Do you remember a moment when something finally clicked for you?

By sharing a particular situation when it all came together for you, it could create a shortcut for someone who’s also in the same situation. Maybe you can open the door for others to make those connections faster.

Do you do things differently now as a result?

Ideas that cause change are always interesting. Contrast the before and after or track your results during a longer time period. Other people could want the same result.

Is this something others are likely to miss?

This is a big one. A lot of thinking patterns are inherited from our environment and can go on for a lifetime without being questioned. Some of the biggest breakthroughs happen behind curtains no-one thinks to look.

Is there a lot of misinformation? Is the information just not readily available?

If you know something that might be unavailable to others, don’t just say “Well that’s a shame.” Be the person who will clear the confusion or compile a repository of knowledge that others can draw from.

Final Thoughts

The more ideas you chase, the more ideas you’ll have. Thanks to neuroplasticity, your brain gets better at anything you start paying a lot of attention to. If that thing is digging around your mind, you’ll get progressively better at digging. Paul Graham again:

Collecting surprises is a similar process. The more anomalies you’ve seen, the more easily you’ll notice new ones. Which means, oddly enough, that as you grow older, life should become more and more surprising. When I was a kid, I used to think adults had it all figured out. I had it backwards. Kids are the ones who have it all figured out. They’re just mistaken.

Jot down anything that stands out in your head, especially if it’s just at the edge of your awareness, and explore it later. Have a list of things that surprised you. Otherwise, you tend to forget what sparked your interest and who knows when it will resurface again.

There’s a social component to this as well. Once you start chasing and sharing, people will come to you with questions. You won’t know all the answers. You’ll be on the chase again, maybe with a group of people this time. Or you’ll be the one with questions, asking people who might know answers. They could very well become mentors for you.

Now I’m off to chase that idea about mindfulness. 😉

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