Dave Barry wrote a humor column for the Miami Herald every week for 22 years. The vlogbrothers YouTube channel has averaged 10 videos per month since 2007. Homestar Runner is an entire universe of animated characters and stories spanning 2,000 videos that is written, drawn, voiced, and maintained by a team of three. Some creators make it look so easy.

I once sent to my list twice in one month and demanded that my wife recognize it as a lifetime achievement. And I’ve been a full-time writer for 12 years! The ability to come up with a neverending list of topics that clients and readers find interesting is, to me at least, orders of magnitude more valuable than being able to fire off 1,000 words every day (obviously both would be ideal but we can’t all be Hank Green). So that’s what I’ve focused on.

Generating a constant stream of ideas worth exploring, like writing output, is more about habits than hacks. I do not have any shortcuts to share on idea generation for the same reason that my appreciation of Cal Newport’s books has not turned me into a content factory. Reading about productivity only helps with becoming more productive insofar as it 1) exposes you to new habits to experiment with and 2) frames those ideas within the context of a pep talk that keeps you motivated to keep trying. And on those two items, at least, I can help.

Brainstorming is rarely productive

One of my favorite bits of etymological trivia is that the word “brainstorming” was invented in the 1860s to describe the uncomfortable panic associated with cognitive overload. The Rocky Mountain News used it to describe watching the silent movies of 1912 as a "breaking down of the brain under the cumbersome burden and the following mental disorders known as brain storms." This is my preferred definition of the word.

Actively focusing on the task of topic generation is, for me, a sort of mental bamboo finger trap. The harder I try, the harder it gets. It’s much easier to pull on the threads that are hiding in plain sight, all around me, all the time. And while it feels trite to recommend a scratchpad, analog or digital, for the out-of-nowhere questions to investigate and topics to write about, I think most people use scratchpads the wrong way. Not enough people take their scratchpad on runs or into the shower, for example, places where I am furthest from any “brainstorming” and therefore most likely to think of something original.

For some, it’s not so much connecting the dots that’s difficult as much as admitting they’ve noticed something interesting at all. “When you ask creative people how they did something, they feel a little guilty because they didn’t really do it, they just saw something.” Steve Jobs told Wired in 1996. “They were able to connect experiences they’ve had and synthesize new things. And the reason they were able to do that was that they've had more experiences or they have thought more about their experiences than other people.” It’s hard because the act of noticing and the habit of curiosity are next to impossible to measure or quantify. But they are things anyone can get better at!

“There is no Idea Dump, no Story Central, no Island of the Buried Bestsellers; good story ideas seem to come quite literally from nowhere, sailing at you right out of the empty sky,” Stephen King wrote in On Writing. “Your job isn't to find these ideas but to recognize them when they show up.” And he wrote that before Wikipedia, YouTube, and the Internet Archive gave us near-infinite research to reference.

While writing this article, the word “fecundity” (a richness of imagination or invention) kept coming up in my research. It’s a strange sounding word so I let myself get pulled away by its history. Etymonline.com includes Google Books’ Ngram View below definitions and I noticed the word exploded in usage from 1968 to 2008. Was it a waste to spend an hour trying to figure out why that was (seems to be largely related to its other definition, the power of producing offspring, and the book The Population Bomb that came out around the same time)? It was definitely more productive than an hour of staring at a blank page and asking myself what I should write about next.

When the Advanced Research Projects Agency asked Isaac Asimov to help a working group collaborate more creatively, he sent them his essay On Creativity, which argues that “The great ideas of the ages have come from people who weren’t paid to have great ideas, but were paid to be teachers or patent clerks or petty officials, or were not paid at all. The great ideas came as side issues.” This is good news and bad news. There is inspiration everywhere. You do not need trudge through social media or current events to find things to write about. But also, “noticing interesting things around me” isn’t something you can timebox. It’s not a habit you can track with red X’s on a calendar.

The things that have helped me the most are:

• Keeping a scratchpad handy when exercising or doing chores.
• Visiting sections of a bookstore or library that I’m usually not interested in (Kagi’s randomized Small Web scratches this itch too).
• Signing up for newsletter and RSS feeds that get in the weeds on my favorite topics.
• Avoiding algorithms and AI that by design do not expose to you anything novel.
• Following citations even when the quoted or referenced text sated my curiosity.
• Emailing or DM authors absolutely anything you’re curious about after reading their writing.

Above all else, if you want to have a steady stream of new ideas, you must read. “You cannot hope to sweep someone else away by the force of your writing until it has been done to you,” King wrote in On Writing. “If you don’t have time to read, you don’t have time to write.” It doesn’t have to be longform, serious, or even writing related to your work or area of expertise. More than once, bedtime stories with my daughter have led me to later look something up that ended up in my writing.

Still, as much as I deprioritize “active” topic generation, where you sit down and focus solely on synthesis, it is unavoidable. And although you could fill Borges’ Library of Babel (oh look, a rabbit hole) with books and research about the topic of purposeful ideation, only a handful of productive approaches have worked for me.

Never brainstorm alone

Multi-episode story arcs have always been off-limits for The Simpsons. That frees up the writers’ room to work on at least 10 different episodes simultaneously, with jokes often starting off in one script before hopping to another as story beats change and evolve through group collaboration.

Even when I’m working on a personal project, I share links, screenshots, quotes, and anything I find surprising with fellow writers. I almost always get back a “That reminds me of when…” or “Kind of like that time when…” No two people will connect the dots in the same way. And, if the deadline isn’t pressing, I can let the topic sit, confident that anyone who I’ve mentioned it to will circle back with more commentary later. This is a big part of why guest newslettering works so well.

It’s frightening to reach out to people directly when you’re an indie creator or self-published author just starting out. But there’s no harm in asking questions like “What do you think most people misunderstand about…” or “What’s the most surprising thing you’ve learned regarding…” Framing the conversation this way is more likely to get a response and is a filtering function for rabbit holes. One of my primary leading indicators for topic generation is how many strangers I’ve emailed with questions about something I’m interested in.

I reached out to popular rabbit-hole YouTuber Phil Edwards for this very article, in fact. I had no way to network to him and video is his domain while mine is blogging and newslettering. But he responded to my questions about how he comes up with ideas nonetheless. "My method is usually to constantly be thinking of ideas, writing them down, and then figuring out ways to cull them over time. The idea itself matters a lot more in my job than the execution on it," he told me. When I asked for his opinion on why esoteric and obscure knowledge can generate such broad and general interest nowadays, his response was one of my favorites from any recent interview: "People are always looking for a decoder ring for the world they live in, and as our systems and processes become increasingly complex and opaque, even diagnosing the truth about a paper cup or a playground can feel grounding." It's a wonderful time to dive into incredibly specific domains with your audience.

Whether it’s reaching out to someone I’ve never collaborated with or a close friend, I always try to keep active brainstorming narrowly constrained, like Dr. Seuss responding to his publisher’s bet that he couldn’t write Green Eggs and Ham using a vocabulary of only 50 distinct words (this link brought to you by a post-bedtime-story query). And the funny thing is, no matter how constrained my questions or prompts are, they’re surprisingly recyclable for unrelated articles down the road.

A few months ago, I interviewed Clive Thompson, a New York Times writer and creator of The Linkfest newsletter. The topic was how he’s kept his writing habit going, so consistently, for 20+ years. The constraint was to focus on specific tools, topics, and habits tied to specific audience sizes (“What did writing your newsletter look like when your list was 50 people?”). But revisiting it today, he had a lot to say about collaborative brainstorming with his readers. “Even the ones that I didn't meet, we just talked and talked and talked, thousands of words, and they would send me things. They would have pushback or ideas of what I'd written that strengthened or opened my mind in new ways.” Most of this happened asynchronously, proving that you don’t need a whiteboard or a mind map to come up with new topics.

I can’t remember the last time I sat down, alone, to come up with things I should write about. I either wait for inspiration from day-to-day activities, or I invite others to weigh in on some narrowly constrained prompt. For someone just getting started, I recommend that you:

• Email or interview at least three or four people per month.
• Ask friends and interviewees if they have suggestions for people you should reach out to.
• Encourage replies, no matter how off topic, to your articles and newsletters.
• Put boundaries around what topics you’ll cover, and make those restrictions your North Star.
• Segment off a portion of your scratchpad for questions you want to use during interviews.
• Reread your previous articles and newsletters, revisiting unfollowed rabbit holes.

Finally, any time you sit down to talk through topic generation with someone else, write up a post-brainstorming summary. Thompson emphasized during our interview that “research shows that the instant you write anything, even a sentence, two sentences, about something you've learned, you hold it in your mind in a different and better way.” It will slow the process down a tad, sure, but add incredible amounts of longevity and value to the output.

You contain multitudes (of topics)

Margaret Atwood filled two large storage boxes with real-world research for Oryx and Crake, her 11th novel. “Nobody knows where ideas come from, but let us say, if you immerse yourself in something, whether it be music, painting, or writing…you are going to get ideas about it.” That’s all it takes, really, being interested in something enough to spend time learning about it and asking people what surprised them most about it.

I could finish a lot more writing projects if I wasn’t always playing detective to the random combinations of ordinary goings-on. And, yes, sometimes it would be better to turn it off, to read Dr. Seuss to my daughter without reminding myself to research where he got his ideas. But overzealous curiosity isn’t the worst problem, all things considered. Especially when it pushes me to meet new people and keep in touch with all the rest I’ve met along the way.