OK, so how do you think?

Here’s an example from 2002, when I was running product at Google News. My friend Krishna built this script that crawled 15 sources and clustered stories by topic, using k-means clustering, which is an AI technique. We hired five news “sourcers” to find a comprehensive set of news sources from around the internet. There’s the obvious ones, but there’s others, like Layla’s Knitting News.

We started talking to some of the big sources, saying, “Look, we have this little tool. We don’t know if it’s going to become a thing.” The Times, Reuters, The Washington Post were hemming and hawing about whether to be in. They finally consented. I had decided once we had two or three, we’d just go.

So we just went ahead and crawled 4,000 sources and launched with all of them. We were prepared for a bunch of people asking to be taken out. But the opposite happened. By noon, we had 1,500 more sources, sources we hadn’t found, that now wanted in.

Right after that, we hired an attorney who had worked in news licensing. We ended up in a who’s-on-first conversation. He said, “How did you get 4,000 publishers signed up? All the demands from all those different companies must have been insane.” I was like, “We just put them in and let them opt out.” He was like, “No, no, no. I need to have the terms.” He thought we had negotiated 4,000 contracts. He’s like, “How many did you reach out to?” I was like, “Three.” He said, “No, no, no. You don’t understand what I’m asking.” I said, “I’m not sure I do know what you’re asking.”

You really didn’t get it.

I’m 26, 27 years old—and I’d never worked in news. I didn’t know anything. But that naivete was better than knowledge. The experience of that attorney would’ve gotten in the way of doing something like Google News. Inexperience can create innovation.

Decisionmaking is a mental process you take seriously. And you seem to embrace something most of us hate: being overwhelmed.

That’s true. It’s important to overwhelm yourself with options. You roll around in a lot of different choices, and get to know what you value and what you don’t—that overall prioritization. Yes, you’re going off your gut, but you first consider enough possibilities that the decision is well-informed.