How One Editor Built a Career by Wondering ‘Why’

Conventional wisdom says that trying to make a living in publishing is a rough road. We read constantly about the death of print media and that the gig economy has decimated freelance writing. You might have as much chance of being a Hollywood actor or playing in the NBA as to be a working writer or editor who can pay the bills, right?

And yet some people are succeeding in building careers as writers and editors. So how do they do it?

One example is James daSilva, who I’ve known for nine years and who I worked with at SmartBrief. He oversees SmartBrief’s leadership and management content, and I talked to him about how he built his career.

For James it all comes down to pursuing his curiosity, and cultivating it. He has been curious about the world, about his audience and about other people in his professional orbit. And most importantly, he was curious to see where that curiosity would take him.

Here’s what his journey to successful editor looks like.

Discovering His Curiosity

James says he knew early on that he wanted to work at a newspaper. “Growing up, we got USA Today, we got the local paper, we got The New York Times on Sundays. So there were a lot of newspapers around,” he says.

James consumed these papers and discovered he loved finding out what was going on — in his community, in the world, anywhere. But what interested him even more was the “why.”

“I love finding out why something is happening — not just the what is happening, but the why is it happening,” he says. “And I like being able to help other people learn about that — ideally without just bothering them — and I've always found that the editing side for me was much more the route that I wanted to do. … I didn't keep a journal. I was just constantly looking at words and examining sentences and comparing what I was reading.”

Most people who imagine making a living in the business of words jump to being a writer, but James says he never really seriously entertained that idea. “I don't really have that same spark to necessarily say, ‘Hey, let me go write something like that,’ ” he says. “... I think there's a lot of stuff about writing that I don't naturally have.”

Instead, he says, he has found that editing allows him empathize with the curiosity of others. "I would say the editor skill set, especially specifically in my work, is being able to set myself outside of just my own head about how other people might read [something], about what other people might want to find out about it.”

Finding New Worlds of Wonder

James says he double-majored in communications and philosophy in college, and that the philosophy classes have played a key role in his career.

“I took semester-long classes where we got through one book, if that, but we just dug into every chapter, every section and every line: ‘What does this mean, and why does it matter that it's written this way versus being written some other way?’ So the philosophy aspect was really very much about a couple things: The literal editing and understanding the words, but also thinking through ‘What are you about? What are you trying to argue here?’ Those two things I got a lot out of from those philosophy classes.”

After college, James put his skills and interests to work on the copy desk of a small newspaper in upstate New York. “The most important thing that has served me well was having a curiosity about what other people are doing — and by other people, that can literally mean anyone in the company and even beyond the organization,” he says. “From the beginning, I wanted to know ‘How do the reporters work?’ I wanted to learn their voices so that I could edit them better. If I had to rewrite their words, I wanted to be in their voice, so I was curious about them.

“I was curious about how the printing process worked. Why couldn't we do inside color reliably? How did the mailroom work, which was helpful if a reader called and said they didn't get the paper. Who would I talk to about that? … I got to be on the editorial board and that was a very interesting thing to see how that process worked.

“That curiosity, I think, both makes you aware of opportunities internally but also makes you a prime person that people look to when an opening opens, because most of my career is just people leaving and then me inheriting stuff.”

Looking for What’s Fresh

James says he applies the lessons of curiosity to the content he oversees every day. “Nobody cares if I run a story on a company doing X or Y,” he says. “But if I run something about how to get better,” then people are interested. “I think that gets back to the differentiation. If you just put a list of fairly agreeable concepts without any depth, they already know that. They can't do anything with that. It doesn't mean that I go at my audience and just tell them ‘You're doing everything wrong.’ It's more about ‘Hey, what if you tried this, or have you thought about this?’ ”

He says he ran a story on better sleep recently that got tons of clicks because it offered something surprising. “I'd rather somebody take one of those ideas, write 700 words on it, and show me that you have some new take on it or even write something that your audience might disagree with. That at least will force people to think about it,” he says.