If you've been upset by something you read in The New York Times' Style section, that was by design. "[The] Style desk covers change, it covers generational change, it covers change in how we talk about gender, it covers young people," says the section's editor, Choire Sicha. "It covers technology, and it covers love, marriage and how we look. Those are all things that are incredibly fraught at this time, and they're supposed to upset people."

Inter-generational conflict is a hot topic (even before the paper of record revealed the collective Gen Z eyeroll that is "OK boomer").

So is the massive cross-industry known as wellness. But how do you cover that responsibly?

"We're not talking about people's parents or people from the outside, we're talking to people and for people who actually do this stuff," Sicha said. "The Times historically will have been one step removed from that, which sounds funny to call out, but that is what we did: 'Hey, what are those kids doing in their bedrooms?' And it's like, 'We need to go in the bedrooms.' That sounds weird, but you know what I mean."

Sicha joined the Digiday Podcast to talk about the freedom that comes with being funded by 4.9 million subscribers, his own take on Gen Z and how he feels about the end of Deadspin.