Confrontational Questions
We answered. Now who else should we ask?
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You’re peeking in on the email correspondence between Jade Chang and Ann Friedman, two best-selling authors (and friends!) who host workshops for writers. We spend so much time in conversation about the creative process that we thought we’d share some snippets with you. This newsletter is 100% free. If you, too, enjoy overthinking the writing life, please subscribe.
In this edition: We’re breaking with our normal BCC format. Instead, enjoy our dishy answers to some confrontational questions…
JADE: Here’s how it started: In the last, late hours of a dinner party, when just a few die-hard friends were lounging on the rug, someone said, “Let’s ask each other confrontational questions.” We were close enough and reckless enough to ask truly exhilarating things. Sample: “OK, now that you’ve won [redacted huge award] and you’re still not happy, do you think you’ll EVER be happy?” Yikes!
A few months later, when Ann and I were putting together the curriculum for our UNSTUCK workshop, I told her about this moment, and we co-opted the idea. Maybe a good confrontational question could jar our writers out of feeling stuck?
ANN: And it worked! We started each session with a confrontation, and workshop attendees used them as launchpads to approach their work in fresh ways. The format has been on our minds ever since, and we thought it would be fun to start a Confrontational Questions interview series. This is how we’re going to use our Instagram—for short, tell-all interviews with writers we love.
But we couldn’t make other writers answer them without first facing the questions ourselves…
ANN’S UP FIRST:
Why should other writers hate you? I mostly enjoy writing.
What’s the worst writing advice you’ve ever heard? Wait for inspiration to strike.
What kind of external validation do you wish didn’t matter to you (but totally does)? I want other writers to find my work interesting.
Do you have any writing superstitions? My words will be sloppy and floppy if I try to do serious writing in soft pants, no bra.
What’s a little detail you care about more than anyone else? I loathe an “I think.” You’re writing this—we know it’s what you think!! (This message is directed at my own first drafts.)
What are you bad at? I’m not sure I’ve ever been in a “flow state”? Well, maybe once or twice.
NOW JADE’S TURN:
Why should other writers hate you? A sip of beer activates my flow state.
What’s the worst writing advice you’ve ever heard? You must have a morning routine.
What kind of external validation do you wish didn’t matter to you (but totally does)? Residencies (because I’ve never gotten into one!)
Do you have any writing superstitions? I can’t actually write a new book unless I get a new laptop! (Might explain the decade between books)
What’s a little detail you care about more than anyone else? Overused metaphors! (I hate them with the fire of a thousand suns.)
What are you bad at? Transitions.
Speaking of transitions…hi again! We’d love your thoughts. Are there any questions you want answered? We think the key to a good confrontation is riding the line between a little risky and genuinely cancel-able.
What other writers should we confront with these questions? Let us know in the comments!
Before we go… a reminder: Early bird pricing for our 2026 workshops ends on December 13h! Check out UNFURL: 12 Weeks to Your First Full Draft with brilliant guest writers Angela Flournoy (author of National Book Award nominated The Wilderness) and Xochitl Gonzalez (Pulitzer finalist and author of Anita de Monte Laughs Last).
This has been a missive from Jade Chang and Ann Friedman, aka the Midwives of Invention. We’ll forward another one soon.
If you, too, enjoy overthinking the writing life, please subscribe. We’ll roam in your inbox 100% free, no paywalls. To join the conversation in real time, check out our upcoming workshops. We’d love to have you!
I both love a confrontation and am allergic to it. Either way I love this idea as an ice breaker/ exercise!
If you're not wearing a KN95 or N95 mask in indoor public settings, why aren't you? (This might sound snarky or like a gotcha but it's not! Covid is still out there wreaking havoc and everyone's just sick all the time but the propaganda worked so well that most people I know are just like * shrug emoji * isn't Covid over?)