A quick note first: Going forward, instead of every week, you’ll hear from me twice a month—one essay, one recommendations list. Glad you’re here.
I got an email recently from a reader who had a book idea.
“I’m working on a book. Would love your advice on getting it published.”
That was the whole email.
No context about the book. No sense of who she was writing for. No indication of whether she had done any research on her own, whether she wanted to self-publish or pursue a traditional deal, whether she had a platform, whether she’d written anything before.
I’ve received hundreds of emails like this. And I never know what to do with them—not because I’m withholding, but because there’s nothing to grab onto. To respond usefully, I’d have to ask a dozen clarifying questions first. I’d have to do the work she hadn’t done.
We’ve all heard the saying: It doesn’t hurt to ask.
The premise? The most you risk is silence or a simple “no.”
But that premise is wrong.
The worst outcome isn’t silence. It’s burning a bridge before you ever crossed it.
It doesn’t have to go that way.
Consider a different version of that same email.
“I’ve been writing online for two years and have a small but engaged following. I’ve read that non-fiction authors typically need a book proposal to land a traditional deal, and I’ve started outlining one. I’m stuck on defining my audience—I see two possible readers and I’m not sure which to build around. Would you be willing to tell me which of the two feels more relevant to you?”
This email would get a response from me. Not because it’s shorter—it’s actually longer. But because it shows the person did the work first. They’ve narrowed the field. They’re asking me to weigh in on a specific decision, not hand them a map of territory they haven’t explored yet.
You wouldn’t message your therapist friend: “I’m feeling bad, any thoughts?” or “Can you read the first 10 pages of my journal and let me know what you think?”
You’d never do it because you know those aren’t real questions—they’re outsourced problems. Yet those are exactly the kinds of asks that land in my inbox. Often from people who are themselves professionals—who bill for exactly this kind of expertise in their own work. People who would be quietly horrified to receive the same type of ask.
That asymmetry is hard to ignore. An unformed ask, whoever it comes from, quietly says: I didn’t really think about you before I reached out.
The most generous thing you can do before asking someone for something is to think about them first. What work is yours to do before you reach out? If you haven’t done that work, the ask isn’t ready to be sent yet.
That kind of consideration isn’t just polite. It’s rare.
And it’s the difference between a request that opens a door and one that quietly closes it.
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