The Truth About Connecting Online: Tips for Book Country Writers from Amy Webb

Posted by March 25th, 2014

DATA A Love Story coverThe awful truth about connecting with strangers online is that it’s hard. Plume Books author Amy Webb wrote a hilariously honest book about just what a huge task it was to try to find a husband online: The memoir is called DATA: A Love Story, and it combines two things Book Country is highly engaged in: understanding what drives people to connect online, and of course, great writing!

Brandi and I both loved the book and wanted to hear more from Amy, who’s not just a top-notch nonfiction writer but also a brilliant digital media strategist (and a now-happily married wife and mom).


Lucy Silag: Did you start writing DATA: A Love Story by drafting, or did you come up with a nonfiction book proposal? How did you organize yourself in terms of writing chapters, meeting publisher deadlines, and revising?

Amy Webb: I was very fortunate to have worked with Sam Freedman when I was a student in the Columbia University Graduate School of Journalism. Sam teaches a class that he hand-picks. It involves an audition, an interview and a lot of writing — that’s before the semester begins. The purpose of the class is to work on longform narrative nonfiction, and part of that process involves learning how to write a compelling book proposal. So in terms of my process, I followed what I learned in his class. I started out as a journalist, and while reporting and writing is something that I still enjoy doing, developing a book wasn’t necessarily in my 2012 client calendar. I had to essentially treat the book as a project and schedule out the time for it.

I’ve always worked from extremely detailed outlines. I started with a map of the basic elements of the book, then filled that in and had a final outline that was more than 200 pages long. I’ve found that for me, if I do the right kind of thinking in advance, putting together the story in writing is a lot easier. I kept an elaborate spreadsheet in Google docs, and I shared my work schedule with my editor, the marketing team at Penguin and my husband. So once I knew what my deadline was, I plugged the work into the spreadsheet. I wanted my editor to read and comment on the detailed outline before I sat down to write the book — it would be better to make any structural changes earlier in the process, rather than after handing in a finished 400-page draft. Many of the revisions therefore happened during the detailed outline.

I’m not one of those people who can sit down and wait for the words to come. I’m also not satisfied with getting one great page done a day. I work best with deadlines and structure, even if both are totally self-imposed.

LS: In your memoir you were candid about taboos like cigarette smoking, which a lot of readers might not relate to.  Were you ever tempted to avoid details that might turn people off?

AW: I think a lot of readers will relate to cigarette smoking. Or a different skeleton hidden somewhere. Being relatable, showing flaws — this evokes relatable emotion in a lot of people. If anything, being honest with one of my flaws, I knew, would draw them into the book. It is a very public book about a lot of issues that are private. I only shared the details that I was comfortable with other people knowing. There is plenty of me left that people know nothing about. But again, my book is memoir. The best memoirs are those in which you as a reader can place yourself, and hopefully learn something in the process.

LS: There are a lot of books about husband-finding marketed to heterosexual women. I haven’t seen another as forthright and specific as yours.  Were you conscious of the genre your book was about to become a part of?

AW: So here’s a lesson about publishing that I learned. Books do better when they’re not square pegs in genre holes. I’ve always seen this book as reported memoir. I didn’t write it as a self-help guide, or a s a reference book about finding a husband. The New York Times did a story about my book and a few others last year, talking specifically about a new kind of memoir category: self-help. I don’t see my book as a self-help story, either. I was asked by the publisher to add int the few pages of how-to tips at the end, which to be honest I was against. I think that not having a set, easily-defined category was probably a disadvantage to all of the various marketing efforts. Amazon doesn’t even have the category right — it’s tagged as a Web 2.0 book in the computer section.

LS: Can we interpret your work as an argument for women to be more specific (and less hypocritical) about what they want in a husband?

AW: Women should absolutely be more specific when looking for a mate, but I’d argue that the same is true for job hunting or even getting published. They should be more specific, they should feel more empowered, and they should see themselves as equals.

LS: Our members use Book Country to find writers to work with (not people to date—that we know of!), but I feel like you could probably give us some great tips on what to avoid in our member profiles.

AW: One of the biggest problems is in oversharing. People who spill way too many details too early. Long profiles don’t fare well. Those that create curiosity gaps, that cause an insatiable desire in the reader to learn more, do much better. In essence, writing great copy for a dating profile is just like writing any great marketing copy. Who, exactly are you targeting and what will draw that audience to the product? Except in this case, you’re the product you’re trying to sell.

LS: One nugget of wisdom from your book was learning how popular women on dating sites weren’t afraid to make the first move. Should Book Country members who want to find a writing community send similar messages to the ones you learned to send in your book: “I like that you [detail from profile]. I’m interested in [detail] too.” Would this work for a writing community, too?

AW: It’s fascinating to me that digital media has polarized our communication style. Some people look into their screens and become absolutely paralyzed — they can’t initiate a conversation, for fear of rejection, being ignored, exploiting their own privacy and the like. Yet these people would probably strike up a great conversation if they were sitting next to you at a conference. Meantime, other people post content continuously without any regard as to who might be on the receiving end. Would they walk up to a person the real world and say “Hey! You! Pay attention to me! Look at my shoes! I got them on sale! Hey! Look!”

The hardest thing for most people to do online is to just act normally, like they would in real life. The easiest way to get the ball rolling is to nudge it. Reach out, explain why you’re contacting another member (for example, you think their book looks interesting), and offer something specific (a review trade).

About Amy Webb

Amy Webb author photoAmy Webb is an award winning journalist who wrote for Newsweek, The Wall Street Journal, and other publications before founding Webbmedia Group, a digital-strategy consultancy that works with Fortune 500 companies, major media companies and foundations, the government, and others. You can learn more about the scope of her work by watching her swizzle reel, and you can also watch her chat with the ladies of The View about DATA: A Love Story here. Amy also did a TED Talk about her experience of online dating that you can watch here. Connect with Amy on Twitter and her website. Follow Plume Books on Twitter, too.

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