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The Leap - Part 4: Agent Big Fish

Last time, Gina got her first big break as a freelancer when the New York Times Magazine published her personal essay. Her plan, which was simply to get an impressive clip that might attract an agent's attention, more than paid off when an editor from Doubleday saw the piece and contacted her. As we'll see in this episode, that led to even more opportunities - and some harsh lessons.

The Leap
Part 4: Agent Big Fish

Question: What's the quickest way to have your manuscript rejected by a Doubleday editor who approached you after reading your essay in The New York Times Magazine?

The three-part answer:
1. Hire a big fish agent who treats you like plankton.
2. Ignore your instincts.
3. Rush your work to the editor.

Eight months before the Doubleday editor e-mailed me wondering, "Have you ever considered writing a book?" a former Hartford Courant colleague introduced me to a friend's agent, Big Fish. Ms. Fish thought my ideas for a book I had in mind were too "niche" for her interests but she liked my writing. "If you ever have anything that is general trade non-fiction," she wrote in a letter, "I'd be most interested in a proposal."

The Doubleday editor had expressed interest in the expansion of my essay along the lines of a memoir. Ten years earlier, as a cathartic exercise, I had written a collection of stories about painful episodes in my childhood but never with intent to publish. One of those became the piece that The New York Times Magazine published.

Pre-NWU, I simply would have phoned the Doubleday editor for an exploratory conversation to better understand what she had in mind. But at six months post-NWU, I had learned just enough about book publishing to be dangerous - to myself. Paranoid about the vagaries of the industry, I was convinced that without representation, Doubleday would at best, not take me seriously, or worse, take advantage of me financially at contract negotiation time.

My presumptions had run amok.

The good news: Through my union local, I met a fellow aspiring book author at a networking event in Amherst, Mass. She had experience with agents and impressed me as a clear-thinking person. So I asked her for help and received this stellar advice: Write a letter to Agent Big Fish. Remind her of her interest in your writing and then tell her about Doubleday. Fax. Wait 24 hours. "If you hear nothing by then," the writer said, "You don't want her."

Ms. Fish called me in three hours.

After reviewing my essays, Agent Fish said the problem was that, while each packed a wallop on its own, as a group, they didn't make a cohesive manuscript. She said that if I wanted her to send them to Doubleday as is, she would. But she felt that "with very little work" I could create the "connective tissue" required for a narrative thread.

The stand-alone power of my essays was exactly what I had intended. Though I cared deeply about the individual essays and had invested much of myself in them, I cared little for stringing them together. I had already told the story of my childhood the way I wanted to tell it - for myself, in 30 sharp snapshots. To unravel those individual threads and weave them together coherently would be no small task. But Agent Fish assured me that she had been in the industry long enough to know what editors sought.

I should have trusted my original impulse for writing the essays - one that came straight from the gut, not with an eye to the marketplace. I should have trusted the positive feedback I had received from scores of readers over 10 years, and from The New York Times Magazine editors. Instead, I forsook everything my intuition was hammering at me to do - send the essays to Doubleday in their original form - and instead followed the agent's advice. The Doubleday editor rejected my "memoir," which she accurately termed "a cobbling together" of essays.

I kicked myself, and went back to Agent Fish to re-pitch the book I really wanted to write. I rushed to complete a sample from the proposed manuscript before the editor could lose interest. Doubleday, and three other hefty publishers, rejected it.

Things went downhill from there. So enamored was I of Agent Fish's reputation and author roster that I had failed to conduct the due diligence that would have informed me sooner, rather than later, that she and I were not a good match. Though I wanted to believe that she held a sincere interest in my work, it became embarrassingly clear that I had hooked the Big Fish only because I was dangling the bait of a big publisher's interest.

When I sought advice for next steps from Agent Fish, she had disappeared, leaving in her wake only a "Dear Gina" letter that said my 15 minutes were up.

Look for the next episode of "The Leap" when Gina picks herself up, dusts herself off, and…?