Dealing with Setbacks

Ever doubted yourself when you’re trying to do something extremely challenging? Wondered why you’re putting yourself through painful feelings of inadequacy and moments of intense vulnerability when you could be safely binge-watching Netflix or curling up with a hot cup of tea and a bestselling novel?

If your answer is yes, you’re not alone. Every writer I’ve worked with has struggled with self-doubt, though some more than others, and everyone in their own way. Some worry about whether they have what it takes to write something other people will want to read. Others suffer from “imposter syndrome” and worry they aren’t “real” writers. They worry their work isn’t sufficiently clever or insightful or original to deserve anyone else’s attention.

As a book coach, one of my jobs is to help writers kick their doubt to the curb so they can get back to work.

But what if, as a coach, I’m the one suffering from self-doubt? Coaching a writer is challenging. Deciding what’s working and what isn’t in a manuscript is always a judgment call, and there are so many variables to consider when preparing feedback. Even if I manage to correctly identify the main trouble spots in a manuscript, I still have to decide what to provide feedback on first so I can help the writer target revisions in a way that will result in the most improvement in the least amount of time. And then, of course, there’s the writer’s personality and tolerance for critique to consider. How much feedback will be enough to make a difference, but not so much as to overwhelm? It can be tricky to find the right balance. Trickier still to have enough confidence, day after day, to be decisive.

This past week, a writer I’d been working with for over a year let me know she wasn’t happy about being asked to make (more) changes to her manuscript. How could I still be telling her, after a year of hard work, that there was more to cut and add? She needed to be done, she said. She thought she’d be getting ready to pitch to agents by now.

Her main goal wasn’t only to write the best book she could; she had hired me, a professional book coach, specifically to improve her chances of getting traditionally published. She’d already worked with two other editors, prior to seeking my help, and had revised her manuscript several times. So, this wasn’t a first draft we were talking about. Her frustration was understandable.

My skin started crawling with doubt. A year did seem like a very long time, especially for a manuscript the writer had once (well, twice) considered “done.” What kind of book coach works with a writer for a year—on revisions!—seemingly without getting them much closer to the finish line? Could I even tell her how much longer it was going to take? Did I even know what I was doing?

Doubt wouldn’t leave me alone. You have no business coaching writers. You should start looking for a new job. Baking bread, perhaps?

The more I thought about her situation, the worse I felt. I started having trouble sleeping. I lost my appetite. I needed to figure out what I’d done wrong, how I could make it up to this writer, and what I could do differently the next time. Not knowing how I’d failed her was driving me crazy.

Luckily, I have access to a coach of my own—a coach for book coaches— and she was very reassuring. She told me that revisions typically take three times longer than most writers initially estimate, and that doesn’t even include the time it takes for copyediting, proofreading and preparing a pitch. Revising is an iterative process, and it can take a long time to go through multiple rounds. Which is why, she said, I should have spent more time at the start of the project with the writer, developing a very clear plan and setting realistic expectations for the work that needed to be done.

Oh. Right. That made sense. I felt foolish for having missed what seemed obvious in hindsight.

For anyone who’s wondering how I could have been so clueless as to start a revision project without a plan, let me offer a brief defense. It’s not that I didn’t have any plan at all. I began with an evaluation of the manuscript and wrote a summary of what I saw as the strengths and weaknesses. The evaluation included suggestions for what could be done to improve the existing draft. The writer and I then spent several weeks discussing why she wanted to write the book, what the story was really about, what she was and wasn’t willing to do, and her level of commitment to the project. Once we had all those planning documents in place, she began the work of revising her story in 20-page increments, sending the revised pages to me for feedback.

The process seemed to be working, more or less, but in the back of my mind, I feared the small changes she was making wouldn’t be enough. We had a plan, but it wasn’t particularly strategic. (That was my biggest mistake.) I was trying to help her fix everything at once, and I was too afraid of being wrong, afraid I might make things worse if I asked her to change too much.

A few times, when I had questions about the story that would require changes to multiple scenes or chapters, I asked the writer to return to the initial planning documents to make sure the story hadn’t changed and was still on track. She wasn’t thrilled but changed the plot here and there, and then went back to revising. I continued to gently push and query and offer suggestions each week, hoping the cumulative effect of the changes would lead to a major improvement.

Unfortunately (but, in hindsight, predictably), when the major improvement didn’t materialize, both the writer and I ended up feeling frustrated and disappointed.

I think if I’d had more experience managing a revision project before I started working with this writer, I could have done a better job of coaching her. Instead, after many months of working together, I had to break the awful news that she wasn’t as close to being done as she’d hoped. It was a hard conversation to have, made even harder because we hadn’t had it sooner. If I’d helped her to prioritize the revisions—made sure she would be dealing with the major problems first, saving the smaller stuff for later, figuring out a set schedule for everything—she would have known what to expect and how much work was left to do. It wouldn’t have had to come as such a shock.

Realizing where I’d gone wrong, I wanted to go back in time and start over. I thought about quitting and referring the writer to another coach. I was at a low point and believed anyone would be better than me.

But that seemed cowardly. How could I keep telling writers that not doing everything perfectly the first time around was part of the process, if I didn’t apply that to my own work? I couldn’t allow myself to be derailed by a setback. I decided that even though I’d made a mistake, I could still try to do my best work going forward.

With help from my mentor, I pushed myself to stay in touch with the writer. We exchanged many emails and had several long conversations by phone, and that helped to clear the air. I asked if she’d be willing to re-examine the overall cause-and-effect trajectory of her story to figure out whether all the scenes she currently had in place were truly working to move the story forward, and she said yes. At my request, she sent me a 100-page document for feedback (even though our weekly max is usually 20 pages), and I spent hours working on it. We also set a target date for finishing.

To recover from the setback, I’ve devoted easily five times as many hours as I’d usually spend on a client, but it has been worth it. I can now go to sleep at night knowing I’ve done everything I could. The writer seems to have appreciated my honesty and extra effort, because she’s decided to stick with me. I’m grateful for the trust she’s placed in me and will work hard to avoid disappointing her.

No matter how good you are, as a writer or a coach, it’s unrealistic to expect your work to be flawless at all times. We’re all going to make mistakes, and we’re going to have times when we doubt ourselves and our abilities. That’s just life. But when doubt strikes, do you have a plan for dealing with it? Have you thought about how you’ll prevent a setback from kicking your legs out from under you and stopping you in your tracks?

I didn’t before, but I do now.

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