Into the Wilderness

I was watching the playoff game between Alabama and Oklahoma. There was a guy on Alabama who committed a penalty and Head Coach Nick Saban went bananas. Threw his headset to the ground. Screamed at the player when he walked past him on the sidelines.

I sat on the couch thinking, "When's the last time I've been screamed at?" Or, maybe a better question, have I ever been screamed at with a Nick Saban level intensity?

The answer: Nope.

The world of writing, at least in terms of shouting matches, is about as far away as it gets from Alabama football.

But the process itself of preparing a book is surprisingly similar to trying to win a high stakes football game. Especially once you get into the editing stage of the project. At this point in the journey, the author has to become as obsessed with even the tiniest details in the same way Nick Saban strives for absolute perfection with his team. A misspelled word in your final draft is the writer's version of a 5-yard-penalty; it doesn't necessarily cost you the game, but it does make you want to throw your laptop out the window.

Even though your Supreme Court of Editors is not screaming their feedback at you, it can still feel pretty personal to hear or read through their honest notes. It's easy for the brain to interpret "Here's what you can improve upon" as "Here's what sucked." It's easy to look at 3-10 pages of notes and think, "Wow, is there anything I did right?" And then, the hardest one of all, separating the idea of "this rough draft is not ready" from "I'M not ready." This can easily spiral into the doubts of: Who am I to write a book? Just look at everything I screwed up.

These next 2-4 weeks (which can easily stretch out to be 2-4 months or 2-4 years) are the hardest part of the writing journey. You're going into the wilderness. The notes from your editors are your compass but circling around you are all the doubts and fears and reasons to quit/move on to something else. The wilderness is hard because it's a complete change in mindset. What worked in the rough draft stage was, "Just write! Doesn't matter if it's good or not, you only need to get the words down on the page!" What works in the wilderness stage is a little more intense. "Just write" becomes "Just edit" or "Just cut this part out entirely."

In the wilderness, your story can no longer be pampered. It's time to break some headsets Nick Saban style.

The good news: Yeah, it can be intense, but you can absolutely get through this next stage. I'll focus on a few things that have helped me out and some strategies I'm currently using with my next book, Here or There.

First thing's first: Your book is not fragile

When I first entered the wilderness, I carried my rough draft close to my chest as if one misstep could shatter the whole thing into a million little pieces.

This piece of advice will sound incredibly simple, but it's an important thing to remember as you begin to rewrite and revise:

Don't forget, you emailed a rough draft to all the people in your Supreme Court. Worst comes to worst, you can download that copy and start again.

At first, what tends to happen is writers look at their rough draft like it were the Mona Lisa. There's a ton of caution. The fear is that one bad edit will be like spilling paint, or drawing a mustache, and thus ruining the entire thing.

This fear could not be further from the truth. Go ahead and break things. This isn't about catching commas and making minor changes. Go bigger! Experiment with some major twists. Test out some more dramatic switches and see what happens.

For example, with my novel Toilet Bowl, the rough draft had Brad, Mark, Tim, and a fourth character named Adam. In the revision I asked, "Could Tim and Adam just merge into one character?" That was a big thing to change four years into the project. But I rewrote one scene and thought, "Hey, this kind of works."

Rewrote a few more chapters and realized something even bigger: this story worked better as a first-person narrative from Tim's perspective. Think about that, Tim went from being a supporting character ready to be merged with another to becoming the main character of the book. The one telling the whole story!

But, had that switch from four characters to three not worked out, that would have been okay too. I could have written a few of these chapters and decided, "You know what, this was a failed experiment. Adam needs to be a separate character."

It's never a waste of time to write these scenes. They almost always improve the book.

Rewriting vs. Revising (or "I thought I was almost done...")

I wrote that last part about Toilet Bowl as if it were good news. Four years in and I changed the whole thing and spent three more years rewriting the book. Isn't that great!?

One of the fears in the wilderness is that you'll discover something about the book that reveals you're not weeks away, but years away from being done. That you may have to rewrite the entire thing. This makes you feel like Odysseus being sent back to sea.

Couple thoughts on this. First, the Adam/Tim edit happened before the Supreme Court stage. By the time I sent it out to nine people, I had already rewritten the book from Tim's perspective.

If I had sent the book earlier, the feedback would have been things like: "I had trouble picturing Tim" or "I couldn't really picture Adam." I remember getting this exact feedback in 2010-11 from a Hope College professor but, at that point in time, I ignored it thinking that my way was right.

If you see a common theme of people saying that they're: "having trouble picturing" or "having trouble connecting with," these are signs that you have some rewriting ahead.

For non-fiction (and fiction too) one of the best things to measure at the editing stage is how long it took for your Supreme Court to get through the book and whether or not you heard from them during the process. Now, this isn't an exact science, because some people in the Supreme Court may be extra busy that month with life and work, but here are some signals to watch for that can help determine if your book is more in the "Full Rewrite" or "Revise a few things" stage.

• You give people a month or two to read the rough draft and, at the end of this timeline, you hear back from over 2/3 (or more) of the Supreme Court (Revise stage)
• You extend the reading window by a month. Then another month. You send out a few texts that say, "I hate to be this guy, but wondering if you could give me your notes by the end of the week? Just trying to start the editing stage." (Rewrite stage)
• Multiple people text you during the "reading month" with screenshots or quotes of a part they really liked. "I'm reading Chapter 16 right now, I was cracking up at this part." (Revise stage)
• The notes you get back are pretty vague. "I liked it." "I thought it was really pretty good." But not a lot of specific notes on what worked and what didn't. (Rewrite stage)
• People are sending you 1-2+ pages of notes with very specific adjustments. (Revise stage)

That last one feels counter-intuitive. Wouldn't 10+ pages of notes on what I should fix be a really bad sign? Look how much I did wrong...

But think about it this way, take something like Dancing With the Stars. For the bottom contestants, the feedback is never very specific. It's something like, "Hey, Grocery Store Joe, you tried" or "You know what, I liked this week's better than last week's."

For the top contestants, the judges are able to give more nuanced feedback. "Here's what you need to do with your feet at this point in the song." "For this type of step, you need to do this with your left elbow." Specific feedback is a sign that you are closer to the finish line. If your rough draft is still far away from being a final copy, then your readers will likely be giving more of the vague, hey-nice-job type of feedback.

Or ghosting the follow-up emails entirely...

Avoid the checklist mentality

When you receive the notes, it's easy to get into a grocery store checklist mentality. You have the list pulled up on one monitor, manuscript on the other. In Chapter 2, you wrote this, I think you should do this. Alright. Head to that paragraph. Make a change. Check. What's next? What's next?

Since you'll be spending a few weeks editing, it's important not to lose the creative mindset. Come up with some new scenes to write just for fun. For Toilet Bowl, I thought, "Hey, what if I did one when the guys were in middle school at a basketball camp." I had no idea where it would fit in the story, but it was a nice break from the paragraph and sentence level editing. This middle school scene ended up going in the final draft of the book.

And a couple other scenes didn't make the cut. Maybe they'll go into another book. Who knows. But the main point of doing these extra scenes is so you can continue the practice of creating things from scratch, even if you find yourself in more of a Final Revision stage of the project.

Here's a quick in-the-weeds tip for editing

As you move from rewriting to revising, to now revising at the real granular level (chasing commas and grammar, the real Nick Saban-y obsessive stuff), here's a trick that might help.

Print out a chapter of your book and cut each paragraph out (or edit copy paste into another Word file). Shuffle the paragraphs around then edit each paragraph one at a time, out of order. When you see the paragraphs and sentences in this way, you are no longer thinking about how they fit into the overall story. You're only looking at the small things within a sentence. For example, f I were looking at this exact paragraph, I wouldn't be thinking about the overall post, I'd be looking at the sentence "Shuffle the paragraphs around then edit paragraph one at a time" and trying to determine, "Do I put a comma after around? Yes? No?"

A good copy editor can help tremendously with this part. Definitely worth the investment, because it becomes harder to spot small mistakes the more times you have read and re-read your scenes.

This is one person's favorite chapter, another person said it was one of their least favorites. What should I do?

This can happen with characters too. You get mixed opinions from your Supreme Court. Who's right? Who's wrong?

A good place to start is assume that both people are right. At least in the beginning.

Even though it wasn't specifically about writing, I found this quote helpful from an article in the Harvard Business Review.

According to Flagship Pioneering founder and CEO Noubar Afeyan, “Early in our explorations. We don’t ask, ‘Is this true?’ Or ‘Is there data to support this idea.’ Instead, we ask ourselves what if this were true?’ Or ‘If only this were true, would it be valuable?’” Out of this process teams are expected to formulate testable venture hypotheses.

So, let's apply this rule to the wilderness. In Here or There, one editor really liked the chapter "Embarrassment is the Emotional Terrorist." Another said it was their absolute least favorite. With each reviewer, I go ahead and apply the "What if this were true?" rule.

"It's one of my favorite chapters."

Great. This is affirmation that it should stay in the book.

"It's one of my least favorite chapters."

Alright. Something about it is not working. Can I revise it? Are there paragraphs I can cut out? Do I need to make any parts more clear?

The result: A more polished chapter that remains one person's favorite and likely goes up the list for the other editor.

The chapters I worry about are the ones that don't show up on either person's "favorite" or "least favorite" list. Look at sketches on SNL. One person might love David S. Pumpkins, the other thought it was stupid. That's secretly a good spot to be as the writer. The ones that fall in the, "Wait, which one was that again?" are more at risk of being cut because there's no emotional connection.

One more example. A member of the Supreme Court suggested turning Here or There into two separate 100-page books. I started with the idea, "Ok, what if this is true?" And experimented with what that would look like. I even got to this "Ah ha!" moment where I agreed I should totally do it. One would be called Here or There, the other called The Master Cup. One is more philosophical. One is more comedic. And then marketing wise it'd be great because both books start with strong first chapters and I could AB test, and, and, and...

I shared the idea with my mom and dad (loyal members of the Supreme Court) and they didn't agree with the switch.

"One thing I like is having those comedic chapters to break up the more philosophical ones," my dad said. "It'd be too heavy the other way around. It works to have the contrast."

Again, two competing opinions. One book. Two books. Both can't be right. So, I weigh them side-by-side and then make a final decision.

For Here or There, I'm siding with my Mom and Dad, doing it as one book. But, because I gave the other opinion a fair shot, I now have a reason behind my ultimate decision. It went from, "I dunno, I just figured it would be better as one book" to, "I think the balance of philosophy and comedy will make the book work as a whole." Now I can obsess over the table of contents to make sure the order fits this comedy-philosophy-comedy flow.

This will sound a little Simon Sinek-y here, but it's a lot easier to hold a conviction once you figured out why you believe it in the first place.

And, if I'm wrong about this change, I can always go back to the email I sent out a couple months ago to the Supreme Court, download the file, and start over.

It's okay to get a little lost in the wilderness.

Hey, this is Chris with Long Overdue. If you're thinking about writing a book for the first time, I think the best place to start is actually with a blog. The blog helps you come up with a bunch of ideas, practice the craft of writing, get comfortable with hitting publish, and maybe even stumble into a book like I had with Here or There. I'm launching a blog writing class end of January called "Starting Five." If you're interested in learning more, please connect/message me on LinkedIn.

Previous posts in this series:

A Blog is Your Whiskey Distillery

Step One: Take Six Weeks Off

Biggest Fan, Toughest Critic

Some of the best Feedback is Behind Your Back