My somewhat insane work planning process

Brandon Crilley recently linked me into a post he did about planning his writing activity during the summer period (he supports his writing habit by being a teacher in the real world, so he has to use his “down time” as efficiently as possible). I responded that I would write a post about my somewhat insane planning methods. This is that post.

At one point, I used to plan like Brandon does—relatively short term, and focused on creating new words. Before I started doing this full time, and before I broke my “business” into traditional and indie publishing activity, that process completely worked for me. But once I started doing this full time, I felt like I should look at the problem differently. Then, once I started the indie route for some of my work, I quickly came to the realization that I needed to get serious about planning.

Part of the issue here is that I work in a squishy world where the product is an element of creativity, and sometimes that process is hard to truly predict (unless one has a very firm deadline). Another issue is that, while I know people who work serially (one thing at a time) I tend to have multiple projects going at any one time, and they tend to be in very different stages. I also write short stories and novels (and have a small degree of a life). But the real truth here is that life as a writer and an indie publisher can get pretty complicated at times. Everything is simple, but there are a billion moving parts and only one me, so the complexity of this process can get overwhelming if I’m not thinking clearly about where I am and where I’m going at any one moment.

I’m also a project manager at heart, which means I can handle almost any level of ambiguity as long as I can put it on a spreadsheet or a Gantt chart.

Anyway, here’s what I do.

Bottom line, I break my work into three separate plans:

1) Year-out Plan: a rolling behemoth that includes all projects I intend to get to in the next twelve months. This is updated every month, of course, with a new month added at the end.
2) Month-out Plan: Basically a focused look at the current (or next) month as defined by the Year-out plan.
3) A WIN (What’s Important Now) plan: A day-by-day plan for what I’m working on this week. I structure this based on things I need to focus on in order to meet the Month-out plan.

Let me touch on each of these in order.


I have evolved this approach over the past year. My goal was to find something fairly concise (fits on 1-2 pages) that can let me see all the work I want to accomplish, as well as the timing of when it needs to occur.

What I’ve come up with looks like this: (click to expand)

As you can see, to fit my goal for planning, I’ve abstracted the high-level tasks a writer does while writing short work and novels, and abstracted the high-level publishing tasks an indie publisher does to create, manage, and launch their products, then laid them all together as items on the vertical axis of a spreadsheet. I then used the horizontal axis as my time flow. This feels very much like a Gantt chart—which makes me happy.

In order to see my specific projects flow better, I color code each work I’m doing. My latest, for example, was completing a novel titled “The Knight Deception.” This book was color-coded in green. My next work is reconfiguring two SF novels (Stealing the Sun 1/2), this work is color-coded in orange and red. By using this scheme, I can see at a glance how projects should flow both through time, and the creation/production process as time moves along.

Month-out Plan:

My month-out plan is really just a focused look at the current month. For example, when I look at the July column of my Year-out plan, I see I really need to accomplish five things:

1) Review the plot and structure of my Stealing-the Sun project.
2) Get a serious kick-start on completing the first Stealing the Sun book (to finish in August)
3) Finish up work on my short story “Running Tribe” (itself another rewrite)
4) Develop the full concept (TOC, etc.) of the short story collection I intend to put out in November.
5) Make a final pass at the print design of the new print design I intend to use while releasing the print version of “Picasso’s Cat” from Skyfox.

WIN (What’s Important Now)

This is where the rubber meets the road. I call it a WIN plan in honor of my last boss’s boss (yes, Srikanth, I’m looking at you), who used this concept to focus the organization on things he thought were important to keep touch with. He used them for bigger, over-arching initiatives. I use the label to identify things that I truly must do now to achieve my longer term goals.

At the beginning of each week I break my tasks into what I intend to get done each day. Of course, I have a form for this. Sometimes, I break form, and just go with a blank sheet of paper, but I like the form because it reminds me of the various categories of my work, and (since I put “Word Creation” at the top) it makes it abundantly clear when I’m kidding myself about my writing. It’s very important that writers create new words on a routine basis, but I’m like most writers I know—quite capable of pretending that all sorts of stuff that doesn’t result in new words are actually “writing.”

Anyway, here’s my form: (click to expand)

On the whole, when I do this well, I find that I generally achieve my weekly expectations (plus more). In the cases where I miss my targets, I move them into the following week, which brings me too …

Managing the Process

Throughout my life as a project manager, some folks I worked with would give me grief about the basic idea of a plan. “It’s never right,” people would say. “You can’t plan for development. You can’t predict invention. You can’t constrain creation!” Or, for another example, I was once at a writer’s workshop, listening to another writer describe his planning methods (some of which I’ve cribbed for myself), when a pair of writers pointed out (with some gently hidden, but good-natured snark) that his plan didn’t include possible acts of nature in it.

Of course, they were all correct. But that’s not the point of a long-running plan at all.

A plan is just a plan. It is, by its very nature, the one way you can pretty much guarantee your project will not actually happen. I mean, seriously here … something is guaranteed to go wrong. Something will happen in a way you did not plan. This is the way of life. So you have to realize that by planning things, you’re not attempting to actually predict anything. Nobody, including me, cares if something happens exactly as I planned it or not. What I’m attempting to do is to think about things the surround my work, and manage them in whatever way is optimal for me at the moment. I’m creating a guiding framework that will let me control the way I adjust my course when change (positive and negative) occurs.

My experience is that I miss many of my specific daily plans, but just taking time to think about my goals and jot them down makes the process an exercise in swapping out work between days due to random issues rather than because I just didn’t do something. I also find that I have to adjust my annual plan about every two months to account for new projects or slippages that occur due to life changes (or due to my optimistic planning model—yes, I admit that I often think I can get more done in the big picture than I actually do, so I sometimes need to slip my “schedule” out).

This is just fine. No one ever really beats me for missing a deadline (and in fact, even in my corporate days, the fact that I could talk with my boss weeks and months ahead of a potential schedule slip made it all work out better). Of course, I want to hit my plan or exceed it. But to me the important part of having a plan is that it helps me make wise and proper decisions that lead me to my goals—not that it act as some kind of whipping device if I don’t.

A Final Word

So, there you have one writer’s semi-insane planning process. I need to admit that I don’t really stop here. I, like many other writers, I suspect, keep fairly detailed records on how I work. On another spreadsheet (naturally), I log the hours I work every day, and the words I write or rewrite. This is how I know, for example, that I’m working easily 50+ hours a week (even though it doesn’t feel like work a lot of the time). It’s how I know I’ve done about 680,000 words of work this year so far (130K new, 550K in some form of rewrite…there’s a whole ‘nother blog post waiting to happen there).

It’s important to me to track this level of work, too. It makes me feel better to know if I’m spending my time well–and, in fact, I find that when I’m feeling uncomfortable about life in general, I can often point to my charts and graphs and see that these moments correlate strongly to times when I’m not creating many new words…which is interesting enough, eh?

Perhaps, though, that discussion can also wait on its own long and boring blog post.

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  1. Project manager, indeed! I don’t think I’d call this semi-insane, man – I’m really impressed by this. As you saw on my post, my planning right now is very rudimentary, and definitely linear; I used to have a lot of projects on the go at once, since I enjoy dipping between multiple worlds, or writing a draft of a story, then letting it ferment while I write the draft of a different story, and then going back to the first one for rewrites. I found I was jumping too much and having trouble keeping track of things, but if I had a plan like yours, I’d be in business. I took a look at that Gantt chart, for example, and that definitely appeals to me.

    More than anything, I can see the necessity of having your layers of planning. And I hope others you follow you scope this out, since at least for me it’s the first concrete look I’ve gotten at how a writer/publisher might structure their time. I especially like that you have personal and life stuff factored in there, as well; it’s too easy to forget about home stuff between work and writing, and so factoring it into the same schedule, I imagine, makes it easier to balance both and not let one conflict with the other.

    Thanks for posting this, Ron. It was an awesome read.

  2. Oh nice.. .I like the spread sheet with the annual plan. I have kept trying to find calendars that work for me and none of them do for the full year but a spread sheet… yes… now when I have some time to waste, I’ll be setting up that template…

    Rubs hands and gets all excited because you know, spread sheets… (yes I’m weird).

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