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Indexing as Deep Work

Photo by Nathan Ziemanski on Unsplash

Deep work, as defined by Cal Newport in his book of the same title, is “professional activities performed in a state of distraction-free concentration that push your cognitive capabilities to their limit. These efforts create new value, improve your skill, and are hard to replicate.”

As I was reading Newport’s book on this topic, it struck me that indexing is ideally suited for deep work. Especially as I work as a full-time indexer, with often a handful of deadlines in a month, I need to spend several hours every day, sitting at my computer, indexing. I need to be able to see, understand, and hold in my mind both the overarching argument or structure of the book (as well as the overarching structure of the index) as well as the smaller details that flesh out that argument and structure. I am creating a document from scratch that to some extent is unique to me, in that other indexers would write their own variations. And the index will, I hope, add value to the book and for readers. It is not something that is easy to replicate. 

Newport identifies shallow work as being the opposite of deep work. This is work that is low value, non-cognitively demanding, and easily done by someone else. The trick, to reach professional goals or to simply stay on top of deadlines, is to focus on performing deep work—what does drive value—and to minimize or eliminate shallow work. 

I think this distinction between deep and shallow work also applies to indexing, and is highlighted by the contract nature of freelancing. Being a freelancer gives me a lot of freedom in how I use my time—which can be used poorly to read the news or watch Youtube videos. It also means that I need to be aware of and responsive to my email inbox, both for new project offers and to be responsive to existing clients. I would say this is all shallow work, because while I do need to communicate with clients and have a method for accepting new projects, I don’t get paid for checking email. While I do need some breaks throughout the day when I index, news and Youtube can serve as distractions and prove to be less effective as breaks if they are taking me away from indexing. While shallow work is not necessary bad, if we do not prioritize deep work and find ways to keep shallow work at bay during those times, then deep work is unlikely to happen.

So how to prioritize deep work?

Newport’s book has challenged me to rethink how I work. In particular, what are my distractions and how do I handle them? Distractions, even ones that seem fairly innocuous, pull you out of a state of concentration and it can take several minutes to return to the task at hand. This happening once isn’t too bad, but if it is repeated throughout the day those minutes can add up. In my experience, distractions also build upon each other. If I follow that sudden urge to check a fact on Wikipedia, I am likely to have subsequent sudden urges that will be harder to resist. I find distractions can also cause a lot of stress and anxiety, because while a part of me is enjoying the distraction, another part is aware that I am falling behind on the task I should be focused on, which creates a vicious cycle. The more anxious I become the more I seek distractions to sooth the anxiety.

As I have come to realize, the costs to the quality of the indexes I write, how quickly I can index, and the stress I inflict on myself through distractions are too high. At least, I do not want to pay them anymore. I know I can’t eliminate every single distraction, but I can do a lot to eliminate most of them, at least the ones that are self-inflicted. 

So far, I’ve come up with a few strategies to better facilitate deep work. Here are three of them:

  • I use the Freedom app to block myself from most news sites and blogs that I typically frequent. The only day I allow myself to browse these sites are Sundays. I have a different block for social media. This does not work perfectly as there are, of course, other news sites and blogs that I have not yet discovered (and which I subsequently have to block), but overall I do feel much more focused and less anxious. And to be honest, I find I don’t really miss the news. I still get a general sense of what is happening in the world from talking to other people and hearing snippets on the radio, and I have enough interesting things to focus on among my own work.
  • I have stopped checking email in the mornings, and I try to only check email twice in the afternoon. I have been surprised at the results. I have come to value my distraction-free mornings, which is when I can create my best and most important work. So far clients have not noticed or commented on slower replies.
  • I take a long break in the middle of the day. I go to the local YMCA, and depending on the day I either join a circuit training class or I swim. I also eat lunch. All of this takes about an hour and a half. What makes this work is that if I get out of bed on time, I have three hours of deep work in the morning, and then another three and a half hours of deep work in the afternoon. The exercise gives me a chance to rest my brain and recharge for the afternoon session.

These new habits do, I realize, introduce some inconveniences for myself and others. I am not likely to reply immediately to an email. There have been times my wife has forwarded me an interesting news article which I cannot read because of the internet blocks I have in place. Last Sunday, I was surprised to learn that the Super Bowl was happening, and realized I had completely missed the buildup. 

I think the trade-offs are worth it, though. If my clients are hiring me to index, and if indexing requires long periods of concentration, and if I want to produce quality indexes while also preserving time for rest in the evenings and on weekends, then I need to structure my workday and put safeguards in place to make sure that indexing happens in the scheduled hours. I wish I could say that I did not need these safeguards, but I have come to realize that I do. 

The questions are fairly simple: What are my priorities? How do I create lasting value for myself and for others? What do I need to do to make sure these happen?

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Making Friends with My Calendar

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Happy New Year! 

I hope your holiday festivities were heart-warming and restorative. My wife and I started ours with our car dying the night before we planned to hit the road, though the holidays did get better from there and we are thankful for a few days with family. 

I don’t usually make New Year resolutions. I think that is largely due to a fear of failure, and of not knowing how to actually implement these goals and aspirations. Change is hard. But I have been thinking recently: if there is one thing I could change this year that would have a significant impact on my life, what would that be? I have decided that that one thing is to make friends with my calendar.

What do I mean by that? Why do I often feel like my calendar is my enemy, or at least a puzzle that is impossible to decipher? There are a number of reasons. Especially as my business has grown in the last few years, I have often felt like my schedule controls me. I feel like I need to work on evenings and weekends in order to meet deadlines, which means making trade-offs with other activities that are also meaningful. I realize this may not be so much a scheduling problem so much as an I’m-accepting-too-much-work kind of problem, but either way it boils down to feeling out of control and overwhelmed.

The problem goes deeper, however, as I have struggled with setting schedules for myself since university. This seems counterintuitive, as I actually thrive on routine. And therein lies the problem, I think. My tendency, when I devise a schedule for myself, is to stick to it as rigidly as possible. Interruptions or other unplanned changes cause me to panic and get disoriented, and eventually I abandon the schedule for a more reactive, and stressful, mode of being. I seem to be in a bind where not having a schedule is not serving me well, yet my typical approach to scheduling and calendars is also not serving me well. I need to find a better way. 

So how do I become friends with my calendar? I mentioned this resolution to my wife, and she astutely pointed out that it is quite an abstract goal. 

I agree with her, and I am okay with that. I am realizing that my relationship to my calendar and schedule is multi-faceted. There is coming to terms with my years of fears, anxieties, and frustrations with schedules. There is learning how to productively handle changes within a schedule. There is finding a scheduling framework that seems to work for me. There is understanding my own biorhythms so that I am working with myself, rather than trying to cram myself into an artificial construct. All of this will take time to figure out and understand.

One book I have read recently is Make Time: How to Focus on What Matters Every Day, by Jake Knapp and John Zeratsky. What I appreciate so much about their book, compared to some others I have read about calendars and schedules, is their acknowledgement that everyone is different. They offer eighty-seven tactics to try, but fundamentally their approach is to experiment and be reflective about what works and what doesn’t. I found it incredibly freeing to realize that I don’t need to have the perfect schedule right away, but I can take time to develop it, and that setbacks along the way are part of the process. Indeed, as I age and other life events happen, my schedule will probably continue to evolve. 

The book also discusses a scheduling technique from Cal Newport, who wrote the book Deep Work. In this technique, you write a new schedule for yourself every day, and leave room to revise the schedule as needed. This provides a mechanism—which I have been sorely missing—to thoughtfully acknowledge that change can and will happen, and to recognize that the remaining time can still be reallocated and used productively. I’ve been trying this for a week now, and it has been a helpful tool for reflection. I have handled interruptions better, and on the flip side, it has also helped me stick to my schedule when I’ve been tempted to change for no good reason. 

Another new initiative I’ve been using for about six weeks now is to put up white board wall stickers in my work space. This has been a fantastic change for me. I think I am still learning just how tactile and visually-oriented I am, as I am enjoying both seeing my work on the wall and the physical labour of writing, crossing out, and erasing. Borrowing the concept of sprints and burndown charts from a book I indexed, I list all of my current projects for a two-week period so I have the constant visual reminder of what I need to accomplish. I also graph my progress each day, so I can see where I am with each project. The whiteboard is also a great space to brainstorm, to write notes, and to make lists. I use it every day.

I already have some ideas for what else I want to try this year to become more comfortable with my calendar. I am happy with some of the results so far, and I am sure more ideas will come up as I experiment and reflect. I am hopeful that 2019 will be the year I finally get a handle on my schedule. I wish you all the best in your endeavours this year too.

What are some of the ways or resources you use to keep your calendar in order?

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Three Indexing Mind Hacks

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It has so far been a busy summer. That means tight deadlines and renewed thoughts about how to be more efficient in my indexing process. I mean, indexing is tough. It is constant analysis, understanding what the text means and discerning how to make the text accessible to readers. If there is a way to simplify or expedite part of the process, it does make a difference on overall indexing time and cognitive load.

Learning how to effectively use indexing software is one approach that is commonly advocated for becoming more efficient. I agree, and I think there is more that I can learn with the software I use, Cindex. 

As I have written about earlier, practice is essential for becoming a more efficient indexer. I find so much about indexing is understanding the different ways a book can be structured, understanding the different ways an index can be structured and written, and understanding when to go with one approach versus another. For me, at least, the only way I can learn this is by doing, over and over again, and being mindful of what I am doing so that I can learn with each index. I think that I am more efficient now than I was even just a year ago. I hope to continue to improve. 

Recently, though, I have been thinking about three techniques I use. These are all ways to externalize and capture my thoughts so I do not have to keep everything in my mind all at once. 

Mind Mapping

Mind mapping is a way to quickly diagram relationships. I find this exercise most helpful for understanding difficult books. There is something about writing down the different components of an argument, and physically drawing lines between them, that boosts clarity. It can also be a way to see if I have captured the full scope of the book in the index, as I compare the mind map, based on the book, to the index. I have been finding it so helpful that I am starting to do a quick mind map for all indexes I write, usually before I start the final edit. It only takes about ten minutes, and it gives me an opportunity to reflect.

There is a website on mind mapping, if you want to learn more. Software is available, both free and for a price. I occasional use Scapple, but honestly, I usually just use a pen and a scrap piece of paper. 

Notes

Another technique I have used for years is keeping notes. I use Notes, a program on my MacBook. I have one note per project, and I simply keep a running list of whatever I want to remember for later. These are often notes about terminology, if I am trying to decide between two or three options. Or these can be questions for the author, or errors that I am finding which I want to share with the client. Sometimes I just free write, in order to understand a concept or a relationship. For some books, I will just have a couple of notes, while for others I’ll end up with a page or two. 

By making a note, I am removing the thought or question from my mind, and I am giving myself permission to move on, knowing that I will be able to come back later and resolve the issue. There is too much thinking going on while indexing to remember every last error I found and question I have, so writing the note down frees up a lot of cognitive space. This is also a recognition that for a lot of issues, I will not know the answer until I have read further in the book and seen how the issue is addressed elsewhere, or perhaps I do need to ask the author. In the meantime, I have to keep working, and making notes that I can refer to later allows me to do that.

Labels and Highlights

Coming back to indexing software, there is a feature in Cindex, the software I use, that I am appreciating more and more as a form of note-taking. This is the ability to label, or highlight, entries. I assume the same can be done in other programs, like Macrex and Sky. 

When I label entries, I am flagging the entry with a colour to remind myself to take action at a later date. I will often use two or three different colours to remind myself of different things. The most common is for an entry I might want to cut. Especially if space is tight for the index, it saves a lot of time at the end to be able to search for the labeled entries and hit delete for all of them. I use a different colour if I think I might want to remove subheadings. Another common reason is for entries I want to revisit, but I am afraid I will forget if it is not labeled. 

As with notes, using labels is about externalizing my thoughts so that I can put that thought away for later.

Working full time as an indexer is often about finding ways to be efficient, so we can maintain a full schedule without burning out. These are three mind hacks that I use to process my thoughts more efficiently, and to focus better without being distracted by a host of other thoughts. If you are an indexer, what techniques do you use? I am curious.

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How to Marinate an Index and Other Time Factors

“How long does it take to index a book, anyway?”

This is one of the most common questions I am asked by non-indexers. It is a fair question. What is this alchemy of words and numbers that I do from which an index is created? Do I actually have to read the whole book?

This is also an important question for editors and authors who are looking to hire an indexer. How much time does the production schedule need to allow for indexing? If a rush job is required, how rushed is reasonable?

To answer this question, I often say that I can complete most indexes in fifteen to twenty-five hours. These are hours spent at the computer, actively working on the index. This is true enough, in that I time myself and these are the numbers I get. But it is still a simplistic answer. A better answer is, if I have no other projects on the go, I can complete an index for a 200 page book in three days. Three long days, depending on the book’s content, but still, three days. A week is more comfortable for me, for most books. I currently index, on average, 4-5 books per month.  

Most of my clients, when they send me a project, give me two to four weeks to complete the index (different clients have different schedules). Occasionally I am asked to complete an index in less time, which I might be able to do, but I still prefer at least two weeks. Why is this? Does this not contradict what I wrote above about completing an index in three days? Even three days is a somewhat simplistic answer. There are a number of factors that affect how long it takes to write an index. 

Length and Complexity

Let’s start with the easiest factors. A long book will usually take longer to index than a short book. A more complex book—as in complexity in structure, argument, or subject matter—will also usually take longer to index than a simple book. This is usually the different between a book intended for a general audience and a book intended for a specialist or scholarly audience. If you are an author or editor, think about the audience for your book and how it is written, as well as the page or word count. That should give you an idea for how long it will take to write the index.

Overlapping Projects and Deadlines

Some indexers prefer to work on only one project at a time. I see value in that. It is easier on the mind to not have to switch back and forth between projects. For that reason I try not to work on more than two indexes at a time, though I am currently working on three. When I edit an index, I also tend to double down and not work on anything else until I am done, in order to maintain focus and to keep the big picture of the index in my mind. 

But still, I often do work on more than one index at a time. I also usually have one or more projects waiting on my desktop for me to start. This means what while I may have three weeks to complete an index, I am not actively working on that index everyday for those three weeks. I am sorry if this bursts your conception of how I work. Please know, however, that sometime in those three weeks I will write the best index for you that I can.  

Why do I work like this, with multiple overlapping projects? The main reason is that publishing schedules often change. When I book a project, I mark those dates on my calendar and I try to space projects in a reasonable way. I also believe that my clients are being sincere about the dates they give me. But, dates change. I may learn about changes a few weeks or a month in advance, or it might just be a few days. I have decided that in order to maintain a full schedule, so that a change of dates does not leave a big hole, it is worthwhile to have overlapping projects. Having two or more weeks to complete an index, while technically more time than I usually need, does allow me to work on more than one project at a time, as well as provides a cushion when schedules slip. 

Time to Think

This, in my opinion, is the most important factor when thinking about the time it takes to write an index. If I am indexing a short book that will take, say, eight hours, I could conceivably write the index in one day. But I would never want to do that. Why? Because that kind of compressed work does not give me time to think.

What do I mean by this? Surely I am thinking all throughout the indexing process. There is reading the text and understanding what it means. There is thinking at the micro level, about what main headings and subheadings to use, and how to word them. There is thinking at the macro level, about the index structure. Then there is the final edit, which is a different sort of thinking from reading the book and creating the initial entries. In order to edit with a freshed mind, I prefer to start editing the day after I finish reading the book. So, yes, a lot of thinking goes into the index. 

By time to think, I also mean time away from the index, time that is not captured in those eight hours. These are insights that come to me when I am at the gym, washing the dishes, or driving. Sometimes if I am stuck I will simply go for a walk, hoping that the break and the change in activity will stimulate my thinking. I find that these moments away from the index, when I give my subconscious a chance to hum along while I do something else, are crucial to writing the index. In a way, the index needs time to marinate. The index will be better for spacing the work out over a few days.

Time to Rest

Related to time to think is time to rest. This is both for within a project and between projects. Reading sixty or a hundred pages per day, and created index entries, is a lot of information to process. My mind often feels like mush at the end of the day, and I need to take time to rest so that I can do it again the next day. The same is true between projects, especially as I prefer, as I mentioned, to double down on editing to keep the big picture in my mind. This can make for some long days editing. Depending on how I am feeling, I might take the next day off, or at least work fewer hours, to give my mind a chance to recover.

Rush Jobs

I mentioned rush jobs at the beginning of this post and how they fit in. When a client asks for a rush job, it usually means that I am being asked at the last minute, and the index is due in a week or less. Given that I am already often working on a couple of indexes, I usually turn down rush jobs. If you are lucky, another project has slipped and I have an unexpected hole in my schedule, but that is usually the exception. The other exception is if I really want to work on the project, for whatever reason, or if I am doing it as a favour to the client, at which point I am probably working evenings and the weekend to fit it in.

Figuring out the time it takes to write an index is complicated. Being a freelancer and working with multiple clients means a fluid schedule. There are the deadlines, and then there is how I structure my days and weeks to actually meet those deadlines. If you are an author or editor, hopefully this blog post will give you a better understanding of what you are helping to set in motion when you say, please complete this index in two weeks.  If you are an indexer, what factors are at play for you?

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Plotter vs. Pantser? The Indexer Edition

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If you read my previous post on genre, I’d understand if you think that this is another post inspired by the When Words Collide writing festival that I attended mid-August. This post, however, was actually inspired by Larry Sweazy’s keynote address at the joint ASI/ISC indexing conference I attended in June. Summer is a great time for conferences.

You fiction writers may already be familiar with the terms plotter and pantser. They refer to how an author approaches the process of writing a story. Do you first plot out the story before writing, or do you start with a blank page and write by the seat of your pants? Larry Sweazy, who is both an established indexer and an award-winning fiction writer, adds a twist to this concept by applying it to indexing.

Pantsing an index is to read through the text and simultaneously create and input the terms into your indexing software, without prior reading or planning. To plot would be to read through the text, either the whole text or by chapter or section, mark it up so that you have an idea of what terms you want to use, and then create the terms in your indexing software based on your notes and rereading of the text.

There are excellent indexers who fall on both sides of this divide (just as there are excellent writers who swear by both). Pantsers say that they can always revise and finalize the index later, during the editing phase. Plotters take the view that they produce a better index, and have less editing to do, if they can first understand the text.

My take? I think a lot comes down to experience, though certainly work styles and how you process information are important too. When I first started to index, I would plot out the index, chapter by chapter. Eventually I started to pants. Part of my decision to change my indexing approach was from learning from other indexers that this was an actual, viable option. Time was also a factor. I was getting more work, feeling crunched, and wondered if pantsing would speed me up. The biggest factor for me, though, at least in terms of successfully transitioning to pantsing, was experience. I had indexed enough books to have a rough template in mind that I could use when indexing blind. I was confident that making a decision, and then revisiting that decision during the editing phase, was sufficient for creating an excellent index. Plotting added an extra step, in that I would make a decision while marking up the text, and then revisit that decision twice, while inputting the entry into the index, and again while editing. I decided that extra step wasn’t necessary.

Still, I sometimes do get a particularly difficult book to index, and for those books pantsing is not as effective. For those I may decide that I do need to do some plotting. Perhaps not pre-reading the entire book, but certain key sections that illuminate the whole.

I have also increased the number of notes I make for myself while I input the terms, which I skim when I am ready to begin editing. These are to remind me of potential trouble spots that I will want to revisit during the editing phase, or these notes serve as brainstorming of alternative terms, or of similar terms I am seeing in the index and want to mull over for which is best to use. I also sometimes use mind maps to help me organize and understand what I am reading. I find visualizing the relationships between terms to be a quick and effective way to understand the structure of the text and hence the index.

For the pantser, I think plotting can still play a role in certain circumstances. The trick is to recognize those circumstances, and adapt your indexing strategy accordingly.

Now as a writer, do I plot or pants? I have to admit that I usually plot. I can often get away with pantsing short works of nonfiction, but fiction is another story. Right now I am experimenting with different plotting techniques, seeing what works best for me. I wonder if this will change too as I gain experience.

And Larry Sweazy? A pantser all the way, in both writing and indexing. That man has it figured out, or, better said, doesn’t, but knows how to finish the project regardless.