Article
May 13, 2019
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by Stephen

Should Freelance Work Come with Trigger Warnings?

Photo by Skitterphoto from Pexels

I laughed when I first came up with the title for this blog post. It was a laugh at how absurd the title sounded, and also a laugh of recognition. Suddenly this issue was starting to crystallize into words.

Work seems so innocuous, being something we do everyday. How can indexing or proofreading hurt me? Yet I have worked on the occasional project that provoked painful memories or fears, and which in hindsight I should have declined.

Taking a step back from the term “trigger warning,” there is also work which is simply emotionally difficult to process. It may not trigger a sharp or personal response, but it can still be emotionally draining. I remember the indexers for the Canadian Truth and Reconciliation Commission report, about residential schools, commenting on the emotional weight of their work.

I am not quite sure what to say about this subject. It is deeply personal; how I react to a text will likely be different from how someone else reacts. I am also no expert on mental health. Still, I think it is a subject that is at least worth mentioning. Freelancers are still people, after all, underneath our professionalism.

I know I am certainly tempted at times to take on projects with difficult content. Sometimes it is for the income, while sometimes I tell myself that as a professional I should be able to handle anything. In reality, though, the professional course of action would be to recognize my own limitations and try to screen projects accordingly. Catching an emotional curveball is not worth the few hundred dollars that may accompany it or the effects that that turmoil might have on the rest of my schedule and life.

At times it may not be the book itself which is so problematic, but rather something else happening in my life which is causing me to be less emotionally resilient at that particular time. And then there are the projects that seem innocuous, and which turn out to be very different, in a bad way, from what I anticipated.

I find that I am getting better at handling these types of difficult projects. The first line of defense, as I mentioned, is to try and screen projects and turn down ones that seems to be too much or not right for me at this time. It is important to recognize here that just because a book may be triggering or emotionally heavy does not mean that it is necessarily a bad book. It may be a very important book about a difficult subject, like the Truth and Reconciliation report. So I try not to blame the project itself, but simply recognize that not every project is a good fit. Also, knowing that what I find difficult may be fine for someone else can provide permission for passing a project along. 

If I do accept a difficult project, either by accident or because I think I can handle it, there are a few ways to make the work easier. I try to cut myself some slack by breaking the work into smaller chunks, while also taking more breaks to rest and process what I am reading. Acknowledging my emotions, instead of burying them under a professional veneer, can help with setting the emotions aside so I can focus. Keeping the ultimate purpose of the book in mind, if I think the book has something valuable to offer, can also help me stay focused, as I do want to contribute to the greater good. It can also help to remember that this is just one project and will soon be over—I will outlive the work. 

Be kind to yourself. Be honest about what is doable and what is too much. Get help or support if you need it. Keep the project in perspective. If you find yourself with an emotionally difficult project, you can get through it.

Article
April 14, 2019
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by Stephen

Mastery Before Speed

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I have been reminding myself recently to not get frustrated over my slow progress writing fiction. 

It has been a dream of mine since I was a kid to be a writer. In grade four I managed to turn a two-page story assignment into an epic that was at least ten pages long. I am not sure now if it was ever finished, as I remember hiding on the top floor of our house the morning it was due in a frantic last-minute attempt to finish.

Yet I have to remind myself that I still have a lot to learn about how to tell a good story, and that I do have a day job, after all. I am not going to publish a book overnight. 

And yet, I get frustrated.

If I can lean into the frustration, though, it is a good opportunity to focus on mastery. 

The need for mastery was first drilled into me my first summer tree planting. Tree planters are paid by the tree, and since prices averaged ten or eleven cents, it was in our best interest to plant fast. Yet speed without proper technique (by which my foreman meant planting a tree in a single fluid motion before striding three steps to plant the next tree) and the ability to read the ground (to find the best spot to plant the tree in) isn’t really speed. Sure, you’d be faster than someone who was slow and had poor technique, but the best combination was technique first and then speed. 

I see this too with indexing, both in my own career and in some of the new indexers I talk to. Since freelancing is (usually) for employment and income—and for some people, they do not have a backup source of income—speed is often seen as key to success. But attempting to go fast without mastering the basics is usually going to lead to greater stress and more time wasted trying to fix errors made in haste. I do believe that newer indexers are capable to writing great indexes—it is just going to take a little longer, most likely, and that is okay. Taking the time is part of making a new skill second nature. 

Bringing this back to writing, part of my frustration is that I can see that I have a much higher mastery of indexing relative to writing fiction. This makes sense, because I have spent most of the last nine years focused on indexing. I realize that I need to put the same time and focus into writing as well. And yet I wish I could just transfer mastery from one domain to another and bypass the work. Especially as making time for writing is, well, another issue. 

Still, mastery before speed.

I have to keep reminding myself of this order. I can see how it got me through tree planting and then indexing. Now, I need to put in my time with writing, to accept this time of learning the craft and becoming grounded in the basics. Speed will come soon enough. 

Article
April 7, 2019
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by Stephen

Cross-Training for Freelancers

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In her book Ten Characteristics of Quality Indexes, Margie Towery recommends taking a nap as a way to boost concentration and attention. Other suggestions include going for a walk, meditation, or yoga. As she puts it, “the trick is to be aware of when your productivity is suffering and then be proactive in finding a remedy.”

This is excellent advice, and one I have been thinking more about recently. While indexing forms the bulk of my work, it is not practical for me to be working all of the time. How I choose to spend my time outside of work can also have an impact on my work hours. 

I am starting to think as some of these other activities as cross-training. This is a concept from sports, in which the athlete trains in two different sports in order to improve overall fitness. The role of the second sport is to support the first. As an indexer I am using my mind and I also do a lot of sitting. So when I think about cross-training, I am looking for ways to both either rest or use my mind in a different way, and to also get out of my chair.

Since the New Year, I have been taking part in a noon-hour circuit training class at the YMCA three days a week. It is 45 minutes of rotating through a series of exercises, which usually results in a full body workout. I have been finding these classes helpful for my indexing in a number of ways:

  • Being at noon, and combined with lunch, they provide a good midday break. I find afternoons more enjoyable and, I think, more productive.
  • I think I do feel more alert when I am physically fit. 
  • Going to the gym provides a bit of social interaction in a day when I am otherwise working alone. There are some other regulars at these classes too. 
  • If I am having a bad morning, working out removes me from the situation and gives me a chance to reset and start over in the afternoon. 
  • Psychologically, pushing my physical limits in the gym helps me to push past mental blocks I face indexing. Working out provides a boost of confidence that I can transfer to my working life. This is the reason that provides the most incentive when I don’t really want to go.

I also read a lot outside of work for my own enjoyment. This surprises some people, but I do enjoy fiction and have other interests I want to keep on top of. I am also a periodic knitter, which I do partly to engage my brain in a different way. In my ideal world, I would also have access to a sauna, where I could relax and let my mind drift. 

I think there are plenty of options for cross-training as a freelancer. The trick is to find something that is enjoyable and rejuvenating, to keep us focused during the hours when we are working. Because who wants to work all the time? More to the point, who is capable of working all of the time without burning out? Not me, certainly. And so I look to see how else I can use my time. 

Article
March 24, 2019
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by Stephen

Why Hire an Indexer?

Photo by Clem Onojeghuo on Unsplash

A couple of months ago I wrote a free email course on indexing. It provides an overview for how to write an index, from start to finish, as well as pointers for what makes an excellent index. 

When I first announced this project, I got a few puzzled reactions. One friend commented, “That is either a great idea or you are completely undercutting yourself.” I understand what he is getting at. My work as a professional indexer depends on authors and publishers hiring me. Why give people the tools they need to avoid hiring me or another professional indexer?

This also raises the question of why pay? While I recognize that there will be a subset of authors and publishers who will not want to hire an indexer no matter what (these are some of the people I hope to reach with my course), I also believe that there are at least three good reasons for hiring a professional. These are not specific to indexing, as I also consider these factors if I need to hire an accountant, mechanic, or plumber, for example. But I think these are still worth being reminded of all the same. 

Expertise

The reason I most hear from other indexers and indexing societies is that the professional has the expertise. Most indexers have received specialized training, usually through a course, and have years of experience. This is certainly an important reason. I have been indexing books since 2011, for example, and have written over two hundred indexes. I believe that someone indexing for the first time can certainly learn, but they will not have this body of experience. Unless one plans on indexing several books, it might just be easier to hire someone than to struggle through the learning curve.

Interest

Another reason for hiring a professional, which I also think is important, is that of interest. There are many tasks that I could do, but I am just not that interested in them. Doing my own car repairs would fall in this category. Lack of interest can make a task seem tedious, and will probably make procrastination much more likely. If indexing feels like a chore, maybe delegate it instead and spend your time more productively on something else. 

Time

This leads us to what I think is the most compelling reason for hiring a professional, which is to buy time. I spend about twenty hours, on average, writing an index (length and complexity of the book are the main variables). If you hire me, you are not just buying my time, but you are also buying yourself time to do something else. Ideally, you will spend that time doing what you are an expert in, which will maximize the value that you present to the world. 

What Does Hiring an Indexer Enable?

Ultimately, the question is, what does hiring an indexer, or any other professional, enable? Yes, hiring an indexer can be expensive. You may have fears that the job will be poorly done. You may feel like you don’t have time to find an indexer. But if you did hire an indexer, what could you be doing instead? Answer this question, decide which of the two—writing the index yourself or doing that other thing—adds more value to your work, and you might have your answer for whether or not to hire a professional.

Article
March 17, 2019
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by Stephen

Mindful Communication with Clients

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I do not check email in the morning.

Depending on the day, I either first check around 12:30 pm or 1:30 pm and respond to what I can within half an hour, though I often don’t need that much time. I then check again around 5 or 5:30 pm, though I have to admit that as the afternoon wears on, it can get harder and harder not to check in the interim. Especially if I am expecting a reply from someone. 

This is a new practice I have been cultivating over the last couple of months. The purpose is to spend the hours reserved for work actually focused on my work, instead of being distracted by emails that may or may not (mostly not, in my experience) need an immediate reply. So far this has been a positive experience. If clients have noticed, they have yet to comment or complain. The biggest change has been in myself.

I had previously noticed, when I would check email first thing in the morning and then continue to check every hour or couple of hours, that my motivation for checking email was often a mixture of boredom and anxiety. I would feel bored with my task and the prospect of a shiny new email was enticing. I would feel anxious about my task or about something coming up in the future and checking email was a way to avoid the anxiety. More often than not, my inbox would be empty or only contain junk mail or other messages that could be easily left for later, and so I would have to return to my task, only this time with my attention fractured. It would then take additional time to get back into the task, which meant I would often accomplish less in the day than I wanted, which often led to more anxiety. The more I checked, the more fractured my attention seemed to get and the harder it would be to return to my work. While email is still my preferred form of communication (my phone is usually on vibrate and out of sight in my bag), I came to realize that the way I was using email was not actually helping me, either with my work or with my mental health.

Nowadays, I can still get bored or anxious with a specific task. I am still tempted to check email as a temporary balm. These are separate issues not directly tied to email. I also find that I am often much happier in the mornings because I have the time to myself and I can focus without fear of being interrupted. Afternoons can be more difficult, in part from simply getting tired as the day wears on, but if I can stick to my email schedule and temporarily forget again that email exists, the afternoon can also be quite focused and productive. While I still need to find ways to manage anxiety and boredom, at least I am not escalating those issues through mindless email checking. 

But what about responding to clients in a timely manner? What about missing out on possibly work opportunities? In talking to other freelancers, this seems a common concern. I have heard some say that they try to reply to emails within five minutes of receipt. If that was me, I do not think I would get any work done, as for me focus seems to be all or nothing. And so I want to push back a bit on this expectation of instant communication.

Most of my work comes from repeat clients and I have found that they are usually willing to wait a few hours for a response. I still try to reply within the same day. I do get some queries from new clients, some of whom I know are contacting multiple freelancers at once. I probably have lost some work from these people due to a slower response, and I am okay with that. These account for a small percentage of my work, and for me the improved focus, productivity, and sense of well being outweighs the lost projects.

I have also realized that I don’t actually get very many emails in a day that require an immediate, or any, response. Most emails I receive are newsletters, notifications, or from listservs, all of which may have some value but are hardly critical. I am not adding value to my day by frequently checking these types of emails. 

It has also been important for me to realize that my work is valuable and deserves to be protected. This is both for my own sake, so that I can complete projects on time with less stress, and also for my clients, because I think that my work is better if I am less distracted. This is understanding that communication is a tool in service of the work rather than the work itself. 

I realize, of course, that my email schedule will not work for everyone. New freelancers, especially, who are trying to book every project they can, may want to check more frequently. But even with more frequent checking, I think it is possible to be more mindful about how we communicate and how communication impacts and intersects with the rest of our work. Perhaps less and higher quality communication will actually help us serve our clients better, as well as keep ourselves more focused and engaged in what we do. 

Article
March 10, 2019
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by Stephen

Tips for Taking a Sabbatical

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Last week I wrote about what I accomplished during my sabbatical. I have also had some people ask how I was able to take the time off, as six weeks, or even four weeks, is a sizeable time commitment as well as lost income. So I want to cover some of those questions today, as I believe that a sabbatical is achievable with the right planning.

Setting a Date

Although I had been thinking about a sabbatical for probably over a year, I finally made the decision in early October of 2018. But I did not immediately stop work, mostly because I still had projects scheduled into December. So, I decided to start my sabbatical in January, when my schedule was clear. It was also nice that January coincided with the new year, and having a couple of months until my sabbatical started also gave me time to plan how I wanted to use that time.

What actually happened was that due to a couple of unforeseen circumstances, December was far busier than I anticipated and a few projects had to be pushed into January. This wasn’t too much of a problem because I simply pushed back the end date of my sabbatical, but it would have been nice to start on time. Next time I will be more watchful for potential scheduling issues.

Money Matters

This seems to be the question at the top of everyone’s mind: how were you able to afford to take the time off? I have to admit I did not put a lot of thought into the finances. My wife and I are fortunate to not have significant debt or a mortgage, and when I checked our bank account I saw that we had enough money to cover expenses for a couple of months without an income. 

If cash flow is an issue, I think a sabbatical is still possible with a savings plan in the months leading up to it. To paraphrase Michael Hyatt, from whom I got the inspiration for a sabbatical,  “What do I need to do in order to make this possible?” Framed this way, options can start coming to mind. 

Will My Clients Leave Me?

One fear I had to confront, which I think can be common among freelancers, is the fear that I will lose clients because I am not available. Personally, I have come to believe that this is a fallacy if you are an established freelancer with a good reputation. If clients want to work with you, they will come back when you are ready.

The other side of this fear is learning to become comfortable with missing out on work opportunities. This was surprisingly difficult because my default is to say yes, if my schedule is open and especially if it is a repeat client. There were a number of times when I had to remind myself that my calendar was actually full because I had a prior commitment to myself. 

During this sabbatical, I was not sure if I should tell my clients the reason I was unavailable. In the end, I did tell two of my clients and I was pleasantly surprised at how supportive they were. For other clients, I simply said that my schedule was already full and told them when I would be available again. I still ended up with a few projects booked for after my sabbatical, so my relationships with my clients seem to be alright.

Plan and Anticipate the Benefits

In the months leading up to my sabbatical, I created a list of possible goals and tasks that I wanted to accomplish. When I actually started my sabbatical, I then edited the list into a workable plan. While the sabbatical should not become another chore, I think spending a bit of time thinking through why you are making the time and how to achieve the benefits you are looking for will help make the sabbatical a more enjoyable and satisfying experience, even if the plan is simply to spend four weeks at the beach to unwind. Keeping the benefits in mind will also help with saying no to projects or with sticking to the financial planning to make the sabbatical possible.

In the end, for me, the sabbatical was definitely worth the planning and the temporary lack of income. I am already thinking of doing it again.

Article
March 4, 2019
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by Stephen

What I Accomplished During My Sabbatical

Photo by Daria Nepriakhina on Unsplash

Taking a sabbatical has been one of the best decisions I have made for my business. I am already thinking about doing it again next year.

For those of you who don’t know, I recently took nearly six weeks off work, from mid-January to the end of February. I did this for two main reasons: I was feeling overwhelmed and a bit burned out from a very busy year in 2018. I also realized that I no longer had a clear vision for what I wanted to accomplish through my work. When I first started freelancing, my goal was to earn enough money to support myself, and for a few years that was enough to keep work challenging. Now that I have moved beyond the start-up phase, I found that simply being busy was not enough. I needed a new challenge to focus on.

So my goal during this sabbatical was to figure out what that new thing should be. 

I thought the answer was going to be writing, because I do enjoy writing and as my wife can probably attest, it is something I frequently talk about. It is really because of writing that I sought to work in publishing in the first place. 

But looking deeper, the reason I enjoy writing—and why I enjoy indexing and blogging and introducing people to each other—is because I enjoy connecting people to new ideas and information. I enjoy being the facilitator who enables other people to accomplish what they need. 

Part of this shift, for me, came from listening to the audiobook version of Authority, by Nathan Barry. The book is about making the mindset shift from being highly proficient in your particular skill to becoming a teacher of that skill. Part of me quails at the thought of calling myself an indexing expert, especially knowing indexers who have ten, twenty, or even thirty years of experience over me. Yet I also have to acknowledge that I am no longer a novice and that I do have experience and knowledge that I can share. 

So this is my first pivot. I will continue to index, and I also want to find opportunities to share the indexing knowledge that I have.

I actually did just that during my sabbatical, by writing an email course on indexing. The course provides an overview of the components of an index and the indexing process, from the initial pre-planning to the final edit, in seven lessons delivered over seven days. It took me five and a half days to write and publish the course, and I have to admit I had a blast doing so. If you are interested, you can check it out here.

Writing is still important, though. The shift for me was to realize that while I still want to publish fiction, I am also just as happy writing nonfiction. Writing is one of the ways that I can teach and facilitate, in a more direct way than indexing (though indexing is also in service to the reader, making the text accessible). This is my second pivot, to be intentional this year about making writing part of my business. The finer details of how this will happen still need to be worked out, but I have a few ideas for writing projects and have dedicated 9-10 every morning to writing, to make sure that words are produced. 

I did some other things during my sabbatical too. Besides a week away visiting friends, I still showed up at my office almost every day. In addition to what I have already mentioned, I spent time brainstorming and writing a two page vision document; read several books to help me reflect on my work; worked my way through the exercises in the writing book Story Genius, by Lisa Cron, to improve my fiction; established a new daily and weekly schedule; and I finally finished setting up investments for retirement, which is something I started a year ago and then let fall to the wayside. In a way, I used this time to try out and practice new habits and new forms of work, such as writing the email course. Without this time, I would have felt too stressed and squeezed to invest the time and effort. I also made sure that I spent evenings and weekends resting, which was sorely lacking before. 

Returning to this theme of vision and purpose, I think the biggest benefit from this sabbatical is that I do feel energized again about my work. If I had done nothing else, the sabbatical would have been worth it to have accomplished only this. I have a much clearer sense for what I want to accomplish in the remaining ten months of 2019, and most importantly, I am excited to get going.

Article
February 16, 2019
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by Stephen

The Lazy Person’s Guide to Business Development

Photo by Samuel Zeller on Unsplash

The title for this post is, admittedly, tongue in cheek. I am not suggesting that those of us with our own businesses are lazy. It does point towards the reality, though, that it can be so hard to make time, or even know where to start looking, when it comes to business development. 

I think we know that we should be doing something beyond the day-to-day busyness of keeping our business moving along. We know that professional development keeps us sharp, that the market we are currently working in may change in the coming years, or that there are aspects of our business which could become more efficient. But none of these are, at least right now, immediate concerns. We will get to them someday, right?

I struggle with finding time too. My recent sabbatical, which I am almost finished with, is a more extreme attempt to make time for business development and growth. It is not the only way, though. 

Another approach, which I have been doing for a few years now (and which is where I first got the idea for a sabbatical) is a more passive approach. I have made it a habit to regularly listen to podcasts related to business and writing, and to read books on business and personal development. I try to read one book a month in this area. Occasionally I also attend webinars that come to my attention.

I describe this approach as passive because while I do make choices about what I read or listen to—and I do sometimes seek resources on specific topics—for the most part I am just going by whatever seems interesting and by whatever happens to come to my attention. I don’t yet know if there will be something of value that I can apply to my business. Not everything has gems that I can use, but the main point is that I keep reading and I keep listening. 

I think it is important that this has become a habit. I am regularly exposing myself to new ideas, increasing the chances that something useful to turn up. It helps that this also does not usually feel like work. I do enjoy learning, nor is there a deadline I need to meet, though there are times when I need to learn something that I don’t enjoy as much. 

Of course, if I do come across information that I think I can and should apply to my business, then I have to put in the work to do so. I am not saying that change and growth is always easy, but at least identifying the path towards growth is fairly easy. 

To illustrate what I mean, I would like to mention five examples—three books and two podcasts—that I have either read recently or I regularly listen to, which I have found helpful and would recommend. Your list will probably vary based on your interests and needs, but maybe this will give you some ideas for what you can look for.

Lead to Win podcast

Michael Hyatt bills himself as a virtual mentor for leaders. He spent most of his career in publishing, becoming CEO of Thomas Nelson, and now runs his own eponymous company offering various products, mostly focused on leadership and achieving goals. His podcast Lead to Win, co-hosted with his daughter and COO Megan Hyatt Miller, is free. He also has a previous podcast, This is Your Life, which is similar and also quite good.

I don’t find everything discussed in these podcasts to be relevant. Hyatt’s main audience is leaders in companies with actual employees, much bigger and more complex than my freelancing outfit. That said, because Hyatt is working at a higher level of business than I am, the podcast does introduce me to topics I wouldn’t normally have considered before and it does inspire me to think big and push beyond my comfort level, which I think is good for me. 

The Prolific Writer podcast

The Prolific Writer is a podcast that challenges my writing goals. It is hosted by Ryan J. Pelton, often features interviews with other indie authors, and is dedicated to prolific writing. Pretty much all of the authors involved publish multiple books a year. I am still trying to write my first book, so I am not in that league yet, and I am still a bit incredulous at what some of these authors are able to accomplish. The value for me, though, is that it does challenge my beliefs about what is possible, and besides being inspirational I do pick up nuggets here and there about writing, self-publishing, and the writing market. 

Deep Work, by Cal Newport

I mentioned this book in my blog post last week. Deep work is deliberately spending long periods of time concentrating, without distractions, on high value and cognitively demanding tasks. I’ve been aware of deep work for a couple of years, and finally read the book last month. I am convinced that indexing requires deep work in order to be done effectively, and reading this book has helped me to reconfigure my workday to minimize distractions and maximize the amount of focused time I spend indexing. I highly recommend it.

Make Time, by Jake Knapp and John Zeratsky

Make Time is another book I have read recently and referenced in a blog post. It is also about how to remove distractions and to make time for what is most important. This is more of a how-to book, as it contains over eighty techniques that you can try. What I found most helpful was their experimental approach. The authors acknowledge that different techniques are going to work for different people, and that everyone is unique in their work demands, their goals, and their biorhythms. So they encourage readers to try different techniques, keep a journal of what works and what does not, and to gradually figure out a personalized schedule. I also recommend their book Sprint, which is not easily applicable to someone working solo, but I still enjoyed learning about their approach to problem solving and product development.

Perennial Seller, by Ryan Holiday

I read this book last year, and the ideas it contains continue to stick with me. Holiday discusses how to create and market items that will continue to sell year in and year out. These may not hit the bestseller lists, but that’s okay because their value will continue to grow over time. This really resonates with my own beliefs about producing quality work. The book read like a road map for the direction I knew I wanted to go in but was not sure how. 

What resources do you find helpful for growing your business?

Article
February 8, 2019
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by Stephen

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?

Article
January 8, 2019
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by Stephen

Making Friends with My Calendar

Photo by rawpixel.com from Pexels

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?