How to be productive while living with chronic illness (or any sort of unpredictable life situation): Part I

how to be productive while living with chronic illness image of planner and pen

This post is one of a two-part series designed to introduce you to a different way — my way — of remaining productive while living with chronic illness.

Listen to me read the below here (because I’m away from home, this audio is recorded with my phone, which is why the quality is of lesser quality than usual):


I geek out over productivity. Organizational systems make me swoon. From Filofax to Omnifocus, from Emily Ley to ToDoist—and everything in between; if it’s created and marketed to convince me that a more organized, more highly productive future is just within my scrabbly grasp, and it’s been created somewhere within the ballpark of my aesthetic standards, I’m probably going to give it a go. After all, I’m the woman who bought a whopping seven different paper planners for 2014. One might consider it a fixation.

Despite my preoccupation with productivity, few of the “productivity hacks” I’ve come across satisfactorily apply to my situation, or to the situation of thousands of other people in a similar position to mine. Is it true that, as countless Pinterest pins would have me know, we all have the same 24 hours in a day? Well… yes and no. (More on that later.)

My guess is that this isn’t only my unique problem to face. This post is one of a two-part series designed to introduce you to a different way—my way—of remaining productive while living with chronic illness.

Why most systems don’t work for me

So I live with chronic illness—multiple chronic illnesses, if I’m to be specific about it.

The problem with 99% of the systems I’ve investigated, and the reason I decided to share my own hodgepodge method, is this: most systems out there presume that I can predict, with some degree of accuracy, what my days are going to look like. This might mean something far-ranging, such as the notion that I’ll be able to make a 1 PM appointment on the following Thursday; it might be as specific and close-ranging as the idea that I’ll be able to “work on X client project” from 2-4 PM on Tuesday, or even to work on a client project at any time at all on Tuesday.

In my case, life with disability and chronic illness means that I can’t predict what I’ll be capable of doing from one day to the next, or even from one hour to the next. As an example of this, I decided to chart my symptom and energy levels for three weeks to see if they operate with any kind of rhythmic regularity. (They don’t, except to say that I’m most likely to be at my most functional in the very early morning. See below.)

hot pink chart of energy graph

Perhaps you don’t live with chronic illness, but you do have some level of unpredictability or limitation in your life. Maybe you have newborn triplets, live with an ailing parent, or care for a health-compromised companion animal; perhaps you have a side job that might ring you up with a command to jet off to Dubai without a moment’s hesitation.

The truth is, unpredictability is the stuff of life. We do like to pretend that we’ll be able to rely on the next hours or days to be as we anticipate them to be, but anything can happen. And this is where a different sort of productivity hack comes in handy.


While I am going to share with you how I go about my daily tasks, I’m not at all promising that this is a one-size-fits-all solution. What I do hope is that my method can inspire you to find your own way, no matter what sorts of obstacles or limitations happen to jut up on your path to greatness.

What I do about appointments

Before I get into the nitty-gritty of how I actually get things done, a few words about appointments.

Appointments are a part of most people’s lives, including mine. Here’s how I deal with them.

  • I try not to schedule more than one appointment (e.g. client call, therapy appointment, coffee date) per day. To do otherwise is to put me at a greater risk of having to cancel one due to illness, or to wind up forcing myself into going to an appointment that I actually don’t have the reserves for, and making myself sick and/or resentful in the process — not to mention disappointing other people.
  • I don’t, under most circumstances, make appointments for after 3pm. If it can’t be helped, I’ll stretch that to 5 PM; if I feel like taking a gamble for something that I can cancel without anyone’s hardship, I might even agree to do something at 5:30 or 6. This is solely based on how I understand my own biological rhythms.
  • Once made, that appointment then becomes a priority. If I’ve scheduled a call for 11am, I’ll be in bed for an hour or so prior to then, resting so that I can be at my best when the call happens. If I have an especially big event (say, a speaking gig) happening on Friday, I might spend all day Thursday resting in preparation.

Organizing the day-to-day: Project management

There are three main ingredients to my productivity system: ToDoist, the Passion Planner, and my own To Do lists (download available in Part II, coming next week).

ToDoist (free, with a paid Pro option): Despite its name, I primarily use ToDoist as a project management tool, rather than as a To Do tool. I prefer ToDoist and not, say, Asana, Trello, or Basecamp for a number of reasons: I don’t work with a team; I prefer its interface and aesthetic; it’s simple to use. (Thank you to Susannah Conway for introducing me to this product.) Implementing ToDoist allows me to see all of my projects, and their corresponding tasks and due dates, at a glance.

todoist screenshot

See the screengrab above? The most important thing about the way I use ToDoist is that it allows me to categorize the (seemingly millions) of projects going on in my life, which are available at the left of the screen. Though Content Creation is an overarching project, Journal and Legacy Notes are separate projects beneath that category, and the tasks that go with those projects are handily listed when I click on their project name.

ToDoist is a cornucopia of functionality, allowing me to, say, create a recurring due date for “Creating a Journal mini-essay” every Monday, to be published on Tuesday; I’m sure that it’s possible for a person with similar circumstances to mine to figure out a way to use ToDoist effectively as a daily task assignment tool. However, I find myself most gratified—and efficient—when I use pen and paper, which is where the Passion Planner and my To Do pages come into play.

Part II will pop into your RSS feed in a week’s time (you do have the Journal in your feed reader, don’t you?) In the meantime, feel free to let me know in the comments if you have specific questions about productivity and chronic illness. Perhaps you have your own techniques for getting things done (that have nothing to do with David Allen’s GTD); I can’t wait to hear them.

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  • I appreciate this glimpse into your planning process, Esme! Like you, I have a weakness for planners and organization but my obstacle to tight, rigid scheduling is children (you never know when they’ll throw your schedule into a tailspin) and a husband that travels far, wide, and frequently at the drop of a hat. I used to get so frustrated having to mark through things I couldn’t get to for one reason or another. I’m a big fan of Evernote myself but then I’ve never had someone explain the benefits of ToDoist as clearly as you have—I definitely need to give it a second look. Sorry to write a novella in your comments but this post resonates with my planner-loving heart. Thanks!

    • Yes! That’s exactly what I mean when I say that so many planner systems don’t seem to take into account a world where unpredictable things happen. Actually, the planner that I use now (the Passion Planner) is one that I enjoy, but COMPLETELY don’t use the way it’s supposed to be used; the maker intends for you to fill in time frames in which you plan to do things. I tried this, and found it disheartening and, frankly, pointless. Thank you for sharing your experiences!

  • Ah! I have a chronic illness and out of happenstance, our methods converged similarly! (My love planner is Polestar Business planner. It has a similar layout.)

    That must mean we’re on the right track. : )

    • Ah! I’d love to hear more about your planning methods–but yes, I took a look at the planner you use, and it seems very friendly to open-ended planning!

  • That is very interesting! I have debilitating migraine that interferes with my functioning. Sometimes it leaves me alone for long periods, and sometimes it preys on me over and over again. It’s unpredictable. I am only learning to accept that I have to slow down. This single acceptation is making me feel much, much better… even if the migraine is still present. Thank you for writing this.

    • Go you! It sounds like you’re really accepting and healing, which is, I believe, the best thing we can do for our chronic illnesses. xE

  • I have bookmarked this journal article Esme so that I can return to it again and again – your insight, hints and tips are priceless. I too am a LOVER of all things organisational, but I have finally accepted that this obsession only becomes useful for me if I actually put all of my Todos (work-based, and ‘life-based’) into a single planner and can see them visually on a calendar-type view, else I just play with organising but conter-intuitively don’t actually get anywhere (I am very talented at procrastinating).

    I’ve just downloaded a few of the planners you mention, and for me, I have found myself leaning towards Asana, as I really click with the beautiful calendar view, I can assign some life-tasks to my other half (mwoahaha!) and I can sub-task things up to i) give me a sense of achievement, no matter how small my tasks are ii) split tasks into the optimum sizes for my working-personality-type (opposite of a completer-finisher!).

    Thank you again for this post Esme, you have alerted me to some great Project Management tools and given me more confidence in optimising my day around my illness – that given the right organisation and tools, we CAN achieve!

    • I am so very glad that this has been so helpful to you! Thank you so much for telling me about how you’ve used it; I’m glad Asana has been a pleasant discovery. xE

  • God, yes, this is something I’ve been struggling with since I had my baby last December: my obsession with planning and my inability to actually plan thanks to postpartum depression and new motherhood.

    Much like you, trying to stick to a rigid timeframe is setting myself up for failure. What I’ve been doing, instead, is dividing my day into thirds (mornings, afternoons, and evenings), and committing myself to one important task per block. I tend to not plan anything big in the evenings because I’m exhausted by that point. Instead, I simply set aside some self-care (usually a hot bath + a book once my husband gets home). It works, for the most part: I don’t feel frustrated and defeated by seeing all these blank time slot. Now I need to tackle planning the finer details, like my writing and tarot study, and the study group I’m running on Facebook. I may have to look into ToDoist again!

  • Never thought I would find this kind of perspective. Very heartening to know that others struggle with such issues.
    However, please explain: What is an RSS feed and feed reader?

  • Thank you so much for this! Todoist looks like exactly what I’ve been looking for. I’m highly intrigued to hear how you use your Passion Planner. I just bought my first one this year. I love it, but I’m continuously tweaking how I use it. I really like to hand-write my planner & to-do lists, which can be really difficult when you need a flexible schedule.