5 Tips for Modern Task Management

Office 365

I am a self-employed, independent Office 365 and SharePoint consultant. One day, I was having lunch with a great friend of mine who is a self-employed, independent animator. We were talking shop and when I asked how business was going he said “Great! Except for when I feel like I have nothing to do!” I joked that “I wish I knew what that felt like!” But the look on his face was that he really wasn’t kidding. The conversation carried on and we dug into the heart of what he was really feeling, overwhelmed. My brother, another self-employed, independent consultant with an MBA once told me that “Being self-employed is great! Except for when you have no work…or when you have too much work!” It seems counterintuitive, but at times I have felt most uneasy during BOTH feast AND famine. So, it is with that notion in mind that the idea of, if you can control your workload and really get your hands around it, you can sleep better, feel less overwhelmed, and actually enjoy the calm moments when you “don’t have anything to do”, or at least know what to do next

The “system” I use is based on having been a disciple of first, Hiram Smith (Franklin Planner), and later Steven Covey (7 Habits of Highly Effective People). I also use a little Getting Things Done (GTD) sprinkled in. There are two elements that make my approach work for me — my approach to work (my thought process) and my technology. The technology only enables or realizes my thought process. Through practice, I have discipline that I have developed. Failure and success is based on 5 “truths” that I observe in my life. So here it is, the basic tenants of how I get stuff done:

  1. There are only so many hours in a given week for me to get MY work done. There is a difference between my work and the work I do for others.
  2. There is a tradeoff between “scheduled work” (client meetings, giving and watching webinars, other things that must be done on a schedule) and unscheduled work. Unscheduled work may or may not have a deadline, in my world I put a deadline on the stuff that doesn’t have a deadline, otherwise it will never get done.
  3. Plan for the unexpected. I don’t fill my week (40, 60, 80 hours) because I’ll never get all that work done. I place a block on my calendar to “get caught up”, so that when I get behind I know I have time in my schedule to get caught up. My rule of thumb is 60% of my week will be productively spent on “work”. The rest of the time is either “getting caught up” or see #4.
  4. Covey called it “Sharpening the Saw”, I schedule time to learn new things, research ideas and blog or other “creative” activities.
  5. I am a morning person. I am most creative, most verbose, and most focused in the morning. I also get up early, I have a lovely dog named Ruby and she loves our “alone time” first thing in the morning. I plan my workday around these rhythms. I do my creative writing early and leave more mundane mindless tasks for the afternoon.

With all that in mind, I can manage my workday because I plan my work week ahead of time. This planning affords me a lot of freedom. I know it sounds counter intuitive, but I try to have a picture in my head of my week so that I don’t stress about the details of any given day. I do that using the following 5 tips.

Plan with One Calendar

This is huge, for me, as I have two different personas. I am a consultant for Aptillon and a trainer, blogger, MVP, and everything else as AbleBlue. My AbleBlue calendar drives my life. So, when I set up a meeting through Aptillon, I have inbox rules that ensure that my AbleBlue calendar is kept up-to-date and is always the one source of the truth. My inbox rule looks for meeting invitations or updates and forwards them to my AbleBlue account. Nothing fancy here, it just works. (BTW, I know a lot of folks have more than 2 personas; it becomes even more difficult the more calendars you have.)

Task Management Inbox Rule

You might say, “Wait, what about calendar overlays in Outlook.” There are three problems I encounter with calendar overlays:

  1. They are only in Outlook. I don’t see them on my phone.
  2. Coworkers I share my calendar with don’t see them.
  3. They do not reflect my true Free/Busy status on tools like https://freebusy.io.

By using only one calendar for all MY scheduled items my wife can easily check my calendar and bots like FreeBusy.io accurately reflect my status on any given day. On my phone, I don’t have to try to reconcile my appointments across multiple calendars. Peace.

Track Tasks with One Task List

I have used several task lists over the years. Starting with paper in my trusty Franklin Planner, graduating to Outlook Tasks (OHHH how I miss the custom metadata in Outlook Tasks!), later Toodledo (the Evernote of the Task list world), and now I use Wunderlist. Is it “perfect”…no. There are things I cannot do in Wunderlist that would make it perfect, like creating additional fields and custom sort order. I still miss the “A,B,C,1,2,3” of the Franklin Planner. I make do with Wunderlist by using due dates and stars (more on this later.)

Write Everything Down

One of my favorite questions to ask on a new engagement is “What keeps you awake at night?”. I anticipate answers like, “Is my server farm backed up?” and “Am I going to meet my deadline?” But occasionally I get much broader answers like: “I cannot forget to do XYZ” or “I just had a great idea or dream I don’t want to forget”. The answer to this is simple…“Write it down!” Keep note paper and a working pen by your bed side. Write it down and go back to sleep! The same applies to EVERYTHING else. I write, collect, and catalog everything in Wunderlist. If I am reading and see something I want to read later, Wunderlist. If I am interested in a new technology, photography technique, or recipe…Wunderlist. If I need to follow up later with someone, Wunderlist. Even if I scribble something on scrap paper, I collect the scraps before the day is over and put them into Wunderlist. Then I throw the paper away. (In GTD these are your collection points.) In this way, my task list is EVERYTHING I want to do. Not today, necessarily, but it does reflect everything I want and NEED to get done. From the seriously important (like life insurance) to the mundane (like reading an article on dog training.)

Take Time to Get Things Done

My process involves weekly (for me Monday morning) review of my ONE task list. I review the things I meant to accomplish last week and decide if they are still a priority this week. If I really need to finish them, I honestly evaluate WHY I didn’t do it last week. For example, I am working on a new class. The first few weeks I was blazing through the material. It was crazy how much I was writing. I had 3 tasks: “Finish Labs 1-3”, “Finish Labs 4-6”, and “Finish Labs 7-9”. I knocked them out in two weeks. I was killing it. The following week I created a similar set of tasks for the lecture content: “Finish Lecture 1-3”, “Finish Lecture 4-6”, and “Finish Lecture 7-9”. When I got to the end of the week I had finished Lecture 1-3, but had not even started on the additional lectures. “Why?” I asked myself, honestly. I was tired, getting a bit board, and needed a little variety. So, in addition to going to a movie and taking a day off (I am self-employed after all) I also changed the tasks to smaller “chunks”. I created “Finish Lecture 4”, “Finish Lecture 5”, “Finish Lecture 6”. I also used the next technique to be sure I had the time to get things done.

The key here is to assemble a “reasonable” to-do list. Break the tasks up into reasonable chunks. A mentor of mine called them “attainable goals”. A gross example would be the difference between “Write Entire Course” and “Write Lecture 1”. I can wrap my head around Lecture 1. The other key to planning and using Wunderlist is the use of “sub-lists” (Wunderlist calls them lists) to break up the focus of each task list. I have lists for House Projects, Read Later, Home Depot, and My Class. I also have shared lists for projects I collaborate on with other folks outside my organization. This is the real value of Wunderlist. I can share a task list with other people and keep tabs on their progress.


Another thing I do, and you can see this in the video around my webinar appointment, is I block additional time around meetings for prep, technical checks, and after meeting follow-up. In the case of a webinar, I prep my demos and run a technical check before I start the webinar. After the webinar is over, if there is a recording, I usually review the quality of the recording before posting it for the public. All of this takes time. If I am traveling to a client meeting, I add the travel time to my calendar. That prevents anyone from adding a last-minute meeting to my calendar that would cause me to be late for my client. It is little habits like this that make it very easy for me to maintain control of my calendar.

Plan to Get Things Done

The last tip is how I pull it all together. Most people will look at their calendar and then their task list and decide “If I have time…do this task, if I don’t I’ll go to the meeting”. I don’t do that. I put things on my Task list on my calendar if they are going to take more than 30 minutes. If it takes less than 30 minutes, I do those anytime someone cancels a meeting or ends a meeting early. In other words…when I find myself with free time. I create time for my tasks by adding “appointments with myself” to my calendar. I know this sounds very basic. But if you don’t AND you have a deadline, all the urgent (but unimportant) stuff will eat your time.

What do I do with the urgent emails that arrive and need attention, but not right now? What do I do with the TLDR emails that I want to read, but will take me out of context just long enough that if I start to read it my whole day is lost? I do this: Schedule time to read it. Yep, this is one of the coolest features of Outlook you have never seen. Start where you can see the email and the calendar icon at the bottom of the left tool pane. Drag the email onto the icon while holding the right mouse button, then let it go. The context menu pops up that offers options for what to do with the email. I usually choose Copy Here as Appointment with Attachment.


That way, when it comes time, I have the context of the email directly on my calendar. If I know that it’s going to take me an hour to read and formulate a reply, I schedule an hour for the message.


Monday with Ruby

OK, so I am sitting on the couch Monday morning with coffee and a Golden Retriever (who has been fed and walked) falling asleep on my legs. I look at my calendar. I get an idea of what my week looks like, because I have been building this week in all my previous weeks. I look at my task list and begin to schedule the stuff that must get done. I put it right on my calendar (I might use due dates in Wunderlist, but I don’t rely on them. I create Outlook appointments for everything that will take 30 minutes or more to complete.) I also leave time, usually afternoons, open here and there for the unexpected. The only items that go on the calendar are ones that I have “starred” in Wunderlist, because, at some point, I also indicated in Wunderlist that they were important. If they are done…woohoo! I mark them done. And if they are no longer stars, but need to stay on the list, I un-star them. This activity takes me only a few minutes each Monday morning…30 minutes tops.

That’s it! I run my week by my calendar. Occasionally, I make adjustments. I may choose to move items around. If they don’t get done, I make time later. They don’t get marked as complete until they really are completed. Bottom line is, I don’t lose sleep over my tasks and calendar. I drive my productivity with my calendar and my desire to get things done. I have to say, the underlying habit I have developed is based on these great resources. If you have not read or participated in a workshop, I highly recommend it.