I’ve been using a technique lately to try to get more stuff done. I wanted to share this technique in the hopes that it might help somebody else.

Ennui and the Overabundance of Things to Do

I tend to be a list-maker. On each of my computers I have a list of things to do, my phone has a list of things to do, and I have (literal) piles of books to read. I realize that I have years and years of material piling up, and I keep adding more to it because hey, there’s always something else to learn and I’m sure I’ll get to this thing…someday…

The problem is that the list (or collection of lists) gets big enough that the best option is to give up and play video games all day. That makes the list grow larger and creates a vicious cycle. Sometimes it means that I ignore a technology which fades away quickly (hi, Silverlight!) but other times it means that I’m late to the party on something important (like, say, neural networks).

Over the past couple of months, I’ve been working through a technique to try to handle things better: calendar entries.

The Spark

There was a person I worked with at one point in time who had calendar entries for everything. This seemed a bit silly to me: yeah, calendar entries are good for meetings and reminders to go someplace, but this got down to ridiculous levels like filling out paperwork, working on certain projects, sending e-mails, and even the mundane (which I won’t go into here to protect the guilty).

While I was at PASS Summit, I was thinking about all the things I needed to catch up on and how I had been neglecting too many things for too long. But although guilt is a powerful motivator, it clearly wasn’t enough to get me to do more. Nor were to-do lists sufficient for getting me, well, to do things. That’s when I thought about the silly idea of calendar entries everywhere.

Calendar Entries Everywhere

At Summit, before I left for home, I decided to start filling in calendar entries. As I’ve gone along, I’ve gotten a bit better about it, but here’s an early week as an example. I’ve marked out a bunch of entries which are private (appointments, personal to-dos, that kind of thing), involve work, or that I just don’t want to share with the broader world. I also didn’t show all of my calendars here, so my days end up a little bit more packed than it may appear at first blush.

I think I can slot you in between 2:24 PM and 2:29 PM on Thursday.
Bonus caption bit: Operation 10% was where I decided to throw away a lot of junk which had accumulated in my house over the past several years. This is what happens when I’m actually at home for a couple weeks in a row: I start getting hare-brained ideas and actually implement them.

As you can see, there’s a lot going on here. That leads into my next section, which starts now:

The Silly Psychology of Calendar Entries

By itself, calendar entries don’t really do much. But what I do is that I turn on notifications for these—that way, my phone pops up a message and Google Calendar has a JavaScript popup box which shows that hey, it’s time to go do something. These messages spur me to action and remind me that I should go do something. Not surprisingly, I then tend to go do something—sometimes even the thing that multiple devices are yelling at me to do!

This discipline technique works both ways: it’s a way for Present Me to get Future Me away from playing video games all the time, but it’s also a way for Future Me to remind Present Me that there are only so many hours in the day to do things, so if I want to work on a presentation, I can’t also read a book, write a blog post, do work, and review material at the same time. That, says Future Me, is why he plays so many video games all the time. Future Me is also really good at coming up with post hoc excuses.

Tips from a Practitioner

Here are a few tips I’ve learned the hard way:

  • Try to plan out the next 3-7 days in advance. If you need to, block out some time for that as well. In my case, I usually spend about 10-20 minutes during slack times thinking about what I want to do and creating those entries for the next week.
  • Be generous with your time allocations. I tend not to fill out anything less than half an hour, and typically use 60-90 minute blocks of time. Things always seem to take longer than you’d expect, so instead of estimating 15 or 30 minutes, go with the full hour if there’s any doubt.
  • Try to limit the number of distinct things you have going on. I want to learn a bunch of things all at once, but to keep things from getting jumbled, I try to have two or maybe three separate topics a week.
  • Variety is great. I’m the type of person who has trouble staying on topic for more than 60-90 minutes, so I want to switch things up during the day. Occasionally, I do get in the zone and blast through something for 3-4 hours straight, and when that occurs, I can always move calendar blocks around.
  • If you feel like getting started early, do it! The calendar entries aren’t strict edicts; they’re reminders of what you have going on.
  • Similarly, if you can’t do something at the appointed time or are completely unmotivated, no worries. Either move that block to another time or delete the entry. But even this is nice because it forces you to think about what you’re doing and if you’re simply procrastinating, that little bit of guilt might be enough to get you going.
  • Leave room in the calendar. Things will come up and you’ll want some flexibility. Also, even if you have an entire day to yourself, you won’t want to fill it with 12 hours of work-like stuff. Leave some gaps between things so you can take a break. That’s one of the big things I learned since the week that I listed above—even on a busy day, I tend not to book more than about 8 hours, and I tend to leave slack room for daily life (i.e., multiple multi-hour naps).

Conclusion: Will this Work for Me?

You might be asking that question. If so, I have no idea—I’m not you and I’m not making money on this so I don’t have much incentive to convince you that it would.

My best guess is that people with the following characteristics will probably get the most out of this technique:

  • You have some flexibility in your schedule right now. If you’re already booked solid for the next six months, there’s not much we can do here.
  • You can commit to performing some action for a block of time. Having young children will likely make this technique all but impossible.
  • You are at least a little neurotic. If you don’t care at all about skipping appointments or ignoring mechanical devices blinking and buzzing at you, this technique probably isn’t going to work.
  • You have a semblance of a plan. One important thing with this technique is that you can switch to the task without much mental overhead. A task which reads “go do stuff” won’t help you at all. By contrast, a task to continue reading a book is easy: you pick up where you left off. For things that are in between, you can always fill out the calendar entry’s description with some details of things to do if that helps.

One nice thing I’ve picked up from using this is that it seems the technique is one you know pretty quickly after starting whether it’s working for you or not. Since I started creating calendar entries everywhere, I’ve skipped a few tasks and had things come up, but it’s been very helpful in keeping me on track by reminding me of the things I need to do each day in a format which is a bit harder to ignore than to-do lists.


6 thoughts on “Getting Things Done Using Calendar Entries

  1. David Sparks, aka MacSparky, has blogged and podcasted about this idea. He calls it “hyperscheduling”. At the risk of link-spamming you, here’s a few items about it.


    If you google “macsparky hyperscheduling” there are a few other people talking about it.

    I’ve tried it in small doses and it does seem to help; the hard part for me is obeying the calendar.

    1. Thanks. I expected that I wasn’t coming up with something novel (heck, I ripped it off of someone myself), so it’s good to see how it worked (or didn’t work) for others.

  2. Thank you for this vulnerable and helpful post, Kevin. Speaking of productivity, can you speak to how you blanked the calendar entries in the image? One of the most tedious aspects of blogging for me is presenting screenshots in an attractive way. The ways to blank the entries that come to mind are: (1) Delete the text in Outlook (or whatever client) and then paste them back afterwards and (2) Use Paint to create filled rectangles of the same color as the calendar entries that opaquely cover the text.

    Both solutions are tedious.

    1. This one was Paint and tedious. Sometimes I use SnagIt which is less tedious, but I was on a machine without that installed. Screenshots are definitely one of the more time-consuming parts of blogging for me, particularly when there’s “post-production” work like that.

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