Hyper-Scheduling Feedback 

I’ve had a lot of feedback about my prior posts about the hyper-scheduling experiment and implementation details. Here are the prior links:

The Hyper-Scheduling Experiment

Hyper-Scheduling Mechanics

This whole thing has turned into a short series here at MacSparky.com. There may be another post or two about this, but today I'd like to share some of the feedback. I’ve received a surprising amount of email/tweets/feedback on these posts. They fall into several categories:

Hyper-Scheduling is Insane

I recently spoke at the ABA Techshow, and at some point an old lawyer-nerd friend cornered me. “David, are you really doing all that crazy stuff with your schedule?” (That quote is nearly perfect. He didn’t use the word “stuff”.)

This sentiment boils down to a lot of people who have never tried something like this marvelling at what an extraordinary investment of time hyper-scheduling appears to be.

I agree putting something like this in place takes time, particularly when getting the habit started. However, having been doing it now for awhile, the time investment is not nearly high as someone who has never tried it would think. I schedule each day and the end of the day prior. Using the mechanics I explained in the last post, most of the scheduling is simply selecting prior instances in the calendar week view, duplicating the item, and then moving it into place. For me, most days start with some Field Guide Work for two or three hours and most days end with shutting things down and planning the next day and in between comes a whole lot of legal work and podcasting that varies on a daily basis.

A key competent of all of this is having a task management system that can help you keep track of all of your tasks (so you don’t have to) and unearth those priority tasks out of the database on a daily basis. I’m pretty adept at OmniFocus so it usually doesn’t take me long to find those tasks that will get checked off the day before and assign appropriate time blocks to get the job done.

For me, the trickiest part about setting it up is being realistic about how much can be accomplished in the next day and not biting off more than I can chew. The practice of hyper-scheduling however, has provided an excellent tool for me to get better at that skill. At this point, hyper-scheduling takes me about 20 minutes. As explained throughout this series of posts, a 20-minute daily investment for all of these benefits is a no-brainer.

Hyper-Scheduling is Unrealistic

No plan survives contact with the enemy.

–Helmuth von Moltke

This second category of criticism boils down to the above quote. It doesn’t matter how much time you spend scheduling if you walk into the office to find it on fire. I’d generally agree with that criticism. Several times since I’ve started hyper-scheduling, I’ve had days where a true client or family emergency appeared requiring me to sweep aside my carefully laid plans and spend the day manning the fire hose.

I guess the real question for these critics is exactly how often do they find that the office is actually on fire. If that’s a routine thing, I think that is more of a problem with the office than hyper-scheduling. The lawyer equivalent of a fireman is a litigation attorney. I was in that racket for 20 years and can tell you at the time I experienced a lot more fires than I do these days. If you have a job that requires you to put out fires on a daily basis (and you’re okay with that), I don’t think hyper-scheduling is for you.

Conversely, however, I’d ask you to make sure the there truly is a fire. As my law practice has transitioned to a transaction-heavy practice and away from the sausage factory that is modern litigation, before hyper-scheduling I was acting like there were daily wild fires where, in hindsight, there were very few. Too often I’d let the smallest problems derail me. Hyper-scheduling has given me more perspective so that a lot of things that I was earlier treating as four-alarm fires now just gets blocked into some time in the next few days and I’m able to stick with the original plan.

Hyper-Scheduling is Nothing More than Sophisticated Procrastination

One reader wrote me and opined that my hyper-scheduling seemed like re-arranging the deck chairs on the Titanic. The argument is that Hyper-scheduling is a way to fiddle, instead of doing work. I think this could be true if you were too precious with your scheduling. The minimum block of time for me to deal with a specific problem is usually no less than an hour. I don’t Hyper-Schedule by making a dozen 15-minute project blocks that I then carefully arrange like a jigsaw puzzle. That would be a waste of time. All of the little, important things I do every day get OmniFocus flags and lumped together in the “Capture Flags” block. I agree someone could implement hyper-scheduling in a way that gets too fiddly. However, I think someone that gives it the smallest amount of thought and deliberation could avoid that trap.

Hyper-Scheduling Doesn’t Actually Give You any Additional Time


This was my own biggest source of resistance to the experiment in the first place. Scheduling myself for ten hours a day does not magically give me 20 hours of work. It’s still just 10 hours. While that is true, adding the planning and deliberation to the day has allowed me to get a lot closer to 10 hours of work done in a 10 hour day where before I was getting more like five or six hours of work done in a 10 hour day because I spent so much time blowing in the wind.

For me, Hyper-Scheduling adds a sense of purpose to the day and lets me be much more deliberate with my time and the projects I spend my time on. Either way, while it’s true this technique doesn’t magically give you additional time, it lets you use the time you do spend on important work much more efficiently.

Hyper-Scheduling is Nothing New

These are my favorite emails. I’ve received lots of affirmation from readers that have been doing this in some form or another for years and ask me, in one way or another, “What took you so long?” Some folks call it block scheduling, others call it fancier things like value-based time management. I'm certainly not the first guy to this party, and I find that comforting.

Hyper-Scheduling Mechanics

Last week I wrote about my anal-retentive hyper-scheduling method and got a lot of surprisingly positive feedback. One of the most popular questions was how exactly do I implement it. It's not that difficult. The night before, I take a look at my appointments and essential tasks are for the next day and start laying things out. Whether I am on my iPad or my Mac, I do this in Fantastical. A lot of times I'm using blocks that I recently used in the past few days, so I set it up in a week view, select the applicable block, such as "Email and Social" (which is the 45 minutes or so where I deal with all of my email and check in on social media), hit the keyboard shortcut command (Command + D) to duplicate, and then drag the block into the appropriate space. You can do the same thing on an iPad with a long press, but it feels like it takes longer and setting the duplicated block to the next day with your fingers is less precise than doing so with the mouse.

Here is yesterday's calendar in Fantastical. I usualy include more detail, like client names, but those were removed for this screenshot. Click to enlarge.

I treat the blocks of time more like versatile soup ingredients than a rigid jigsaw puzzle, so I am happy to move them around as I'm planning the next day. The only things that are locked in are the specific appointments I have made with other people. I know some folks who have done this by creating repeating events where they have the same block of time for the same event every day. My life isn't that simple, and these blocks nearly always move around depending on what I have on deck for the next day. Setting these as repeating events won't work for me, but maybe they can work for you.

I map days out the afternoon before and it is an organic process because the whole time I'm also looking at my pile of tasks in OmniFocus and trying to make big boy decisions about what exactly gets my attention the next day. At the end of this process, I have a pretty solid looking calendar for the next day. I set alarms for the block events that start at the time of the event, so I get a little kick as I go through the day and need to change into the next block. The Siri watch face on my Apple Watch helps with this.

The last part of my process, and this is new in 2018, is writing it down with a fancy pen in my Baron Fig Confidant dot grid plus-sized notebook. I have a page for every day, and at the top is a list of events and big rock tasks to finish for the next day. I keep it open on my desk as I work. Writing it down takes additional time but only a few minutes, and there is something about having it written down in ink in front of me as I work through the day that keeps me rolling. I received some very satisfying affirmation on this last bit when I saw that Shawn Blanc does the same thing.

Underneath this section of the page I draw a line and below that I take notes and summarize progress at the end of the day. Like I said in the last post. The whole shutdown thing is a post for another day. Here's a picture of my list for yesterday. At the time I took the picture, I still had one event and one task left to complete. Sorry about my terrible printing. If I'd thought about it when I set up this day, I would have tried to make it neater. Click to enlarge.  

The Hyper-Scheduling Experiment

For the last month, I have been conducting an experiment with more deliberate scheduling of my time. For lack of a better word, I have been calling it hyper-scheduling. 

Historically, I have kept two things in my calendar: 1.) appointments and 2.) big rock-style projects. For example, if I've been meaning to write a certain complicated client contract for a few days and it wasn’t getting done, I would set aside several hours in my calendar specifically for that project.

With this hyper-scheduling project, I have taken that to a different level. For instance, here is my schedule from a few days ago:

6:00 – Shower, shave, and meditate

7:00 – Bicycle to Starbucks

7:20 – Write Smith contract

9:20 – Review email and social media

10:00 – Write Field Guide

11:00 – Bicycle to bank, market, and home

11:45 – Lunch

12:15 – Capture “Flags”

13:00 – Legal Work

15:00 – Field Guide screencasting

17:00 – End of day email audit

17:30 – Daily shutdown 

21:00 – Jones call 

A few of these require further explanation. 

  • I have a cool bike that I use for most of my local transportation. Anywhere within five miles of my house, I am probably biking. (Hooray for California!) I have to build that time into the schedule. All the pedaling also helps me fill my rings.
  • Flag capture is the process of knocking down flagged tasks in OmniFocus. Every day I have 5-10 tasks that I have flagged to make sure I get done.
  • “Legal Work” is me working through OmniFocus tasks in my legal perspective that are not flagged. I don’t truly hyper-schedule time in that block of time for each specific task I'll work on. When I set up the day, I am not even sure what I will be doing during that time except that it will be legal work. I just have a block set aside to make calls and get non-critical client work done.
  • One of the biggest advantages of this practice is the commitment I am making to spending time on the next MacSparky Field Guide. Before I started this experiment, there never seemed to be time to work on my books. Now it is built into the schedule.
  • Shutdown is a whole thing I do (which I will write about another day). Relevant to this post is that as part of that shutdown, I hyper-schedule the next day so I can wake up and hit the ground running.
  • Normally after I do the shutdown, I am done for the day. On this particular day, I had a conference call with a client in India so I had to get back on my horse later in the evening.
  • Not all of my days are this ideal. Some days I spend driving all over Southern California meeting clients or going to the dentist. The system still works on those days too.

After doing this for a month, I am sold. The extra work involved with planning the day gets paid off with interest in productivity the next day. 

A couple of things I have learned along the way with this experiment is to make sure and set up my schedule the night before. I am pretty sharp in the mornings, so I want to spend that time on client or creative work, not scheduling. Also, there is nothing wrong with setting a block of time as a commitment to types of work as opposed to a specific task, such as generally getting client work done as opposed to a specific client project.

Another thing is to accept that despite my planning, none of this is carved in stone. If a client calls in with a true emergency or I find out a friend is in the hospital, I can blow the daily plan up fairly easily. Because of the planning, on this day I knew I had about 45 minutes of flagged must-do tasks. If something came up, I would know that I need to find 45 minutes in the day to deal with the flags, and the rest could be scratched.

Most people who have thought a lot about calendars and planning preach that you must put space between events on a highly scheduled day. That is probably good advice, but a month in, I still haven’t done that and I am not feeling particularly bad about it.