My Calendar Tricks Webinar

Digital Calendars are way more powerful than the paper calendars we humans used for hundreds of years. The problem is, that most of us are still using them as if they are just paper calendars … and they are so much more than that.

Not only can our calendars now give us things like alarms and repeating events automatically (that’s the easy stuff). With a little out-of-the-box thinking, you can get a lot more from your Calendar. You can now easily schedule blocks of time to get the work most important to you into your schedule and make sure all the little stuff doesn’t get in the way of the big stuff. I call it hyper-scheduling.

You can also use calendar blocks to limit your time on things that are usual time-sucks. For instance, I have a one-hour block of time to process email and comms. That’s there so I only spend an hour (not three!) dealing with email.

And don’t forget digital calendars are free. You can make as many as you want. This lets you transform your digital calendar into a planning calendar.

I’ve got a lot of ideas on way to use digital calendars to your advantage. I shared them in a recent webinar and now you can watch it. Enjoy!


Fantastical Field Guide (Free)

The Plan vs. The Day

One of my big takeaways from Cal Newport’s book Deep Work was the concept of tracking time blocks. I’ve written (and talked) a lot about how to use hyper-scheduling to get your most crucial work moving forward.

It’s pretty easy to visualize how hyper-scheduling works. Here you have a day, and you set aside blocks of time for your most important work.

8:00 – AM Comms

8:30 – Field Guide Recording

10:30 – Podcast Recording

13:30 – Legal Work

16:00 – PM Comms

16:30 – Shut Down

I haven’t, however, written much about the aftermath of a block-scheduled day. Sometimes things go sideways. Maybe a client calls or your kid gets sick, or you wake up realizing that today you just don’t have it in you. I call that “The Plan vs. The Day”. How do you manage that on a blocked schedule? How do you keep track when carefully planned blocks and reality go to war?

The short answer is that you get over it. Sometimes things just don’t go as planned. You deal with it in the moment, and the next day you start again. Yesterday, I had a great plan but, in the afternoon, decided to take an extended nap. You can see how that blew a few things up for me. I keep track of those derailed days. Then when I go back later and do my weekly/monthly/quarterly reviews, seeing how often my blocks didn’t reflect reality gives me data I can use for future planning.

A case in point is my recording time for Field Guides. The pandemic happened, and my kids all came back home from school. I had to move my studio around the house and suddenly found a trend of routinely not hitting Field Guide blocks. That lead to some changes.

So how do I keep track? There are several ways:

On Paper

Get a piece of paper or a fancy notebook and write the hours down the center of the page. The night before or the morning of, I write the plan down. As the day goes along, I can update the right side with what actually happened. Here’s a sample.

This is one of the easiest ways to track the plan vs. the day. So long as you keep your notebook nearby, it’s easy to update throughout the day. If you want to keep a more permanent copy of notebook musings, just taking a picture of the page at the end of the day. I do this and save them to my Day One database.

With Digital Paper

GoodNotes for the iPad is a great app. If you usually have your iPad with you, you can record the plan vs. the day on a GoodNotes page. You can easily make a GoodNotes template page that looks just like a paper page. Then you can use an Apple Pencil to fill it in as you work through the day or type it in using a keyboard. With digital paper, you get the advantage of backups and sharing, but you lose the satisfaction of using analog tools that I know many folks dig.

With MultiMarkdown

MultiMarkdown has a table-building function using the pipe character. It’s easy and lets you put your day vs. plan comparison in a text file. Here is an example plan vs. day table in MultiMarkdown:

|The Plan|Hour|The Day| |---|---|---| |Start Up|7| ✓ | |DEVONthink FG| 8 |Journaling| ||8:30|DEVONthink FG| ||9| ✓ | ||10| ✓ | ||10:15| Shower & Tai Chi| |Client Contract|10:30|| |Client Contract|11|Tisha Call| ||11:20|BHPS Work| ||11:40|Client Contract| ||12|| |Legal Work|13|| ||14|| |Automators Planning|15|| |MacSparky|16|| |Shutdown|17|| |Liana Visit|18|| ||19|| ||20|| ||21|| ||22|| ||23|In Bed|

And here it is rendered using Obsidian:

The advantage of this method is that you can work on it without jumping to a paper notebook or an iPad. The downside is that it is more fiddly to maintain as you go throughout the day. You can script the entries, but this is not nearly so simple as a pen and paper.

On Your Calendar

Calendar plan v day.png

Keeping both your planned and actual events isn’t all that hard with a Calendar app. The secret is to make a new calendar called “The Plan” or something like that. Then as you get through the day, you just duplicate your events. Move the original calendar event, as planned, to the “Plan” calendar. Then adjust the copy to reflect how things went down. If you throw a block overboard during the day, you just move the original to the plan calendar. Here’s an example day reflecting both the plan and the day as it went down.

No matter how you go about this, I recommend not getting too hung up on tracking your blocks to the minute. Thirty-minute blocks are as granular as I ever go.

If you’ve made it this far in the article, you probably still think tracking the plan vs. the day is a pretty good idea. If, however, you’re having doubts whether all of this is worth it, I recommend you try it for 30 days. I find the feedback loop of routinely seeing my plans smack up against reality gives me a much better picture of how I’m doing and how much I can take on. The real trick is not getting too granular. You’re looking for significant trends here.

In terms of what is the best method, that is up to you. I’ve tried all four of these methods over the years. I currently am primarily doing this with a pen and paper. (If you must know, a Platinum 3776, medium nib with an architect grind and Rhodia A4 paper that I punch for a Levenger disc system.) In a jam, however, I can use any of the other methods as well. The point is that there is no single right way. You just need to find a way to consistently keep yourself honest, whether with a text file or a notebook.

If you want to try tracking the plan vs. the day for 30 days, grab a pad of paper and start. Set your timer for 15 minutes and write down what you think will happen that day. It doesn’t have to be perfect or pretty. Just do it every single day for 30 days in a row. After a month, you’ll be able to look back at how those plans compared with the actual outcomes of each day.

Remember: there is no single right way to do this, so find one that makes sense for you and stick with it for 30 days! At that point, you may find you’ve built a habit, and then you are home free.

Hyper-Scheduling Technology

Yesterday I wrote about the task management and your calendar. Today, I’d like to share some of the technology behind how I go about blocking these schedules. Creating calendar items can be tedious. Using a tool like Fantastical makes a big difference, but when blocking a whole week out, you want some automation at your back. For me, it’s been an evolution.

Block and Copy

You can copy and paste calendar events in most calendar apps on the Mac, including Apple’s own Calendar app. Command + C and Command + V are your friends. If you have similar blocks you use throughout the week, you can set them up once, then copy, then paste as many times as needed. You may need to make adjustments to start and end times (or even descriptions), but that is way easier than starting from scratch. Blocking and copying calendar events on the iPhone and iPad are not as easy and more time-intensive. Block and copy is a perfectly acceptable way to set your blocks, particularly if they vary a lot from week to week. As my schedule started getting more consistent, I looked at other options for automating calendar blocks.

Setting a Repeating Event.png

Repeating Events

All calendar apps can create repeating calendar events with a high degree of customization. If you want a block every Tuesday at 1 PM or on the last Sunday of every month at 3 PM, you can do that. I tried this for a while but eventually gave up on it for two reasons.

First, I was not too fond of the confirmation box that shows up every time I adjusted a repeating calendar event. It was like hitting a speed bump multiple times every day. It started as an annoyance but quickly became unbearable.

Second, recurring events go into the future, potentially, forever. If you block most of your days going months (or years) into the future, Scheduling anything in the future become more difficult because, according to your repeating events, you are already very busy every day, forever.

Automatic Event Creation

As I explained in yesterday’s post, I don’t want to plan blocks much more than a week into the future. As Yoda said, “Always in motion the in the future.” Blocks planned out more than a week in advance rarely go down as planned. Yet there is enough consistency in my schedule that I’d like to automate the process of generating the 25-ish calendar events I want every week.

Shortcuts Weekly Blocks Script.png

The easiest way I found to do this was with a Shortcut that runs through a “Create Event” task for each day in the following week with my standard blocks. You can download a simplified version on your iPhone or iPad with this link. I run this script every Saturday afternoon. It takes just seconds and fills my week with blocks. Since they are not repeating events, I can move and change them at will without seeing that blasted confirmation box. Moreover, since they only go one week into the future, if I’m planning an event for a month from now, my calendar isn’t overly cluttered.

In addition to generating the calendar events, my Shortcut script also inserts alarms for most events to trigger when the block starts. This reminds me to change gears and helps me from getting lost in any particular block.

Daily Evolution

Often, but not always, I need to make adjustments to these blocks as I go through the day. Stuff happens. It’s okay. I do, however, adjust the calendar to reality when that happens. Sometimes it means moving a few blocks around in the coming days. That’s okay too. Regardless, I take a screenshot of my weekly calendar on Sunday night, and I always go back to look the following weekend to see how the week went down compared to my plans. Sometimes I learn a thing or two comparing reality to the theoretical.

The Paper Option

I’ve also tried blocking entirely with paper. For that, I’d recommend a nice pen and a notebook that makes you want to use it. The trouble with doing this on paper for me was that I didn’t have the notebook with me at all times. Digital events are in my pocket, on my wrist, and send me notifications.

The Relationship Between Task Lists and Calendars

I’ve written about hyper-scheduling and using my calendar to keep myself in check when planning tasks. Those posts often get questions from readers about the exact relationship between my calendar and my task list. If you keep both a calendar and a task list, it can get confusing to figure out what goes where. Of course, you know the dentist appointment goes on the calendar, but if you are going to get the most out of that calendar, it should be used for much more.

Your task list should be the keeper of all tasks. It is the full inventory of things you plan to do. If, however, you’re like me, that inventory is pretty full. There is no way I’m going to wake up one day and complete every task on my list. Honestly, there are years worth of work in my OmniFocus database.

The purpose of the task list is to bring order to that chaos and give you a framework to hang current and future tasks and keep them in perspective. The goal is that when you plan your days and weeks, you can easily pull the wheat from chafe in that task list and know that out of all of those things, which are the ones that move the needle for you right now. Figuring out what is essential right now is the entire reason I’ve invested my time in mastering OmniFocus (and made the OmniFocus Field Guide). I want to get to the tasks that need my time with the smallest time investment on a daily basis.

It’s at that point that my calendar joins in the dance. Once I have picked my tasks for the day or week, I need to plan when I will accomplish them. To do this, I need to answer a few hard questions:

  1. How long will this take?
  2. Do I have that kind of time available?
  3. Exactly when will I give it that time?

Let’s break that down further.

How long with this take?

As humans, we are generally terrible at estimating how long it takes to get something done. We usually vastly underestimate the amount of time required. If this is new to you, I recommend taking your initial time estimate and doubling it. Let’s say one of your on-deck tasks is a client proposal, and you immediately think “one hour”. Make it two. You can always scale back later, but if you are using calendar blocks and they are too short, you will fail at it. If it ends up taking one and a half hour to make that client proposal and you have a one hour block, you’ve already crashed. If instead, you had a two-hour block reserved, you can take a break for thirty minutes and play with the dog or work on something else. Bad time estimates are where most people have trouble when calendaring tasks.

You may find that you also have a set of essential but small tasks that also need to get done. I don’t block time for small tasks, but I will block time to handle a pile of small tasks. In my case, I often have a one-hour calendar block called “Legal Flags”. Those are small flagged client items in my OmniFocus database that I can lump together and get through quickly.

Do I have that kind of time available?

This process starts with a small list of tasks and you setting time estimates for them. Even with a short list of tasks, you may find you run out of time. There are only so many hours in a day. If you have realistic time estimates, you may find that you don’t have enough time for all of your selected tasks. That’s okay. It happens to me nearly every week. You then have to decide what gets done now and what has to wait for later. This process is the payoff of combining your tasks with your calendar. It allows you to be realistic about what can (and can not) get done in the time you have. It’s the difference between a realistic list of tasks for the week that you can feel good about finishing and an unrealistic list that may sap all of your energy by Wednesday as you realize you have no hope of getting it all done. I guaranty you will get more done with a realistic list than an unrealistic one.

Exactly when will I do it?

The final step is to put those task blocks on your calendar. They are just as crucial as dentist appointments and will help you keep on track throughout the week in getting those most important tasks done.

So in answer to the question of what goes on my task list and what goes on my calendar, I’d say while all of my tasks are in my task list, only a select few graduate to the calendar. I’d also avoid going through this process for tasks any further than a week out. Everything is continuously in motion, and it isn’t easy to know what will be the priority more than a few days from now.

Want to see what technology I use to pull this off? There’s a post for that.

Time Estimates and Self Delusion

A few weeks ago, I re-opened the Pandora’s box of hyper-scheduling, and the email started pouring in. One common problem I heard from folks implementing their own hyper-schedules went something like this. “Dear Dave, I tried your nerdy block schedule thing, but it was a bust by lunchtime. Even though I spent a bunch of time planning my day, nothing was getting done on time and I had to abandon it.” The reason for this particular problem is our shared inability to estimate how long it takes to get work done. If you try block scheduling but make the blocks too short, you’ll make yourself crazy. 

Hyper-scheduling requires time and space.


If you are going to try this out, give some thought to your time estimates and how long it will actually take to finish a project. Consider all the nuances and expected complications and figure out how long that would take. Then double that number. I’m not kidding. If you reserve time that doubles your initial estimate, you’ll be able to get the work done. Maybe, after a while, you’ll get better at realistic time estimates but start by doubling.

By increasing the time blocks, that means have fewer of them. That’s a feature, not a bug. Hyper-scheduling is about making a realistic evaluation of the work to be done during the day and actually getting it done. It’s easy to load your self up in the morning with more tasks than you can realistically complete. You then spin your wheels all day and end up accomplishing little. Instead, make a plan and stick to the plan. You’ll get more done.


You also need to build space into a block schedule. I’ll often leave some empty one-hour blocks in the day to deal with unexpected issues. I also give myself space after any particularly intensive project to take the dog for a walk and clear my head before diving in again.

Making the blocks forces you to make the hard decisions about what you’re going to accomplish in a given day before you start working. It’s the difference between “ready, aim, fire” and “fire, aim, ready”. Being realistic about time and space is what lets you get those important tasks done.

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 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.