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.

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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

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.