Category: Weekly Playbook

Weekly Playbook #5: Handling Email

For an overview of this series, see the debut post on my morning routine.


I’ve been using email for more than half my life. While it was available to me in college, I didn’t begin to use it until I started at my job a few months after I graduated. That was 1994 and I was 22 years old at the time. Nearly 27 years later, I think I’ve done a pretty good job with handling email. My inbox rarely contains more than a dozen message at any given moment. I frequently hit “inbox zero.” I’ve been through a variety of models for managing my email over the years, from an elaborate folder structure to the minimalist structure I’ve used for the last fifteen years or so.

Until recently, I kept up with my email more or less in real time. I’d clear out messages as they came in, respond as they came in, prune and refile throughout the day. As I developed my morning routine, one of the things I wanted to try was to see if it was possible to handle my email once a day, in the mornings, after I’d finished my writing. This playbook is what has come out of that experimentation so far.


  1. Reply to email messages I flagged the previous day. Use canned replies, if possible.
  2. Move the replied-to message to my Archive folder.
  3. Scan my inbox for messages that can be deleted without being read. Update filters to weed these out in the future, if possible.
  4. Delete the unneeded messages.
  5. Read the remaining new messages
  6. Take action on the email if action is quick. If it takes more time, snooze the email for a later date/time.
  7. Move messages that don’t require a response to my Archive folder.
  8. Flag messages that require a response and leave in my Inbox. I use the Pin function in my mail client for this.
  9. Compose any new messages I need to send


Example: Handling this morning’s email

My basic philosophy here is to try to deal with email once per day. So far, this doesn’t work out quite this way in practice, but I’ve found that it means I am checking email much less frequently during the day. And it does help me to make sure I am replying to email only once each day. Here is what my inbox looked like as I composed this post:

My morning inbox, before running through my playbook.

The first thing I do is to reply to any email messages in my inbox that I flagged the previous day. If possible, I’ll use a canned reply. I have a few of these. One common example is when I get unsolicited requests to do a guest post on my blog. If I find that I am writing the same reply over and over, I will also use this time to compose a reply that I will turn into a canned reply that I can use in the future. Once I’ve replied to a message, I immediately move into my Archive folder. This morning was nice. I had no email that I flagged for reply.

Next, I look for email that can be deleted without being read. Often these are newsletters I didn’t subscribe to, or notifications from service I use that I don’t need to see. For the former, I’ll see if there is an easy way to unsubscribe. I’ll also use this opportunity to improve my inbox filters so that messages like these never make it to my inbox in the first place. The MetLife Dental Claim email is a good example of a message I can just delete as I know it contains no useful information (just a link to the site).

Next, I’ll read through what is left. I always enjoy Melanie Novak’s posts which is why I subscribed to her blog. No action other than to read. For blogs, I’ll use the email as a reminder to go to the blog itself to read so that the blogs get the views. Besides, I prefer reading on the blog than in email. It makes it easy to comment. Once I’ve opened the blog in a browser, I’ll delete the message from my inbox.

The Ring message requires an action on my part, but it is not something I want to do now, so I’ll snooze that for Friday when I know I will have time.

Dan Roberts is the CEO of Ouellette & Associates, a great company I’ve worked with in the past, and from which I have received some of the most practical project management training I’ve encountered, to say nothing of their outstanding customer support training, which focuses on moments of truth. I saw that Dan is starting a podcast, and the action here was to get more information about the podcast and when it drops.

The message from Capclave (my local science fiction convention) has been sitting in my inbox for almost a week now, which is rare for me. Since it is going to take more than a few minutes to handle this, I’ll snooze it until Friday.

The nice thing about this morning is that I have no email that requires a reply, so there is nothing to flag (so far). This is where I tend to dip into email throughout the day, checking to see if there is anything I need to reply to and flagging it so that I can reply tomorrow. I also don’t have any new mail to send out, so it was a quick and easy morning for me. At the end of the process, my inbox looked like this:

My morning inbox after running through my playbook: inbox zero achieved!

I don’t achieve inbox zero every morning, but as I said, I usually don’t have more than a dozen messages in my inbox at any one time. One nice side effect of this is that people can expect to get a reply from me first thing in the morning, the day after they’ve sent me a message. First thing in the morning is also when I sent out my new messages, if I have any.

Filing my email

When I began using email in 1994, I was using a Unix-based email system that allowed for the creation of folders in the same way you could create folders in a file system. I had a fairly elaborate scheme for organizing my email into folders. back then, but about fifteen years ago, I moved to a much simpler scheme, consisting of four active folders. The four folders are:

  • Inbox – where I process new email.
  • Archive – where I store all email that I want to keep
  • Sent – where I store copies of email that I sent, including replies
  • Upcoming Travel – where I store current messages related to upcoming travel (confirmations, tickets, etc.)

It occurred to me that the power of search made it simple to find pretty much anything I needed without spending a lot of time figuring out where to file a message. So if a message doesn’t go into the trash, it goes into the Archive folder. Travel-related messages take a detour to the Upcoming Travel folder until they are no longer needed, at which point they go into the archive folder as well.

If I need to find something, I just run a search and can usually find what I am looking for within a few seconds.

My mail apps

Currently, I am using the Spark mail app for handling mail on my computer. On my phone I use the Spark mail app for iOS. I just like the simplicity and functionality of Spark better than the native Mac mail app.

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The Weekly Playbook #4: Finishing a Notebook: Transcribe or Scan?

For an overview of this series, see the debut post on my morning routine.


I am rarely without a Field Notes notebook in my back pocket. Several times a day, I pull out my notebook to jot something down: an idea for a post; notes from a podcast; the names of people I meet; items to pick up at the grocery store; the name of the server in the restaurant we ate at; funny lines I hear at a gathering. I do this so that I can remember these things later. Some of them find their way into posts I write, some into stories. Other things are more ephemeral, but even a server’s name in a restaurant can be useful if I am searching for a character name in a story.

I’ve filled more than 30 of these notebooks since 2015. They sit in a nice row on a shelf in my office. Occasionally I go back to them, to look for something, like when I was searching for a particular brand of beer recently. The problem is, I only have access to them when I am sitting here in my office. It would be nice to have access to them no matter where I was.

my 30 completed field notes notebooks with an index notebook on top
My 30 completed Field Notes notebooks, with an index notebook on top.

This weekly playbook is a kind of experiment. I began with the idea that I wanted to be able to access these notes anywhere. I had two ideas:

  1. Transcribe the notebooks into Obsidian, where my other notes live, or
  2. Scan them into Evernote

I decide to try both in order to see what worked better for me. The playbook section below has the procedures I followed for each. In each case, I used my most recently completed notebook, book #30. I’ll describe my findings in the commentary.


Transcribing notebook into Obsidian

  1. Create a Field Notes folder in Obsidian
  2. Create a new note called “Book 30 – March to June 2021.
  3. Begin typing in the notes using the following guidelines:
    • Make each “day” a header in the notes
    • If my handwriting is unintelligible, put question marks and move on.
    • Wherever I have a dividing line in my notebook, include a divider in the notes file
    • Use only one file per notebook

Scanning notebook into Evernote

  1. Create a Field Notes notebook in Evernote.
  2. Using the Scannable app by Evernote, scan in all 48 pages of my notebook #30, including the cover and inside cover.
  3. Once scanned, put the note in the Field Notes notebook
  4. Title the note “Book 30 – March to June 2021”
  5. Set the create date of the note to March 1, 2021
transcribed notebook page in obsidian
A transcribed notebook page in Obsidian
scanned notebook page in evernote
A scanned notebook page in Evernote


It probably took me an hour to transcribe the first 15 pages of the Field Notes notebook into Obsidian. After an hour I stopped. It is easy enough to estimate that a full notebook would take me a little over 3 hours to transcribe.

On the other hand, it took about 15 minutes to scan the entire notebook into Evernote using the Scannable app. (I think Evernote’s Scannable app does a slightly better job at scanning than the regular iOS app does.)

For me, the Evernote scan is the better over all option. There are several reasons for this:

  1. It is quick enough to make it worthwhile. Investing 15 minutes to have the contents of the notebook available to me anywhere is a worthwhile investment of time. 3 hours is a little much. I am not likely to invest 3 hours, but 15 minutes is no big deal.
  2. The notebook really is available anywhere. The screenshot above is from my phone. I can flip through the pages just as I can with any PDF.
  3. Scanning preserves everything in my notes, include occasional sketches and diagrams that I make.
  4. Evernote uses its AI to attempt to make the PDF searchable. It is supposed to be able to recognize handwriting. I made several attempt, but I think my handwriting is too messy. Still, for people with very neat writing, the notebook is searchable. I keep the notes in their own notebook in Evernote for this reason: when I want to search for something in a Field Notes notebook, I can limit the search to notes in the Field Notes notebook so that I don’t get results from other sources.

There are a few cons to using Evernote over Obsidian:

  1. The notebook is not as searchable as it would be if I transcribed it into Obsidian. I could probably find things faster in Obsidian.
  2. My notes would be in plain text format and could be manipulated like any plain text.
  3. I could do more dynamic linking of my notes to other notes using Obsidian. (You can link to other notes in Evernote, but there is no practical way to do this in scanned documents.)

Another consideration is that I want to get my entire backlog of notebooks in a format that I can access anywhere. Transcribing 30 notebooks into Obsidian would be an investment of nearly 100 hours of my time. Scanning 30 notebooks into Evernote is an investment of 7-1/2 hours. From a practical standpoint, this is a no-brainer.

Then, too, since the notes already exist, they fit into the model of using Evernote for curation and collection, and using Obsidian for creation.

Remember, my goal at the outset was to be able to access the notebooks from anywhere. My goal wasn’t to make them as searchable as they could be. I’m fine flipping through a PDF to find what I am looking for. It usually doesn’t take very long, so it seems like the investment in time to manually transcribe all of my notes would be overkill.

Going forward, when I finish a notebook, I’ll follow the procedures for scanning that notebook into Evernote.

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The Weekly Playbook #3: My Evening Routine

For an overview of this series, see the debut post on my morning routine.


Recently, I wrote about how I form my habits. In light of that post, I thought I’d write about my evening routine since it helps to reinforce the habits that I have been working to form. I wrote about my morning routine in an earlier post. That routine covers the first two and a half hours of my day.


From start to finish, my evening routine covers the last two and half hours of my day. Bold items are ones that I try to do every day regardless of circumstance.

  • Blog edits (30 min)
  • Mind dump (10 min)
  • Prepare tomorrow’s to-do list (10 min)
  • Journal (10 min)
  • Workout (50 min)
  • Update habit journal (10 min)
  • Shower (10 min)
  • Meditate, unguided (10 min)


Like my morning routine, my evening playbook doesn’t have fixed clock times associated with it. I usually try to get started by around 7:30 or 8:00p, but that can vary. I’m more focused on how long it takes to do the things, than when I actually do them.

Blog edits allow me to re-read the posts that I have coming out the following day, make tweaks, add finishing touches, and try to catch typos that I am famous for making. This is relatively new. In the past, I was willing to trade accuracy for speed in my posts, typing fast, but occasionally making mistakes that I didn’t worry too much about. But I’m trying to do better here, and so this gives me the time to review. I’m usually two or three days ahead in what I’ve written so I focus on the post coming out the following day. If I have time after that, I will review other posts, or continue to write ones that I started in my morning writing session.

In looking for ways to improve my sleep, one of the things that I’ve been doing is attempting to clear my head of anything that will keep me awake. The mind dump, journaling, and meditation all work toward this end. The mind dump is a very GTD-esque task. I take a sheet of paper and jot down everything that I’ve got on my mind. At first, I left work-related tasks out of this, but I found that I think about work when falling asleep so I’ve started to really try to dump everything I can. This gets it out of my head and onto paper, my simple manifestation of David Allen’s inbox. I don’t spent more than 10 minutes on this. I avoid looking at my to-do list or email or other things when doing this because if something isn’t on my mind, I don’t want to put it there by mistake.

I use that list to put together my to-do list for the following day. I pick the three things I want to get done at home, and the three things I want to get done at work and write them on an index card, which I keep in the back of my current Field Notes notebook. This sets up the next day for me and I don’t need to fall asleep wondering what I need to do.

Journaling at the end of the day allows me to get other thoughts out and provides a context for my overall day. The last thing I do is 10 minutes of unguided meditation as a final way of clearing my head, or being okay with whatever I can’t clear. I started with 20 minutes of unguided meditation, but that was too long for me so I scaled back.

I give myself 50 minutes for a workout to allow for stretching before and after. As I write this, I am focused only on stretching so that as I work my way toward cardio and light strength training, I don’t end up hurting myself. I alternate between a 30 minute stretch session one evening and a 15 minute the next.

In my post on how I form my habits, I mentioned my habit journal. I try to keep this updated throughout the day, noting when I wake up, what I eat, mistakes I made along the way, my exercise. I go to bed making sure it is up-to-date.

These playbooks are designed to be living documents. I tweak them as I make adjustments, figuring out what works and what doesn’t. So far, the playbook for my evening routine is working out pretty well.

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The Weekly Playbook #2: Curating Photos

For an overview of this series, see the debut post on my morning routine.


I don’t know about you, but I’ve got too many photos in my photo library and I don’t know what to do with them all. They are all digital, of course, so they don’t take up space. But there are three problems that plague me:

  1. Duplication: because there is no limit to how many pictures I can take, I tend toward taking a lot of the same thing.
  2. Ephemera: there are pictures I take so that I can use for a specific purpose: like the brand of detergent I need to pick up at the grocery story. These could be thrown away after I use them, but they never are.
  3. Lack of curation. Almost none of my photos are tagged, labeled, or otherwise curated in any way.

Recently, I decided to tackle this problem, and I developed a playbook for curating my photos. Here is what I do.


  1. Open the Photos app on my Mac.
  2. Select the “Weekly Photo Curation” Smart Album
  3. For each photo in the album, so one of two things:
    • Delete the photo
    • Give the photo a title, and optionally, give it keywords
  4. Repeat step 3 until all the Smart Album is empty.


I use Apple photos for managing my photos. As of this writing I’ve got over 25,000 photos there, many of which are duplicates or ephemera, and most lack curation.

I decided to tackle this problem by stopping the bleeding first. Thus, this playbook.

Defining the Smart Album

The “Weekly Photo Curation” Smart Album is defined as follows:

I search for any photos in the last 7 days that do not yet have a title. Since a Smart Album is a “live” album of the photos that match the criteria, each time I either delete a photo, or add a title, the photo drops out of the album so that I know I am finished when the album is empty.

What goes into the decision to delete or save? Mostly experience. I usually ask myself a few questions that go beyond the usual keeping a photo out of sentimentality or personal documentation:

  • Is the photo a duplicate or close enough to be considered a duplicate?
  • Is the photo distorted (blurry, etc.)?
  • Is the photo unique enough to keep for use on the blog? (I prefer to use my own photos on the blog than ones that come from curated sources online.)
  • Do I need this photo to be available in my Photo library? (Is it available somewhere else?)
  • Have I needed to find similar photos to this one recently?

Selecting a title

If I choose to keep a photo, I try to give it a succinct title that is specific enough to be useful in future searches. For instance, this morning I took a picture of the sunrise coming up behind the 7-Eleven which marks the halfway point of my morning walk. In this case, I simply titled the photo “Sunrise over 7-Eleven.” I try to be conscious that Apple Photos, like Google Photos, uses AI to be able to identify things in photos. Sunrises are one example that Apple Photos is probably good at. But the 7-Eleven in the photo is from the back, so there is not much of a change for the AI to identify it as such so I throw it into the title.

sunrise over 7-Eleven
Sunrise over 7-Eleven

Tackling the entire album

At some point, I’d like to go back and clean up the entire album, but with more than 25,000 photos, that seems an almost impossible task. Maybe at some point, I’ll put together a playlist which would allow me to review a month of photos at a time, slowly working my way backward. But for now, I’ve got too much on my plate already so I am focusing on ensuring good meta-data quality on photos going forward.

Also, I am trying to be more present when doing things, and am less likely to take as many photos as I used to. Every little bit helps.

I try to do this on Sunday mornings, immediately after completing my morning routine. I guess you could say that this has become part of my Sunday morning routine. That allows me to get the past week’s photo’s curated just as the new week is beginning.

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The Weekly Playbook #1: My Morning Routine

Introduction: Playbooks are Practices

Welcome to the inaugural post of my new column, “The Weekly Playbook.” Each week I plan to feature a playbook that I use to help make my life a little easier. What is a playbook? A playbook is like an enhanced checklist that provides steps or outlines for a specific task that make it (a) repeatable, and (b) flexible. Playbooks help to save me time, build habits, and avoid making mistakes. Repeatability is key because it means I am not reinventing the wheel each time I am trying to perform some task. Flexibility means that playbook has built-in alternatives for when things go sideways. Over time, I kind of mentally absorb the playbook. In this sense, the playbook becomes the practice.

I first learned the value of a checklist when I was taking flying lessons in 1999-2000. Checklists are there to reinforce memory so that you avoid missing things. Back when I was flying, I learned to touch each item referred to on the checklist as a way of reinforcing that I was doing it. Playbooks came a bit later. I started to develop my own playbooks for work initially. After rolling out some big piece of software, I found that a standard manual or user guide wasn’t as effective as lots of short, focused lists on how to handle different situations. Over time, I began to create playbooks for myself in order to reduce the number of decision I had to make or the time I spent looking up information. They are also great at helping to form habits. In some ways, the Going Paperless series of posts that I wrote about Evernote where a set of playbooks in narrative form.

This series is different. First, the playlists that I’ll write about here are much wider in scope than the Going Paperless posts, which focused on the possibility of using digital tools like Evernote to replace the paper in my life. Second, the Going Paperless posts were more narrative in form. As you’ll see the playbooks I discuss have three parts:

  1. Background: Why I use the playbook or how it came to be.
  2. Playbook: The playbook itself which is often just a list and a set of alternatives.
  3. Commentary: Some words explaining the playbook in more detail.

I decided to post this series every Friday so that people had a chance to explore them over the weekend, when there tends to be more time. We’ll see how that works out. Given that I just began my creative new year with the goal of becoming a full-time writing in ten years, I thought I’d begin with the playbook that I worked up to help support his goal in the most generally way: my morning routine. Enjoy!


Project Sunrise is a codename I’ve given to my effort to improve my writing and writing opportunities over the next ten years so that when I retire from my day job (ten years hence) I can begin working as a full-time writer. The project involves more than just improving my writing, but also my overall health and well-being. Given that I still work full time and am raising three kids, I needed a way of ensuring I am getting time to write, analyzing and improve what I write, as well as improve my health and well-being into an already full day. This playbook outlines my newly revised morning routine. I’ve been beta-testing and tweaking this routine for a few weeks now, but began using it “in production” on July 1, 2021.


From start to finish, this playbook takes 2 hours and 35 minutes to complete each morning. Bold items are the ones I try to do every day regardless of circumstances.

  • Walk (45 min)
  • Meditate, guided (10 min)
  • Shower (10 min)
  • Write (1 hr)
  • Journal, email, blog comments, etc. (30 min)


  • Bad weather? Replace walk with elliptical (45 min)
  • Short of time in the morning? Move writing to evening routine (1hr)


I have my morning routine list posted in a few places so that I can reference it at a glance. It is posted in my office above my screens so that I can see it when I am sitting at my desk. A copy of it is also taped into the back of the current Field Notes notebook that I carry around.


Note that there are no clock times associated with the playbook? To be as flexible as possible, my playbooks focus on duration, but not start or end times. As I’ve worked out this new routine, I try to get started at 5:50 am. But this list works just as well if I start at 7 am or 9 am. Everything just shifts relative to the time it takes. I’ve tested out each of the times listed to make sure they are reasonable. That way I know how long it will take to get through the routine.

It is important to me to have alternatives readily available. Nothing throws off a habit as much as an unexpected situation? What do I do if I am traveling? What do I do if the weather is bad? What if I have an early work meeting? Have a pre-defined set of alternatives means I don’t have to think about the answer in most situations.

Order matters to me on these playbooks. I walk first thing because it wake me up. I gave up caffeine 74 days ago (as I write this) so I no longer have that as an aid to alertness. The walk gets me fresh air and some immediate exercise and I come back to the house alert and ready for the day.

I use the Calm app for meditation. My preferred guided meditation is Jeff Warren’s “The Daily Trip” series. These last anywhere from 9-12 minutes and allow me to clear my head before getting started.

A shower after meditating helps wash away any residual sleepiness. Even though my showers are quick, it is also where my mind wanders and I try to guide it toward what I plan to write that day.

After the shower, I write. For instance, I am writing this post after my shower on July 1. On my walk and in the shower I was able to frame how I wanted to present these playbook posts (context, playbook, and commentary). I give myself an hour to write. Maybe I can write only one post, maybe more than one. Maybe I’m not in the mood to write. That’s okay, but I don’t allow myself to do anything else in that hour.

Finally, I give myself 30 minutes for journaling, handling any personal email, and reviewing any blog comments that I need to reply to.

Playbooks are designed to be living documents. I adjust them as needed as I learn better ways of doing things.

I also have a playbook for an evening routine, but I’ll save that one for another time.

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