Writing / Blogging Workflow

VirtuallyGeeky’s Blogging Workflow
VirtuallyGeeky’s Blogging Workflow

I am still working through my workflow, but similar to a productivity system, it should be a living thing that evolves with you as you continue to learn and grow.

In my quest to create more content, I have run into various problems that I needed to solve for, so here are some things that I have learned. Hoping they can help others as well. I have to be honest that I stole most of what I talk about, but modified things slightly for my wants/needs. A lot of this came from MacSparky’s workflow.

Workflow Requirements

  1. Idea generation
  2. Content creation
  3. Editing/grammar checking
  4. Reflection
  5. Publishing

Let’s unpack these one at a time.

I put a list of the tools/apps I use at the end of this article in case anyone is interested.

Idea Generation

I have gotten inspiration from both David Sparks at MacSparky as well as Shawn Blanc, who I found through the MacSparky blog! I have purchased most of the available training from Shawn Blanc’s sites, The Sweet Setup, and The Focus Course. Both David and Shawn talk a lot about their creative process for their blogs, and it helped me grapple with my desire to blog more. So, here are the basics of my idea generation and capture process.

Reading — Both reading books as well as listening to books via audiobooks. I try to learn all the time, and in this process, lots of great ideas come to me. If I get an idea while I am driving and listening to an audiobook, I simply open Drafts from my Apple Watch and speak the idea into my watch. That converts my speech into text, and it’s sitting in my Drafts inbox (on all my devices) for when I can get to it later. I use this method even if I’m not driving because it’s so damn easy! If you don’t have an Apple Watch, you can use the Drafts app on the iPhone in a similar fashion, but it’s just not as streamlined as you can imagine.

The Drafts complication on the Apple Watch - Tapping this opens up a new note in dictation mode, so you simply start talking
The Drafts complication on the Apple Watch – Tapping this opens up a new note in dictation mode, so you simply start talking

Podcasts — If I’m not listening to an audiobook, I am probably listening to a podcast. There is so much great content to learn from podcasts out there. My capture method is the same as when I am listening to an audiobook.

Web-browsing — If I am on a device and find something that sparks an idea while browsing the web, I will usually just share it from Safari directly into Ulysses. I can either send the main link and type my idea, or I can highlight text in the article and then use the share sheet to get both the link and that highlighted text into Ulysses. The nice thing is, I can either dump it in my main Ulysses inbox if I need to move on quickly, or I can choose the exact Ulysses group where I want it to land.

In some cases, a simple snippet of text or the URL to something isn’t enough. If I want to save something more involved or for longer-term retention, I use Keep It, which I found through a recommendation on The Sweet Setup. I also use Pocket to read stuff later (I’m still trying to figure out the best tools here and how to use Pocket for my needs).

Everything Else — Pretty much anytime I have an idea I either get it into my Drafts inbox to deal with later, or I open Ulysses and capture it there. It’s just a matter of how much time I have at that moment for capture. Drafts is the fastest by far!

Once I have my ideas, I will poke at them now and again to add a little color or start to write a little bit. If I get spun up on one idea and start putting a lot into it, I will move it from Ideas to Cooking. That’s when I move into full-blown content creation.

Some of my groups (folders) in Ulysses. I love the ability to use icons for the groups for visual queues
Some of my groups (folders) in Ulysses. I love the ability to use icons for the groups for visual queues

Content Creation

“Moving the cursor from left to right,” as they say. Sometimes this is super easy, and other times something will stall out a little for me. Or, maybe my mind is really on another idea I have. If that happens, I move the idea to my Backburner group to keep it warm. While it’s there, I can continue to pick at it and keep it fresh. If it is no longer feeling fresh at all, I will move it back to the Ideas group, where I can always pick it up another time.

When things are clicking, it is more about finding the time to work on it (I have a busy day job). For this, I have to be somewhat opportunistic and chip away at it wherever I am that I can find that availability. Luckily, having an iPad with an external keyboard and cellular data makes writing anywhere a total breeze. This capability goes back to the ubiquity of Ulysses being on all of my devices and being in sync across them. So I can even tap away on my iPhone while using the bathroom if I feel so moved.

Sometimes an article is short and quick, and sometimes it is relatively lengthy with quite a bit of research and lots of thinking and re-working things. When I get into one of the more extensive articles or need to gather resources and research, I create a group in Ulysses for the material to keep track of it all easily. The resources and research can be links, images, pieces of information I want to incorporate or quotes, etc. This research gathering doesn’t have to only happen while I’m actively trying to finish an article. If I have an idea that requires a lot of research, I can create the group while it’s still in Ideas and start the gathering process over time. Then, once I feel like I have enough to get cracking and I want to work on it actively, I can move the whole group into Cooking.

Once the article feels complete, I then move it to Baked (edit) and move on to the grammar and editing phase.

Editing / Grammar Checking

I happened upon Grammarly while reading MacSparky’s blog and reading through his workflow. I’m just using the free version for now. I haven’t decided to pay for the Premium service yet because it’s not cheap (at the time that I’m writing this it is either $29.95/mo if you choose to pay monthly, $19.98/mo if you pay quarterly, and $11.66/mo if you pay annually) and I’m not sure if I will truly stick with blogging regularly. My track record hasn’t been stellar over the years, so I’m giving it time to see how I get along. If, however, I stick with this and get a better following, I will surely pay for it annually.

A couple of things about Grammarly: 1) It doesn’t work everywhere, and 2) It poses workflow challenges to work around. On workflow challenges, if I have any hope of sticking with blogging/writing, it has to have as little friction as possible. The good news is, I found a killer trick to make things easier!

The first problem of Grammarly not working everywhere really has to do with using a computer rather than a mobile device. I am 100% Apple, but the problem exists on Windows as well. There are plug-ins for Office on Windows (not on a Mac), but that still wouldn’t solve my problem since I use Ulysses for writing and barely ever use MS Word. Grammarly has browser extensions so that it can monitor your grammar as you type in a web browser, which is fantastic, but I found out it doesn’t work with WordPress.com and its new block editing. Mine doesn’t work at all in the blocks using Safari, but I read somewhere it should work on a per-block basis if you use Chrome as the browser. I don’t like Chrome, but even if I decided I would just use it for publishing my blog posts, it still wouldn’t consider the entire article for voice, tone, context, etc. So it’s less useful. Also, I write my posts in Ulysses, so it would be great to have Grammarly work right in Ulysses. No dice.

As I was writing this article, I was notified that Antidote, a competitor to Grammarly, now works with Ulysses. I looked into this as an option briefly, but it looks like the workflow isn’t much better, but is at least somewhat automated. The price is relatively high as well (it’s comparable to Grammarly if you pay yearly), and it didn’t seem that attractive to me. The iOS app isn’t anything more than a reference tool, similar to a dictionary or thesaurus, and since I am using my iPad so much, this was pretty much a deal-breaker for me. Plus, as you’ll read in the next couple of paragraphs, I think I have an excellent solution (for me).

Grammarly, then, creates a workflow challenge, because it doesn’t “just work” with my current workflow. My basic workflow is to write in Ulysses and then publish to WordPress as a draft. I then make sure all looks right on the web before actually scheduling when it will go live. So, to me, the best area to have Grammarly work would be in Ulysses, but it doesn’t. So most people are grabbing the text from Ulysses and pasting into the desktop Grammarly app, making the edits there, then copying and pasting it back into Ulysses. That’s not ideal, but I guess it’s workable.

I have been using my iPad for nearly all things I do lately, so I like to make sure whatever I do works well on the iPad. Ulysses works wonderfully, including publishing to WordPress from Ulysses on my iPad, but knowing that I need to check grammar, etc., I went to look for the Grammarly app on iOS. The only thing that exists is a Grammarly software keyboard. 😑 I never use a software keyboard on my iPad unless I leave my external keyboard at home and need to use the on-screen keyboard. I pretty much always use an external keyboard to type. That means, just like TextExpander’s keyboard, it doesn’t work as you type on the external keyboard. But, I searched to see if there was some way still to use the Grammarly functionality with an external keyboard and I happened upon a short video by “81gmedina” where she shows how she types with her external keyboard, then brings up the software keyboard and switches to the Grammarly keyboard. Once the Grammarly keyboard is up, you can tap on the “G” in the upper left, and it scans the entire body of text and then makes its recommendations!! I tried this in Ulysses on my iPad with a previous article that was very long, and it worked beautifully!!

Tap the “G” on the Grammarly keyboard to review the entire document/article
Tap the “G” on the Grammarly keyboard to review the entire document/article

Note, on my iPad and my external keyboards, I had to tap-and-hold on the little down arrow on the bottom right of the screen to get the regular software keyboard to come up.

Tap and hold the downward arrow on the right to bring up the software keyboard and then switch to Grammarly
Tap and hold the downward arrow on the right to bring up the software keyboard and then switch to Grammarly

Once I did this, I was able to switch to the Grammarly keyboard and have it work successfully. I am guessing Apple made a change in the software that doesn’t allow what she was doing, or maybe it’s just her keyboard that works the way she shows. When I initially tried bringing up the keyboard selection without having the software keyboard already showing, I had to select something else before I could get Grammarly to show up and work properly. Finally, after you choose Grammarly as the keyboard, that selection persists even if you minimize it and continue to use the external keyboard, which means when you tap-and-hold that bottom right arrow to bring up the software keyboard, it brings up the Grammarly keyboard from then on… nice!

Now, this still doesn’t work on my iMac Pro, but I’m okay with performing this step on my iPad even if I happen to be working on my desktop. My iPad is never far away, and Ulysses synchronizes changes so quickly and well… this step is much less of a burden than trying to swap text in and out of Ulysses and Grammarly and the potential to lose links or formatting. I could even use Ulysses and the Grammarly keyboard on my iPhone for this step in a pinch, and that’s pretty badass!

Screenshot of Grammarly reviewing whole article while an external keyboard is still attached
Screenshot of Grammarly reviewing whole article while an external keyboard is still attached

I originally started writing this article on March 20th when I only had a free account with Grammarly. I then received an email from Grammarly on March 26th, offering me 40% off for 48 hours only on a premium subscription. Based on the workflow trick I figured out above and the fact that I can use Grammarly for much more than just my blog, I decided to pull the trigger and bought an annual premium subscription for the 40% off the price (under $90 for the year, which came to something like $7/mo). I added a reminder in my calendar so I can choose to cancel before it renews if I find that I am not using it enough. Anyway, I am now a paying customer of Grammarly.

The editing portion I am referring to in this section is mainly reading through the article from top to bottom to make sure the thoughts are cohesive and in order. Sometimes I need to add words, sentences, or even whole paragraphs to make things work better. Each time I think I’m done, I need to run Grammarly against it again to make sure all is well.

Once I am happy with things, I publish to WordPress as a “draft,” meaning it isn’t truly published to the public yet, which leads to the reflection period.


Once I publish the article as a draft on WordPress, I may immediately go through and check how things will look on the site for formatting and image placement, etc., depending on whether I have time at that moment. However, this initial phase isn’t to finalize things.

Then I wait at least 24 hours before reading through the whole thing as the end-user will read it and make sure it still makes sense, doesn’t need anything, and looks good.

If all of that leads me to believe it is ready, that’s when I schedule the article to be published. I have been scheduling posts to publish on Monday mornings at 6 am Eastern time, with the thought that people tend to check social media before their workday gets started. I have no idea if my timing is right, but so far, those posts have gained far more traction than anything I publish later in the day or week.


One beautiful thing about WordPress.com (or your own hosted WordPress site) is the ability to schedule posts for a specific day and time and to automatically post to social media sites, so people see that you made a post. I know other blogging sites also have these capabilities, but the fact that WordPress.com does all of this on their free site AND that I can write my articles in Ulysses and publish to WordPress directly from Ulysses is a killer workflow for me. I am guessing I will eventually pay for a WordPress.com site to remove the ads, but for now, I am loving free.

Final Thoughts

Just while I have been writing this over the past week, a couple of things happened: 1) I received a notice that Grammarly was offering 40% off all of their plans for 48 hours only, and 2) WordPress.com offered me a 20% discount on a paid plan.

For Grammarly, I saw too much potential benefit for more than just blogging, and 40% off was too good to pass up!! For WordPress.com, I was going to skip it and stay with the free service. I already own my domain through a registrar, so I just didn’t see the point other than removing the ads, but I am trying to be cost-conscious. Before the discount expired, I decided to look at the pricing again. I was about to skip it and close the page when it hit me… I just spent $7/mo on Grammarly, and yet the “Personal” paid WordPress plan was only $4/mo without a discount, so I decided just to do it and bought a two-year Personal plan to remove the ads for my readers. With the 20% discount and the further discount applied for the two-year commitment, it comes out to only $2.80/mo! Not bad.

I figured it might be helpful to others to list the tools I use at the time of this writing:

  1. Drafts app for capturing ideas as they come to me
  2. Ulysses for writing (and several other things)
  3. Pocket and Keep It for web content research that is more than a snippet. I can link to things in Keep It with an x-callback-URL to get right to the content.
  4. Grammarly for spelling/grammar/voice/tone/etc
  5. WordPress app or web site for final polish and review… and also scheduling the post to be published

All in all, I am pretty happy with this workflow. I just hope the ideas keep coming and that I can find the time to keep writing for this blog. I am enjoying myself and hope others do as well.

Productivity Pitfalls —OR— Why GTD always failed for me

Originally written on 03/19/20

Best Intentions

I think people generally have a real belief that they are “going to make it work this time” when they decide to “buckle down” and stick with a productivity system. I know I do. Maybe it’s finding a new system, maybe it’s finding a new productivity application that catches your fancy or has some new feature/function that you find appealing. Maybe it’s a New Year’s Resolution or you set a goal to become more organized and productive. Perhaps it’s trying to create good habits around being productive.

In all of these cases I believe people have the motivation and conviction. But it seems no matter how much you are committed, it doesn’t last or simply fails. Why is that? I can tell you this much… the problem is not that new app.

What Goes Wrong

It’s not that difficult to start out strong… maybe even last a couple months! But over time we slip back into the same behavior that got us in trouble the last time, and the time before that… and the time before that. <sigh>

So what is the problem if we are using great tools/systems? The problem is us and how we process information. At least it is for me. If you are one of those people that never feels bogged down by a growing list of tasks or never loses any piece of information, then I have to ask… what are you doing here?!? Go read something more pleasurable! For everyone else, you are probably a lot like me.

I will not claim to have it all figured out, but I recently learned an issue that keeps putting me back to hectic and lost. It is a lack of review and planning. EVEN if I start out planning, the lack of review has things getting lost in the shuffle or continually pushed forward in an endless losing battle (it feels like). “I just don’t have time for review and planning,” I say in my head, “I just need to start getting work done.” But busy work without review and planning is most often lackluster in actual productivity at best. At worst, you realize too late that you are working on the completely wrong thing and have to scrap your work and start over or on something different.

Decisions, decisions

But it’s also more than just review and planning. You have to actually make up your mind, you have to make decisions on what action to take! You see, I often find myself in a rut, especially with email, on not knowing what action to take. This indecision results in emails being read by me, but staying in my inbox for my future self to deal with. Then, later that day or even days later, my future self looks at it again… has to re-read it and understand what it is (a waste of time) and then try to make a decision this time… except, maybe I’m still not ready so I do the same thing again. There are times when I will have read an email for the 4th or 5th time before I’m able to decide what to do with it. And, while these emails are itching to linger in my inbox, it is both confusing to look at and wastes even more time because I am unsure what actually needs action out of the mess of emails left in my inbox.

I used to work with a guy who would delete all of his emails once he read/acted on them. It literally blew my mind. I asked him how he referenced things at a later date… his answer? He searched for them in his trash. 😳 I was dumbfounded. But, here’s the thing… his mind was free. Whether you completely agree or disagree with his methods, HIS mind was free. He didn’t have things clogging up his vision. If there was an email in his inbox it needed to be processed. Same with his task list.

But, please don’t take this line of thinking to mean it is an email only problem. It applies to things on your task list or physical mail sitting on your desk. ANYTHING that needs to be processed requires you to make a decision on how to process it. For task lists: am I really going to complete this today, or is it just something I’d like to complete today? — that’s just one example — For physical mail: is this junk mail, a bill, something that needs to be filed or shredded (etc.)? You can come up with lists of things like this for many facets of your life.

In fact, part of what causes your indecision is not wanting to lose track of things… isn’t it? You leave emails in your inbox because you figure if you move it out before taking the right action you will forget about it. You let things build up on your active task list because you don’t feel like you have a place to put them where you won’t forget about them.

So, you have all these things that require your decision on actions to take… yet you are paralyzed most of the time. How do you fix this?

Changing How You Think

I have read countless books on the subject and even purchased and taken training around this. You probably have too… we know the answer, but we can’t seem to do the right actions to combat this same problem.

I already said the solution above — review and planning — but why is it so elusive?

Well, I also already mentioned why we skip this step… we put a higher priority on “taking action” rather than sitting quietly and analyzing what we should actually be working on… what actions will mean the most or make the biggest impact.

By the way, it’s more than simply scheduling the time to review and plan… you literally do have to change how you think when it comes time to make those decisions, but if you are consistent in your review and planning habits, the task of making a decision is much less difficult or scary.

What Clicked For Me?

For whatever reason, whether it was where I am in my life, the delivery of the content, or maybe it was simply hearing similar things for the hundredth time… it is starting to sink in. I can think of two things that have had the biggest impact on me recently regarding all of this. 1) The “All The Things (Pro)” training by Shawn Blanc from The Sweet Setup and The Focus Course, and 2) the book “Atomic Habits” by James Clear where he mentions both the “1% better” rule as well as “habit-stacking”.

Just for clarification, I have zero sponsorship on my site at the time I am writing this article (who knows what the future holds), so anything I am personally recommending has no kick-back to me. I have also personally paid for everything I talk about out of my own pocket. Any and all ads you see on my site are because I have a free WordPress.com site, and that is how WordPress capitalizes on my site… not me.

There are some sayings that have stuck with me and I can’t remember where I originally heard them (even though I am trying to keep a commonplace book with quotes), so I apologize for not providing appropriate credit:

If everything is a priority, then nothing is —AND— If we focus on everything, then we focus on nothing

There is a misperception that “doing things” is the same thing as “being productive”

Less is more when it comes to either goals or task management

These sayings help frame how you have to think differently. You can’t make everything a priority at the same time. We truly can’t focus on more than one thing at a time (multi-tasking is literally bullshit… anyone who appears like they can multi-task is simply very good at task-switching very quickly, but it’s still less efficient than pure focus). Also, simply “doing things” isn’t what I would define as productive unless the result of those things actually produces something useful/wanted, or your desired end-state.

Side-note on multi-tasking for any computer nerds reading this: Computer CPUs don’t actually multi-task either… well, not in their most simplistic form. Almost every CPU these days, even mobile phones, use multi-core CPUs. But, each core is actually a processor. A processor can only handle one compute task at a time, but because CPUs have many cores it can schedule many different compute tasks across them at the same time and, in essence, multi-task. But, you should think of each core like your brain… our brains don’t have multiple brains inside it. 😉

Shawn Blanc covers a lot of the topic of focus in his All The Things (Pro) training by limiting himself to only 3 things per day (outside of his regularly scheduled appointments), but also talks about actually scheduling the time it will take to accomplish those “things” in your day. I mean, it makes complete sense… if you don’t block off the time to complete those tasks, how can you ever expect to actually get them done?!? And I know this has been my downfall for many years. I think to myself, “I’ll find time throughout the day to get to my task list”… yeah right.

I also love how he talks about making sure one of those 3 things is something longer term and more personal. How else will you remember to work on those longer term goals/projects and make enough progress?

Making Those Decisions

Personally, I think you have to have it clear in your head what the possible decisions are and what those actions or filing steps/places are. The reason I say this is because you want to be able to get through the decision process quickly. I don’t necessarily think getting this figured out is easy, but it’s crucial to making sure you know what to do and can do it quickly. Quickness is key because taking too long either slows down the process to the point that it is unwieldy and doesn’t get done, or you never even start due to indecision. I know this is what was happening to me with my email and task management that had it completely clogged up.

I also believe this is a living, breathing matrix that will evolve over time as you and your system matures. So don’t worry so much about getting it right the first time once and for all. Just figure out what makes sense and get started. As you work through things you may realize some of those decisions or filing steps/places needs to be altered… make the change and keep going.

Each person has a unique way of looking at things and requirements, so you really need to figure these out yourself, for yourself. You can look at what other people do as a starting point, but you really need to make it your own. I wrote a post on what I started to do around decisions and getting to inbox zero. You can use this and modify it for your own needs to suit whatever it is you are trying to decide around. The basic framework may still apply. BTW, I have since changed some of the tools I use and how I do some of those things. But that doesn’t matter and that’s my point… it’s a living and evolving system that you should feel free to change as needed.

Having Security in Your System

Getting back to what had paralyzed me, and may be what’s paralyzing/holding-you-back, it is the frightening thought that you might lose something or forget about it after you file it away in that someday/maybe thing.

For me it was the matter of not understanding how I get reminded of those things that I file away somewhere. How will I ever find it again down the road? You could say “search for it”, which was my thought process… until you can’t seem to remember any words related to that thing as it sits in your system. I used to throw stuff in Evernote thinking I would just find it later via search, but a year or more later I would try to find something and it would take many different attempts and methods to try and find things. Sometimes I would just give up because I would keep striking out. This didn’t help my anxiety around this topic at all.

So then, how do you feel secure in your system? Well, I think it is two things:

  1. Be more purposeful in your “filing” of things — By this, I mean you should only file things away that you believe are important enough. Also, you need to be able to provide enough “context” around that thing so that it makes sense to your future self. This “context” might be a project name, an area of your life (work, personal, dad, husband, coach, hobby, etc), tags that you will remember in the future (tags should be clearly defined and minimal in number to be manageable), or notations around it. I have decided to be much more mindful in what I put in different places to make sure it makes sense.
    1. For “quick capture” I use an application called Drafts. This is on my iMac Pro, my iPhone, my iPad and, most importantly and most useful, on my Apple Watch! Whenever I think of something I don’t want to forget I tap on the Drafts complication on my Apple Watch that opens a new note in Drafts and starts listening to provide voice to text. Then I just say what’s on my mind and click done. I do this in the car while driving, in the walk-in closet while getting dressed, in the shower, ANYWHERE! If I am already on one of my other devices I can open Drafts and it opens to a new note for that quick entry. All of these things/notes sit in the Drafts “inbox” to be dealt with later. When “later” comes, I can move those bits of text to their appropriate location, and Drafts even has some great integrations with other apps or you can create your own. It doesn’t matter whether that thought is a task for Things, an appointment on the calendar, an idea or thought for a blog post in Ulysses, etc. The “later” piece is in that review portion I keep mentioning… Drafts’ “inbox” is simply one more inbox to get to zero throughout your day/week.
    2. Help reduce the noise of your system by adding “no sooner than” timing parameters around things that don’t need to be looked at or thought about for a period of time. This could be snooze folders (you could have folders for the month names, or quarters of the year, etc), actually adding some future date like in a task management system, etc. Why continue to spend brain cycles on these things constantly if they don’t need an action or decision at this time? This is like leaving things in your email inbox… every time you see those read emails that still exist you start to think about them again. It’s wasteful and stressing.
  2. Schedule time to review the different areas where you file things — Some things need more frequent review than others. Daily review is for things like your remaining tasks that maybe didn’t get finished (Do they still need to get completed? Should they get filed again or scheduled?), the tasks that should be looked at for tomorrow/today (depending on when you are doing your planning/review), your inboxes (email, task management, quick capture, maybe even physical mail, etc). Things that require less frequent review are those someday/maybe things… things that don’t have a definite due date or that aren’t as pressing. Those are the things that tend to get lost and forgotten, so if you know that you will review them later you will stress less and feel better about filing them away.
    1. When you go through these various areas you can decide if something needs to be brought into the present with a date/time to work on it, if it should be pushed out further, or maybe you can just delete/get-rid-of-it! If something is no longer valid, discard it so you don’t have to think about it any longer. Don’t burden your mind with unnecessary or unhelpful things… you have enough to think about. Prune these areas regularly and mercilessly.

The first part, the filing and context, is incredibly important for your future self and brain (you will thank yourself later), but the second part is why you will ultimately feel secure in your system. The pruning part is also very important to help reduce your potential list… which brings us to the next section.

Caring Less

Boy, that’s a strange subheading… but this was really key for me. We are human beings with limitations and there is no way to get it ALL done or not skip something. The GTD system was great for emptying my brain, but I also felt like I had to track everything that came out of it. Like everything was equally important. But it’s not all equally important. Some things don’t actually need to get done.

In fact, one of the things that I learned in the past year was that letting things sit, on purpose, has a way of telling you just how important or critical it actually is. Some times those things fix themselves or become unnecessary. Sometimes the fire-alarm gets louder and that’s when you realize it does need your prioritized attention. But you would be amazed at how well this tact works. Try and let things stew a bit and see if they still seem important after hitting the pause button. If they aren’t, prune them!

Another way to think about “caring less” is about setting appropriate expectations for yourself on what you can actually accomplish. How I relate this to “caring less” is because I have always had this almost panic that everything needed to get done… it was all P1 and it needed to get done right away. So my daily task list was nearly everything on my overall task list. This is ridiculous and unattainable. Maybe you disagree that this falls under a section titled “caring less”, and that’s fine, but if you are one of the many people in this world who thinks they need to check off 20 tasks in a day, then one of two things is true: either your tasks are remedial bullshit (maybe that’s too harsh, but I mainly mean very small and quick to complete tasks instead of larger and more impactful tasks), or you are trying to bite off WAY more than you can chew. I’m betting it’s the second part, as it was for me. But it actually took a lot for me to get it, and I still fall prey to trying to worry about too many things at once or in a single day.

As mentioned earlier, Shawn Blanc talks about this in the All The Things training, only choosing 3 main things to accomplish that day. They should be the most important things that help you move your priorities and projects forward.

And then I just read an article this past week on Harvard Business Review about this very topic and people getting down on themselves about not finishing up their daily todo lists. The problem? People had too many things on their daily lists!! I like one part in this article in particular on how to prove it to yourself if you still don’t think it’s a problem:

Perform a forensic analysis. Grant recommends trying an experiment. Each morning, write a regular to do list, and at the end of the day, see how many things you managed to complete. Do this for a week or two. “Then ask, on average, how many items am I crossing off?” Your goal is to get a feel for how much work you actually get done in a day, so you can learn to manage your expectations about what’s realistic.

It then goes on to say that, with this data, you need to “right-size” your list to only include what you can actually get done. They say this may wind up only being 2-3 things in any given day.

Getting back to the All The Things training, it’s not just that you only choose your 3 top priority items for the day, but you actually estimate (over-estimate is what Shawn recommends) how much time each thing will take to complete and literally schedule them into your calendar! This last part is SO hugely important that I can’t overstate it. If you don’t understand the importance of this you can also run another test for yourself. Run one week estimating the time of your tasks and actually schedule them into your days. Then, run one week NOT estimating the time they will take nor scheduling them into your day. See which week you are more successful in getting your tasks actually done. You probably see my point.

I know that when I don’t schedule my tasks they rarely get done. But estimating the time they take before scheduling them serves another purpose… it allows you to see if you even have the bandwidth available in the day to get to them! For example, I have 2 days a week that are literally back-to-back-to-back calls from 9am to 5pm… and those are just what are scheduled. I am leading or participating in those calls and need to pay attention, so there is no notion of being able to “multi-task” while I’m on those calls. I know there isn’t much I can do on those days and I have to do things before 9am or after 5pm if I am going to be able to get to them. Other days that have appointments scattered throughout the day are times when I can try to tackle some of the things on my list, but this is also where it is key to make those time estimates and truly schedule them into my day. Free calendar space tends to get booked, so I create appointments for my tasks. If they are important enough to make my short list, they are important enough to schedule time in the day for. When I don’t schedule my tasks, they almost never get done.

Without a plan you become a prisoner of events. Likewise, without review you cannot effectively plan.

Heard the first sentence when listening to the book Measure What Matters, by John Doerr. I added the second sentence myself since it is what occurred to me when I heard it.

Finishing this section off, “caring less” to me means:

  • Hit pause on things to see if they are truly important or worth it — don’t be so reactionary
  • You don’t need to actually do everything that makes its way to you or your list — prune your list mercilessly
  • Stop worrying about losing stuff and trust your system — regularly review

How To Improve (The 1% Rule)

In the book Atomic Habits, James Clear talks about the idea of compounding interest as it pertains to yourself. This can apply to almost any aspect of your life, but in the aspect of a productivity system I see it working like this:

  • Don’t try to bite off too much change at once. It’s too shocking to the system and generally unmanageable. Start off with smaller incremental changes and build on to them over time.
  • Every time you are able to take things 1% further, you are taking them 1% more from the last incremental bump, so each additional 1% delivers exponentially greater results than the last.

1% is just a metaphor, in my mind anyway, for small incremental changes that are more easily digestible and manageable that ultimately lead to much bigger total changes over time.

Let’s look at a real-life example:

  • You want to get better at reviewing and planning, but you struggle with spending the necessary time on it and instead of doing any review and planning you simply skip it.
  • Instead of trying to do it completely “right”, which may actually mean spending 30-45 minutes each day, just set aside 5 minutes each morning or night (choose one).
  • After a week of this much time being successful, bump it up to 10 minutes.
  • The next week bump it up to 15 minutes, and so on.
  • After 6-9 weeks you will be up to 30-45 minutes of reviewing and planning (you can start to add even more time each week as you start seeing the benefits, because it is easier to justify in your brain. Meaning, instead of only bumping it 5 minutes per week, in the 3rd week you may bump it 10 minutes and the 4th week bump it 15 minutes and be up to 35 minutes in just 4 weeks).

The Easy Path To Committing (Habit-Stacking)

When I was reading the book Atomic Habits, the concept of habit-stacking was a major ah-ha moment for me! The idea is this: if you already have a habit that you never miss, simply stack a new habit to the end of it.

We don’t rise to the level of our goals, we fall to the level of our systems.

James Clear, Atomic Habits

For example, for the past 5 months I have been religiously writing every morning and night in my journal app, DayOne, using a modified 5 minute journal template (I’m going to write a post on this soon). I wanted to start a new consistent habit of reading “The Daily Stoic” by Ryan Holiday and write about how I can apply the message to my life in a shared Apple Note with my very good friend JJ. Since I already had a working habit with my journaling, I simply add The Daily Stoic habit to the end of the first habit (i.e., When I finish writing my 5-min AM journal I will read the day’s message and write my thoughts in the note). This worked perfectly! A couple months later, and very recently in relation to me writing this, I realized my Things 3 “Today” view was overcrowded and not working the way I needed it to. The problem was lack of review and planning, so I stacked that to the end of my Daily Stoic habit (i.e., When I finish writing in the shared Apple Note, I will open Things 3 and decide what I will actually work on today). This has been working out for the last week or so, and I am planning on stacking another habit at the end of that, which is performing my planner review and planning. The point is, I am not trying to change everything at once, but adding things to the end of something you already stick to makes the new habit that much easier to stick to and remember in the first place!

When You Fall Down, Pick Yourself Up

Everyone is human and everyone is going to miss now and again. Maybe something comes up that gets in the way of these daily habits that legitimately blocks you from doing them… maybe you just simply miss on your own without any situational help. The point is, don’t miss again.

James Clear talks about this in his book, but I also had my sister mention this to me when I was talking about diet/eating habits. She told me, “Yes, we will mess up… but that’s just an opportunity to do the right thing next time!” I really liked her wording. James Clear was more forceful when he said, “I don’t let myself miss twice.” The reality is I sometimes do miss again… sometimes I can miss for a whole week on certain things. My sister’s point was, stop beating yourself up about it. Just decide you can get back on track and do it. No fanfare needed… no 50 lashes with a wet noodle needed… just course correct and don’t look back!

Doesn’t that seem like a better way to look at it? It does to me. (Thanks Big-Sis!)

Whether the habit/anti-habit I am trying to maintain has to do with productivity or health related, it seems much easier to get over the hurdle of a miss if it’s no big deal to simply start back up. When I used to think about it in more rigid terms, like James Clear talked about it (I was already hard on myself before reading James Clear), I felt like I had already failed. Like it was too far gone already. How silly is that?? I can laugh at myself now, but I wonder if others think that same way?

So, if you are like I was (and sometimes I can start to revert back to), just take the pressure off of yourself. Just try and do better. Try the 1% if what you were trying was too much in one go. In fact, James Clear also talks about that 1% possibly being only to think about the thing you want to do on the daily. He used an example of fitness. Start with the thought for a week. Then get dressed in fitness clothes (without going to the gym) for a week. Then add driving to the parking lot of the gym without going into the gym. Eventually, he said, you are already dressed in workout clothes and in the parking lot… you may as well go in.

Like I said, I really like so much of the Atomic Habits book and ideas on how to create habits. I will definitely be reading it more than once. As some wise man once said, you never actually read the same book twice (because you grow and change yourself, and therefore find/learn different things each time).

Critical Path for Success — Review/Planning

It’s not like this is a surprise ending… I’ve been sprinkling this in from the very start of this article.

I guess my closing statements are these:

  • Make the time to review and plan and DON’T miss it (pretend it’s an appointment with someone you wouldn’t want to disappoint)
  • Force yourself not to take on new things (reactive) until you review and plan (strategic) what things should actually be on your task list (this means you can’t be a “yes” person)
  • Review means you don’t lose track of things, which means filing things for later review is less scary — I’m not saying I never lose my way or slip backward into indecision… but if I realize I am doing it and find my way back to the review and planning phase, all is not lost.
  • I also continually fall down… but, as long as you pick yourself back up, dust yourself off and get back to the right activities, you are doing much better than most.

When I review and plan my day I feel great and get done what I need to get done. When I don’t review and plan and am only reactive, I feel frazzled.

At least if I review and plan my day when something comes up that is reactive I have my plan in front of me and can decide if I want to skip or move something, but I still feel good about my day in the end.

– VirtuallyGeeky

This article turned out to be way longer than I thought it would, and I know it was a lot to read. If you made it this far, thanks for staying with me. I hope you got something out of it. I was hoping to get it out on March 9th and even to publish something additional on the 16th, but this topic was so important to me and my life right now that I decided to just finish it. I toyed with making it a 2 part series, but where would you split this up?? Also, even if I did that, it didn’t feel right to leave anyone hanging for the ending.

This blog and writing these topics really helps me think through things and have a conversation with myself. If it helps anyone else at the same time, then my time was even more worth it. Please feel free to leave comments and start a conversation with me and anyone else that visits!

Free Time Management Course from "The Focus Course" during this pandemic

I have only talked briefly on this blog about how much I love the people and their training over at The Sweet Setup and The Focus Course, founded by Shawn Blanc. I just got an email this morning (because I’m a paying member) that they are offering their course, “A Focus On Time 2.0“, at no cost! It’s normally $247, so this is a pretty sweet deal. I have personally paid over $1,000 for their various trainings so far and have zero regrets… so an opportunity like this is pretty awesome!

It looks like they are running this promotion through the end of March, but I wouldn’t wait! No cost and no risk, what do you have to lose??

Click here to be taken to the promotion page where you can get the training. The promo code is on the page several times, but if case you miss it, it is “WFH“… as in, Work From Home.

I just signed up myself and this was the welcome letter I got:

Thank you for joining our flagship Time Management course.

This course has several lessons that are specifically relevant to work-from-home creative folks as well as full-time, stay-at-home parents. Which is why we are making this course available at no charge to help anyone who could use a re-alignment of their time management skills in context to the current state of things.

I am honored to have the opportunity to connect with you and help you become a little more focused and relaxed during your day.

I have been meaning to post something once a week and have failed the past 2 weeks. In that time I have been busy with work and life, so it has been a struggle to put in the time on writing for this blog. With that said, I have been putting in quite a bit of time and effort on a meaningful post that got much bigger than I originally expected, so I hope the wait is worth it. I contemplated splitting it into 2 separate parts to be able to get things out weekly, but that felt wrong to me, so I waited and finished it all. I should have it posted by Monday morning.

I hope everyone is safe and healthy during this strange time with this pandemic. I would guess that this will still get worse before it gets better, so make sure and prepare your psyche for what’s to come.

Peace and love to all!

Creating a Working Productivity System

Written on 02/29/20

I came across The Sweet Setup as a result of looking at some custom page templates that David Sparks had on his blog on MacSparky. After looking at the training on The Sweet Setup site and looking at the Ulysses app, which I had looked at before but didn’t want to pay the subscription fee for, I decided to get ALL of their training as a package. I already had and used all of the other apps they had training on, other than Ulysses, and I like supporting people that create amazing content. I’ve since figured out that Ulysses is an awesome app, so I’m happy I took the plunge. I think it will greatly help me write more content and do more blog posts. In fact, I wrote this blog post using Ulysses and it even publishes directly to my WordPress blog from within the Ulysses app whether on my iMac Pro, my iPad or my iPhone! Talk about convenient!!

Some Background

The EVO Flow System

I originally took the EVO Brain Type Assessment maybe a year and a half ago, and then bought their physical planners. I really like a lot of things about their planner and system, but some of it just doesn’t make sense to me. The planner notebooks are superb quality, truly lovely and a pleasure to use, but it just felt a little off when using it. But there are definite benefits to their content.

I also recently paid for and took their newer, more involved (and expensive) EVO Elements Assessment and got the results of that. I think there is a lot of great content in there, and I will need to go through that multiple times to truly get it, but I believe it will be helpful in understanding myself, my needs, and how my brain works and sees the world.

I like the act of writing things down in an analog/physical fashion, but the fact that it’s not digitized and searchable is a downer and a little frustrating when trying to find something. I think it still has its place and I could also take pictures of things to digitize them, but I never do. So I started to lean toward using the iPad and the Apple Pencil to be able to still write my notes by hand, but have them already digital and searchable.

Physical, Digital, Multi-Device, Frustration

Over the last few decades (man I’m old) I have flip-flopped between both physical and digital uses for various things within my productivity systems. Physical planners have a strong place in my heart. I love using them and writing with really nice and expensive pens, but I never seem to stick with them. Plus, flipping through pages to reference things later is kind of a pain.

I have used several different digital planners and calendars, but never found a single thing that fully met my needs. I used many different task management applications and they all felt limiting to me until I found OmniFocus and later Things, as I write below in this article. But there is still a problem… which you’ll read about below.

Then there was the issue of wanting to have all of this information no matter where I was. Before “cloud” applications became a thing I had to choose my phone for that single source of truth. But phones are not the best device for all cases with their small screens and that also led to frustration. These days, the apps I am using sync across all of my devices in near real-time and I can move seamlessly from one device to another. Progress is a wonderful thing.

More importantly, the latest iPad Pro devices are so good, and now that iPadOS is out with it’s enhancements to make the iPad more like a laptop (if wanted) I am using my iPad more and more. While I still use my iMac Pro at my desk, I almost never use my (work) laptop anymore. I am super excited about that. I will write an article about the iPad and how I have been using it. I have another blog for my photography hobby where I wrote some articles about both the iMac Pro and the iPad if you are interested in reading some of my thoughts. I need to write part 2 to the iPad article now that iPadOS is out and I have been using my iPad so much more.


So, with some of the background out of the way, let’s talk about what I am doing and using today. I will talk about the applications/tools I am using.

GoodNotes FTW! — Handwriting in the Digital Age

I had come across GoodNotes quite some time ago as I mentioned from finding it referenced on the MacSparky blog, but I never bought it. One of the coolest things about GoodNotes is that it has handwriting recognition, so this means your handwritten notes are actually searchable! I downloaded David’s page templates thinking I could even print them out and use them physically in my Circa notebooks if I didn’t use them digitally, and it gave me the idea to create my own custom planner pages. But then I struggled with what to put on my own page templates, got analysis paralysis and gave up. I still would like to create my own templates and need to flesh this out graphically to brainstorm ideas. I also realize that I can keep iterating on them, so it doesn’t need to be perfect the first time.

David Sparks also mentioned Shawn Blanc and his templates that led me to The Sweet Setup and their training (mentioned and linked to above).

GoodNotes Training

The GoodNotes training from The Sweet Setup was good to understand the app and give some ideas of how to use it, as well as some good page templates to use, but the real benefit was from the All The Things training where Shawn Blanc goes through how he uses a notebook and his productivity system. It is a Hybrid system that uses digital apps for calendar (Fantastical, which I’ve been using for years) and task management (Things 3, which I only started using from this training), but then analog — or writing in GoodNotes on the iPad — for the Planner portion and note taking.

We will see if I can keep up with the notes in GoodNotes, but I like the system so far and have been using my iPad in place of a physical notebook for a couple months now. I mostly use handwritten notes during customer meetings since the perception of people is that you are paying attention to them while writing, versus typing the same notes on a keyboard (I even fall prey to this assumption myself when someone is typing notes of what I’m saying). Something to keep in mind if you are planning on taking notes and don’t want to offend the person speaking.

For the planner portion, The Sweet Setup training provided some page templates to use as planner pages, and those were decent, but it still felt lacking to me. This brought me back to searching for planner pages and/or making my own templates. However, right around this time I got an email from Blanc Media Group that they were about to release a digital planner for 2020 that would work in GoodNotes! I thought maybe this would be the solution I needed.

2020 Digital Planner from The Focus Course

Since buying and taking much of the training from The Sweet Setup that I talked about above, Shawn Blanc and his company released a digital planner for 2020 that is more like a full physical planner. I purchased that and have used it… and it’s nice, but I honestly haven’t kept up with it. It has all kinds of cool links between pages and the planning/review stages, but something still feels a little off to me.

I don’t think it’s that the planner doesn’t meet my needs, because it’s nice and should work. I think the problem is that I don’t set aside the time to put in the planning/review work like I should/need to. I keep living my life in reactive mode because I don’t make the time. I know this is going to become its own blog article because it’s a HUGE issue for me (and I’m sure others in my situation).

As a side note, when I bought the digital planner, they offered access to a larger training package (The Focus Course) that normally is only open for registration a couple times a year (or something like that). I took the financial plunge on that training but haven’t set aside the time to go through it yet. I’m sure I will learn a lot more through that training as well, and will surely write here about my experiences with it.

My Own Templates

I will probably share the templates I create once/if I get them done. Maybe even how I make them… I may use OmniGraffle, but I seemed to be struggling with the controls in OmniGraffle, so may need to use something else if I can’t get that figured out.

I still haven’t fully figured out what I want, but I had the idea of using some components from the EVO planner and some from other planners I have used and combining them in a way that makes sense for me… just like David Sparks did and talked about in his blog post.

Calendar App — Fantastical

As I mentioned above, I have been using Fantastical for years (I think since version 1 actually) and have enjoyed it. I bought BusyCal some time last year and tried to switch to that instead. I also bought BusyContacts for the Mac from the same company as it tracked appointments and emails to individual contacts. Both applications are nice, but I missed Fantastical and went back to it (I still use BusyContacts on my iMac Pro). Flexibits recently released Fantastical version 3 and I have been using that for a couple weeks now. I am actually having some issues with it on my iPhone, but I am going to try deleting it and reinstalling to see if the problems go away… because I’m not hearing about others having the same problem. The problem I am seeing is when opening the app, it seems to lock up for several seconds while it updates itself. This is crazy frustrating when trying to look at an appointment or trying to add a new appointment quickly.

Deleting the app and resinstalling it solved my problems! So, very happy to say that the iPhone app is running smoothly.

Fantastical allows you to create appointments using natural language and I just like the various viewing options available to you on the various devices. I also LOVE how it combines duplicated appointments across different calendars into one, which helps make things less busy looking. I often duplicate my work appointments that have travel onto my personal shared calendar with my wife so she can see when I am away from the house. The fact that Fantastical combines these into one event to look at removes clutter from the daily and list views.

Task Management App — Things

I used to use OmniFocus and even got some amazing training around OmniFocus from David Sparks… in fact, I got multiple versions of his training over the years on that app. OmniFocus is a great app, but there were a few things that I found frustrating and ultimately had me looking elsewhere. Namely, you couldn’t manually change the order of tasks in a list, and while it was EXTREMELY powerful, it almost felt too complicated. I still think it’s a great app and wouldn’t fault anyone for choosing it. There are a lot of things you can do with it that you can’t with other apps.

In my search for the GoodNotes templates, I happened upon The Sweet Setup training and saw they had listed Things as their favorite task management app. They had some blog posts around this as well as some videos and I figured I would give it a try. If memory serves, I think I downloaded a trial version of the Mac app and tested some things out.

Two things about the app got me hooked:

  1. You can manually change the order of tasks within lists, which allows you to manually create an order of priority or order of completion.
  2. You can email messages to Things while changing the subject line and the x-callback URL link it creates still gets back to the original email even after you archive it. With OmniFocus, if you changed the subject line it would break the link.

I have since changed to using a different x-callback URL method for linking to emails that I also found on MacSParky that utilizes AppleScript and TextExpander. This new method also allows me to link to emails in Things and Bear Notes or anywhere else. It is SUPER simple and very useful.

I have been using Things for quite a while now, and I actually started falling into the same bad habits that made OmniFocus mostly unusable for me. I just wrote a post on this because it is something I need to fix, and the issue is NOT the application, but rather me. When I made the switch from OmniFocus to Things, I did a monster purge of tasks to get my task management app cleaned up. But this was only a temporary solution to the underlying problem. Not that I was blaming OmniFocus for this problem, nor is it why I switched to Things instead, but the complexity of OmniFocus and lack of manual rearrangement capability didn’t help matters. I will absolutely be writing a post around my trouble with task management as a whole and how I intend to fix the problem. This alone seems like a journey unto itself.

iPad Productivity Center

Essentially, the iPad is the center of this productivity system because of the digital planner. When I only had the 12.9” iPad Pro (2018 version with cellular) it was a little cumbersome because the 12.9”, while MUCH smaller than the original iPad 12.9” Pro (without FaceID), it is still too big to be truly take-anywhere. I recently gave the 12.9” 2018 model to my wife as a laptop replacement and bought the 11” iPad Pro (2018) with 1TB of storage and cellular to replace it. I was worried that I would feel like I was missing screen real estate, but I haven’t felt that even once since switching. And, in fact, when I use my wife’s 12.9” now it seems insanely huge to me. So I am very happy with the change to the 11”. The only bummer is that there is a rumor that they will be releasing a newer model in the Fall of 2020 (this year), so I am sure there will be some slight regret for not waiting. But honestly I am still happy because I am using it so much more.

While the iPad is the hub due to the planner being mainly useable only on the iPad, I can still get to GoodNotes on my iPhone or iMac Pro and look at things. The good news is that Fantastical and Things work extremely well on all of the devices individually, so the only real limiting thing is having to use the iPad for the Planner portion. And since I use my iPad so much more and take it with me to more places, I usually have that access.

What’s Next?

For my next article on productivity I will start talking about the changes to my mindset on how to deal with productivity and the struggles I have overcome and those I still have to work on. I will try to offer some advice around these things as well. In all of this, I hope it can help others that have similar struggles as I do and it helps me to “think out loud” through writing these articles.

Things 3 not working out the way I thought it would —OR — Why I shouldn’t put everything on the Today view

February 14, 2020

It’s my fault because of how I am using Things, but I’m not sure how to fix it just yet. If I’m being honest with myself, I knew switching to Things from OmniFocus would not solve my overarching task management problem.

The problem is that I mark things as “Today” so I don’t lose sight of those tasks, but I have zero intention of actually doing them today. In fact, they may even be things I don’t intend to do for over a week. I think I do it “so I don’t lose track of them”, but all it does is clutter my “short list” and make it long and difficult to see what I actually need to do right now. Things 3 allows you to organize the tasks into any order you want, and in the beginning I was doing that so the things I need to focus on first were at the top of the list descending in order of priority or order to complete.

So, to fix this I really should clear out my “Today” list of everything that I don’t intend to complete today. The question is: How do I not lose track of tasks? Or, maybe more importantly, how do I break the habit of thinking I will lose track of things if they are not in front of my face??

Maybe I can utilize some of the things I am learning from Atomic Habits in my task management processes. I feel like I will lose track of things because I don’t religiously review and plan. If I am reviewing and planning, then I won’t miss something and I’ll be more intentional with my time. So, the real problem is that I don’t religiously review and plan.

How do I make review and planning a habit… Make it something that is completely automatic and regular?? I have been successful in making journaling a daily habit (using my modified 5-minute journal AM & PM templates in DayOne), as well as my Daily Stoic practice with my good friend JJ in a shared note in Apple Notes.

Habit Stacking, talked about in Atomic Habits, may be the way I can do this. Habit Stacking is essentially adding habits to the end of other habits you already have. As an example, you want to increase fitness by doing pushups every morning. Maybe (hopefully) you already brush your teeth every morning as an automatic habit. You could specify that, after you brush your teeth you will drop to the ground and do your pushups.

For my needs, since I already have a morning and evening habit/ritual of doing my 5-minute journal, both in the AM and PM, I can stack reviewing my tasks directly after writing in my journal. So far I have written in my journal every day for the last 141 days, so that is a pretty solid habit now. I will try this starting tonight.

Productivity, a Journey – Part 1 of… Forever

Originally written on February 14, 2020

In the beginning, there were things to do…

…problem is, those things often got overlooked, forgotten, or procrastinated on.

I didn’t mean the title of this post to seem ominous or depressing. On the contrary, it is meant to be a great journey or quest where you always look to improve upon something as you evolve over time and your needs change or you learn new ways to do things more efficiently.

A Productivity System for People with Analysis Paralysis

I am one of the unfortunate people that can’t ever seem to get a system to consistently work for themselves. I see other people who have systems that work for them and I am jealous. I try to implement their system, and maybe it even works for a few weeks, but inevitably it fails for me because I don’t keep up with one or more important pieces of that system. I’ve thought I had the right system several times. Maybe even kept up with something for months. Ultimately it fails and gets too overwhelmed, whether email or task lists, and becomes paralyzing.

I think one problem is a lack of both planning and review on a daily basis. Another problem is indecision, especially around deciding on what to do… including what to do with emails (do I archive, delete, take action, save somewhere for reference, etc.).

To make this easier to talk about, I am going to break things into two topics. One will be calendar/todo, and the other will be email. Because email has a lot of action items it will be similar in discussion points, but it is still different. Also, if an email happens to be an action item outside of email, then it should get placed into the regular todo system.

All of what I will talk about will be a bit of a work-in-progress, which goes back to the title of this post. Productivity systems, for me at least, are constantly evolving. The techniques I mention are a result of various things I have tried or got from other peoples systems that seem to work for me to some degree. However, I am not perfect at following my own advice, or others, and am human. Even with my latest system I falter and usually have to try and “catch back up”. I hate being reactive, but my new job role has me rather busy and same with personal life. The key seems to be scheduling time for both the planning and review that I mentioned earlier. That way, if you are starting to fall behind on things, you can schedule some blocks of time to get things back under control. And similar to ensuring that “taking care of yourself” is a priority, which I am also not good at, you need to make “staying organized” a priority. You are at your best for both yourself and others when you are not running around like a chicken with its head cut off, so it is worth your time whether other people, or you, agree with that or not.

The “part 1” portion of the title relates to there being many more posts to come after this one pertaining to productivity. I will try to categorize them all as such and maybe even link between some of them where it makes sense and is directly related to the topic of discussion. Ideas are coming to me all the time, and to be timely I will try to post things as they come to me… but some of my intended posts require more thought and planning, so they won’t be coming out in any truly organized fashion. One post I am working on behind the scenes is my overall current system I am trying to use and stick with. I already have a side-note post around one of the applications I am using called Things 3 that I will probably post before I get the overall system post published.

I welcome feedback and questions if you decide to come along with me on this journey. Hopefully I can learn from others as well.

Task & Email Management – Inbox Zero!

Inbox Zero!

A little over 2 weeks ago (writing this on September 21, 2019) I decided I needed a clean start with email. My inbox literally only had maybe 3 months worth of clutter because 3 months ago I tried to get a clean start back then. The problem the last time, and several similar attempts before that, was that I didn’t fundamentally change the way I was processing email. When I couldn’t or didn’t need to take immediate action on an email, I left it in my inbox so I knew I had to deal with it still. Other things I just didn’t know what to do with. They weren’t really a task, nor immediate if it was a task (like something to read or reference), so I just left them in the inbox marked as read so I could get to them when I needed to. Finally, for things that I absolutely needed to take action on, I might flag as well as mark unread so I knew I still needed to take action on it.

What a HORRIBLE freaking way to use email!!

I have read and watched countless videos on how to obtain inbox zero nirvana… but I never made the decision internally of how to deal with email and be consistent with it. I’ve read GTD by David Allen and many other blog articles and self-help productivity books and articles. But until you change they way you look at email and can compartmentalize it in your head quickly, you will most likely fall prey to a cluttered inbox like I have for decades. My physical desk is similar, and that’s something I still need to tackle.

What did I change?

I had to come up with a method to process my emails in a very simple and tidy fashion. This means that emails need to fall into one or more categories, and each category has a processing action associated with it. I’m not saying this methodology is perfect, and I expect it will morph as required while I use it and find inefficiencies. In fact, over the last couple weeks I have already made some changes. The categories and actions I am about to list are current as of September 21, 2019, but I started this out using Microsoft Todo as my task management solution, which I’ll explain later and why I switched. Where I list OmniFocus below (I use this on my Mac and iOS devices, but they recently released a cross-platform Web version too!), it could be whatever task management app you want to use.

Categories = Process Actions

  • Immediate Action of less than 5 mins = Reply/Forward/Act-on as necessary
  • Garbage/Don’t Need = Delete/Unsubscribe & Delete/@SaneBlackhole
  • No action, but not trash = Archive
  • Reference material = Save to Evernote (unstructured) or OneNote (structured) and Archive email
  • Action item, but not immediate = If email related, forward to OmniFocus not changing anything in the subject line, then rename from within OmniFocus. If non-email related, forward to OmniFocus with appropriate task name as Subject Line
  • Something to deal with later in email = Either use SaneBox Snooze folders to have the email reappear in my inbox at the appropriate time, or the iOS Outlook app “Schedule” feature to snooze email to return to inbox at appropriate time SaneBox folders are universal across any email client —

How to start with a clean slate

Each person is going to have a different starting point/situation. The first ever time I tried to do this I had literally tens of thousands of emails in my combined inboxes. When you have something that massive, the only thing for it is creating a new folder in each email account labeled something like “Clean Slate” and dumping ALL inbox items into that folder. In this way you can start dealing with your inbox in an uncluttered way and follow the process you choose to deal with items. At the same time, you can go into that “Clean Slate” folder to start searching for things you may need to really deal with. If, like me, you have tried the clean slate approach before and only have a couple/few months of email in your inbox, you can use the method I used.

Sidebar: I have been using SaneBox for the last 4-5 years on all of my email accounts (the Dinner subscription is what it was called when I purchased it) to automatically filter unimportant email OUT of my inbox so I can deal with it later in batches. I get a daily digest every day around 4-5pm and opening that digest in a browser allows me to very quickly take action on those emails by seeing who they are from, the subject and a quick blurb of what’s in the email. From there I can chose to delete it (even delete many of the emails in one click), archive it, send it to my inbox just this one time, or train things to different folders (like maybe something should actually go to my inbox all the time, or maybe I want to Blackhole all future emails like this so I never see them again).

At first, you may think the cost of this service is expensive, but once you figure out just how amazingly useful and powerful it is, it is indispensable. It’s also universal, meaning it has nothing to do with any individual email application and is visible across all email applications as well! You can use Snooze Folders and create your own custom folders to do all sorts of things. I have some folders that filter stuff about hobbies and automatically forward all emails to Evernote where I can search for them later.

The link to SaneBox I am using is a special link that would put money towards my SaneBox account if you sign up for the free trial, so I’d appreciate you using my link if you decide to sign up. But even if you don’t, I’d still recommend you using this service.

While it will not completely solve your problems, nor get you to inbox zero, it definitely helps with inbox zero.

The first thing I did was filter my inbox for unread email, since these were things that I either literally never looked at or marked as unread because I needed to do something with them. I went through these very quickly and made decisions on how to deal with them based on the above categories/actions. Next, I filtered on flagged items and went through the same process. Finally, with only unfledged read items, I quickly scanned for anything that jumped out as important and processed those, and then selected ALL items and Archived.

Let’s Talk Task Management

While Inbox Zero has been working for email for over two weeks for me, I was worried that some tasks were getting missed. Using a tip from someone I respect that always has a clean inbox, I had started flagging emails with due dates and reminders. I was doing this in Outlook, which is what he uses… only on Windows, not a Mac. While I do like Outlook for Mac, it is NOT the same as on Windows and is missing one critical feature for this to work perfectly. That feature on Windows is the ability to have a task list below your calendar to see tasks that are either due or available to work on. I thought I had a solution, which was to use Microsoft Todo application, which is available for the Mac and iOS (and other platforms as well). This seemed to be working for the first week.

My work Exchange account seemed to be working fine with Todo, but my personal email accounts don’t seem to work with flagging and showing up in Todo. I believe it works with any Microsoft email account, like Outlook.com, but I have 4 other personal email accounts that aren’t these and there’s no way I am pushing all my email through my Outlook.com email (at this time anyway). What I started to realize was emails I was flagging to then show up in Todo and that I would not lose track of weren’t ever making it to Todo. That means Todo wasn’t my single source of truth!

You might say, just use Tasks within the Outlook app! That would only work if I only used the desktop version of the app, because Outlook on mobile only contains email and calendar… not tasks. I even thought about using Reminders, but again, only flagged emails from my work Exchange email were showing up in Reminders… and while Reminders has its uses in my family (shared lists) it is NOT my go to task management app.

I thought that I may need to go back to OmniFocus, which at least now tracks email IDs correctly (meaning, within the task notes there is a hyperlink that opens your default email app to the correct email, EVEN if you archive it or move it to another folder – this works on iOS and macOS!), but in order to do that I can’t edit the subject line or it treats it as a new email thread and you don’t get back to the original email. Since the subject line becomes the task name, this means forwarding emails to be linked don’t have a very descriptive task name. Also, this means I couldn’t possibly automate parsing the subject line with due dates and projects, etc. All email ends up in the inbox of OmniFocus, so the ONLY way I can make that work is to religiously clean out my OF inbox too. Up to this point, my OF inbox has been much like my email inboxes used to be, so that means I need to come up with solutions to clean it up quickly with very few decisions, similar to how I am processing emails.

I abandoned Todo from Microsoft recently because the app isn’t flexible or automated enough. There is no single view that automatically populates with stuff I should work on today. There is a “My Day” view, but you have to manually choose what goes on that day, which is idiotic! There is no unfiltered view to be able to see everything on a single page… so I’m done with it. Pretty much, the ONLY nice thing about the app is that it automatically imports flagged emails, but only from my work account. Which means that it’s inconsistent, and I was flagging emails from my personal accounts thinking they would be in Todo, but they never show up and I forget about them. It’s better to always simply forward the email to OmniFocus and clean up the OF inbox on a daily basis. At least that is consistent, if not the perfect solution.

My gripe with OF is that I can’t change the subject line of an email if I want to be able to get back to the email from OF. Since the subject line becomes the task name, the subject of the email almost never matches up to what the task should be called. There also is no native way in OF to parse inbox tasks based on tags/keywords in the subject line anyway, and even though there are some scripting automation solutions that can parse emailed tasks, since changing the subject would break the email link it is not worth it.

This means that I have to take an extra step later by looking at the contents of the emailed task to determine what the task actually is. I suppose if I emailed the task to OF and immediately opened OF and changed the task name it would still be fresh in my mind, but I tend to batch process my OF inbox.

Finally, if the task doesn’t involve actually replying/forwarding the original email and is simply something I need to get done outside of an email app, then I CAN change the subject line to the actual task name when forwarding to OF… because I don’t need the task to link back to the original email. Again, though, this requires additional thought at the time of the forward and is less “automatic”, and still requires me to choose if it should be deferred/due on a specific day and if it’s simply something I merely want to do.

Cluttered Task Management

I have owned and been trying to use OmniFocus for many years now. David Sparks (MacSparky) has some incredible field guides/videos and blog posts around how best to use OmniFocus, but he can’t fix my/your brain to process items appropriately. I have purchased two versions of his OmniFocus field guides, and they really are amazing and super useful… I would recommend them to anyone, and I get nothing myself for saying that. They are that good. His latest version is amazing and easy to navigate thanks to his new training site. You can jump around the content to get to what you want, which is perfect for review/reference down the road.

One of my biggest failures with OmniFocus has been a very cluttered view… to the point that I had so many things I could be working on that I couldn’t figure out what to work on. This is in part because I was trying to use David Allen’s GTD method of a single inbox to empty your brain. My problem was everything I put in was “active” and therefore “available” to be worked on. I suppose you have to understand how OmniFocus works to better understand this, but some of these things are what make OmniFocus so powerful and customizable.

I started to try and “defer” things in OmniFocus, but I also used a lot of due dates arbitrarily so things didn’t get lost in the sea of available tasks. I also would flag things that I felt were important, but didn’t have a timeframe I needed to get them done… this was another way I ensured I didn’t lose things. It just kept the clutter and I’d still waste brain cycles looking at those items to decide I didn’t need to work on them.

Not EVERYTHING actually needs to get done

I read an article from an OmniFocus user a while back that was having the same issue as me. His solution was essentially to only have two major categories for tasks: either Want-to or Need-to. The concept is actually quite simple. Either you want to do something, but there is no real hard time limit/due date or even penalty if you don’t do it, or you need to do something, which means there is either a hard time limit/due date or a penalty if you don’t do it. With this, Want-to items relate to Someday/Maybe from the GTD principals, and can therefore be “paused” in OmniFocus, which means they do not show up as available tasks. Need-to items are active, and therefore available, but sometimes things need to wait or at least don’t need to be worked on right away. So you use “defer until” dates to make them only show up when they should be available to be worked on. Other times tasks literally need to be completed on/by a certain day. For those you actually set “due dates”. And, if something has a due date but doesn’t need to be started right away, you can also set a defer until.

Using these two major categories, most things will likely end up as Want-to and therefore won’t clutter your daily task list. But then you may worry that they will get forgotten. For this, you can either schedule review times for certain projects or simply go through the list occasionally to see if any tasks should be moved into something more active.

Get over FOMO (fear of missing out)

Almost my whole life I have suffered from fearing that I was going to miss out on, and this translated to my email and task management. I think it has only been recently that I decided this fear was counter productive and I needed to get over it. The bottom line is, if something truly needs to get done, you will figure it out even if you “pause” that thing or don’t have it in your face all of the time. This has been a relief on both my brain and stress levels. I am okay if things get missed because I had other more pressing matters to deal with. Not everything is a priority. Focus only on what truly matters the most… the rest you can do in your spare time.