Sometimes I ask myself, how do I do it?
According to Todoist, since August of 2016, I’ve completed 2,640 tasks, which translates into:
- 563 tasks a month
- 140 tasks a week
- 23 tasks a day (6 days per week)
Now when you take into account that this does not factor in my daily routines, meetings or delegated tasks to my assistants, it’s a feat I’m quite proud of.
1It’s incredible how far I’ve come from where I was a few years ago. I was struggling to get anything done, and I obsessed over finding the right systems (i.e. I was addicted to productivity porn).
After reading about GTD, I set out on a mission to find the best system. I ended up trying all sorts of different task management apps over the years, from Nozbe, Wunderlist, Asana, Trello - you name it; I've tried it.
In fact, I spent more time switching apps than I did doing actual work. I thought the reason for my productivity issue was not having the right system and I was associating getting work done with using the right tools.
While software matters to a degree, it’s not as important as how you use it. Much like in the photography world, they say it’s not the camera you use but rather the person behind it that determines the quality of the photo.
The system I describe below is a culmination of years of experimentation and constant reiteration. In fact, I recently rolled it out to my entire company at SupportNinja, and it has increased productivity and communication across the board.
The entire company now assigns tasks to others, and we have a weekly business meeting where we review any unassigned or overdue tasks while reviewing existing ones to determine their priority as a team. Most companies never teach their employees how to process email in their inbox, but we do. This is the only reliable way to ensure that email can be relied on to be an effective communication tool to all the employees and that information won’t slip through the cracks. Between Slack (short questions), Email (long-form collab) and Todoist (tasks) we try and label different tools for specific types of communication.
While it’s by no means perfect, it’s much better than not teaching a workflow to your employees at all. In that scenario, you might have Steve from IT giving his department tasks through email or John from HR who only uses Slack. It’s like everybody is singing to a different tune. You might be able to patch something together from a cultural perspective, but I find it’s a better long-term strategy to set the standards from a hierarchical standpoint.
Below, I go into detail to describe the system I’ve setup for myself and my company. What’s great about it is that it doesn’t matter if you’re just one person working by yourself or somebody who has a team put together. This is a productivity workflow that has worked well for me and subsequently my company, which has in some ways validated the method to the degree that I feel comfortable writing about it.
Now, I don’t advocate that this particular method is the best, nor do I advocate that you copy this way exactly. However, if you have no framework in place for yourself or company, then this one can be an effective one to start with. I encourage you to make it your own while maintaining a kaizen philosophy of continuous improvement.
Let’s Dig in.
After hopping on my computer, before digging into email, I check what’s in my “Tasks due Today” section of Todoist and then highlight the most important items I want to work on that day and mark it with a red flag. Some like to use a Productivity Notebook where you write in 3 tasks you want to do for the day; this is just a variation thereof.
Next I open up Gmail, but first - let’s see how I have it setup.
My Philosophy on Email
By default, the Gmail interface provides various tabs where it attempts to auto-group individual emails. I’ve never found this helpful and found it more distracting if anything, as every time an email hit one of these labels I felt compelled to click on it to see what emails were hiding in the tab. It’s just like the addictive Facebook notifications which give us a little dopamine rush every time we give in and check. It took me years to realize that this was a huge contributor to my procrastination problem.
I took a step back and asked myself, instead of trying to develop the willpower to stop looking at my inbox every 30 minutes, how can I design a systematic way of processing my email so I spend more time on deep work?
I’d like to comment on a method Tim Ferris has described that works for him, which is chunking his email habit into blocks of time at the beginning and end of the day. I’ve found this impossible to do when you’re at the helm of a company. I also find it to be true by many founders, executives and regular employees who work in organizations with a culture of constant communication. In many ways, a company could unintentionally create a dangerous cultural norm by introducing the idea that in order to make it seem like you’re working, that one should respond to others quickly. As Jason Fried of 37signals says, a company culture is everything that isn’t in the handbook.
So basically, my method is one which changes the habit of checking your email into a system of processing, not responding.
To start, I split my Gmail layout into three specific parts:
- Starred Emails
I like to use Starred emails for two reasons. The first is to mark an email which might carry important information that I might need to recall on in the future. I find this mostly ends up being related to travel (at least for me). The second is when I’m processing my inbox (as described below) and there exists an email I want to reply to at the end. Such a response shouldn’t take more than a few minutes, but sometimes I encounter a little bit of resistance as it would require a change in mental modes from processing to thinking (about a response or next action). The reason that it’s at the top is so that it’s where I end up at since I start from the bottom.
- Important Emails
95% of the emails I reply to are marked as important emails. These are emails with a little yellow flag next to them and was previously rolled out in 2010 as the Gmail Priority Inbox. It’s been largely overshadowed now by the tab system.
[alert type="info"]Lately, Gmail has been trying to roll out a more integrated Email system called Inbox which tries to act as a central system where you can store reminders, follow-ups and have easy access to relevant information. They haven’t switched Gmail to this because it’s somewhat of an experiment by using AI to help manage information and collaborate. While I think it’s promising, I don’t think it replaces having your own system that is customized and suited to your needs and the needs of your organization. At the end of the day, if you have a system that works for you then great, use it - however, Inbox is not a system you can just throw 100 people at and expect them to all use it in the same manner.[/alert]
- Everything else (unimportant emails)
These mostly end up being newsletters, password resets, forums, statements, reports and other misc notifications. Most of these emails don’t require any reply.
You can configure this setup by going to Settings inside Gmail. Then clicking on the “Inbox” link. Then make sure you select “Priority Inbox” as the type and then setup the sections as follows:
Now the beauty of my method is not unique to the layout. So feel free to customize the Inbox section to your liking. This is just what I use … and I like it. ¯_(ツ)_/¯
The race to the top
I used to be stuck in the email hamster wheel. I’d spend my entire day in my inbox, and it felt terrible. It was one of those bad habits you don’t realize you have, to keep email open as my number one tab at all times. It had a dedicated button on my bookmark bar. I tried many things to change it.
At first I tried disabling email notifications, but still found myself just checking it more often. Then I tried to remove it from my bookmark bar, but then I just started typing it in the URL bar. I even tried using a time limiting extension like InboxPause but found myself disabling it when it blocked access to my email for random calls or conversations with others.
[alert type="info"]While I don't use InboxPause, I do currently use something called Inbox When Ready and find it to be a great addition to my inbox. It allows you to hide your inbox instead of attempting to pause it. A simple button click can hide or view your inbox. This means it's not annoying to bypass, yet it does create a small barrier that can help you to avoid looking at your email if you're aware that you're doing it.present enough in the work that you are doing. [/alert]
That wasn’t even the worst of it though.
Whenever I looked at my email, there were emails I dreaded, so I just let them pile up at the bottom. It was a constant battle to reach what is now popularized as “Inbox Xero.”
The moment of realization for me when I discovered that I was reacting to other people and working out of my inbox. Everything I did, centered around what was in my inbox, and as a result, I never had time (or the willpower at the end of the day from responding to everybody else’s requests) to work on the items that actually pushed the envelope further, so to speak.
Occasionally I’d find the time to clear my inbox. However, it was an odd feeling to have no emails, as that meant I had accomplished what I was stressing out this whole time to do. It’s a little bit like winning something and then realizing you have no greater purpose or goal in life.
Either way, it was a constant stress that I had to tackle. After a bit of reading, and lots of time I discovered I needed to rewire my email habit and become more disciplined by holding myself to a higher standard.
With that said, let’s talk more about my method.
I’ll start the day by scrolling to the bottom of my inbox and working with the unimportant items. Why the trivial ones you ask? I find it easier to transition into email processing mode if I start out with mostly informational emails where the only action for me to perform is to read and archive.
I like to think of it as stretching before the real game begins.
[alert type="info"]Speaking of games, there’s something called the Email Game for Gmail, which is a utility that forces you to process emails with a countdown clock. While the concept is brilliant, It's a habit I never really adapted. One of the reasons is that the company behind the game is the same one that owns Boomerang, a popular app which returns emails to your inbox when the recipient doesn’t respond. While I don’t have a problem with what some might refer to as a “growth hack”, it doesn’t fit with my current system.
Regardless, Boomerang was one of the first companies to spark the idea of returning an unanswered message back to your inbox, and I used it for quite a long time because of it. Since then, many competitors have popped up, like RightInbox and TheTopInbox. Myself, I currently use MixMax for this purpose; however it’s mostly irrelevant to my Email Processing System.[/alert]
The goal is to have nothing in my inbox after processing my email. The other goal is to close my email or at the least, change my focus to my Todo program discussed below.
I primarily follow the 2-minute rule popularized by David Allen in his GTD book. If the email is under 2-minutes, I reply to it right then and there. If it’s over 2-minutes, then I convert it into a task. As I mentioned that Todoist is my todo framework of choice, I particularly am fond of the Gmail integration they have which adds a button to Gmail which allows me to convert an email into a task.
Here’s what that looks like:
Now as I mentioned above, if it’s an email I know is a quick response, and I feel halfway about converting it into a task just getting it done, I star it. I'd compare this to how sometimes you have clothes, and they’re not entirely new so you don’t want to put them back in the drawer with your unworn clothes, but you don’t want to put it into the hamper either; so you put it somewhere in between? Oddly, I find that this odd analogy applies in multiple facets of our lives.
Since starred messages are at the top, I then stop thinking about the email, but I don’t archive it either. Once I star it, then refresh the page by clicking on the “Inbox” link, it reverts to the top, and then I look at the next email currently at the bottom.
So basically you’re starting at the bottom, archiving emails once you're done processing them. This could be simply archiving emails that require no action, replying to the email, or converting the email into a task.
Email Delegation Strategy
I’d like to discuss shortly a slight variation of the method above. At an early point I found myself with hundreds of emails a day; however, most of them were not relevant to the work I was doing. So I decided to see if my assistant could help sort some of my emails for me.
Every morning before I got on, he’d send me an email report. My EA (executive assistant) has access to my inbox through a feature called Gmail Delegation which does not require me to give my password. He would then archive mostly informational emails, and I was even able to train him to become more advanced by even providing additional information for me on particular types of emails, especially those that required me to login to their service or app to obtain the information that they were notifying me about.
Here's what a typical daily email report looked like:
However most of the time, it was considerably longer. And could contain dozens of email links. When he came back, he’d have to do this for hundreds of emails.
At some point, I asked my assistant how much time he was spending on the daily email report, and he indicated it could take on average between 30-60 minutes a day, and I was a little shocked. I realized that a part of being a leader is also valuing the time of the people below me, so I set out to find a better solution.
At around the same time, I stumbled upon Sanebox with an AppSumo deal, and I’ve been hooked ever since. Their algorithm automatically compiles emails it deems as unimportant. Any new emails automatically get shifted from my inbox into a folder called @SaneLater which I can check anytime. Every morning it sends me a daily email report that allows me to scan all the new emails quickly. It then allows me just to move that single email to my inbox, or whether to train it to allow future emails to go to my inbox or a third option which is called a Blackhole. I find the Blackhole to be an easy method of getting rid of aggressive newsletters (and unwarranted) drip campaigns from companies and individuals trying to push their agenda.
Another side point about Sanebox is that it means you could potentially remove the need even to have an “Everything Else” section. The downside is that you can never 100% trust the sorting algorithm and I occasionally still get important emails that end up in the @SaneLater folder. Some mornings I’ve even missed sending an important email to my inbox, whether I was tired or just scanned through the report too quickly.
[alert type="info"]If you’re using Sanebox then the “Everything Else” section of your Gmail layout can essentially be removed. However, it might not prevent you from needing to check the @SaneLater folder multiple times a day to make sure you don’t miss something potentially important. Either way, the methodology surrounding the @SaneLater folder is different anyway, as here you don’t process the emails inside of the folder, so there is no urge to clear them from your inbox or even respond to them until you move them to the Inbox the next day in the daily email report from Sanebox.[/alert]
Let’s recap my Email Processing Principles:
- If the email will take under 2-minutes then handle it right then, right there.
- If you want to handle the email right after you process your inbox, but need to give it a few minutes of thought, then Star the email and process starred emails once they’re the only thing in your inbox.
- Remember to update the Priority Inbox algorithm by marking emails via the yellow “Priority tag” next to each email in your inbox. This will separate relevant work emails from less valuable information. If you have Sanebox then this could mean dragging emails from your Inbox to the @SaneLater folder, where it will then automatically store future emails from that contact.
- Always start from the bottom up and don’t skip emails or “pick the easiest ones” as that’s a bad habit you don't want. If I find my willpower is weak, I'll either revert to Pomodoro or just find something else to do. Much how they say in the weightlifting world about maintaining good form. It’s never a good idea to compromise form just to get an extra rep or two in.
- Consider the processing of your email much like an untimed Pomodoro session. You aim to process your whole inbox in one sweep. However if worst comes to shove and you still find yourself with the email tab open all day, commit to forming the discipline of either replying/tasking or archiving any emails you open.
Wow, that was a lot.
Now if you get into the habit of being able to follow this disciplined approach to email, then it shouldn’t take you more than 30 minutes a day to handle whatever comes in your inbox. The next part of the process is to switch to “work” mode which involves my favorite Todo application called Todoist. It’s by no means perfect, but it’s rare for me to have stuck with software like this for as long as I have, so that must mean something.
My Todoist Workflow
So the Todo workflow as I describe here is still relevant to most other applications and can be applied in some form to most systems. Other software that is most similar to Todoist includes Nozbe, Wunderlist and OmniFocus. There are a ton more that I could list, but I don’t want you to become addicted to productivity porn as I was.
Regardless, I start off my day in my Todoist inbox. What exists here is a collection of thoughts, reminders, tasks, emails and from time to time, even revelations I have to myself and company.
Much like email, the goal is to handle any items that would take under 2-minutes, then the rest of them should be considered on a variety of levels:
- Do I clearly define the next-action associated with this task?
Often I'd find myself procrastinating on things only to realize it was because I was running away from what seemed like big mountains I’d have to climb when in reality I simply hadn’t given it much thought. If it’s a big thing, I might create a new Todoist Project and then create a series of tasks with the intention of breaking it down into smaller bits. Most of the time I don’t have to do this, but it teaches you to make sure that everything you add is actionable, or at the least, you recognize when you need to add more clarification or thought to something.
- How important is this task to me right now?
There’s a whole other topic about Pareto’s principle that I’ve briefly touched on before involving the somewhat known 80/20 rule, where typically the top 20% of your efforts will have the greatest impact. One of the biggest applications for this rule is with our work, and this combined with a looming sense of dread over not completing things constantly stresses us out when we don’t do things that we don’t need to do in the first place, or at least we don’t need to do right now.Nonetheless, what this means is seeing if this is a long-term item or reminder about something to handle in the future I’ll set a blind due date in the future and move it to a project I currently call “Backburner” which I simply used to call “Future Tasks.” This method allows me to separate items from my plate at the moment and potentially relevant items I don’t want to forget, but don’t necessarily want to burden myself with this very moment.It also allows me to keep moving the due date of tasks inside the “Backburner” project if upon the due date I still deem it is irrelevant to the current situation of the company. Sometimes if a task comes up repeatedly, I may even move it to a project called “Trashed Tasks.” Much like the clothes metaphor I mentioned above, it’s easy to delete tasks you type accidentally and much harder to want to delete something you can’t fully decide if you want to do. So, move it to another project, remove the due date and move on!
- Do I need to do the task, or can I delegate it?
While this is a topic deserving of its own blog post, I tend to delegate most administrative tasks to my assistant team who have varying levels of access to my life that can do things like handle communication with a contractor to get something done. Most of the time I simply care about meeting the objective and have trained my assistants to use critical thinking to solve problems on their own. I’ve become a little bit more elegant since my cruel methods involving LMGTFY with my early years.
At the end of my “Inbox” sorting within Todoist, I should have no items in my Inbox. It’s at this point when I pat myself on the back and then visit the “Today” view inside Todoist.
Now I must admit that running my life through based on what is in my task list is not always perfect. There are some days where I have so many meetings or just feel completely burnt out that I don’t even have time to open Todoist. While the need for self-discipline is necessary, the same goes for anything that you’re trying to achieve that requires effort to reach an attainable goal.
While I hold myself to a higher standard than I did just a few short years ago, I’m careful not to criticize myself on those inevitable “bad days.” A book called Radical Acceptance has considerably helped to improve my perceptual view of myself and how I work.
On that note, if you find yourself with an unproductive day or week for that matter where you don’t get anything done, this can often lead to “work anxiety” where you fret all the overdue tasks and projects you still have to do. As much as I try to remind myself to simply be present and accept that I will get done whatever I get done, there still exists some level of anxiety regarding this sometimes; so naturally, I developed a system to help with this.
Finding the right Due Date
While I touched lightly on this earlier, I’d like to reiterate the importance of mindful work, as it’s so easy to get caught up in one thing and realize that we only did that to avoid the dread of a larger and more important task or project.
It’s easy to beat ourselves up over this; however, a systematic way to alleviate this is by asking during my morning review if this particular task is something I need to do today. If it isn’t then, I’ll only reschedule it to a future day. Now what I like in particular about Todoist is its ability to show you what your workload is like for other days of the week as you can see below.
So if it’s 5 pm and I still have 20+ tasks due today, I will mindfully pick the ones I will focus on for the remainder of the day and find another day with less going on to do it.
Sometimes though you might wake up and see you have 10, 20, 30+ tasks overdue from days before. An essential part of my workflow is never having anything overdue. Before I re-assign the due date, I ask myself if this is actually necessary to do today or even this week?
As I mentioned above, I will often move tasks to the “Backburner” and assign a random date in the future, sometimes weeks or months out. Any tasks inside this project though don’t come with the same burden of having to complete them. As when they become due I simply ask myself if this is a task that is still relevant (which I archive/delete if it isn’t) or if it is, but still not right now, then I’ll just re-assign it to another future date.
You don’t want to be using the “Backburner” method though for tasks that are relevant and that you’re just trying to avoid. In that sense, you don’t want to get into a bad habit of continually reassigning those tasks to a future date.
There are many books and articles dedicated to how to stop procrastination, but at the end of the day you simply have to must the self-discipline to start working on it. Much like how in the 12-Step program from AA, the first step is realizing you have a problem. Simply getting myself in the habit of adding a “procrastinating” label to tasks I’m continuing to move to the future serves as a reminder to my inner consciousness that I’m probably avoiding this task. Much like how we often tell others that we didn’t have the time to do something, but what we’re really saying is that it wasn’t high enough on our priority list for us to do it. So simply being able to recognize when I’m procrastinating has had a huge impact in helping me to formulate a strategy to help me with it.
Speaking of procrastination, there will inevitably be enormous projects you’re assigned or vague objectives you have to complete.
Before I reassigned the date, I’d ask myself if I accurately identified the “next-action” for the task. It’s quite easy for us to assign ourselves something like “create a content marketing strategy” without thinking about it. While I mentioned before that breaking a task into smaller, more actionable bits is necessary, sometimes it’s not enough to really get ourselves moving.
Pomodoro & Me
Anybody familiar with productivity is going to be familiar with the idea of Pomodoro, which is breaking tasks down into smaller bits and mainly trying to override that part of our brain (limbic system) that craves constant fulfillment for our present selves.
While I’ve been familiar with this technique for a while, I never incorporated it as a part of my work regime until recently. I always thought that I was too good for it, and didn’t need it. There were times I’d use it and would work consistently beyond the 25-minute timer I’d set for myself. At some point, I asked myself why I was even using it and fell off the wagon, so to speak.
What ended up happening, of course, should be no surprise. Procrastination crept itself back into my life, and at the end of the day I’d ask myself what did I get done today, and more often than not I couldn’t name any meaningful work for that day.
Today, I can honestly say it’s been incredible at helping me to experience “Flow” again and complete more tasks consistently that leave me feeling a sense of fulfillment afterward. Let’s dive into how I do this with Todoist.
Todoist & Pomodoro
It’s human instinct to want to pick the low-hanging fruit among our todo-list. In fact, it’s even been suggested as a productivity tip that you should create more daunting tasks for yourself, so your brain ends up picking something that seems easier to manage.
When I encounter a task that I find myself having to add the label “procrastinating,” more often than not I move it to a project called “Pomodoro Session” in Todoist. Alternatively, you could just create a tag called “Pomodoro,” whatever floats your boat.
Sometimes I’ll run into a task that I experience resistance with, and it takes mindful practice to recognize when it’s something that should be done inside a Pomodoro session.
Speaking of doing a session, if I didn’t schedule time in my calendar to go through Pomodoro I’d never do it. At the beginning of each week, I check my calendar for open spots and then schedule a 90-minute Pomodoro Session with myself each day. The goal is to be able to spend 25 minutes on 2-3 items that I know I’d be procrastinating on otherwise. The very simple idea of telling yourself that you’ll only spend X amount of time on something is stronger than most people give it credit for.
I can't recall the amount of times I was procrastinating so heavily that I was able to convince myself to only spend 5 minutes on it, and halfway through there was a little voice in my head that said "F*** it, might as well do the whole thing"
The idea of creating a time-block could be used even outside of Pomodoro. You could use it to schedule a “thinking” or “creative” session with yourself where you eliminate distractions or even use an app like Freedom to minimize them.
While the app or method you use isn’t important, I like to use a program called Vitamin-R which has all sorts of hidden nest eggs and goes talks in detail about the psychology and motivation behind how the developer made it. I particularly like how the “Motivation Level” and “Resistance level” attempts to sort several time slices into relatable terms. In effect, this helps to minimize over-thinking and allows you to set a time slice for 5 minutes, which the app indicates that such a task comes with it, low motivation and high resistance.
There are a host of Pomodoro apps though, so don’t get too caught up in trying to find the “perfect” one.
Note on the Todoist Inbox
Much like sorting your mailbox, you don’t reply and answer snail mail in your mailbox as it’s simply a collection spot. Now you might have a place where you always put your mail for further processing, and it’s that idea which should be applied to tasks of any sort.
Throughout the day, you may get interruptions from coworkers about things you need to do or even things you recall on your own. The first step is to just get them out of your head by writing it down. The Todoist inbox serves as a sort of collection box for tasks whether from co-workers or myself. No need to worry about the due date, or description. This is, in effect - the beauty of the Inbox inside Todoist – as it serves as a collection spot for all this and much more.
This method allows me to jot tasks down from anywhere, whether in the shower or out and about with the mobile app. Then I can forget about it as I know it will be processed in due time.
Much like how I process my email, I process my tasks in my Todoist Inbox in a similar way. If it’s under 2 minutes, I just “get’r done” right then and there. If it’s going to take longer than I’ll decide when I’m going to do it, or I delegate it to somebody else.
I only go through my Todoist Inbox once a day to avoid getting hooked on small one-off tasks that can often be nothing more than distractions when there are more important things to do.
Once my Todoist inbox and Gmail inbox is clear, then I go to my “Today” tab, and that's when I consider my work day to have started.
Having a structure like this prevents me from forgetting important tasks when I’m away from my computer, as well as prioritizing my work to maximize efficiency.
Note on Daily Tasks
When it comes to daily tasks, I try to keep them out of Todoist or any other task list manager. I’ve always found it cumbersome when I have a gigantic/totally procrastinating on a series of tasks and I’d find myself doing my daily tasks instead. Doing this actually increased my procrastination as I felt fatigued after having completed a few small tasks.
Instead, it’s better to try and incorporate daily tasks in a separate space in your life that you do solely based on habit. Once you’re able to make something a habit, no longer do you have to try and muster the willpower to try and do it. The benefit of keeping it outside of your regular todo-list manager is you won’t have to decide when/whether to do it over other pro-active work.
One method I use is requiring myself to go through a series of small habits when I sit down at my desk in the morning. I use an app called 30/30. This creates a time-pressure to do these items, and it’s premeditated by the cue of sitting down at my computer. I use it in a variety of ways, and surely you can find a way to implement your own foundational habits when at the computer or any place else.
- Start the day by asking yourself what you have to get done that day. Then sort through your email, handling any emails under 2 minutes and converting others into a task or marking with a star. Then audit the “Inbox” of unsorted tasks inside Todoist. Again, if it’s under 2 minutes just do it, otherwise break it down into smaller tasks, prioritize, then assign a due date.
- For the rest of the day, I spend most of it handling tasks in the “Today” tab. I use Red priority to indicate a task that I positively need to get done that day. Orange tasks mean that my resistance on the job is high enough to warrant using my Pomodoro App. Lastly, yellow tasks are recurring items simply to separate them for other tasks.
Remember that optimizing your productivity is a journey that's a part of work itself. You'll learn more about yourself by simply doing good work instead of obsessing over how you're working. Only doing good work will result in achieving the objectives you’ve set out for yourself. My method above only describes the current framework that I use in the hopes that it will be valuable to you and your own workflow.
“The Principle of Priority states (a) you must know the difference between what is urgent and what is important, and (b) you must do what’s important first.”
― Steven Pressfield, The War of Art