Tame the Chaos

The single most important thing you can do to increase your output is to manage the external world’s input

Organization doesn’t come naturally to me. It never has. It’s something I have to consciously pursue or it won’t happen. Like most people I got by in life with the occasional one off todo list or tracking it all in my head. This worked fine for a while, even much longer than everyone said it would, but in the later part of college where I was doing undergrad, grad school, and working simultaneously it became too much. I did research, experimented, and eventually landed on a system that works well for me.

During my professional career, I’ve been truly staggered by how disorganized most people are. It makes it hard to get things done as their communication is inconsistent. It also just looks stressful. It probably hits me worse since I have ADHD, but I can’t imagine it’s comfortable for anyone to live each day not knowing if they’ve missed anything that’s going to blow up later. When I’ve given advice to those that have asked for it they tended to find some value, so today’s post is a discussion on how I approach things.

Keep in mind each person’s mind works differently, but it should be of value because the considerations informing my choices are relevant to all and even if the exact regime isn’t suited to you maybe parts of it are.

Background & Principles

There are two classes of people for task management. Primarily calendar people and primarily todo / task list people. If you don’t know which you are, try the todo system. For a calendar system to work it requires a level of discipline and time estimation skill you’re unlikely to posses. Even as I’ve become more disciplined, I’ve found it’s just not how my brain works and have stuck with todos. The issue many face with the calendar approach is that if you fail to accomplish something on time, it breaks the rest of the schedule. You then have to spend time fixing it and are more likely to just give up on your habit change. If you’re the type of person, like me, who shrugs and says now that I’ve messed up, the day is shot and the proceeds to do nothing else, then you’re not a calendar person.

Units of Work

No matter which you pick, the purpose of each tool is unchanged:

• Task List - Works in Tasks. Tasks are units of work that have a deadline, but can be done early. For example paying your taxes is a task. It must be done by April 15th, but you can do it earlier.
  • If you don’t have a deadline it’s not a task. It’s a backlog of ideas you’d like to work on. It’s the place where you pull new ideas in to make them a task once you’ve run out of other things to do.
  • Deadlines can change. The point isn’t that it’s immutable, the point is there is a plan for it.
• Calendar - Works in Events. Events happen at a specific time or a specific time + place. Another rule of thumb is if it involves other people, it’s an event. After all, how are you supposed to work with others if you’re not showing up at the same time?
  • If you have a dedicated period to accomplish things, it can be helpful to have a task list tied to that calendar event. Let’s say you and a partner are reviewing finances. You have a calendar event for reviewing, but a list of tasks for each “review X account”.

If you’re a calendar primary person, it’s possible to convert tasks into specific events which is why there’s a subjective element here. For example, doing taxes is often time consuming so you might schedule a dedicated time to do it. It may be tempting to do this in general, as if you just have a bucket of tasks to do each day what ensures you’re allocating enough time for them all? I think this is fine for big critical tasks like taxes, but when in doubt try to stay away from this conversion. Taking the trash out takes 2 minutes. You don’t need to schedule it as event, even if you forgot you can do it right before bed easily.

Visibility of Work

There is lots of great content on the topic of task management, but I find it usually misses a critical topic. There’s a distinction between work that is tracked solely by you and work that needs to be trackable by others. I don’t think these should generally be colocated. Doing so means you’re sacrificing communication or tool quality in some way. It also increases noise to have your irrelevant personal items in the team space. Moreover, even if you disagree it’s usually not your choice. For software engineers there is always a work item board of some kind your team uses. Rather than fight against that, lean into it. Different tools for different classes of work.

My recommendation:

• Use a simpler todo list app for your personally tracked work. Todoist, Microsoft To Do (integrates with Office well), Google Tasks (integrates with GSuite well), and Apple Reminders are just a few of the hundreds of options out there. Hell, even pen and paper can work.
• Consider a multi stage board for tracking team work. If I care about visibility, it’s usually because something you’re doing is complicated enough that I need to track it. This means a simple yes vs no is finished state isn’t ideal. Instead your work should go through phases. Kanban boards are great for this, and they’re not just for factories or software development. You can make them for support tickets or even the sales pipeline.
  • A normal todo list works, and Kanban boards like Trello aren’t the only alternative either.

Separate Church and State

Don’t mix your personal items with your work items. Even if you’re self employed. It can leak data, introduces noise into the system, and generally isn’t good for your mental health. Take the exact same approach to each area, and even consider using the same tools, but keep separate accounts for each. For example, I use Todoist for task list management. I have an account with my personal email and one with my corporate email.

Some items do impact both though. Your dentist appointment goes on your personal calendar, but now you need to be marked out of office on the work one too. The way I handle this is I share my work calendar with my personal calendar. This means there’s an additional layer I can toggle on and off to overlay my work schedule when planning appointments or time off, but I can toggle the layer back off for normal use.

Email & Instant Messengers (Teams, Slack, etc)

Email is a dreaded pit of despair, a maelstrom of human suffering. Email is bad because we don’t consent to what we receive, and it’s a mix of so many things. It’s notifications, copies of information, discussions, announcements, assigned tasks and general communication. Because email is inevitably a mix of things, I accept that. I have some specific rules for email, and then I apply my rules from before to email as well.

Rules:

1. Always block or unsubscribe unwanted communication. Learn how to use rules and filters. Don’t let them sit there, don’t just click delete each time. You’re squandering so much of your time by doing so.

2. If it’s not important, delete it. Don’t hoard it forever just because storage is cheap. It’s just making it harder to find things you do care about.

3. As soon as you are done with something archive it. Don’t let your inbox go on forever. Rule of thumb, if you have more than ~30 emails in your inbox you’ve fallen behind. Ideally you have fewer than 10 after each use.

4. DISABLE ALL NOTIFICATIONS. Notifications are cancer. They disrupt flow, leak private information when screen sharing, and create a false sense of urgency on both sides of the conversation. Unless you have an atypical job like Director of Blah or you’re someone’s assistant, I promise it isn’t that urgent. It can wait until the next time you check your email or IM app.

   If I see notifications on a screen share call, I immediately cringe. Not cool man. Respect the privacy of the others :)

5. Email is not a dashboard. Do not use email to distribute automated reports, status updates, or periodic monitoring. There are dedicated tools for these things that do a better job, have fresh data, and can be accessed anytime you want.

If you follow these rules, you’ll notice that email itself has become a sort of pseudo todo list. That’s precisely how I recommend using it. It strikes a balance, you keep information and are fairly efficient while ensuring you never miss anything either. So if it’s a todo list, what constitutes “done”? Any of:

• I read it, and there’s no follow up. If I might care to reference again I archive, otherwise I delete.
• I was assigned a task and converted it to another item (personal list item or team app work item). If there isn’t context in the email needed and the followup isn’t over email, you should convert it. Otherwise, leave it in email as a todo. Don’t waste time tracking it a second time. The fact that it sits in your minimal inbox means you’ll still see it needs to be done.
• I was assigned a task and completed it.
• It’s been sitting there for a few weeks and I’ve acknowledged this isn’t important enough to actually get done, so I cut the task.

My System

• I use a todo based email system for both my personal and work email.
• A personal calendar and my company calendar.
• For todo lists, I use Todoist. A personal account and a work account.
• For team todo tracking, I use Kanban boards (specifically in Azure DevOps since I work for Microsoft as a software engineer, but I’m not married to any particular tool for this).

I schedule blocks of time for different things. Personal, work, side project work. When I’m in one of those time blocks, I use the same tools (mostly), but use the associated account. For work it’s easy, it’s a different computer so it’s only logged into the work accounts.

Examples

1. Recurring biweekly sync with my manager - Recurring calendar event, company calendar
2. Give the new hire access to our test environment - This was an email, gets converted to a work account todo list item
3. Implement a bug fix - Work item in the team’s Kanban board
4. Take out the trash - Recurring task, personal todo
5. Work at Microsoft - Recurring calendar event, personal calendar (this is to make it easier to plan my other personal stuff around. It’s one big block, no details about the actual work)
6. Skeet Shooting - Recurring calendar event, personal calendar

How to Get Started

If you’re unsure where to start, you’ve probably got some debt to clear out.

Have a Backlog

It’s worth keeping in mind, time is finite. There will always be more things you want or even need to do than are possible to do in a day, week, or lifetime. Be realistic about this. If you’re regularly pushing back the deadline of the same task over and over again, something is wrong. When you constantly push it back, you’re wasting time and forming a bad habit. To be clear, it’s common and expected to not finish your list each day. But if you’re not finishing the same things each time, that’s an issue.

The solution is to have a backlog. Have a separate list of tasks that’s your task wishlist. When you’re feeling inspired, motivated, or just have unexpected time, you can come back and pick something. The backlog is just a bulleted list, so you can track it however you want. A written note, notes app, word doc. Some task manager apps have “projects”, you can create a backlog project and move items there.

Email and Instant Messages

This one is simple, just declare “Email Bankruptcy”. If you have 1000’s of emails, it’s not reasonable or necessary to go through them. Most of it is junk and what you’ve missed, you’ve already missed. Select all emails, and move to your archive. If you have too many, create a temporary rule to auto move and let that run for a while. Delete the rule when the inbox is back to 0.

As you get new emails, filter noise. Unsubscribe or write rules to automatically delete them. Don’t archive spam. Check your email at the beginning and end of the day. You can also check it periodically during down time say between meetings if that’s not a distraction for you. Just stay on top of it going forward, and you’ll be surprised how manageable it will become.

Document the Chaos

Open a notes app, or get a piece of paper. Write down:

1. What are the things you need to do every week?
2. What are the things you need to do every month?
3. What are all the random things you need to do that are on your mind? Get as many as you can, but don’t worry, it’s impossible to think of them all. You can add them later as the pop back into your mind.
4. What are all the random things you want to do right now? If you had more time, energy, etc. These will probably go on your backlog.

Be really specific here! Include seemingly stupid, trivial stuff that you already have habits for like showering.

Grouping and Expanding Items

When you dump your mind onto the page, there will be tasks that are tiny minutia and others that are far too large. You should take a second pass over your list to group small items and break down large items.

Chores can be a good example of too small. Clean the sink, the toilet, the shower. Group all of these tasks into a “cleaning” event. If there are too many, group them into a couple events such as “clean kitchen” and “clean bathrooms”. These can be scheduled as reoccurring events in your calendar, with the small tasks in a checklist or in the description. This way you’re not overloading your task manager with dozens of small tasks each week, which can be distracting or even overwhelming.

For large tasks like “fix my car” or “build a table”, we want to do the reverse. What are the concrete, small steps that you need to take to get to the goal? A common pattern is setting goals, then research, then acquire resources, then execute the plan. Each sub step there may have multiple steps themselves. Outlining this all ahead of time makes it easy to schedule. In general, I recommend keeping these types of things as tasks in the task manager.

Bonus: Reusable Checklists

Once you’ve gotten the basics down and your life in order, keep an eye out for situations that require a list of things in your mind such as packing for a trip. Create a packing checklist. This makes sure you bring what you need, and that you bring it back with you. Think about what kind and length of trip it is. You’re probably bringing more or less the same things each time, so why not keep the list for future instances of this type of trip?

Ideally it lives in a digital notes tool as a reusable checklist. Then you can check items off as you pack, and reset the list when it’s time to pack again for the trip back home. It works great for local things too. Going skiing or camping? Have reusable checklists for each activity.

Keep it incremental

Finally, remember that habit change is incredibly hard. Do go through the getting started process in its entirety, but extend yourself some grace with missing deadlines and not tracking things at first. Having a clean slate will make it easier and lead to immediate improvements, but full discipline takes time to build.