Eleven Experts Share The Secrets of Scheduling Everything in Your Calendar

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Question: “What is your best advice for managing all your tasks in your calendar?”

Read on, as ten experts give their point of view on how you can maximize the use of your calendar by using it as a tool for managing (almost) all your tasks. There are some important differences of opinion, and a variety of approaches depending on which approach the expert happens to use. It’s the first post of its kind on this topic anywhere, so I’m glad to have you here!

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Ultimately, successful people live their lives by design, i.e. an effective plan of execution. When we plan to use concrete resources such as space, or money, we’re very conscious of the available resources vs the demanded resources. But, when it comes to time, it’s much harder to plan because time is not perceived as a concrete resource like space.

Those who have been successful with concretizing time used their calendar as the framework to transform their time demands into tangible blocks. However, there are very limited number of skilled individuals that have made it to this level of discipline. What hinders most people from scheduling all their tasks in a calendar are interruptions, lack of control over mood and energy, shifts in priorities and incorrect estimates of task duration. So, any attempt to schedule tasks leads to frustration.

Fuzzy Planning is the middle ground between not scheduling, and scheduling. It tries to offer the benefits of concretizing time, yet provide some slack in the execution to make it as practical as possible. It leverages machine thinking to augment the planning process. So far, in SkedPal beta we have converted many people with a to-do list to Fuzzy Planning to reduce the overwhelm in their lives.

Our first implementation required total task scheduling. In other words, every time demand was thrown into the calendar. Our study and analysis of user behavior showed that this method was very highly prone to the planning. Once again, we tried to find the middle ground and offered a new solution where we encourage scheduling tasks for only the near term and leaving the rest of tasks on a conventional list. This way, users can maintain a small list of active projects in their current focus to be scheduled using Fuzzy Planning. This has led to a greater success rate, and has dramtically reduced the number of failed plans.

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I have found three things to be key in making calendaring my tasks work for me.

First, there have to be blocks of time that aren’t scheduled. The more I try to do, the more unscheduled time I need. Even within the working time blocks, I give myself a break. So if I’m scheduled to work on a writing project for an hour, I take the last ten minutes of that block as a break.

The second key is to use blocks of time for certain tasks based on my ideal schedule. I work on blog and podcast tasks from 1-3 in the afternoon, for example. Limiting related tasks to that timeframe helps me get more done and feel that I am moving all my projects forward. In the past, my tasks might be scheduled all throughout the day, leaving me feeling scattered.

Finally, when I finish scheduled tasks early, I do not schedule anything else. This means that in using Skedpal (my scheduling program of choice), I do not hit the Reschedule button. Doing so makes me feel like the work never ends. A scheduled list should function the way a traditional to-do list does in that once it’s done, you’re done.


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Let the old fable of rocks, pebbles and sand guide us through this simple framework for scheduling.

Rock it with Deep Work

You see, the purpose of total scheduling is to not to fill up every minute of your day, but rather to free up good chunk of your day for the most meaningful and fulfilling work of your life. What is it for you? Raising your kids? Helping people in your community? Making a dent in the universe with your creations? You can achieve any and all of your dreams, if only you would work on them every. single. day. In your waking 16 hours a day, do you think you can have 3-4 chunks each 2 hours long – to do things that are most important to you? I’m sure you can, and here is how: you take the glass of your daily schedule when it’s still empty, and place these rocks of Deep Undistracted Work sessions in there. Done. And you still have at least 8 hours a day left.

Pebbles of Recovery

Pebbles, beach… The thing about these arch-important Deep Work hours is that they require your full presence and attention. And attention is limited resource. Good news is that it is also a renewable one. So, to ensure peak performance, stick a few recovery activities in between. It might be a healthy meal (you know, the one that doesn’t put you into food coma), or a trip to gym (that might be a Rock itself – an example of how you can kill two birds with one Rock :), or play with your kids (another likely Rock), or just a walk around the block (or to the cooler). No, checking your Facebook feed is not a good recovery technique – it actually drains your attention reservoir. And don’t forget about THE recovery activity – sleep. But how you possibly could – it already blocks 8 hours out of 24, right? By now, we have ensured that we have both time AND energy to move the proverbial needle every day, even if little by little.

Sand of shallow work

Guess what? There is still time left in the day! You can spend this time however you want, completely guilt-free. Checking your email, or your site stats, or chit-chatting with a friend, or whatever gives you the kick of immediate variable reward (or the kind of reward you prefer). And even these can be scheduled strategically, for checking off a bunch of little things can give you a) momentum and b) peace of mind. In other words, it can make you feel productive (feeling is a good thing, as long as you don’t confuse it with actually being productive), and it curbs the temptation to do these when you are trying to focus on work that really matters. For these reasons, you can even do some shallow work before (gasp!) deep work, just don’t let it eat into the deep work time. And again, beware of the little things that shatter your ability to focus. But hey, sand on beach feels so good.

Be water, my friend

In the extended version of the fable, a student takes the turn and demonstrates the wise professor that the glass full of rocks, pebbles and sand can still take in a surprising amount of liquid (vodka or beer, depending on the origins of the fable-teller). And in our framework, water plays an important role too. “Be water” is Bruce Lee’s way of saying “go with and not against nature”, and our way of saying “the best schedule is the schedule that works for YOU”. Water moves everything in the river for the optimal flow. Likewise, experiment and find the exact placement of Rocks, Pebbles and Sand that keeps you in the Flow.

Curious to see this framework in action? You can see my actual workday schedule here

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If you desire to manage all of your to-do items in your calendar, I’ve found it’s effective to treat larger projects and smaller tasks differently. With larger projects, I recommend blocking out chunks of time to complete them.

For example, you may put in two, two-hour blocks to work on a proposal. Or you may block out a couple of days to work on a large project. This is important because larger projects can’t just be “squeezed in.” Setting aside the hours needed to get them done helps you to visualize how the work will fit in your workweek. It also gives you a sense of realism for how much you can actually accomplish.

For smaller tasks, making note of the exact time you’ll get them done can get cumbersome and tedious, so I’ve found it’s helpful to take a modified approach. One possibility is to put them in as tasks or all-day events that appear at the top of your calendar on the day you intend to get them done. That way, you know that you need to complete them but you can have flexibility around when they fit in throughout the day. A second alternative is to schedule a calendar event for grouping small tasks such as “finance work” or “client follow-up.” Then within the description or notes section of the calendar event, you can record the specific tasks that you need to complete as they come up.

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Francis Wade asks, “What is your best advice for managing all your tasks in your calendar?”

I find blocking time to be very useful in several situations: when I’m overwhelmed when I’m facing a lot of empty and unscheduled time with several tasks on deck, or when I feel that I am just not dedicating myself to a task enough.

However, more generally, I work from a well-curated small list of tasks. So-called “hard landscape” items, such as meetings, line my calendar. Projects and batches of small tasks find their way in between as the day progresses, by some finely tuned balance of task review, habit, and even whim.

So, with Francis’ permission, I’ve changed the question to:

“What is your best advice for managing tasks in your calendar?”

When managing tasks on your calendar: Consciously buffer time to close your sessions of work.

Blocking time is a useful method to help set aside other work. When we have a sense that other work can wait, we have a better chance of focusing on our present work.

However, there are other ways to lose focus within the session, too. If we realize that we are making a mess, we may start to worry if we’ll start the next project in time. Or, if we’ve made a mess in a previous session of work, that session’s files become clutter and can distract our present work.

Therefore, the better we set work aside at the end of a session, the better it will stay off our mind during other work.

However, doing so takes time.

Setting work aside consists of:

  • Having a sense as to when we will return, perhaps scheduling it
  • Storing the work and readying it for next time, perhaps with a clearly written and well placed next action
  • Clearing the work out of the way of other project paths and stations, perhaps creating it a home

Because all of these benefit from time in thought, it is often useful to set an alert as to when you would like to consider ending your current session of work*. Doing so allows you time to close the session.

Notice, setting an alert to close a session is quite different from the usual practice of setting an alert as to when to start something. When you set an alert to start work, often, if not always, you are in the midst of something else. That leads to either dropping what you’re doing while leaving a mess or starting the next work off schedule, either of which can be problematic.

Instead, as you begin your session of work or when you realize you are creating a mess:

  • Consider when you might begin closing the current session of work?
  • Consider setting an alert to accommodate time to do so, giving yourself plenty of time before starting the next session.

Often, you’ll find better focus, better quality, and even an enjoyable engagement.

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To make time blocking a regular habit:

1) conduct a weekly planning session where you plan and block out activities for the upcoming week and

2) keep your calendar open each day, refer to it often and re-plan appointments on the fly as you go throughout your day and based on how long tasks actually take so that you have a record of how you spent your time.

Visit my website at https://paulminors.com

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“What is your best advice for managing all your tasks in your calendar?”

Total task blocking is irresponsible.

Hold on, I am saying this because it is unrealistic. All tasks are not created equal and should not be treated as such. Really, you know better.

1. Only schedule the tasks that you are actually going to do.

You create more wasted energy in re-planning and the disappointment of not achieving something. Evaluate the time it takes to do the task and then schedule what is most important. You can have an overflow list to look at when you have extra time.

Notice, have you have moved the task more than 2 times? If so, evaluate if you really need this task to be on the priority list or if it should go to the overflow list.

2. Evaluate excuses

Evaluate the excuses you use when you move it or delete it. Why are you moving it? Did you just delete it? It obviously wasn’t a priority if you deleted it. Stop scheduling tasks that just get deleted.

It isn’t about getting things done but getting the right things done. That isn’t new. But the dopamine that is released when we get stuff done has us focused on unimportant stuff because the important stuff may be harder, or outside of our comfort zone so we opt for what is easy.

3. Focus on the Result

Listing out each and every task in my experience doesn’t get me the result faster or more effectively. I focus on the result and chunk my tasks.

To me, listing it all out is an unnecessary planning effort. You are looking to achieve the result so start putting more focus on the result than the task.

By doing that you may find a better way of doing things and being open to the fact that the tasks might change.

4. Build in flexibility

Build in flexibility and become more strategic in your thinking versus tactical.

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Take inventory of all the recurring daily tasks and set them up as a recurring activity.

For example, if every day, you need a sum total of 1.5 hours to handle the day’s emails, then enter a 1.5 hour block on your calendar and make it a daily recurring activity, let’s say from 9:00 to 10:30.

Now we all know emails don’t come in like that; they come in throughout the day at random. But by reserving the time as a continuous block, it allows you to realistically understand exactly how much time you really have left for other tasks. So, do this for all your known recurring tasks: email, meetings, anything you know you have to deal with every single day. Reserve that time now. This will show you just how much time you really have for those other activities.

Drag your ToDo list.

If an item on that list needs to be done today, drag it onto your calendar and make it a real appointment. Make it tangible. Make it account for its own duration.

Manage Expectations.

Give yourself time to communicate with the people who are expecting responses from you. Let them know the status of the task, even if it is going to be taken care of later than they had hoped. Managing expectations reduces your stress level, which helps increase productivity.

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Working with your strengths rather than against them is a critical, yet underutilized principle of Total Task Scheduling.

You account for your strengths when you manage your energy, focus, and environment in ways that maximize your productivity. Optimize your efficiency and increase the number of tasks completed.

Your energy level naturally ebbs and flows throughout the day. When you have the most momentum is the time to schedule tasks that require the most brain power. Similarly, planning more routine obligations, or those of less value, during low energy hours allows you to maximize your efforts without draining your energy.

Focus management relates to energy level. Your ability to focus will vary according to your interest in the activity, its level of difficulty, and the number of distractions while working.

Unfortunately, interest-level and duties are sometimes at odds with one another, especially in our professional lives. If we only did tasks we enjoyed, many jobs would never even be started! As such, it’s advisable to schedule less appealing assignments during a stretch of higher stamina because that’s when we have the best focus. Note, I didn’t say during your “highest” energy. We experience a continuum from very low to very high momentum. As such, some tasks require our peak energy and others need sufficient stamina-neither the highest or the lowest.

Another aspect of focus is the complexity level of the assignment. The higher degree of difficulty, the more important it is to reserve a high energy time-slot  Alas, we are prone to procrastinate challenging tasks which usually means we’re tackling something hard when we are tired. It’s important to reverse that trend!

When using your calendar for Total Task Scheduling, design your day around your energy capacity and focus level to increase your overall effectiveness.

How does your “environment” correlate to organizing tasks? When your workspace is arranged in ways that appeal to you, it is easier to main your energy and focus. Here are some environmental features that you may want to consider: noise level, accessibility of materials, comfortable as well as ergonomic furniture, amount of light, and water bottle for hydration.

If Total Task Scheduling is your goal, it is crucial to take advantage of your strengths. Take a moment and answer these three questions:

  • How can you change your current scheduling tendencies to benefit from your peak energy times?
  • What small modification will increase your focus?
  • What one alteration will create a more conducive work environment for you?

Choose one area and experiment with small adjustments until you find what works best for you!

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What Can You Achieve in 30, 60, & 90 Minutes?

When I ask my clients where they found the biggest benefit in my How to Use a Calendar program, they often reply: “Scheduling for 30, 60, or 90 minutes.”

It’s tempting to block off a massive chunk of time for a big project. Whether that massive chunk of time is an afternoon, a day, or a series of days – doing so subtly encourages procrastination in two ways;

  • It doesn’t specifically define the desired outcome
  • The extended duration of time allows you to constantly say, “I’ve got plenty of time to figure it out.”

Overcoming both of these requires peeling apart the project into smaller, more discreet, incremental tasks. Then estimating the time to accomplish each of those specific tasks. Finally, scheduling those tasks with their corresponding estimated duration on your calendar.
This has three subtle benefits:

  1. Timeboxing each task mildly increases the sense of urgency to complete it, for this is the only time available for this part of the process (er, project).
  2. Increasing the number of completed tasks makes it easy to see progress and build momentum toward a larger goal.
  3. Discrete task level scheduling makes it easier to confidently communicate expectations of progress to yourself and your collaborators (at whatever granularity is appropriate).

I encourage my clients to use the following estimation framework I talk about The Power of When:
• 30 minutes for a small, known* task.
• 60 minutes for a small, unknown task.
• 60 minutes for a large, known* task.
• 90 minutes for a large, unknown task.
• Tasks taking longer than 90 minutes should be broken up into more smaller, more specific tasks.
*known = something you’ve done before and can confidently complete within minutes

Why 30, 60, and 90 minutes?
  1. Nothing takes less than 30 minutesOnce you factor time for preparing to do the work (including switching mental contexts), reviewing the work to ensure it has, in fact, created the desired outcome, and properly closing out the work – nothing takes less than 30 minutes. Not even replying to that important email or phone call. This is before factoring in any disruption or interruption.
  2. If you can’t achieve the outcome in 60 minutes you need to step awaySixty minutes is a long time to be intensely working. In endurance running it’s here at 60 minutes where you need to start considering additional food & water to counteract the physical and mental fatigue. The same goes for intense creative work. Fifty minutes into a task, you know if you’ll reach the intended outcome within the next ten minutes or not. Either way, stop after those ten minutes, step away from the work environment, and get something to eat and drink, take a walk around the block. I’d be willing to bet when you return you’ll have a new perspective – if not a breakthrough.
  3. After 90 minutes you’re fried. Maybe you figured, this tasks is just a little bit bigger, a little bit unknown, but totally do-able with a little push past the 60-minute mark. Ninety minutes would get you to a more substantial milestone and more resilient stopping point. Fantastic. Go for it. Know that at the end of it, you’ll be completely fried, totally mentally drained. The break we talked about at the 60-minute mark? Yeah, it’ll need to be longer and even more re-energizing than before. Especially if you’re expecting to do it again when you return. The best place for intense 90-minute tasks is the very first thing in the morning and the very first thing after lunch.

Now, what if you reach the outcome before the estimated time is up?

  1. Review it thoroughly to confirm it is in fact completed. You might be surprised to find one or two more small, quick, easy things that could make it that much better.
  2. Pat yourself on the back for beating your estimation and take a break.
    If you’re interested, I wrote this post in two 60 minute sessions with an hour lunch in between.

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Use Temporal Containers to Carve Out Time for “Flowing”

Most people describe Total Task Scheduling as a method for placing all their tasks in their calendar. But there’s another opportunity that can transform your performance: you can use it to consciously program periods of super-high productivity.

“The Flow State”. “Deliberate Learning”. “Deep Work”. These are all examples of periods of intense focus described by authors and researchers. They are times we produce our best work, using our most developed skills to accomplish a short, challenging objective.

The big problem is that the modern workplace is not set up to facilitate these sprint-like sessions. Instead, you are expected to sacrifice them on the fly for meetings, email, slack messages, watercooler talk, and other even lesser reasons. Plus, if you have the misfortune of being seated in an open floor plan, you must also be prepared to overcome visual and audible distractions.

While open plans represent a huge cost saving for the person who writes the checks for furniture and rental space, there is a huge, invisible price to pay. Now, you must scrounge around to find quiet spots in the basement, or stay at home, or spend afternoons at Starbucks; all in order to “actually get some work done.”

If you are serious about “Flowing,” you simply cannot leave these sessions to chance. But even more important than finding quiet places is the need to schedule them far in advance. In fact, they need to become a regular feature of your calendar because time is the only element that’s required: the others are optional.

The most productive people set aside containers of time, using as many recurring appointments as possible. They may not know exactly what each session will be used for, but it doesn’t matter. The mere fact that it exists means they have a unique resource banked for later consumption.

Now it’s easier to stay on track. Before the session starts, the time is protected against arbitrary meetings. While it’s running, barriers are erected against interruptions. They can be used to gain the kind of momentum  Arno Rafael Minkkinen talks about, where one discovery leads to others.

My breakdown of the core behaviors of Flowing shows them to be exquisite and rely on a number of other skills, such as the ones we teach at ScheduleU. If you’d like to gain some valuable insight into your Flowing skills, here’s a free assessment. It’s part of an introduction to the MyTimeDesign Plus+ program where we take a deep dive into Flowing.


As you can see from these ten expert contributions, there is no single, one-size-fits-all solution.

Novices mistakenly believe that scheduling everything means blindly throwing every task into your calendar. As some of the experts point out, that’s a recipe for disaster, even if you use a powerful auto-scheduler. The truth is, “Scheduling Everything” means using your calendar in nuanced ways, assisted by technology to achieve peace of mind.

I encourage you to find the approach that fits your circumstances as a first step. Then, make a plan for the development of your future skills which uses the best technology. Learn how to take these steps by signing up for my complimentary program – A Course in Scheduling.