Introduction

Everyone wants to maximize productivity and work-life balance with better calendar management and scheduling. Over the years I’ve learned two key tricks. First, plan with the calendar instead of a task list because the calendar controls real life time allocation. Second, manage inbound and meetings within predefined calendar blocks instead of reacting, because calendar whitespace will always default to what other people want you to do via meetings and inboxes.

Let’s just get straight to the tool; a simple four step process; 1) we’re changing from reactive to proactive with time management for processing the inbox, then we 2) schedule personal time to ensure balance, 3) schedule project time, and 4) schedule meeting blocks to minimize their impact on project productivity.

After we review the tool, we’ll go into detailed background context to understand what motivates this time management system and how to apply it to become massively happier and more productive.

The tool

Schedule each of these four activities in priority order, creating descriptively named meeting blocks for each topic that repeat weekly or every other week as appropriate. When you are done your *entire* calendar should be blocked. Don’t leave any whitespace because whitespace will default to meeting and inbox time.

Inbox time – First, schedule reactive work. This is when you’re going to check your inboxes and agenda for the day. I recommend once in the morning and once at the end of the day (and maybe once in the middle). This has to be planned realistically based on the response times you need to commit to, or it will blow up. When it blows up, you default back to reactive mode and the entire system blows up – you’re back to checking inboxes all the time, and allowing others to control your time and attention based on their agenda rather than your agenda. That’s why I recommend blocking the reactive times first and very thoughtfully, to be 100% certain that they are scheduled at realistic times of day for replying and coordinating. If you find inbound blowing up and these time blocks aren’t working, step back and tweak the system, maybe you need to do it three times a day for 15 mins instead of once a day for 30 min, etc. I also include daily planning time here, normally 15 minutes at the beginning or end of every day to prepare for the coming day.

Personal time –  Second, schedule your personal time. The most important thing is ultimately your physical and mental health, and you’re not going to do anything else at maximum effectiveness unless you put yourself first. Explicitly book your family time, social time, workouts, meditation, therapy, wake up time in the morning, and wind down time in the evening. Fit work around your life not life around your work. It’s fine to schedule personal blocks of time in the middle of your day for workouts or therapy. It’s fine for parents to stop work early for kiddo time if they are out of school before the work day ends, then do another block of project time at night after the kiddos are in bed. It’s fine to end later one day or start later the next day because you want to do a night out during the week. Think like an owner – what matters is your impact, not the exact times of day you are working.

Project time –  Third, schedule your project time. This is the core time where you create the most value, so you should allocate time blocks to each project based on strategic value. Manage your calendar to ensure that your most creative and productive time is allocated to project work rather than meetings. Often you have time conflicts with meeting blocks, e.g. you want to do your creative project work from 8am-noon, but you are in PST and have coworkers in the EU that want meetings in that time range. Projects are generally always more important than Meetings. That said, you have to make some time available when calendars overlap, so it’s a question of getting creative. Can you do some really late meetings some days right before your wind down time in the evening and early AM for your EU colleagues, or have your creative morning blocks 3-4 days a week and 1-2 days a week give up one morning meetings block, then afternoons those days are project time?

Meeting time –  Fourth, schedule meeting time. Distinguish between internal vs external meetings. If you have a role in which your projects are often executed as a sequence of meetings e.g. sales, fundraising, BD, or recruiting, try having schedule blocks where only particular types of meetings are allowed so you don’t constantly context shift and underperform in meetings. For example, if you’re a salesperson with a bunch of calls to emerging growth companies for one product, calls to large enterprises for a different product, and internal team meetings, maybe try to allocate dedicated calendar blocks and stack calls within their respective blocks. I always stack meetings in the same context back-to-back, which allows more time for sustained flow in the same context. This avoids sporadic 30-60 min downtime blocks in between meetings, which can be really difficult to fill with productive work and ‘get in the zone’ on anything.

Background

Timeblocking is an idea that’s probably as old as the calendar itself. Benjamin Franklin was one of the first productivity hackers to evangelize timeblocking.

I want to outline the primary trade-offs that show why it’s important to use your calendar as a time management tool to control your daily work rather than to use a todo list or project management software.

The trade-offs I want to talk about are:

• Proactive vs reactive
• Multiple queues vs single priority queue
• Project vs meeting time
• Work life balance vs just work

Proactive vs reactive time allocation

“I have two kinds of problems, the urgent and the important. The urgent are not important, and the important are never urgent.” – Dwight D. Eisenhower

When the chaos of daily operation sets in, we often end up reacting to things – inbox, meetings, pings on slack, messengers, notifications.

So many new things surface every day, and it’s unclear when to react to it, how and where to capture everything, and then how to prioritize and allocate time to it.. Stephen Covey’s book, The 7 Habits of Highly Effective People, suggests building a system that allows you to focus on important, non-reactive work. Without a robust system in place, you will continuously find yourself lost in daily, interrupt driven, chaos.  The best illustration of this is the ‘Eisenhower matrix’.

Schedule inherently reactive work as ‘inbox time’  – some work is inherently reactive and requires you to react to inbound messages like email, slack and messaging apps. For many busy people it’s unrealistic to look at these inboxes just one time per day. I, or someone on my team doing it on my behalf, will process inboxes once in the morning, once midday, once at the end of the day and sometimes once before winding down for the evening. Go through and archive as much as possible, reply when necessary and can be done in just a few seconds, otherwise cue up tasks in Asana. Importantly, keep inboxes closed and notifications off on all devices when not in an inbox processing time block. Responsiveness is a setting. It’s on you to determine how important it is. Dealmakers like recruiters, sales, or investors who need to move fast and close things are completely different from the creative class of product, design, and engineering – dealmakers might want to commit to a system with much faster turnaround time and check inboxes 10 times a day, whereas creatives might only want to do it once. Cal Newport takes 10-20 minutes at the end of every day to review and review timeblocking for the following day, and I do something similar every Sunday night to prepare for the following week.

Hold boundaries and say no – Lots of activities can be eliminated up front. You set your boundaries with your calendar, but poorly-managed reactive work will be trotted in by people who feel entitled to your time. There will always be a draw into short notice meetings, teammates that need help, work outside your core responsibilities, newly emergent project scope, and surprises manifesting from unknown unknowns. Everyone thinks their stuff is high urgency, high importance; lots is neither and can be discarded or give an immediate no, some is urgent but can still be ignored or delegated, and some is important but there are still greater risks and priorities. So be assertive about not immediately reacting to inbound. As Tim Ferris says, eliminate before you optimize.The beauty of this is that people realize that their request is being run through a process which feels like its going to take a long time, and a lot of things aren’t going to get an immediate response and will probably be a no. They leave you alone and go figure out their problem. This includes not making yourself available for short notice meetings that impinge on your other calendar blocks.

Delegate, do, plan – Once you’ve eliminated everything you can, find anything that you can delegate or should be owned by someone else. This is the next source of limiting your work, so you should be as rigorous about it as you are with eliminating work. It’s also a magnifying effect; you are potentially creating work for many people or even worse, blocking them. Once you’ve delegated or moved ownership to the right place, then your important and urgent items that must be done now should just be done. After that, plan and work on the longer term items. It might seem like you’ll then never get to these items because there will be too much important and urgent work, but that’s not the case – this is why it’s very important to eliminate and spread ownership around as much as you can so that you’re really focusing on your projects. Your job is to shepherd that work into the respective project queues, prioritize it with the other work in each of those projects, and manage the work during the time slots allocated to each project. The time blocks for each project will ensure that strategic time is used in the right way and not just absorbed by the emergencies of the day.

Multiple queues vs single priority queue

As work gets more complex, cross-functional and multifaceted, you need to manage across multiple queues of work. The question arises how do you determine what to do next. In the world of project management you will typically have a queue for each project, and people that need to work across projects consolidate the view of these queues into a single priority queue.  The trouble with this approach is it’s not very effective at determining how to allocate time across the projects. It assumes a world where everything maps into a task you need to do next, and you can easily globally prioritize the order in which to do each of the tasks. That’s just not realistic.  In reality you usually want to top-down define how much time you’re allocating to each queue, block that time on the calendar, and attack the work during that time slot.

As work comes up, capture and organize it into queues – I like to use Asana. If you want help with this and haven’t done a lot of project management before, try something simple like GTD to help you capture and organize tasks. If you get into the GTD stuff, be sure to notice that its creator David Allen has been changing his mind from the looser model he started with to the more rigorous model we’re proposing here. 

Obviously life isn’t perfect and changes will come up or you’ll need to do a big sprint on one particular project on a given week, but the more multifaceted and cross-functional your work is, the more you want to try to be pretty rigid about honoring your time blocks on the calendar as a way of prioritizing time allocation to each queue. You want to avoid allowing yourself to get churned by constantly shifting too much and never functioning at peak performance or focusing long enough to drive important tasks to completion.

Setup the calendar to allocate time to what’s most valuable, and if you don’t have enough work in a given project queue, then you should be doing the work to generate more work. Think top down and be proactive and creative about how to build value in each project.. If you’re a busy CEO then this is very natural because you have many different kinds of projects going on in parallel, but this advice applies universally across an organization. For example, if you’re an engineer, you’ll be very heavily weighted towards writing code, but you can still reserve slots on your calendar for non-code related tasks. If you find that there’s not enough non-code tasks, be proactive. Let’s say you’re just starting to work on recruiting to grow the team but you don’t have any interviews yet for this week.  I like to think top down so instead of turning your interview time back into coding time this week, I would encourage engineers to look through their networks to see if they could reach out to to ask for referrals, or to check on open-source projects or other ways of finding interesting candidates. Try to take that time block to be proactive; surface candidates for the recruiting team or reach out yourself rather than simply coding and waiting for interviews to show up on your calendar. I always prefer to coach people to be more proactive and more top down, because ultimately we’re allocating these calendar blocks because we think that’s what’s going to have the most positive impact on the business,  so the best thing you can do is get creative about how to have impact if there isn’t something obvious in that slot.

The complexity and richness here shows why it’s so important to think about the broader organization, its priorities, your personal priorities, and not just a narrow view of a single task list.

“In this context, the shortcomings of personal-productivity systems like G.T.D. become clear. They don’t directly address the fundamental problem: the insidiously haphazard way that work unfolds at the organizational level.” –  Cal Newport

Project vs meeting time

Another big issue in taking control of your time is acknowledging the need for time blocks and not being open to arbitrary activity at any time during the day. The biggest distinction here comes between heads down time and meeting time. This is especially important for those of us in strategic or creative roles where we need real heads down time to get in the zone for hard problems. We need to be able to put up boundaries around that time that are sacrosanct and will not be violated by meetings, especially on short notice.

Paul Graham referred to this as maker’s schedule vs managers schedule. 

“The manager’s schedule is for bosses. It’s embodied in the traditional appointment book, with each day cut into one hour intervals. You can block off several hours for a single task if you need to, but by default you change what you’re doing every hour. But there’s another way of using time that’s common among people who make things, like programmers and writers. They generally prefer to use time in units of half a day at least. You can’t write or program well in units of an hour. That’s barely enough time to get started…A meeting commonly blows at least half a day, by breaking up a morning or afternoon. But in addition there’s sometimes a cascading effect. If I know the afternoon is going to be broken up, I’m slightly less likely to start something ambitious in the morning.”

We also need to chunk up heads down time for each project. I represent each project in asana, maintain a discipline on adding tasks to asana, and name calendar blocks the same as the project name. So if it’s coming from the marketing project for my company Warmer, the invite will say ‘Warmer Marketing.’ I’m not perfect at this, and I will change my overall calendar blocks probably every couple months, but I notice that when I have broad placeholder categories like ‘Content’ or ‘Heads down’ I tend to be unfocused, have less impact. Being imprecise about your categories tying to specific project queues will also make you less focused on enforcing boundaries more willing to let those blocks be overrun by meetings.

So I strongly recommend starting with time blocks tied to each specific project, and making meeting time blocks explicit on the calendar. Only allow the team to schedule meetings within the explicit meeting blocks, and honor your focus time for each project – work only on that project, in priority order.

Be sure to think about when you are most productive and creative and use that as your project time. I like to try and do more creative work on my own early in the day – it’s sometimes harder to do your best work later on after a day of back to back meetings.  This process is really about you taking control of your time and calendar and so it’s highly personalized with respect to your own lifestyle and how your brain works.  A lot of this is specific to you and depends on how you focus best, when you do your best creative work, the time zone overlap with other co-workers that informs when meetings need to happen, and so on.

You also might want to ensure that certain types of meetings can only go in certain slots.  For example, you may want to limit the number of hours in a day or week for certain types of meetings.  Your team is always going to want as much of your time as possible and people have their own agendas in mind.  It’s entirely on you to define and maintain your boundaries that force people to find other ways to get things done.

Project time should be treated as everyone’s most valuable time, and hence meetings should always be absolutely necessary – avoid scheduling meetings when something could be solved asynchronously. Meetings should start on time, have an agenda, and be well facilitated to avoid unproductive monologues, ratholes, tangents, and fruitless debates. You might want to try various forcing functions for meeting hygiene, for example Ben Horowitz at a16z famously fines people for being late to meetings.

Work life balance vs just work

Perhaps the most important trade-off is work-life balance versus just work.  If you’re not scheduling your life then you’re opening up the door for your work life to overrun your personal life. So I always recommend making your personal life explicit too. 

“The big thing is basically *everything* is on the calendar. Sleep is on the calendar, going to bed is in there and so is free time. Free time is critical because that’s the release valve. You can work full tilt for a long time as long as you know you have actual time for yourself coming up. I find if you don’t schedule enough free time, you get resentful of your own calendar. If I didn’t have this, I’d be in a panic the very first moment I wake up.” – Marc Andreessen in an interview with Sriram Krishnan (more timeblocking excerpts from this interview here)

I actually find it quite helpful for logistics, because for example I ensure breakfast and commute times for my daughter are baked into my calendar so I can’t be disrupted by a meeting driving to and from school, when I need to be present and show she is most important. Folks are welcome to have a meeting and start without me at 8AM, but they know I’m not available until 8:30AM and I will auto decline anything that starts before that.

I know a lot of people with families will stop right at 5 or shortly after for dinner with the family and then they’ll go back for an evening shift after they put the kids to bed so they might work again from 8PM to 10PM for example. I’m a single parent that has my daughter half time, so I pick her up from school half the time and do activities with her right away, so I don’t do afternoon meetings on days when I have my daughter. I also go out a lot now when I don’t have my daughter, so those days I’ll work straight through until maybe 8PM then go straight out to party. As a less experienced entrepreneur without kids, I used to work straight from waking up to going to bed – stopping only to eat or workout.

Balance is all highly personal and can change a lot based on stage of life and how effective you are with your time. When you are doing ‘knowledge work,’ it’s not so time-of-day sensitive, so everyone needs to feel empowered that they can make the work fit their life, they don’t need to make their life fit the work.

Make the work fit your life, not your life fit the work.

The second crucial time of day is the morning — make sure you start the day off with a systematic physically and mentally healthy routine whether it’s meditating, eating a good breakfast, getting a workout in, etc.  Make sure you acknowledge how your mental energy and creativity flows throughout the day.  Many people, including myself, find that we do our best creative work earlier when we are freshest.

It’s totally okay to do workouts in the middle of the day, or take mental health time for therapy, meditation, a walk, a nap, a coffee, etc. What really matters is your impact – what you get done not when you get it done during the day. I personally do my best work with a big chunk of creative activity and creation in the first half of the day. Then I take an afternoon break for a workout, a run, meditation, or a nap. Then i do another big session into the evening.  I find that a break in the middle of the day boosts my energy level.

“afternoon naps are underrated.

afternoon workouts are also underrated.

both give a distinct sense of freshness and clarity for the second block of work, as if you get a free second morning each day.” – @bradfordcross

Introspect and think about what is going to work best for your life, and make the work fit your life. Always remember the ‘airplane rule’ – put the mask on yourself before you try to assist others. In other words, you’re not going to do your best work or be able to help your colleagues if you’re not starting from a place of physical and mental health yourself.