Wonder Tools ⏰ Try Timeboxing

I’m starting this year with a focus on tactics, not just tools. Timeboxing is the tactic I rely on to plan my 100 weekly waking hours. In this post I’m sharing tips and tools to help whether you’re new to timeboxing or a pro.

To read this full post online, visit https://wondertools.substack.com/p/timeboxing

Timeboxing is the practice of scheduling tasks and deep work directly onto a calendar. By specifying how long to spend on each task, timeboxing helps you create a realistic plan taking into account your priorities and available time.

How it works for me

I start the day with 15 minutes of reflection and planning. I usually use a portable notebook or Sunsama. I review tasks, set priorities, and schedule specific time slots for deep work. I allocate time that’s available to me between meetings and teaching responsibilities.

Why timeboxing might work for you

Timeboxing might be a fit if you have the freedom to decide what to do when. It’s especially useful if you have a sense of how long things often take you and know the daily rhythms of your concentration levels, i.e. when you’re best able to focus. It doesn’t have to be all or nothing: timebox a fraction of your schedule if unpredictable work or personal responsibilities limit your flexibility.

Here's a simple process to start timeboxing today:

* Choose your planning time Pick either the end of your workday or first thing in the morning. I prefer a.m. when I’m most focused.

* List your priorities Spend 5 minutes listing your most important tasks for the upcoming work session. Not everything. Just the top few.

* List necessities Spend 5 minutes listing other less-valuable tasks that you have to get done today. Again, not everything. Just what’s most essential.

* List notes and for-later items Spend 2 minutes jotting down anything else that comes to mind that you’ll need to remember later to help you get your work done, or that you’ll need to put on a future work list.

* Estimate durations Next to each task, write how long you think it will take, adding a 25% buffer to account for interruptions or hidden sub-tasks.

* Block your calendar Schedule each task into specific time slots.

* Review at day’s end Consider how long things actually took, what worked well, and what didn’t. That reflection will strengthen the next day’s plan.

Pro tip: Start small. Begin with just your morning or afternoon hours. Start with the simplest tools available to you, whether that’s paper and pen or your existing Outlook or Google Calendar.

Common pitfalls to avoid

* Over-scheduling Don't fill every minute. Leave buffer time for unexpected tasks and the occasional rabbit hole.

* Unrealistic estimates Most tasks take longer than we think. Double your initial estimates.

* Ignoring energy levels Match challenging tasks to your peak energy times.

* Too much rigidity Build in flex time for inevitable disruptions.

* Planning too far ahead Focus on the very next work session, not next week. Who knows what will happen to complicate plans or alter priorities?

How timeboxing supports popular productivity frameworks

* The Eisenhower Matrix This approach focuses on assessing what is urgent and important. While Eisenhower analysis helps you prioritize and decide what to do, timeboxing helps you decide when to do it and how long to spend. It also nudges you to commit to it by putting it on the calendar.

* Eat the Frog This idea suggests doing the most important or most difficult task first. Timeboxing helps give you a structure for putting that task onto your calendar and allocating sufficient time for it.

* The 80/20 Rule This concept suggests that 20% of the work you do delivers 80% of the most important value. It helps focus attention on what's most valuable when you’re deciding what’s worth your time. Timeboxing helps you execute on that prioritization by making it tangible on your schedule.

Recommended timeboxing tools

Graph paper, sand timers, and Post-its

* Graph paper works well. Organize your schedule into boxes, with each representing 10 or 15 minutes. Here’s a nice notebook version.

* Sand timer It’s old-fashioned, attractive, and doesn’t require batteries or a screen. Get one that lasts 15 minutes — or whatever work interval you prefer. Benefit from a visual reminder to stay focused.

* Writing Guru Mallary Tenore Tarpley recommended this sand timer in an excellent recent piece on gifts for writers. Choose between 5, 15, 30 or 60 minute durations for $10 to $13.

* A nice notebook and pen help provide a clean, pleasurable surface for planning. I like the classic Leuchtturm1917 notebooks.

* Post-its Put one 15-minute task or deep work step on each Post-it. Line up eight in order to plan out a two-hour work sprint.

Google Sheets / Microsoft Excel

A free spreadsheet can work well for planning if you work independently and don’t rely on a digital calendar.

* Here's a blank Google Sheets template for planning in 30-minute increments. Click “Use Template” at the top right to make your own private version. Or copy it. Adjust it to suit your needs, or create your own template.

* To access your sheet as you work, print it out, bookmark the tab, or access it from your mobile device.

* Avoid the temptation to decorate or perfect your spreadsheet. Spend brief time planning to maximize time for doing.

* If you do want to get fancy, use checkboxes to mark completed tasks to reward yourself for getting stuff done. Or use color codes to categorize your priorities to get a visual overview of where your time is going.

* Benefits: Google Sheets is free, simple, and easy to use. So is Excel if you already have it.

Google Tasks

Use Google’s free task manager to list out priorities, then drag them directly onto your Google calendar for scheduling. It’s simple, fast and handy if you already use Google Calendar. It works well across operating systems, but doesn’t let you adjust the duration of tasks.

Sunsama

This is my preferred daily planning software. I use it on my laptop — you can also use it on iOS or Android. You can sync it to your existing task lists and calendar, or use it by itself.

When you open Sunsama it prompts you to reflect on the prior day and to plan your upcoming work. You can add new tasks or import them from other apps like Todoist and Asana. You can then drag tasks onto your calendar to schedule your day.

Integrations and pricing: Sunsama syncs with Outlook and Google Calendar as well as Slack, Teams, Trello, Monday, Notion and other tools so you don’t need to flip between apps. At $16/month it’s a well-designed pro option for those with a budget for work tools. Too pricey? Stick to the free alternatives above.

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How my approach has changed

I used to dive into email first thing. I would tackle tasks as they came to mind, or based purely on urgency. I would pause work throughout the day to contemplate what to do next.

Now I plan, set the schedule, and then focus on doing. I waste less of my limited attention on making decisions hour by hour. I worry less about how I’m spending time because I trust my morning planning. I take five minutes at the end of the day to think about what worked and what didn’t so I can plan better next time.

Reality check: I often mess up my intended approach and instead hop from task to task without finishing things. On those days I waste time, dwell on unimportant email, ruminate, self-blame, try structured procrastination, then eventually forgive myself and start fresh.

Timeboxing resources

* How Timeboxing Works and Why It Will Make You More Productive by Marc Zao-Sanders — Read this for a three-minute summary of what’s in Zao-Sanders’s Timeboxing book.

* Primary takeaway: timeboxing makes it clear to you and to others what you’re working on because it’s on your calendar. It helps you plan based on actual deadlines and priorities.

* What’s the #1 Productivity Tool? For Me, It’s Timeboxing. by Neha Kirpalani

* Primary takeaway: by forcing you to find time on your calendar for each task, timeboxing helps you conquer the planning fallacy, which is the tendency to underestimate by 3x how long things will take.

* Tranquility by Tuesday by Laura Vanderkam offers nine ways to make time for what matters.

* Primary takeaway: “Effortful before effortless” is an excellent rule of thumb to encourage putting more consequential tasks first. Why? We’re often in a stronger state of mind earlier on.

* Vanderkam also suggests applying this approach to leisure. We might benefit from spending time on active hobbies we deeply enjoy before passively consuming Netflix.

* Indistractable by Nir Eyal is an excellent guide to staying focused.

* Primary takeaway: to overcome distractions we have to confront our tendencies to avoid difficult work when it is complex or boring, or when our perfectionism stalls us.

Timeboxing vs time blocking

Time blocking means allocating blocks of time for priorities without specifying timing for specific tasks within that block. Timeboxing adds an additional element: you actually schedule tasks and deep work onto the calendar in defined time slots. Having specific timeboxes nudges me to focus fully on that one thing during that part of my day. It also helps me, over time, to better estimate how much time I need for various kinds of projects.

Timeboxing vs working from a task list

Picking what tasks to work on requires mental effort. If you make that effort throughout the day by repeatedly asking yourself what to work on next you’re spending down your focus on decisions that could be made in advance.

Timeboxing vs improvising

Improvising our day may seem an artistic approach. But musicians, painters, dancers and others who do creative work often follow carefully-planned practice regimens.

Even when we’re doing creative work that requires imagination, we benefit from structure. Detailed plans allow us to apply our focus and creativity to the work itself. When we trust in a schedule we’ve crafted, we avoid getting distracted by decisions about what to do next. We can then immerse ourselves in the action.