Timeboxing Your Calendar


Scott D. Clary
Scott D. Clary
6 min readMay 23, 2024


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Timeboxing Your Calendar

Today, we’re diving into a time management weapon that’s changed my game: the art and science of timeboxing.

Time is the Ultimate Luxury

You know this.

As entrepreneurs, our most precious resource isn’t money, connections, or even a brilliant idea.

It’s time. The 24 hours we each get, day in and day out.

Yet, how many of us treat it like a priceless diamond, carefully choosing how it’s cut and polished?

Most of us don’t.

We let time slip through our fingers like sand, reacting to the urgent instead of pursuing the important.

We get sucked into endless meetings, distracted by notifications, and wonder where the day went.

Enter: The Timebox

A timebox is simple: it’s a chunk of time you dedicate to a specific task or activity. It’s like a meeting with yourself, but one you actually keep.

  • Example: Instead of saying, “I’ll work on marketing this week,” you timebox it. “Tuesday, 10 AM — 12 PM: Create social media content calendar.”

This seemingly small shift does something magical:

  • Clarity: You know exactly what you’re doing and when. No more decision fatigue.
  • Focus: You eliminate distractions. Your brain gets the signal: “This is game time.”
  • Accountability: You’re forced to confront your progress (or lack thereof).
  • Efficiency: You get more done in less time.

Why Timeboxing Isn’t Just for Beginners

You might be thinking, “Scott, this sounds like basic stuff.” And you’re right, the concept is simple.

But don’t mistake simplicity for lack of power.

Timeboxing is a tool that scales.

The more complex your life gets, the more essential it becomes to have a system that brings order to the chaos.

Timeboxing is that system.

In the next segments, we’ll dive deeper into:

  • The Timeboxing Mindset: How to think about your time differently.
  • The Timeboxing System: Practical steps to implement this in your life.
  • The Timeboxing Masterclass: Advanced strategies to take it to the next level.

Think Like a Strategist, Not a Firefighter

As entrepreneurs, we’re constantly bombarded with demands on our attention.

Emails, meetings, unexpected problems… it’s like a never-ending game of whack-a-mole.

Most of us react to this chaos by becoming firefighters.

We rush from one emergency to the next, putting out fires as they arise.

This is exhausting, unsustainable, and keeps us from playing offense.

Timeboxing is about shifting from firefighter to strategist.

The Strategist’s Advantage

A strategist takes a step back from the front lines and surveys the battlefield.

They assess the terrain, identify key objectives, and allocate resources accordingly.

Timeboxing is your strategic planning tool for time. It allows you to:

  • Prioritize: Not everything is equally important. Timeboxing forces you to decide what truly matters and give it the focus it deserves.
  • Protect: Your time is sacred. Timeboxing creates a fortress around it, shielding you from distractions and interruptions.
  • Proactive: Instead of reacting to the urgent, you’re proactively pursuing the important. You’re in control.

3 Mental Shifts for Timeboxing Mastery

  1. Embrace the White Space: Don’t be afraid to leave gaps in your calendar. This is where creativity, deep work, and unexpected opportunities flourish.
  2. The 80/20 Rule of Time: Identify the 20% of your activities that generate 80% of your results. Timebox those activities ruthlessly.
  3. The Power of “No”: Saying no is a superpower. Timeboxing helps you protect your time by giving you a framework for saying no to anything that doesn’t align with your priorities.

The Antidote to Overwhelm

One of the most common challenges entrepreneurs face is overwhelm.

There’s always too much to do and never enough time.

Timeboxing is the antidote.

It breaks down daunting projects into manageable chunks, creates a clear roadmap for action, and gives you a sense of progress and control.

Remember: you’re not a firefighter, you’re a strategist.

Start thinking like one.

Your Timeboxing Toolkit

Now, let’s get tactical.

We’re building the system that turns timeboxing from a concept into your unfair advantage.

The right tools are essential for any builder. Here’s what you need for your timeboxing arsenal:

  1. The Calendar: This is your command center. Digital or paper, it doesn’t matter. But it needs to be something you use religiously.
  2. The Task List: A running list of everything you need to do. This can be separate from your calendar or integrated with it.
  3. The Timer: The ticking clock creates focus and urgency. Use a physical timer, your phone, or a timeboxing app.

Building Your Timeboxed Week

  1. The Weekly Review: Start each week with a strategic planning session. Review your goals, identify your priorities, and create a rough outline of your timeboxed week.
  2. The Big Rocks: These are your most important tasks, the ones that move the needle on your goals. Schedule these first, ideally in the mornings when your energy is highest.
  3. The Pebbles: Smaller tasks, meetings, and routine activities. Fit these around your big rocks.
  4. The Sand: Email, social media, and other low-priority tasks. These should fill in the gaps, never dictate your schedule.
  5. The White Space: Intentionally leave blank spaces in your calendar for flexibility, creativity, and deep work.

Timeboxing Tips and Tricks

  • Theme Your Days: Dedicate certain days to specific types of work. This creates mental clarity and reduces context switching.
  • Batch Similar Tasks: Group similar tasks together to minimize mental overhead.
  • Overestimate: Be realistic about how long tasks will take. It’s better to overestimate and finish early than to underestimate and run over.
  • Iterate: Your timeboxing system will evolve as your needs change. Experiment, adjust, and optimize over time.

Timeboxing Beyond the Basics

Once you’ve mastered the fundamentals, you can start experimenting with more advanced strategies:

  • The Pomodoro Technique: Work in 25-minute blocks with short breaks. Great for focus and productivity.
  • The Flow State: Schedule time for deep work when you’re most creative and focused. Protect this time fiercely.
  • The 90-Minute Rule: Research suggests our brains naturally cycle through 90-minute periods of focus. Timebox your work in 90-minute blocks with breaks in between.
  • The Ultradian Rhythm: Our bodies naturally cycle through 90–120 minute periods of high energy followed by lower energy. Timebox your work in these cycles, alternating between intense focus and restorative breaks.
  • The Power Hour: Dedicate the first hour of your day to your most important task. This sets a productive tone for the day and ensures you tackle your priorities before distractions arise.
  • The Daily Highlight: Choose one main goal for each day and timebox it as your top priority. This ensures you make progress on what truly matters, even on busy days.
  • The Timeboxing Ritual: Create a pre-timeboxing routine that signals to your brain it’s time to focus. This could be a short meditation, a few stretches, or a quick review of your goals.
  • The Accountability Partner: Share your timeboxing plan with a friend or colleague who can hold you accountable and provide support.

Beyond Theory, Into Action

I could fill countless newsletters with more tips and tactics, but they mean nothing without action.

Timeboxing is a tool, and like any tool, its value lies in how you wield it.

Take the principles we’ve covered, experiment, adapt them to your unique needs, and make them your own.

This is your chance to not just understand timeboxing, but to embody it.

What’s Next?

Your journey doesn’t end here. It’s just the beginning.

As you consistently apply timeboxing, you’ll witness its profound effects on your productivity, creativity, and overall well-being.

More importantly, you’ll gain a sense of mastery over your most valuable asset: time.




Scott D. Clary
Scott D. Clary

👋 scottdclary.com | Host @ Success Story Podcast 🎙️ | I write a newsletter to 321,000 people 👉 newsletter.scottdclary.com