Time Management Part 2: Use a Rolling Planning

In the first part of this series, we explored the crucial distinction between importance and urgency, learning how to prioritize tasks that truly matter instead of constantly reacting to urgent demands. Now, let’s take the next step: transforming this understanding into a practical time management strategy that ensures consistent progress toward your long-term goals.

 

Rolling Planning: Using Buckets to Avoid Over-Planning

One of the biggest pitfalls in time management is the temptation to over-plan. Many people fail at planning because they try to create the perfect plan, meticulously detailing every step far in advance. This approach often leads to frustration and burnout because:

  • It’s impossible to predict every detail for tasks that are still far in the future. Life is unpredictable, and priorities shift.
  • Over-planning consumes too much time and energy
  • When things don’t go exactly as planned, it leads to discouragement and the feeling of failure, which can make you abandon planning altogether.

The key to avoiding this trap is to not spend too much time planning things that are still further in the future. Instead, use a rolling planning approach that organizes tasks and goals into different buckets:

  • Yearly Bucket: Tasks that you want to accomplish this year but not necessarily in this quarter.
  • Quarterly Bucket: Tasks you aim to work on this quarter.
  • Monthly Bucket: Tasks to be focused on this month.
  • Weekly Bucket: Tasks scheduled for the current week.

The key idea behind this approach is to use buckets as placeholders for tasks and ideas that are still vague and far in the future. You don’t need to define every detail yet. By placing tasks in the appropriate bucket, you acknowledge their importance without committing to specifics that may change over time.

This approach allows you to stay flexible and adaptable but still make progress on things that are important to you. 

Periodic Reviews of your Buckets

Quarterly Review: Moving Items Between Yearly and Quarterly Buckets

At the start of each quarter, take a moment to review your Yearly Bucket. These are tasks or goals that you want to accomplish sometime this year but haven’t yet committed to a specific quarter. This bucket is intentionally vague because it’s meant to hold ideas that are important but not yet urgent.

During the Quarterly Review, you:

  • Decide if any new tasks should be added to either the Yearly or Quarterly Bucket.
  • Move items from the Yearly Bucket to the Quarterly Bucket if you feel that the upcoming quarter is the right time to start working on them.
  • Deprioritize tasks by moving them from the Quarterly Bucket back to the Yearly Bucket if they are no longer a priority.

For example, if you planned to start working on a strategic project “later this year” but realize that the upcoming quarter is the right moment, you would move that project from the Yearly Bucket to the Quarterly Bucket. Conversely, if a task initially planned for this quarter turns out to be less relevant, you can move it back to the Yearly Bucket.

Monthly Review: Moving Items Between Quarterly and Monthly Buckets

Each month, review your Quarterly Bucket to decide which items are now ready for action. This step allows you to gain more clarity on your priorities as the quarter unfolds.

During the Monthly Review, you:

  • Move items from the Quarterly Bucket to the Monthly Bucket if you’re ready to focus on them in the upcoming month.
  • Reassess and reprioritize tasks, moving them back to the Quarterly Bucket if needed.

This flexible approach acknowledges that priorities and circumstances change. By adjusting your focus monthly, you maintain agility without losing sight of your long-term goals.

Weekly Review: The Jar of Pebbles

The Weekly Review is the most crucial step in this planning process because it’s where strategic thinking meets practical scheduling. During this review, you not only decide which items from the Monthly Bucket you want to focus on during the upcoming week, but you also carve out specific time slots on your calendar for those tasks.

This is where the Jar of Pebbles analogy comes into play.

The Jar of Pebbles: Prioritizing What Matters Most

Imagine your schedule as an empty jar, waiting to be filled with pebbles of different sizes. The larger pebbles represent your most important tasks—those high-impact activities that move you closer to your long-term goals. The smaller pebbles are the less important but often urgent tasks that can easily consume your day if you’re not careful.  If you start by filling the jar with the smaller pebbles, there won’t be enough room for the bigger ones. But if you place the bigger pebbles first and then fill the gaps with the smaller ones, you maximize the space and ensure that the most important things get done.

During the Weekly Review, you:

  • Move tasks from the Monthly Bucket to the Weekly Bucket, ensuring that your focus remains on high-impact activities.
  • Block time on your calendar for the most important tasks before the week fills up with smaller, less important tasks.
  • Schedule your big pebbles first, treating these time blocks as non-negotiable appointments with yourself.

This is the key to a successful weekly plan: you proactively decide when you’ll work on your most important tasks before other demands take over. By doing this, you ensure that the important, non-urgent work gets done consistently.

Daily Review: Flexibility with Focus

The daily review is about delivering on the commitments you made to yourself during the weekly review. It involves a quick view of your calendar and priorities at the start of each day, but with a flexible mindset.

The key to the daily review is understanding that you can be flexible with when you work on a big pebble, as long as you ensure that you do work on it. Here’s how:

  • Protect Your Big Pebbles: The big items you scheduled during your weekly review are non-negotiable in terms of whether you work on them, but they are flexible in terms of when you work on them.
  • Allow for Flexibility: Life happens. Meetings get moved, urgent issues arise, and priorities shift. If you planned to work on a big pebble from 2:00 to 4:00 but something urgent pops up, it’s okay to adjust the timing. You can move that time block earlier or later in the day.
  • Don’t Delete or Ignore—Only Reschedule: If you need to move a time block, always reschedule it for another time and ideally on the same day. The rule is simple: you can exchange time, but you cannot remove that time from your schedule.

This approach allows you to remain flexible while ensuring that you make consistent progress on what matters most. You’re not locked into a rigid schedule, but you’re also not sacrificing your long-term goals for short-term distractions.

When to Conduct Reviews: Finding Your Quiet Moment

The timing of your reviews is crucial. To be effective, you need a quiet moment for reflection and strategic thinking. This could be:

  • Quarterly Review: At the start of each quarter, on a day that allows for undisturbed reflection.
  • Monthly Review: At the end of each month or the start of the new month.
  • Weekly Review: Early in the week, at a moment when you can calmly reflect on your priorities. For some people, this is Sunday evening; for others, it’s Monday morning.
  • Daily Planning: A brief review each morning to ensure you’re on track.

The key is to find a moment when you can think strategically, without distractions. This will allow you to make thoughtful decisions about where to invest your time and energy.

Why This Approach Works

This rolling planning method works because it allows you to:

  • Stay flexible and adaptable: Plans are fluid and can be adjusted as new information and priorities emerge.
  • Stay focused on long-term goals: By continuously moving items from bucket to bucket, you maintain strategic focus without being overwhelmed by rigid schedules.
  • Avoid procrastination: The gradual refinement of tasks from yearly to daily ensures that important activities don’t stay vague indefinitely. They gain clarity and move closer to action as time progresses.

By using the Jar of Pebbles analogy and strategically moving items between buckets, you maintain a dynamic but focused approach to time management.

Taking Control of Your Time

Mastering time management isn’t about packing your schedule with endless tasks. It’s about strategically choosing what to focus on and ensuring that the important, non-urgent goals get the attention they deserve.