New Time Management Tool — Milestone Chart with Long-Term Planning

A milestone chart has been the core of my planning for over a year now. The old one focused on the one-week through several-month time frame. The new one encourages you to plan even longer projects.

Each row has a time frame, and each project (or group of projects) has a column. Each cell then has a milestone or goal.

The chart allows you to add as much or as little detail as you like for each time frame, at any time. Even better, you can see the big picture for a November to February project without flipping pages.

You can flesh out an important project first, then see how much time is left each week for other projects. If you need to change something, you can see how it affects both the rest of the column, and your workload for the week.

The chart didn’t convert well to WordPress format, so here’s a pdf of the entire thing.

milestone chart version 2

I still use a separate weekly dashboard each week, and a spreadsheet for repeating tasks.

I update the chart with pencil every few days (usually just marking things done), and spend half an hour updating it on the computer every few weeks.

This process, plus a good estimate of how much project time you really have each week, will encourage you to put some projects into hibernation. It will also cause you to take immediate action on your dreams. Both actions are good.


The first column is the first date each time frame. (Decade, year, month or week.) One time frame for per row, so you will have several rows for January 1, 2010.

The second column is the length of the time frame. Use “a-decade”, “b-year” and so on for sorting. (I abbreviate them so the column can be narrow.)

The third column is vacation, holidays, and anything else that might affect how productive your work week is. (If your husband is away, you don’t want to schedule a heavy week at work.) I even put in “last week of summer,” because my kids are stressed out then.

The remaining columns each get a single project or goal, although I often combine similar projects into one column. The number of columns is limited only by your font size and printer.  Start with one column per project, then combine them as works best for you.

Step 1: Plan the Decade.

No, this is not overkill. It provides perspective for everything else.

Create a row for Jan 1, 2010, with time frame of a-decade. In each column, list one thing you want to accomplish or make good progress on before the decade ends. These might be fuzzy (start my own business) or vague (graduate), or a mix.

Create a row for each year, starting on Jan 1, and with time frame of b-year. For each decade-goal, choose one or more sub-goals or milestones for each year. Remember, the milestone is to be finished during the year that starts on Jan 1.

The date a time frame starts is used rather than the date it finishes. This way, the very first line is your long-term goals.

Format the decade and year rows. You will need 3 levels, or 4 if you go down to the day level.

Step 2: Plan the Year.

Add more columns, one for each project you hope to make progress on before the year ends, that doesn’t already have a one.

Create a row for each month, starting on the first of the month, and with the time frame of c-month. For each goal in the year row, choose one or more milestones for each month.

In the Vacation column, list anything that might affect your how much you get done that month. Very little new work gets done in December, and when your coworkers are on summer vacation you’ll be trying to do two jobs at once. March break, Easter, and the week before cottage opening are also important. Include big gift-buying events at this stage, especially if you have to co-ordinate with someone. You can fill in the smaller ones later.

If a project spans a month boundary, make a milestone for each month. That way, you’ll do the first half of the work during the earlier month. (That also applies to work that spans a year boundary.)

Include the actual dates of deadlines. This will save time when you do the next level. Also, you won’t miss the deadline on the 3rd of the month if you’re late doing the next planning session.

Format the rows.

Step 3: Plan the Month.

Follow the same pattern, except the dates won’t be as tidy. I start on Monday and finish on Sunday. You can flesh out as many months as you like at a time. The system just rolls over at year-end. No more carrying around two books!

Now count backwards from each milestone or deadline and add more details. See sample chart.

This level has as much detail as needed to keep you on track. Some projects are so complicated that I write only a summary here, and the details elsewhere. A generic “keep on track” might work, but it risks a big surprise if you forget what that means.

Pay attention to the Vacation column while doing this.

You might want to move the information from the month rows to the week rows, then delete the month rows.

Format the rows.

You can go down to the day or even hour level if you wish, but you might need to add even more columns for appointments and routine tasks to cover everything you need to do. You can add day-level details in the week row if necessary.

Step 4: Sort and Print

Most of the time, you’ll sort the rows by date, then by time frame.

The first row will be your goals for the current decade, the second will be your goals for the current year, and so on. Down at the bottom will be months and years in the far future.

The next time you do long-term planning, you might want to hide some of the rows. Add an extra “hide” column. Sort by time frame. Put an X in the “hide” column for rows you don’t want to see. Sort by “hide”, and then by date. Or use a fancy spreadsheet function if you know one.

Step 5: Work the System

Each week when planning, look at the current week row (and the longer-term goals above it). Ideally, you won’t have to look at future weeks, but it never hurts know what’s coming up. You might decide to do some things early.

If you realize you don’t have time to do everything you need to do (If?), you will quickly see which things you can move without affecting the entire project. You might realize that, even though this week is busy, the next few weeks are even worse.

Variations and Comments

I like to put the more-important columns on the left. It helps me plan the week.

Very long-term goals that don’t have many milestones in the near future on can be combined into one column for now. You can split them when you add so many details that the column is crowded.

Projects that use similar energy work well in the same column. I only have so many “high focus” hours a week.

You can also use a column to keep track of other resources, such as which weeks your husband needs the car for his carpool.

Projects that are done one-after-the-other work well in the same column. E.g., You want to finish remodelling the family room before starting the kitchen. You don’t care when the basement if finished, but if that slips, then the kitchen won’t be finished in time to bake Christmas cookies. Put them in the same column, so when the first room slips, you see the chain reaction.

Some people work better with “finish by Dec 31” than “finish by end of year that starts on Jan 1”. For me, the benefit of seeing the longer goals on top outweighs the mental gymnastics.

Unless otherwise specified, the goal is to finish the milestone by Friday. You might want to have separate columns for “not office” work.

If you always look ahead a few weeks when planning your week, it’s safe to only put the finish milestone for two-week tasks. However, it might be safer to divide it into one milestone per week.

When reading a text book, list the chapters you hope to read each week. The chart will tell if you fall behind.

If you want to do a bit more detailed planning, but not add the rows for the next level just yet, go ahead and add the details in a higher level.

I record birthdays by when the were born, rather than writing “turns 40” for 3 years in a row.

Tables in Microsoft Word work well for this. Yes, you can sort tables by date, and even multiple columns, in Word. Google Drive Presentation looks like it will work, but the sorting isn’t automatic. I don’t use Excel because several cells will have more than one task.

You can use Excel to create date series, then copy the columns to Word, so you don’t have to enter each date manually.


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