Day Planning – how to Schedule a Challenge School Day

Day Planning in the Challenge YearsIt seems to be a familiar question among Challenge families. How do we get all the work done in a week? I can say from experience tutoring, that is it a common struggle among many (if not most) families who have students in high school.

Most students tend to begin to shift towards more self-guided learning at the junior high level, and mom and dad start to take more of a secondary role in their education. Checking in, grading work, administering tests – these tend to be the standard jobs of homeschooling parents at this stage. But I’ve also seen that many times, without a clear and structured plan for the week, our tweens and teens just don’t have the self-discipline or the organizational skills necessary to be completely self-guided.

Enter: The Day Planner. Because it’s 100% necessary to understand how to organize time.

A quick Google search of “time management” will prove that many people struggle with it, and seek assistance. And we have a unique opportunity as homeschooling parents to teach this valuable skill to our kids.

With regards to Classical Conversations, I have seen many people say that the Challenge Guide will become a day planner for Challenge students. But I must disagree. While the guide does clearly list the expectations of the student, it hardly lays out a plan for accomplishing the work in 4 days time. Further, sometimes what’s in the guide doesn’t break down the steps that need to be taken in order to finish the week’s work.

It’s not a fault of the guide. It isn’t meant to be a planner. That’s our job as parents – to set our learners up for success.

Homeschool Story Student PlannersTo begin, invest in a day planner that has lots of space to write, make mistakes, and revise. I love the planners on Homeschool Story – especially since you can download one for free (or for very cheaply). Each week is a double page spread of a full 8.5×11″ paper! It’s also broken down into 6 subject areas, which is perfect for Challenge! I also really love the bright colors, but it can be printed in B&W and still look great.

When filling in your planner for Challenge, one great way to start is to fill in everything that is due on community day. This allows you to have a quick reference as to what your student needs to pack. More importantly, it helps them create a goal for their work. I believe our teens will strive to reach a goal when it is placed in front of them. Seeing it clearly written out is powerful. When they have an obvious and full understanding of what’s due, they are less likely to procrastinate, and leave it till the last day.

Then, begin filling in other days. We’ve tried 2 different methods for dividing up the workload.

The first is to split the work up across 4 days, leaving an hour for each subject. This allows you to, as CC recommends, to spend time on each subject every day.

Pros: The work gets done progressively each day. An hour isn’t too overwhelming or frustrating a time to focus on one subject. It allows the mind to be regularly saturated by a subject each day, so if repetition is really important, it could be the way to go. Cons: Switching subjects 6 times can be frustrating, especially if your student has a hard time transitioning in and out of things, or takes a while to get organized or focused.

The second is to work on fewer subjects each day, in bigger ‘blocks’ of time.

Pros: When you child is on a roll, they can keep working, presumably allowing them to get more done. A loved subject gets some extra time, while a not-so-loved one only has to be looked at every other day. Cons: Less daily repetition for subjects where that is beneficial, and if you miss a day (illness, field trip, etc…) you’ve missed half the work week on a handful of subjects.

We have found a happy medium, and often approach our week like this:

Day 1
1 hour Math
2 hour Literature
1 hour Latin
2 hour Science

Day 2
1 hour Math
2 hour Debate
1 hour Latin
2 hour Logic

Day 3
1 hour Math
2 hour Literature
1 hour Latin
2 hour Science

Day 4
1 hour Math
2 hour Debate
1 hour Latin
2 hour Logic

Day 5 – Community Day

In this way, we are still getting the repetition that is so beneficial in Latin, and spreading Math out (because 2 hours of math is overwhelming in my house), but are spending more focused time on the other subjects every other day.

And – it is WORKING!

We have seen the immense benefit of approaching our scheduling in this way.

Recently, however, we have used something new for scheduling, and moved beyond the paper day planner. (Not that we don’t love them – we do!) Some changes in our lifestyle brought us the need to schedule more electronically – something we could access from anywhere, and something we could all control and adjust.

TrelloMy husband has been using the Trello app in his office for some time with his team to schedule and assign tasks. We’ve taken his idea and turned Trello into a small scale communication hub for our whole family, and ‘School Stuff’ became a busy board for us to schedule, see an overview of our responsibilities, and keep and eye on how we are progressing through the week’s work.

Trello Task Board

An excellent feature of Trello’s system is the ability to access your boards from mobile devices, no matter where you are. Multiple people can be assigned access to boards, and even to specific tasks on those boards. Cards can be placed on each board, and inside the card, a history of the events can be seen. You can also create a checklist inside of each card, which will allow you to break down each subject into more manageable assignments.

Trello Card


Unpacking each subject into smaller pieces is important, because it helps your child understand the time it will take to complete each task. Many students feel they can accomplish an entire subject the day before community day, only to discover that it’s almost impossible to do so. Having it laid out before them at the start of the week will help them to manage their time, and without a doubt, be more successful, and get more accomplished by community day.

Sometimes we get lazy, and don’t take the time to lay out our week before us. Without a doubt, we always end up regretful, and often find ourselves frustrated and stressed, like crazy people the day before our community day, trying to get everything done. It’s imperative that our students are learning to schedule their time. But they need our help to do it. They may need our help for years!

Take the time to teach your student this valuable skill, which will stay with them far into adulthood. In our busy, high pressure world, there isn’t much tolerance for lateness or incomplete work. Let the Challenge years be a time when your kids get a firm grasp on how to make time management work for them.

3 comments on Day Planning – how to Schedule a Challenge School Day

  1. Amy Wilkerson
    August 11, 2016 at 8:46 am (2 years ago)

    Hi Amy,

    Do you have any advice to a homeschool mom whose oldest child will be starting Challenge A next year, along with a middle child who will be a first year Essentials student, and then a 5 year old who will be learning to read? Beginning first year challenge is intimidating to me and my greatest concern is my ability to support/manage time for all three of my children who will be in very different stages of their education. Any advice or encouragement in regards to this would be very much appreciated! Thank you!

  2. Mary
    January 25, 2015 at 2:39 pm (4 years ago)

    I had never thought of using Trello! My husband and I use Trello to get work done for my blog and music curriculum (he’s my tech guy!), but this online task sheet might work very well for my Challenge student, too. Thanks for the tip!

    • amygarwood
      January 25, 2015 at 3:23 pm (4 years ago)

      It’s working really well for us, and my daughter likes that it’s accessible on her phone (of course). It’s more ‘fun’ than paper and pencil, and I’m totally willing to leverage the fun factor for all it’s worth!


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