Do you have a kid in the Classical Conversations homeschool program? Or maybe you’re a homeschool parent worried about middle school or even high school. Let’s have some real talk about homeschooling teenagers with the CC Challenge program including how to prepare your student, how to adjust your schedule, and how to keep going when it’s tough.

When you’re still trying to figure out how Classical Conversations works in elementary, it’s hard to think several years in the future. You’re tired, and you’re already juggling what feels like more than you can handle. I get it. However… You need to see into the future to truly see the beauty of CC Foundations.

Here’s your “Beginner’s Guide to Classical Conversations Challenge”. 

Disclaimer: Please remember that I’m still forging this Classical Conversations homeschool journey with you. While it is our tenth year with CC, the highest level we’ve reached so far is Challenge II. And every student, family, and CC community is different.

Affiliate disclosure: When you click and purchase a link in my post, I may earn an affiliate commission at no extra cost to you. I promise to only recommend products or places that I have personally want, used, or researched. Thanks in advance for the gallon of gas. 😉


Morning Devotional on Community Day in CC Challenge - Spring 2023
Morning Devotional on Community Day in CC Challenge Spring 2023

CC Challenge Terms to Know

Classical Conversations (and classical education as a whole) has their own vocabulary and language that you need to know before going down the CC rabbit hole.

Challenge Director – This is the teacher who is different for each separate class. Although they work with the Foundations director, each of the Challenge directors are separate entities who collect their own fees, make their own schedule, and deal with their own students. Foundations tutors are under their Foundations director; there are no Challenge tutors because each is their own boss.

CC Challenge Guide – Each year, the student will pay for a new syllabus for their level. This is a requirement and is part of the fees. This breaks down each week’s course load by strand (See next definition) and gives the assignment which they are to work on for the following week.

CC Challenge Strand – Strand is like saying “class”, and within each challenge day, there are six strands. Strand equals subject. However, it gets even more confusing here. The six core Challenge A strands remain the same until Challenge IV. Although the Challenge booklist and subject matter change yearly, they’re still the same six: logic, grammar, research, exposition, debate, and reasoning. However, logic really means math and debate includes geography. Don’t worry about it until you’re there – it’s still confusing.

Art Presentation to Classical Conversations Group in Challenge 2 - Homeschool
Art Presentation to Classical Conversations Group in Challenge 2 Homeschool

Classical Conversations Challenge Themes – The six-year CC Challenge program is designed with over-arching themes which build every year. This Challenge overview is more than just British Literature or American History. These themes revolve around developing character and independence. Just like the CC Foundations program, the CC Challenge program is about developing Christian character over everything else.

CC Challenge level – Level means grade level in “regular school” terms. In CC, there is no 9th, 10th, and so on. junior high years are Challenge A and B; high school years are one through Challenge I-IV, designated in Roman numerals. 

For example, a Challenge A student age is approximately that of a seventh grader; while your homeschool child can’t enter the level earlier than 7th grade, it is possible that there will be an 8th grader in the class. At times, Challenge class ages depend on the availability of a spot in the CC class as the classes can have no more than twelve students.

~~~> If you’re completely new to Classical Conversations, make sure you check out “Classical Conversations: Our Top Ten Reasons After Eight Years”.


Classical Conversations Challenge A Meeting around Table - Homeschool
Classical Conversations Challenge A Meeting around Table Homeschool

What is the Challenge Program for Classical Conversations?

Classical Conversations Challenge program is homeschool for junior high and high school. Typically, it follows completion of the CC Foundations program for elementary school.

Did you know that when Leigh Bortins designed Classical Conversations in 1997, she started with high school for her own children? Yep. These younger years in the CC Foundations and CC Essentials program were developed only after she realized what her younger kids should know in order to truly thrive in the upper years.

Think about that. This very Foundations curriculum that you’re doing right now with your four to thirteen year old and memorizing all the random facts one day a week, it’s all designed to help them in the future. You are currently working on the building blocks for the later construction in junior high and high school. And what a beautiful construction it truly is.

Challenge sounds scary doesn’t it? Sounds like hard work for mom and homeschool student alike. Makes you want to think about your other options. After all, they’re going to want to be in sports and have a job, you can’t add unnecessarily challenging high school work to their schedule.


Dissecting Sheep Lungs in CC Challenge B - Spring 2023

Can I Still Individualize My High School Student’s Learning?

The Challenge program is what you make it. The Classical Conversations schedule is a plan for your whole CC group, but you have permission to tweak it. You can tweak the Challenge work for your family because you are still the ultimate authority.

Your child’s director will have them hand in some papers and research reports, but that is to help you be accountable. They will be tracking your child’s participation in special events and assignments in class. However, they don’t give a grade, just an assessment. You will better know what your child needs to work on, and if they’re high school age, you can use this to help prepare the grade you give them on your transcript.

Your Challenge director has either had a child go through that class, they have personally taught that level, or they have other tutors and groups to lean on for more information. With much consideration, he or she knows what needs to be scaled back and can see the big picture better than you can. Take the time to ask for help!

You are the ultimate authority as the parent. It is challenging, but the beautiful thing about homeschooling teenagers with Classical Conversations is that you are still the teacher. You make the rules.


Girl Standing at Debate Podium in Challenge 2 Classical Conversations - Homeschool

What if My Child Doesn’t Want to Learn Latin? Or Logic? Or…

The tutor’s expectation is that they stay with the curriculum enough to participate and contribute in class. How that looks for every family will be different. The directors need to know how you are adjusting the CC Challenge schedule for your homeschool teenager, but they are there to work with you.

Again. You are still the boss. In the higher levels, there will always be some students who have already filled their foreign language credits or who are doing a dual enrollment program for their writing strand. 

  • When Challenge B Mock Trial is coming up, assign the book to be finished a week earlier..
  • In the upper Challenge levels, pick which lab reports to complete to allow for a debate schedule.
  • Accommodate special sports schedules or family travel if needed. – You know I’m always going to prioritize travel! Sports… not so much. (Wink wink :) )
  • Instead of doing Latin exercises, your child reviews Latin vocab cards while studying Spanish for an upcoming mission trip.
  • This theater mom knows that nothing happens during tech week. Together, we can look at the calendar ahead of time and try to control the crazy.

Challenge kids read a lot of books. However, the Challenge A booklist can be tweaked as needed.. and B, I, II… all the way up. If your child is a reader, you’re in luck. In your child is an anti-book boy, I feel your pain. Challenge books can be listened to on audiobooks; the student can even follow along in a paper book if needed to put sticky tabs on quotations they want to remember. I’ve even had seasoned Challenge director-moms have their kids only look over the CliffNotes version just so their child can participate in class.

You’re the boss! (How many times do I have to say that? 🙂 )

~~~> Speaking of mission trips, remember all that learning doesn’t count as much as character. Check out “Mission Trips: Should You Let Your Teenagers Go?” . I bet you can guess how I feel about the subject.


Homework and Planner on Table - Homeschool

How Can I Prepare My Child to Start Challenge?

My number one recommendation is to make your child as independent as possible. Your child. Remember that’s going to look different for every child.

During our first time through CC Challenge A, my friend and I looked at each other and asked ourselves why we were so afraid of it. Maybe it’s all the new terms, maybe it’s the idea of having a schedule to follow, maybe it’s the size of the load…? But it’s not scary. It’s beautiful.

  • Work on those Foundations presentation skills including having the upper elementary students use a note card as a guide if needed.
  • Teach them how to use a planner and stay on track. (Here’s the one my Challenge kid loves!)
  • Give them a good foundation in writing simple papers. Essentials does an excellent job teaching this with the Institute for Excellence in Writing (IEW) curriculum. The Challenge A students start out the year writing one paragraph papers on animal just like they did in EEL.
  • Train up your child to make their own decisions and not turn to you all the time. I know that sounds easier than it is. Show them how to write a paper in word. Teach them how to use the printer. 
  • Get their supplies organized. Help them set up their binder so they know where papers are. 
  • Set up an email account so they can get emails directly from their teachers. 
  • Learn their learning style – Do they need a desk? Music? How long can they focus before they need a break?
  • Sit with your sixth grader in the CC Essentials class and show them lifelong learning. Model note taking. Show them that they’re never too old to ask questions and admit when they don’t know something. This is your last year to sit alongside them in class; don’t waste it.

~~~~> If you’re headed into the Classical Conversations Essentials program and want more information, head to “CC Essentials: How to Be a Prepared Parent.”


Junior High Boy doing Challenge homeschool homework at home on the bed

How Can I Prepare Myself to Have a Child in CC Challenge?

The best advice I have for you as you enter these upper years homeschooling teenagers is to see the big picture. Understand the basics of the Challenge overview. Even if you have a kid still in elementary school, go see the big picture and sit in some classes with Essentials and Challenge kids. Not only will you have a lightbulb moment as you see why your six year old is memorizing random history facts, you’ll be encouraged and excited about where you are headed.

Challenge is not as scary as you’ll read in the homeschool Facebook groups or from older moms. (Stay away from those overwhelming places if you can!) Remember that every mom has different expectations for their child. Some kids are going to be stressed no matter the level of difficulty. Some moms are going to worry no matter how much there is to worry about.

Honestly, even though I am little biased towards homeschooling high school with Challenge, I know these kids. They know how to lead conversations, how to respectfully present their ideas, how to interact with their adult teachers, how to see God and His creation in everything they study, and so much more. Regardless of what they’re learning, these are the type of kids I want my child to become and I want them to consider friends.

And, I suggest you volunteer or sit in on a Challenge class every once in a while. Host movie night at your house after they finish a book. Help arrange a cultural event. After all, knowing our kids friends and their families is a major perk of homeschooling! It doesn’t stop when the kids get a little older.


Reading in Bookstore Aisle - Homeschool

What Will My Week Look Like as a Challenge Mom?

The CC Challenge A guide is for your 7th grade student. But the strict schedule and all the weekly assignments are not a requirement. Your days and week will like what you want it to look like. Neither of my Challenge kids stick to the “one hour per strand” plan. Honestly, some of the strands take less than an hour for the whole week. They were designed that way in order for the kids to have some lighter loads.

The CC Challenge guide book is designed as an honors course with more assignments than they actually expect you to complete. If you child does everything listed for a strand, that is honors level work. The teacher won’t expect them to do everything scheduled and neither should you.

Just as the Classical Conversations Essentials Guide is followed differently by each family in the upper elementary school, you can make the weekly plan. Know when your kid needs to skip something. Maintain the parent-child relationship; getting all the homeschool self-imposed check marks isn’t the most important.


Can My Kid Enter Challenge Without Doing CC Foundations?

Yes, your kid can start with Challenge if they haven’t done Foundations or even homeschool. However, they will have a bigger learning curve than the other children who are familiar with the method, class-structure, and Foundations memory work.

But don’t let that discourage you. There is so much beauty in the conversations that these big kids are having and the amazing projects they are completing. Don’t have the same expectations for your kids at the beginning – after all, those Foundations years were preparing them for these Challenge years. But if they put forth their best effort and Mom remembers it’s not a comparison game, they’ll be able to soar and make some amazing friendships along the way.

Classical ConversationsHomeschool group gathered at the park

What Does Classical Conversations Foundations Have to Do with Challenge?

l Foundations has everything to do with Challenge! The further we go in our high school homeschool journey, the more I see all the connections being made. Foundations memory songs and the Timeline song are being sung in some part of challenge every week. It brings all the pegs together for student and parent alike.

  • The artists and composers they learn every year in Foundations? Those are the artists they focus on during Challenge II.
  • The Classical Conversations timeline song will be sung weekly… Trust me.
  • Those maps they are tracing and memorizing? They do the whole world Challenge A.
  • The basic music theory with that Foundations’ tin whistle? That’s the Math in Motion book used for music theory in Challenge III.
  • All the presentations they’ve given weekly and paper reading for Essentials? They’re going to be presenting in front of their class every week a paper, presenting a memorized piece, or debating in the later years.

~~~~> Are you a new Classical Conversations family needing CC family presentation ideas and needing idea to make it fun for everyone? Steal my ideas on this post: “Classical Conversations: 20 Easy Ways to Rock Your Family Presentation.“ 


Highschoolers in Debate with Classical Conversations Challenge 2 - Homeschool

If Challenge is This Amazing, Why Do Many Students Not Continue?

That’s the question of the hour isn’t it. I really think a lot of us homeschool parents don’t think we can homeschool high school. The thought of being in charge of upper level math or teaching my child science labs can be overwhelming… But I think if they sought out the wisdom of upper-level parents, they wouldn’t be so worried.

Some families choose to head to a public or private school for easier access to sports or band or… However, at least in my town, those opportunities can belong to everyone. Just ask around!

Dual enrollment may be a concern. Honestly, it’s hard as a Challenge parent to see so many kids who are graduating with associates degrees and all these college hours. It’s so much easier to accomplish that in traditional school. You can do dual enrollment or college credit with Classical Conversations. Lots of people do it. It’s just a matter of making the schedule work for you.

For me, it’s honestly a matter of remembering the focus of our schooling. Yes, I would love for my child to have those extra hours of college paid for – and she will have some – but I’m not going to take away the beauty of the eduction she has right now with Challenge for the chance of graduating college a year early. 

I want her to have extra time for theater practice and travel with family and reading a book for fun and truly enjoying her learning. I want my kids to grow into kids who can think and have amazingly deep conversations with their peers and connect the beautiful curriculum all back to God. I want my kid to be a Challenge kid – because Challenge kids can do amazing things.


Presenting Challenge A Science Fair Project to CC Community - Spring 2023
Presenting Challenge A Science Fair Project to CC Community Spring 2023

Now What? How Do I Join a Challenge Class?

Does that mean I convinced you to stay with CC in high school and that your kid is ready to take on a CC Challenge class? 

CC locations are all over the US and spreading across the world. Now, there may not be the Challenge program you need in your hometown because not every CC campus has the same levels. It depends on the number of Challenge kids in each level and if there is a teacher willing to lead the group. Often, parents have to drive a distance for their kid or even split up their family if your regular Classical Conversations community doesn’t go up high enough – been there and done that (and didn’t like it!). Find a support staff to help and get hooked up. 

If you’re looking for more information about the challenge years? My top advice is to talk to some wise older homeschool moms who can answer all your questions to the best of their ability. Don’t be afraid to ask and ask again. Homeschool moms as a whole love to guide more families and kids to follow in their footsteps.



Bobbie 2022 at garden

I’m Bobbie. As transplants from Texas, my family of six is on a mission to discover all of Georgia’s amazing places, experience amazing road trips across the United States, and create a homeschool life along the way.

Want to adventure like me? Reach out! I’d love to chat. Stop by my Instagram or Pinterest page to discover more of our adventures.

Want to work with me? I’d love to work with your destination and tourism board to help other family travelers see all you have to offer.


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