Tweens, Teens, and other Homeschooling Joys and Challenges (with Jessica Jensen)

Jessica Jensen homeschool encouragement

Jessica Jensen has homeschooled through a host of joys and challenges over the years. Her homeschool journey has included a childhood cancer diagnosis, a chronic illness, and the more typical struggles of homeschooling thru the tween and teen years. We had such a delightful conversation on topics ranging from surviving the middle school years to growing into our own unique homeschool approaches. Read or listen to my interview with Jessica for lots of encouragement and wise homeschool mama perspective!

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Who is Jessica Jensen

Jessica Jensen has been home educating her two daughters in the classical and Charlotte Mason tradition since 2009. In 2019, Jessica co-founded Sola Gratia Fellowship, a Christian classical liberal arts homeschool community.  She is a co-director of Sola Gratia Fellowship and leads in the areas of vision, upper school academics, and continuing education for parents and mentors.  Most recently, Jessica began teaching in the middle school humanities program at Paideia Fellowship Online.  Jessica graduated from the University of Idaho where she majored in architecture and minored in art. She worked for several years in the field of architecture before looking into the eyes of her firstborn and dreaming new dreams.

A west coast native, Jessica grew up split between the city streets of tech-booming Seattle and the wilds of an Alaskan rainforest. She currently resides in Eastern Washington with her family. She loves rainy days, British Literature, and endless cups of chai tea. 

Watch my conversation with Jessica Jensen

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Amy: Hello friends, today, I am joined by Jessica Jensen. Jessica, thanks for being with us today.

Jessica: I’m happy to be here.

Amy: Jessica has been home educating her two daughters in the classical and Charlotte Mason tradition since 2009. In 2019, Jessica co-founded Sola Gratia Fellowship, a Christian classical liberal art homeschool community. She’s a co-director of Sola Gratia Fellowship and leads in the areas of vision, upper school academics and continuing education for parents and mentors. Most recently she began teaching in the middle school humanities program at Paideia fellowship online.

She’s a West coast native and grew up split between the city streets of tech booming Seattle and the wilds of an Alaskan rainforest– that sounds gorgeous. [laughs] She currently resides in Eastern Washington with her family and she loves rainy days, British literature and endless cups of chai tea. Jessica, I gave, obviously, a little bio there of you, but could you tell us a little bit about your family and yourself and then how you guys came to start homeschooling?

Homeschooling in the Midst of Hard Times

Jessica: Yes, so I am married to my husband, Josh, and we have two daughters who are both high schoolers now so we’re homeschooling two high schoolers but we started homeschooling on accident. We did not mean to start homeschooling. It was not on the radar whatsoever but we had some tragedy happen in our family. When my oldest had just turned five, our younger daughter who was two-and-a-half was diagnosed with leukemia. We have a fall birthday, so it’s almost a birthday, it’s in a few days. She’s about to be 17 now so we’re a few years down the road. But back then it was it was like, “Oh, what does this mean?”

We had no idea what it meant and what that would mean for our family at all long-term but we spent the next nine months, literally living at the hospital. We had a child who was in treatment for almost three years and so she was severely immune-compromised, pretty much that whole time. We were basically on house arrest. We could be at the hospital and then we could go home and then that was about it. This whole quarantine thing we’ve got going on here feels very familiar to me. It came time for school to start in the fall and she was five, she was supposed to start kindergarten.

I was like, “Are you kidding? That room is full of germs and kids who are sharing their germs,” [laughs] that can’t happen. That is literally life-threatening to our other child. I tried to explore some other options, but really there weren’t other options for us and so we had start homeschooling. I had no idea what that meant, not even a little bit. I just spent the last almost year figuring out how to be a home healthcare nurse. Now I had to figure out how to homeschool and so I was like, “Wow, okay.”

I went to college for something completely different than this and it really did not prepare me for this at all. When we started– I always laugh about this because my husband was like, “Okay, I guess we’re homeschooling,” but we didn’t know what that meant. He happened to go to this store that we don’t really go to that often, but they happened to have one of those boxes on the shelf, and it was by the people who make hooked on phonics. It was hooked on kindergarten and he bought it for like $20, kindergarten in a box. He bought it for $20, he brought it home. He was like, “Here you go.” I said, “Oh, okay, I guess this is what we’re using.” We just started there.

I was already a library goer and all that kind of thing. It wasn’t too huge of a swing, but you just really don’t know what it is and so it was really hard those first few years. Both because our life circumstances were just difficult and also because I didn’t know what I was doing, but by about January of that first year, I was like, “Okay, if I’m going to do this, I want to figure this thing out.” Then I just started checking out all these books from the library on homeschooling and just got my hands on anything that I could find and I was reading it and researching and trying to figure out what this thing was and how we were going to do it. That’s how we started. It’s dramatic. [laughs]

Amy: Yes, what a dramatic start and then to see how far you’ve come and now you have two girls in high school, it’s amazing. How did you– obviously you decided to stick with it even when it wasn’t necessary for your family for the same reasons. How then did your educational philosophy grow as you started doing more research and how has it changed over the year?

A little Charlotte Mason, a little classical, a little growing into homeschooling

Jessica: I think in the beginning, you’re really worried about doing what you know and keeping up, and I’d gone to school and so that was my background. It looked a little more like school, but we fought with that a lot because it turns out my eldest is a very non-traditional student. She had some learning difficulties, some other things that we worked out over the years but of course you don’t know that right off the bat.

I think one of the first– the first book that really hit me was Susan Schaeffer Macaulay’s For the Children’s Sake, that one really captured me and I was like, “Okay, I can get excited about this vision and this idea for education.” I always rode that line where people would say, “What kind of homeschool are you,” and I’m like, “Kind of Charlotte Mason, kind of classical, somewhere in there.” I think there’s a lot of us who read that book who have stepped on that type of thing over the years. That’s what we ended up sticking with just because it just really captured my imagination and my vision for what I wanted for my kids.

Of course what was going on in our personal lives really formed a lot of what we wanted for our kids too. It made us mature in a hurry. I wouldn’t say that we were immature, but I think I had this vision of giving my kids this really great childhood because my husband and I didn’t necessarily have the greatest childhoods in some ways and so we wanted to just create this stability, these things that we didn’t have. I realized, God convicted me that in some ways, I had created idols out of those things and so I needed a new vision, like, “Okay, hard things are going to happen and they’re going to happen to kids too.”

Really what needs to happen here is they need to learn more about God and what he can do for them and how he can be there for them and how we can grow together as a family, through hard things. That was a big part of what we were learning in those early years too. Really, those early years weren’t as much about academics as they were about just personal growth for all of us. Then after three years or so, we would have been able, theoretically, to put our kids in school and it just seemed like, “This doesn’t seem like it would fit for them.”

My oldest had those learning challenges and we were working those out and then with my young, she had long-term health effects that we were expecting to see, and we never did and we still haven’t so that is such a blessing but actually she was advanced in a lot of ways. I saw a lot of myself in her, she’s way smarter than me though, by the way, totally smarter than me but I saw a lot of those same tendencies that she was going to be bored. We were going to put her in school and she was going to be bored and she was going to shut down because she taught herself to read.

One day she was supposed to have– she had her treatment, over 85% of girls who go through that same treatment have cognitive defects afterwards. Not only did she have none, she taught herself to read a week after she turned four. Because I wouldn’t, she kept asking me and I’m like, “No, no, we’re going to wait, I’m not going to push you,” and she pulls out her sister’s phonics readers and starts blending sounds and reading. and I’m like, well, I’m going to sit here next to you and pretend like I’m doing something.

Amy: That’s amazing.

Jessica: It’s just a miracle in a lot of ways for her and so I had these two very different children and I was like, “Neither one of them would fit well in a classroom right now I don’t think,” and so we were able to finally join a co-op and do some more things outside the house and start joining a homeschool community outside our home and that was really fun. I think that’s how we journeyed through the years, those early years, at least

Amy: I love hearing how you were even able to see how the Lord used even hard times to show you good things that you wanted — and how often the things that we want as homeschool moms, are good things… We want our kids to love one another and get along and we want them to love learning and we want our home to be this peaceful, loving place. We have all these things that we want that are good things, but as soon as our affections get out of order and those become the primary things, sometimes even those good things can become idols. And God is so good to refine us and humble us and point us back to him being our ultimate good, our ultimate end.

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Favorite Parts of Homeschooling over the Years

You’ve talked about some of the reasons why you loved homeschooling, you wanted to stick with it, have there been any other favorite parts of homeschooling over the years?

Jessica: We get to read good books. I get to read good books. [laughs]

Amy: I’m just in this for the books. Forget the kids.

Jessica: I know, I am. [laughs] I remember, my experience in school, and I went to a good school. I was fortunate, I was able to go to a private school through most of my years of my schooling and it was a good school. But I didn’t like school that much. I had my own things I wanted to read and my own things I wanted to study. I remember my relatives saying, “Why is Jessica always getting bad grades in spelling, she reads all the time”. It’s like, “Yes, because she’s not studying her spelling words, she doesn’t want to do that.” I could see some of those same tendencies in my own kids.

I could put them in there and they could check the boxes, but they weren’t going to really be learning. That’s part of what has kept me homeschooling.

The other part is yes, I’m having fun. By the time I got to college, I actually liked learning because you get to choose more of what you’re doing, and it’s more fun. I actually got more passionate about learning then. I really actually think I as a kid, I just didn’t like school. I wanted to learn my own things. It’s been fun to do that. It’s been fun to help cultivate that in them and just set them up now to start and not shut down for a long time because of a system that was imposed on them.

We actually had a really fun conversation a couple of weeks ago. We’re reading Charlotte Mason’s Ourselves Together. We’ve used Ambleside off and on over the years but overall, I felt like my kids needed to wait a little bit longer for some of the books, they just weren’t quite mature enough for them yet. I waited till this year and I have a freshman and a junior in high school this year and we’re reading Ourselves over the next two years. I wasn’t sure how it was going to go because I tried it a couple of years ago and my younger one was like, “I don’t understand this, what is this lady talking about.” [laughs] It’s allegorical in the beginning and she was not getting it.

This year we started it and she did get it, and it’s actually been one of the highlights of our year this year. Reading that together and the discussions that we’re having from it are really fun. One of the ones that we had a couple of weeks ago was just about cultivating your own intellectual life, and it was just really fun to be able to share with them, “You know, I didn’t love school. I didn’t love doing all the assignments I was given. I wanted to do other things. I get you. I get that you don’t want to sit down and write a narration everyday but you’re still going to do it.” [laughs]

Just helping them to form that vision of like, “What do you want to be like when you’re older? What do you want this intellectual life of your own to be, because I want to help you to start developing that now.” To be able to have that conversation and to help them maybe start to see me more as their partner in this a little bit as we make this transition through the high school, it was a really good moment.

Amy: That’s one of my favorite parts too, of the high school years. Seeing these children that are starting to become– they always were their own person — but being able to articulate their own thoughts and ideas in new ways, and to be able to point them towards an adulthood that’s still going to be one of learning. It’s not just about what we do that’s on the checklist and, “You’ve got to do your assignments.” We talk about lifelong learning, but we better be modeling for them that we like to learn as well and give them that excitement: “The rest of your life lies ahead of you. You get to keep pursuing education in it.” It’s just really fun to see that.

Homeschooling through cancer, chronic illness, and the more ordinary challenges of life

Jessica, you mentioned obviously the beginning of your mothering and homeschooling journey came in the midst of great challenges. As the years have gone on and you’ve continued homeschooling, have you faced any other challenges, maybe even small ones in your homeschool, and how have you combated this?

Jessica: Yes, basically my whole homeschooling journey has been challenges. I really feel like that at this point. We got to the cancer thing, we recalibrated to what life would be like, what normal was and that kind of thing, and then we went through some other personal challenges. It ended up, I’ve been living with some chronic health issues since then. For the last seven years or so. This is our 12th year of homeschooling so that’s more than half. [laughs] There were a couple of years where I had really bad chronic fatigue and some other issues going on and I was like, “Go get your books and come to my bed.”

We went from one thing to the next really. I’m in a much different point now but I still have those challenges and I have limits and I have to set them. I really like to set goals and achieve things. This has really had to teach me to step back and trust the Lord that my kids are going to get what is the most necessary. That He’s going to lead us and we’re going to do what’s necessary and He’s going to provide other people to come in and help support and lead them in different areas.

As they’re in high school, that’s actually really a healthy thing too. In some ways I wonder. I’m like, “Would I have been too overbearing if I wasn’t dealing with this? I don’t know.” It may be a gift in that way. I would really like for it to be over, but [laughs] I try to see the good side of it. We’ve always had some sort of challenge like that to deal with.

You go through middle school and I have two girls. I grew up with a bunch of boys. I have four brothers. I do have two sisters, they’re both adopted and much younger than me so I say we had to import more girls because we just couldn’t get any more girls. We’re all boys.

My cousins were boys so I always hung out with boys. When I had two girls, I’m thinking, “Really God, [laughs] what are we doing here? What’s going on?” It’s funny but just dealing with the middle school years have been really hard too. All the emotions, we’re all big feelers in this house, have really big feelings and learning how to deal with them and get along has been a challenge.

Homeschooling Middle School and the Tween Years

Amy: Let’s talk about the middle school years a little bit because I feel like people always talk about, “Those teen years are going to be a challenge.” Every season has its challenges of course but I actually really love the teen years. I think it’s been really fun. I was thrown for a loop with my first born when we started going through these middle school years and it was crazy. It was hard. 12 especially. I don’t know, 11 and 12 was just really hard.

I’m seeing that play out. Now with my third one in that age bracket, I’m not as panicked by the challenges this time around. You’re now teaching middle school as well. Those ages, what are some of your tips and strategies for us as educating them and what should be some of our goals especially as high school educators in that very pivotal and often challenging time of life? [laughs]

Jessica: It’s fun. Nobody told me it started when they’re nine. Nobody told me that. My oldest started going through these things and I’m like, “Oh my gosh, what is going on?” Then they get a little bit older and you’re like, “All of my parenting has been worthless.” [laughs]

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Amy: “I’m a failure.”

Jessica: “I am a total failure. This kid is a hot mess and so am I.” It’s comical the first time. The second time, yes, you are much calmer because you’re like, “We’ve been here before.” [laughs]

Amy: “I know we will survive.”

Jessica: “We will live through this.” Yes, it’s crazy. It’s interesting to read about some of the science too. Their whole brain is being rewired. Of course, it seems like you’re starting over because in some ways, you are. All the changes that are going on in their bodies are pretty wild. As far as school goes, for me, and I don’t know if this is the right way to do it. Clearly my kids are still only in high school and one of them is still on the tail end of this kind of crazy behaviors so we still have some of it happening.

But it’s getting better. It’s really fun to see them move through it and get to that point where they can act a little more adult. It’s trial by fire. I’m like, “Okay, you’re big now and you need to bear some responsibility.” So I throw them at the deep end a little bit. I just say, “Okay, I’m going to treat you as much like an adult as I can especially when it comes to school.” As homeschoolers, we’re always everywhere with them so they don’t have very many opportunities to take on responsibility unless we push it on them sometimes.

There is a rare kid, I’ve heard about these kids. I don’t have one, but I’ve heard that there are these kids who just want to take on responsibility and just start doing this. I don’t have one of those kids, I’ve kind of had to push mine out a little bit into the water on their own, and just say, “Okay, here’s your responsibilities. This is what you’re going to be held accountable for and you need to get it done.” Oh, I give them tools. I give them lots of tools like, “Here’s a schedule thing, here’s various types of checklists, here’s all these things you can do.”

Really it’s just about getting them to do it and they don’t learn until they do it. I don’t know, this just might be my family, we have to learn things the hard way. I give them an opportunity to fail and they fail, then we go, “Okay, let’s pick up and let’s fix this.” Then you can walk alongside them, so it’s giving them the tools, then letting them off on their own to use them, and then walking alongside to remedy where they fall down. And it’s life lessons, that’s just part of life, that’s what we all learn.

I want them to be able to do it while they’re still here. That’s not really fun, it’s a lot easier to control the process and be more hands-on, but I don’t want to have to be hands-on their whole lives. That’s been my approach and it works, it takes a long time. [laughs]

Amy: There aren’t going to be quick fixes, there aren’t quick fixes in general in parenting. There’s not a quick fix for your three-year-old, there’s not a quick fix when your kid’s learning how to read. There’s not a quick fix for the tween years, the teen years either. It’s a lot of patience, a lot of relying on God’s grace. I think the thing I wish I had realized sooner, but things really were transformed relationally with my oldest, especially once I thought to myself, “How does God treat me in my sin?”

The fact that He loved me while I was His enemy and sent His son for me while I still hated Him. I was like, “Oh, He doesn’t treat me as I deserve.” Any parents who are in that moment where there’s just– feels like the overwhelming emotion as the parent, looking at this person who seems to be acting like an ingrate, sometimes — just that, really, that was something that transformed my heart. It was something I could have responsibility for, my own attitudes and my own actions.

Once I changed my mindset and started remembering how much I had been loved and forgiven and could mirror that to my child, that made a big change in our relationship in that season.

Jessica: Yes, for sure. It helped a lot with mine too, my oldest, especially to not be controlling all aspects of her day, that also helped our relationship a lot. I’ve seen it with her that this has worked well. I am seeing my younger one progress and getting close, we’re getting close. It was interesting, this year. My oldest has a lot of outside classes, so she is responsible to other people and she responds really well to other people and being responsible to them. She has a couple of classes still with me, not doing quite as good on that. [laughs]

Amy: I am totally with you right now.

Jessica: I had a conversation with her the other day. I said, “Okay, here’s the thing. You’re pretty much driving this bus, but you’re getting off the route. You’re not doing so good when it comes to my classes. If you don’t want me to get back in the driver’s seat, then you’re going to have to step up and meet these standards.” She’s like, “Oh yes, I don’t want you driving, so I’m going to step up.”

Now I can have that conversation with her, whereas, four years ago, I couldn’t. It just would have been, there was emotions everywhere and there was just craziness. Now we can have that conversation, so that’s really good. I’m seeing that progress also in my younger one and I’m much calmer the second time around, which helps tremendously.

Amy: It’s good if there’s only one person having an emotional meltdown at a time, preferably not the parent.

Jessica: [laughs] Yes, it does. I always hear that thing like, “Put on your Kevlar”, and just like, “Let it roll off”, and I’m like “But I ran out of Kevlar this week, I don’t have any more.” It’s still really hard, but it’s been a little bit easier to get through the second time around. At the same time it’s just like, “We still have to do this?” It feels like in middle school, it’s almost like starting over in a lot of ways because you are putting them in the driver’s seat. I was like, “If you were in a public school, you’d be responsible for all this. I’m not asking something crazy of you. If you were in a school, this is what you would be responsible for.”

I didn’t feel like I was asking too much of them and I gave them tools and coached them and it was up to them to use it. I didn’t feel like that was too crazy, but it does feel like starting over in many ways because it’s also about educationally, just thinking about– step one is getting them to do their work. Step two, I feel like is getting them to really engage in the process for themselves. It’s a really different– high school, especially when you’re classically educated, is just a really different animal than your typical high school.

They really have to be willing to immerse themselves in the process and that’s something that a lot of them have a hard time doing. It might just be they are on the lazy side. That could be it, or they might have a huge fear of failure and they want to know the right answer and the right thing. It’s walking alongside them and helping to figure out, “What are these things that are holding you back from really being willing to immerse yourself in this process?”

Because if you really and truly want to learn and grow, especially into the high school years, this is when we need to figure it out. We need to start trying to recognize our failings and our things that hold us up and to address them and be able to grow past them.

Amy: I feel like those middle school years give you really like a grace period. Because in the elementary, up through fifth maybe even sixth grade depending on the student, you’re really laying a foundation of a lot of just understanding your math, your reading, a lot of your basic tools that you’re going to be using to then delve more deeply in your later teen years, your high school years. I’ve really found that in those middle years, it gives me that flexibility to be like, “Okay, let’s focus on the character and the emotional regulation and the self-control and the scheduling our time, meeting deadlines, meeting other teachers requirements and things like that.”

It also helps you see where some of the gaps may be that have been there. Because really, you’re not necessarily learning anything totally new in those middle school years. When you think about even the math and the science at those ages, a lot of it is repeating what you’ve already learned, obviously in a little bit more deep way, but it gives a lot of flexibility to not freak out at that stage like, “Oh no, we’ve missed something.” You have those years really as this, “Okay, here’s where we prepare for the next stage.” I think it’s really a gift of time and space and not something necessarily to put too much pressure on those years. Especially while their brain and emotions are high.

Jessica: Yes. It’s more about their personal development and their character development than it is about getting some academics in. As far as the academics go, it’s more about making it their own. Because in those elementary school years it’s, “We do what mom says.” It’s very controlled by mom or teacher, whoever. When you get into those upper years, it really is time for them to make it their own, so it’s all part of that transition. It really is, it’s kind of messy, it’s hard. I always feel like as a parent, I not enjoying it so much, but as a teacher, I actually really love it. I actually have a lot of fun just helping them to figure out who are you? Who do you want to be? Let’s start building that, so I do, I really enjoy it and they get my jokes.

Amy: I love that. I hope this is really encouraging, I know it will be encouraging for the mom who’s hearing this. I wish someone had told me what to expect in those years, especially because I was taken completely off guard and thought that it was me or my kid, that we were crazy. I hope that this is just an encouragement, like, “Hey mama, this is normal. It’s normal, you’re going to get through it by God’s grace. It’s going to be okay, persevere.”

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What is Jessica Jensen reading lately?

Jessica, this season, I’m asking each one of my guests the same two questions. The first question I wanted to ask you is what are you personally reading lately?

Jessica: Oh goodness. Besides all the books I’m reading for classes, of which there are many, I have been actually listening to on audio because most of my reading time is actually taken up with books for classes right now. I have a pretty full plate right now. My enjoyment reading has actually been most recently, I’ll turn on an audio book. I have been listening to James Herriot’s All Creatures Great and Small it’s been just such a perfect thing because it’s like, it has so nothing to do with 2020 or any of the crazy things going on in our world right now.

It’s just like being transported to the Dales. I just go with this veterinarian in there. All the chapters are like their own little story, so I don’t have to track any plots. I don’t have to track anything like I do for my classes. It’s just purely relaxation and it’s funny and it’s fun. That’s what I have been doing in my free time.

Amy: James Harriot is definitely the epitome of cozy reading.

Jessica: It is, it’s perfect. It’s my little medicinal reading for the craziness of our world right now. [laughs]

Tips for the Homeschool Day Going Off the Rails

Amy: Love it. The final question for you is what tip would you have for a homeschool parent whose homeschool day seems to be going completely off the rails?

Jessica: It really depends. It depends on how old your kids are, like so much. When my kids were younger, I would send them outside. That’s what number one thing, go outside, go outside and play. Everybody needs to go outside and play.

Now that they’re older, the reasons why it’s going off the rails are usually a little bit different. Sometimes we just need a time out. We seem to need to go to our own places and be alone for a little bit and cool down and try again. That works.

My oldest likes to go for walks. She’ll go take a time out and go for a walk, yes, it’s still going outside, I guess it’s still a thing. Usually now it means we need to maybe get away from each other a little bit, but there are three of us and we’re all in this house all the time right now. It’s a different season for sure.

Amy: Sometimes we just all need to take a break, go to our rooms, get out our cozy read, come back later.

Jessica: Let’s try this again later. Because pushing through, it doesn’t work.

Amy: When everyone’s crying and mad, you’re not really learning all that much anyway.

Jessica: I’m like, “I’m reading you the Bible, you have to–” No, it just doesn’t work. It’s like, no, this is not teaching them anything about the character of God. It’s like, “Makes them do this.”

Amy: Have you eavesdropped in my home??

Jessica: No, I’m telling you about the other day.

Find Jessica Jensen Online

Amy: It still happens. This has been so fun. Thank you for taking the time to chat with me today, and where should people go if they wanted to find you online?

Jessica: I am on Instagram @JessJensenWonders and then I’m on Facebook at Jessica Peeler Jensen.

Amy: Fabulous. I’ve been stalking you online. We’re in a lot of the same little groups, talking about books and things, it’s like, “I like this lady, I would like to get a chance to talk to her.”

I’ll talk to you later. Bye bye.

Jessica: All right, bye-bye.

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