Success Stories to Embolden You typography
by Ashley Wiggers

The following are a few of the highlights from an interview between myself and second-generation homeschooler, Ben Wilson. Ben is the adult son of our columnist, Todd Wilson. He works alongside his dad as the co-host for their podcast The Smiling Homeschooler. He even lives with his family (wife, daughter, son, and baby on the way!) in a house next to his parents’ house. Ben is the oldest of the Wilson’s eight children and like his dad, he is passionate about homeschooling, being a dad and husband, and encouraging others. I hope you enjoy this snippet of our conversation.

Watch or listen to the whole interview here:
www.hs.today/bonus-content
Ben and his family smiling outside

The following are a few of the highlights from an interview between myself and second generation homeschooler, Ben Wilson. Ben is the adult son of our columnist, Todd Wilson. He works alongside his dad as the co-host for their podcast The Smiling Homeschooler. He even lives with his family (wife, daughter, son, and baby on the way!) in a house next to his parents’ house. Ben is the oldest of the Wilson’s eight children and like his dad, he is passionate about homeschooling, being a dad and husband, and encouraging others. I hope you enjoy this snippet of our conversation.

Watch or listen to the whole interview here:
www.hs.today/bonus-content
Second generation homeschooling with Ben Wilson typography
On: Being Homeschool Graduates Now Homeschooling

Ben: One big advantage that we have, and everyone really can have now—you have those who’ve gone before you, a model. Unlike our parents, I don’t have to “reinvent the homeschooling wheel.” I can look to my parents; I can look to other homeschoolers and hopefully not fall into the same pitfalls. There are going to be things that we’re going to think are a great idea and we’ll stumble a little bit, but I’m very thankful for being set up into the place we are.

Obviously, not everyone has the luxury of growing up in a homeschool family. And there are more homeschoolers now than ever before. It’s important to be aware, self aware, of that tendency to want to have it all super structured. There’s so many all encompassing curriculums. I was just talking to some friends and the mom said, “Oh, the community online is so cool.” But you can already see they’re saying, “Here’s all the things you have to do.” And I’m thinking, “I hope it works.” But hearing this makes me wonder if they’re going to be stressing out constantly, and try right from the get-go to make it this huge, huge thing.

Ashley: Yeah, the expectations are huge. You have to reel in your expectations. Sometimes I’ll come up with this great lesson. And I think everything is just going to go smoothly, and then enter actual kids into that. And it doesn’t go as expected. Then they’re asking, “Why are we doing this?” or “What is this about?” or “I don’t really like this mom.” And I realize, okay, apparently I need to be flexible. I need to be willing to pivot, to roll with what’s working and what’s not working.

That takes courage, you know. It takes a sense of ownership over what you’re teaching them instead of being enslaved to what you think is a good lesson plan. Because you have these actual little people and you have to be willing to listen to them and make adjustments based on what’s really happening.

Ben: For sure. Rigidity when working with kids, or with people in general, means there will be a danger that you will either lose them in terms of the relationship or be in a constant battle with them.

Whether it’s because you don’t want to have to admit that maybe your ideal picture is not exactly reality, or you have to step out of your comfort zone—it can be hard to be willing to deviate. If you won’t though, for whatever reason, homeschooling will constantly be a challenge. I think it will suck the joy out of it and the parts that are so wonderful.

You know the saying, “the best laid plans…” Plans sometimes fall apart. There’s so many times where mom or dad would get excited about something like “Oh, we’re going to do devotions, or we’re going to do this thing…” Then we’d all get there. They thought it would be some fun, beautiful moment. But then everyone’s crying or arguing. If they just got angry, it would have completely ruined it, but we have a lot of good memories around some of those moments. Because they were like, okay, we thought it would be like this, but we’re just going to let that go a little bit and take it as it is.

Ashley: Yes, in this world of Pinterest, and social media, where you see perfection all over the place and think that’s reality, then you have moments like you did with your family, and like we did with ours. And you fear there’s something wrong with you as a parent and homeschooler. But the truth is, no, that’s all part of it—the mess, the having to apologize, learning from your mistakes. That’s all such an important part of the homeschooling journey.

It’s not a problem. It’s actually simply a challenging, but important, part of the process. Because as a homeschooling student you find out what your character is in those moments, and you learn from your parents. You learn how to work together when things get hard. There’s so much good in it, if you can see it that way.

Ben: Yeah, exactly. And you’re not doing it “wrong”. You know, hard stuff doesn’t mean it’s all completely wrong. There just isn’t perfection, unfortunately. And know this: you’re just seeing everyone’s highlight reel and comparing it to your reality as the saying goes. That’s tough. I’m thankful back at the time, when we went through homeschooling, my mom didn’t really have any kind of social media or anything like that. I wonder how much different, or how much more pressure, she would have felt if they did have it. That is definitely going to be something that this generation is going to have to fight against.

Ashley: I do. I find myself comparing and looking at someone’s beautiful activity that went so perfectly. Then I look at my kids who I tried to do some playdough thing with, and they just ended up throwing it at me…I know that especially with my oldest, he really does not want to have to follow instructions all the time. He would prefer to create something on his own. And since he’s still so young, I try to honor that. I try not to control him too much, because that’s what I want to do. I want to say no, this is the outcome we’re going for. And he just wants to do it his own way. I think he has that kind of leadership quality in him that I don’t want to squash. So I’m trying to balance teaching him how to follow but also letting him be the leader I know he is. It’s so complicated!

On: Passing on Boldness

Ashley: We’re talking about passing on boldness in this issue. Our first issue of the year was all about developing boldness as a homeschool parent, and now we’re focusing on the part that comes next. After you step into some form of boldness, how do you pass that on to your kids? We thought a great example of that would be talking to you! Your dad, Todd Wilson, is one of my heroes. I think he displays such boldness in his convictions. And you know, what he believes in, what he stands for, and the encouragement that he brings to so many people, because he’s real. He’s not trying to tell another story. He’s actually telling his honest story about the things that were good, the things that were bad, and things that went well or didn’t work out—it’s all part of it. So how do you think homeschooling enabled you to grow in boldness?

Ben: I think one aspect of boldness is being okay with being different to some extent, and homeschooling is different from the general public, so embracing that and being okay with it, not apologizing for it or feeling “less than”. And I think my parents did a great job of encouraging us to just be who we are, and who God has called us to be and not necessarily worrying about what everyone else in the world is thinking. Obviously, there’s still that pressure, and you still want to fit in to some extent, but I think homeschooling allows you to embrace those God given gifts and to really grow in those areas. That’s something I think is really special and unique about homeschooling—if people will let their kids thrive in their strengths. So I think they did a really, really good job in encouraging those areas in us. That intentionality my parents had, of pushing us to know what we believe and to really focus and build our worldview too… they didn’t have to worry about a curriculum that doesn’t teach what they believe. They could constantly reinforce those beliefs over years. And then let us really think, understand, and engage with it on our own. I think that is another area that has allowed us to be bold, and I would hope that is something I’ll be able to pass on to my children. Not bending to the pressure of society, I guess.

“Dad is always being real when speaking, or just talking to people, and trying to reinforce that we do not need to uphold some perfect image because no one is perfect.”

Ashley: Yeah, it really does take courage to step outside of the box. We have so many boxes we’re stepping outside of as homeschoolers, as believers, as people, wanting to make a difference. Fighting for things and saying no to what the world thinks of success and saying yes to what we believe in. It really is so huge and it happens in the subtle, small moments throughout the day. I recently wrote for another publication about legacy because of my mom’s legacy that I’m kind of walking in, and I realized the legacy she left me was built in the everyday moments of life. It wasn’t how you think of it, as some big, giant thing. It was a culmination of the moments that were more quiet and the things that happened at home that nobody else knew about. Those were the things that really mattered in the end. I hope parents will be encouraged by seeing the two of us (as homeschool graduates) stepping into what most hope for, that their kids look back and are grateful for the opportunity of homeschooling, that they plan to homeschool their own children, and that they find joy in their experience as homeschoolers. Hopefully they can realize it’s not some giant thing you have to accomplish; it is in the little things we sacrifice and do to make memories—when we realize something’s not working, and we set it aside, or when we realize we’re comparing ourselves on social media, and we need to take a break from that… it’s all of those little things that really leave a legacy.

When you’ve been working with your dad, how have you seen him be bold? And what impact has that had on you?

Ben: You mentioned it a little bit. But being real takes boldness, because the natural thing that everyone does is to kind of put up a fake face and put up walls, so that they only portray the best, whether it’s in person or social media or anything else. So allowing yourself to be vulnerable enough to be real and to show the hard stuff… it does the opposite of what everyone thinks it does, which is, “Oh, if I’m real at all, people will think less of me.” But generally, it actually makes people think more of you. Because everyone’s had those struggles. The most powerful people in the world still have the same struggles internally. You read any historical biography and it could be someone who literally changed the world, and they still struggled with stuff. Dad is always being real when speaking, or just talking to people, and trying to reinforce that we do not need to uphold some perfect image because no one is perfect. That’s more realistic and it’s more sustainable. And I think it’s something that they passed on, consistently. We’re always trying to make sure that we don’t put on some fake face, especially with the internet making it so easy to do nowadays. And it’s just so damaging. People get discouraged, feeling like such failures to something that’s not even real.

Ashley: And really, for you growing up, not feeling like, they were ashamed of you in any way, because they were always sharing the real honest story about your lives together. Some children have to endure their parents standing up in the limelight and talking about some wonderful family that they don’t have a clue about.

Ben: Right? Sure, because when you’ve set yourself up on a pedestal, it’s really easy to get knocked off. And we’ve seen that in homeschooling circles. There’ve been some very well-known people who thought they had all the answers to everything. And then it turns out, it’s not that cut and dry. It’s different for every child, and hopefully, that legacy will translate to my kids. I think it’s going to be especially important nowadays to teach our children that they’re probably going to be called things that aren’t great because we are going to have to be different from the general idea out there of what good is. So I think the passion for that was definitely something my parents passed on. And I hope I can impart that to my kids that it does not matter. If your friends think they can do math facts a little bit quicker or get to do more parties or whatever it may be. The things that do matter are much more important.

Picture of Ashley Wiggers
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shley Wiggers grew up in the early days of the homeschooling movement. She was taught by her late mother, Debbie Strayer, who was an educator, speaker, and the author of numerous homeschooling materials. It was through Debbie’s encouragement and love that Ashley learned the value of being homeschooled. Currently, Ashley is the co-executive editor of Homeschooling Today magazine, public relations director for Geography Matters, and the author of the Profiles from History series. Ashley makes her home in Lutz, FL, with her supportive father, Greg, her loving husband, Alex, and their precious sons, Lincoln and Jackson.

Ben Wilson smiling
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en Wilson is the co-host of The Smiling Homeschooler Podcast. He has been married to his wife, Rissa, for 6 years and is currently expecting his 3rd child. Ben is a homeschool graduate, the oldest of 8 children, and the son of speaker and author, Todd Wilson, “The Familyman”. In 2018, Ben and Todd started The Smiling Homeschooler, with the goal of encouraging homeschool moms. You can listen to their podcast on all popular podcast apps, or email Ben directly at ben@thesmilinghomeschooler.com.