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Homeschooling & Raising Entrepreneurs w/ Nathan Barry

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Katie: Hello, and welcome to the “Wellness Mama Podcast.” I’m Katie, from wellnessmama.com, and from wellnesse.com, my new line of personal care products, that’s wellness with an E on the end. This episode is all about homeschooling and what you can learn from it even if you are not interested in homeschooling with your family. I’ve heard from a lot of people who are considering it right now as things move more virtual anyway, and I wanted to be able to have a conversation that would give some practical advice if your family is in this situation and is considering homeschooling or if you’re one of our listeners who already homeschools.

I am here with Nathan Barry, who’s a friend of mine and also the founder of a business called ConvertKit which powers my email and newsletter that many of you subscribe to. But Nathan has been a designer, an author, a blogger, a lot of different things. He like me was homeschooled, and like me also dropped out of college, and he now runs a hundred-million-dollar company. And in this episode, we delve into homeschooling both from the perspective of students, both of us being homeschooled, and now as homeschooling parents to give hopefully some very practical advice if this is something that you are considering. But even if you aren’t, we talk about ways that you can foster some beneficial skills and mindset traits with your children even if you aren’t interested in homeschooling them and do this alongside a more traditional school education.

So I think as we’re all learning to navigate this world, that does include a more virtual aspect in many cases, homeschooled or not, I hope that this episode will give you some practical how-to, and if you’re listening, make sure to also check out the show notes at wellnessmama.fm. I’m going to link to a lot of the practical resources that we mentioned, and you can always post comments on there or ping me on Instagram with more specific questions of anything you would like to see me talk about or write about related to parenting and homeschooling in the future. But without further ado, let’s join Nathan Barry. Nathan, welcome. Thanks for being here.

Nathan: Yeah, thanks for having me on.

Katie: I’m really excited for this episode. And I think it’s even more timely than when I first thought about doing this episode because so many families are considering homeschooling right now, or jumping into the world of homeschooling. And we’re gonna go deep on a lot of topics related to that, but to start, for those who aren’t familiar with you, I’d love to hear a little bit of your background and specifically, your background with homeschooling.

Nathan: Yeah, okay, so, right now, I run an email marketing company for creators called ConvertKit. And so we’ve got 60 employees spread around the world, like 30,000 creators using the platform. And so my world is like design and tech and all of that, you know, startups that whole world. But my background is homeschooling. I am the fourth of six kids, we were all homeschooled growing up. I grew up in the mountains outside of Boise, Idaho. So, you know, we had a couple of acres of land and backed up to really a lot of like…sort of a common area for the whole…it’s not really a subdivision because it was in the mountains, you know. But basically, we grew up having lots of land and space to roam and all of that.

And we can get into all the details, but my mom homeschooled us, my dad was involved as well, but not quite as much. And yeah, I was homeschooled. I went to Boise State University for college first for…I started graphic design and then marketing. Dropped out after a few years. And then, you know, just got into software design and had a few jobs. And then I’ve been running ConvertKit for seven years now. And for context, I’m 30, so yeah, born in 1990. So anyway, that’s the super high-level story. I’m a huge fan of homeschooling. I wrote a post on it recently that got a lot of traction. So it’s kind of fun to be back in this world since I’ve been out of it for quite a while.

Katie: I love that. I will link to that post that you’re talking about because that was one of the reasons I thought to have you on the podcast. And we share quite a few similarities. I’m a little bit older than you, not too much. I was also homeschooled, although only until high school. My parents were very academically minded and wanted us to get scholarships. So it was kind of…we went to public high school and we were kind of expected to perform and get scholarships at that point. But I think…I’ve said quite a few times I think I learned the bulk of everything I needed long before high school through homeschooling. And like you, I now also run a company and credit my parents and their teaching for a lot of the lessons that have made that easier, as well. What parts specifically of homeschooling do you feel like set you up for success the most?

Nathan: Yeah. There’s a couple of different things. And, you know, everyone’s homeschooling experience is different. So I always try to say like, this was mine. And I think there’s fundamental things that work really well and make this possible. But kind of the first thing that made a big difference for me is that, you know, with class moving…class always moves at the slowest pace, or sorry, the pace of the slowest student. And, you know, with homeschooling, you are your own class, right? My siblings are two or three years older and younger than me, like, there’s no one else in my grade, and class moves at my pace.

And so what that meant is that, you know, there’s really no speed limit, I can move as quickly as I wanted as I was motivated to. Some days, you know, that was a downside I really dragged and procrastinated and all that as other kids, you know, as is normal. But then like, I really remember this time when I was 11 or 12 and, you know, we grew up in the mountains and so it’s wintertime, it’s just the most beautiful snow coming down. Where like you can practically see the snow accumulate because it’s just these giant perfect snowflakes.

And I’m sitting there, it’s 8:30 in the morning, and I’m like so mad that I have to do Saxon Math. You know, and I’m like, “I wanna be outside.” And my mom just says, like, “You know, school doesn’t have to take a set amount of time. The sooner you complete your work, the sooner you can go sledding. ” And I was just, like, I perk up, you know, it was one of those things that maybe I knew, but no one had explicitly told me that before. And I was just like, oh, okay, there’s 30 math problems and it’s less than I need to… You know, like, just like, stay totally focused and get it done. And, you know, I think an hour later, maybe an hour and a half later, I was outside sledding.

So that was such a key lesson that there’s no speed, you can go at whatever pace. And I actually play this forward growing up, all my friends were older than me, you know, friends from church, youth group and even friends from the neighborhood. And so I had this realization that they were all going to go off to college and I’d still be stuck in high school. And I think I realized this when I was probably 13 or 14, and they were all, you know, 16, like 15, 16, 17, kind of like that. And so I thought, well, I don’t want that to happen.

So I went to my mom and said, “Well, is high school four years, or is it a set amount of work?” And to her credit, she said, “No, it’s a set amount of work.” Like, “Great, can you give me that to-do list form?” And because I had older siblings, you know, she’d already had like, sort of her high school curriculum written out because I’d already had three older siblings go through it. So she’s like, “Okay, you get all of this done with good grades, and yeah, you can go to college.”

And so I just dove in and I said, “Okay, I don’t wanna be left behind as all my friends move on.” And so I…Like one example. Every year we drive from Boise to Seattle, which is like an eight, eight and a half-hour drive, to go visit family. And I remember thinking like, well, I’m always bored on these road trips, because, you know, pre-iPads. And I’m bored when I’m doing algebra so why don’t I just combine the two? And so I would do like a month’s worth of algebra on one drive. And so I had, you know, my older siblings, they’re in the car, and I could ask them for help with questions, and so I would just dive in and get it all done.

And so the result was that I started going to Boise State when I was 15. And, you know, I got to feel like I caught up with all of my older friends. And, you know, now I ultimately dropped out of college and so another claim to fame, I guess, is that I dropped out of college at 17. So before most people drop out of high school, but it worked out well in the end. But I think that was the biggest lesson of, like, there’s no speed limit, you’re in control, you can have all the upside.

Now, there’s the other thing I think, in a lot of normal schools…this certainly isn’t true across the board. But a lot of the time, teachers will give the upside…sorry, they’ll give the downside, but not the upside. So for example, like if you do really well on your school, you can sit here in class for the same amount of time as everybody else. If you do poorly, you get sent to the principal’s, you know, there’s all these consequences, right, you get more homework and everything.

And so when we think about autonomy in school, often it just results in like your upside is really limited, and your downside is, you know, is uncapped. And so I think that was something that was so good about my homeschooling experience is that, you know, both the upside and downside were mine and that set me up for future success.

Katie: I love that. And I would guess there was probably a direct crossover with that into entrepreneurship. Because I think of…like Peter Thiel is kind of famous for asking how can you achieve your 10-year plan in 6 months? And talking about how there is no speed limit or no timeline. And even if you aren’t able to accomplish your full 10-year plan in 6 months, you’re still probably way ahead of someone who expects it to take 10 years. And it’s kind of that idea of controlling the upside and working toward time freedom. Do you feel like that from a functional perspective translated into your life as an entrepreneur?

Nathan: Oh, yeah, totally. And actually, one of my favorite conversations I’ve ever had was with Peter Thiel, at a conference that you and I were both at and where we ended up at a party at Peter’s house. And ended up having a great conversation about homeschooling and it was really fun. And I think that is spot on that, you know, homeschooling, entrepreneurship, everything, it, like, just puts you in the driver’s seat. And so it says, okay, whatever outcome you wanna create, it’s up to you now. And yeah, there are still some constraints, right. Like, in entrepreneurship, we have to follow the general rules of the economy you know, there’s like, basic things, supply and demand, and all of those things, it has to work that way.

And homeschooling, you know, I had a homeschool experience and there’s other communities that would go for more of like an unschooled or, you know, like pushing maybe the limits on education even further. And that wasn’t my experience. But like, generally, it’s like, okay, you still need to play within the bounds of the system of like, at colleges and grades and like we still did standardized tests, for example. But we always treat it as like, oh, if you get below the 95th or 99th percentile on a standardized test, like, were you even paying attention? And so I think in the same way, right, it’s this total freedom but then there are these constraints in broader society and that’s true for both homeschooling and entrepreneurship.

Katie: I agree. And we did the standardized testing as well. I think my parents liked having a metric of just making sure we were able to check all of the boxes. And I think it also was great because the mindset for us was, this is kind of like a game that we have to play but like, let’s just beat the game. And I approached the SAT and the ACT with the same mindset of, like, it’s not that I think this thing is going to help me in my life but this is a game. So how can I beat the game? How can I study effectively for this particular test and just treat it as a thing I’m going to conquer? And did really well on both of those.

And so I’ve now taught my kids the same way of like, I don’t care what your ACT and SAT scores are but if you want to take them, let me show you how to beat the game. I think the other thing you touched on that I loved was the aspect of autonomy. Because I’ve seen this…and I think this is an important thing that we need to be having a conversation about. Even in the adult population, in the workplace and in motivation in general, I think of Dan Pink who talked about the psychology of motivation. And he explains that the ideas of autonomy and mastery are actually bigger motivators in the workplace and in life than even money, reward, and fame.

And how that seems counterintuitive at first, but basically like the human psyche is kind of wired for those things. And not that those can’t be fostered in a traditional school environment. But I think homeschooling is uniquely geared to make that more possible in situations like what you talked about. Also getting kids to think in terms of time being the most valuable asset and moving towards time freedom. Do you feel like that crossed over directly as well, that mindset of autonomy and being in control of all the factors when you started building companies?

Nathan: Yeah, I think so. You know, I was just used to that environment. You know, like, I think we all had friends or heard stories, right, as your leaving high school and going to college, right? You always encounter people where you just see them go off the deep end in some way, right? Whether it’s drugs or partying or whatever else. And usually when I dive into…or like kind of dig deeper into, like, what happened there? Often it was times where someone’s life was really controlled, and they didn’t have a lot of autonomy. And so then they came into this environment where, you know, of college and they had total autonomy and they could make all their own choices.

And like the freedom from that was overwhelming, they didn’t know how to make good choices, or they didn’t have that as their own value or priority. And so I think that homeschooling can work in a really good way of giving people autonomy along the way, and then seeing what each kid does with it. And the freedom from that and then the self-motivation that comes from it. And then that rolls forward into the next thing, usually more freedom, more autonomy, and a more motivating process. And so I think that that’s the same kind of thing in entrepreneurship where everyone that I know that’s quit their job has been like, “Okay, I’m all in on this company that I’m starting. I’m all in, like, let’s go.”

And then they have this moment of like, oh, I’ve been used to building this as a side hustle but now I can spend all my time doing whatever I want. And I don’t know what to work on like the freedom is crippling. And so I think that the more we can give autonomy in education and companies and all decisions along the way, the more success people are going to have. There’s a quote…I’m trying to think I must have been reading Brené Brown the other day. And so I don’t know who she was quoting, but she was basically talking about a lot of times we run the risk of paving the path, paving the road in front of our kids. And so basically preparing the road for our kid rather than preparing the kid for the road.

And it just made me think of a lot of what we’re doing is too structured and too prescriptive. Whereas, you know, certainly, my homeschooling experience was a lot of like, look, this is what the world’s like, here’s…exactly what you’re saying. Here’s how to play the game, and identifying when it’s like this really matters and when it’s like, this is just a game. And, you know, games are fun to play so treat it that way. And that’s…I love what you’re saying about the standardized tests because we thought of it in the same way.

And honestly, I think of entrepreneurship that way now as well of, like…And I’m curious if you think of entrepreneurship the same way, right, because you’ve built a wildly successful company. You’re in the process of building another one that I think is going to be 10 times bigger or more. And so I’m curious, do you bring that whole game mindset into your company as well?

Katie: Very much so. I love that idea that you just mentioned of prepare the kid for the road versus the road for the kid. And that’s something…We now are homeschooling our kids as well and we thought through when we started, what is the actual goal with an education? We’re not just gonna follow a curriculum or a book program, just because it’s an existing program. What are kids actually going to need to know as adults, to be not just members of society, but contributing members of society who work to improve things? Because certainly, you know, the last few months would illustrate there are certainly many things that our kids are gonna need to address and improve over the course of their lifetime.

And we distilled this down to the idea that also does correlate to our companies as well of one of the most common skills that makes someone effective and efficient and prepare them for whatever future path they’re gonna encounter. Because also, I would guess, just like for me, it would be true for you as well your current career probably didn’t exist when you were in grade school. So if someone had asked you what you wanted to be, when you were young, you won’t even been able to know to answer what you’re currently doing. And with the rate technology progresses, our kids will likely face a similar thing.

So we distilled the idea that we needed to equip our children with skills that could not be outsourced to computers, and skills that made them good humans. So things like creativity, critical thinking, connecting the dots, where other people don’t even see dots, thinking outside the box. Questioning and finding out if something is actually a legitimate source of information versus just part of the narrative. And then how do we build on that and teach the things they need to know through that lens versus just through bookwork.

And so we also kind of applied an 80/20 approach to school realizing if I went back and just thought of all the facts that I had learned in my education, I would remember probably a very small percentage of them. And so what things do kids actually need to retain as adults to be effective in whatever area they end up. And so, like the things we’ve done with our kids have led into that kind of business approach that crosses over in our companies as well.

And much like you, our kids finish their traditional bookwork by about the age they would normally start high school. And at that point, we have started an entrepreneur incubator with them, where we work with them to start their own business. And the goal being they have to have a profitable business for a year before they can drive a car, or get their own phone, which has been pretty motivating for them this far. And so it’s been fun to kind of see that overlap and to kind of watch their minds start to engage on the business side.

Nathan: Yeah, oh, man, I love that. I’d seen like some of the public aspects of, you know, what you and Seth have shared on Facebook that kind of thing. I believe, one of your kids did a coloring book, is that right?

Katie: A cookbook, actually.

Nathan: A cookbook, a kid’s cookbook. Anyway, it’s been fun to see that come out, but I didn’t realize that was a rule, you know, for the car, or the phone having the business. And I love that because there are so many lessons that come from that that will really stick with them long term. I just think about everything that has to happen in order to have a profitable business and it’s so many of those skills that you’re talking about. And, you know, you mentioned not knowing where you wanna be when you grew up, like, I wanted to be a landscaper. So clearly that played out exactly how I thought it would. But I wanted to run my own landscaping business so at least I got the business side part of it correct.

But what’s interesting is, yeah, what skills actually matter. Like, my mom had a really strong background in literature, English, writing, all of that. And I remember her making me suffer through all of those subjects. And I’m just like, “Mom, this doesn’t matter like I’m never going to be a writer, I wanna be a landscaper.” And she’s like, “Okay, that’s fine if you’re never gonna be a writer or anything like that, but like, writing is such a crucial skill, you have to get it right.”

And now what I realize is, what she was stressing is communication matters and clear writing leads to clear thinking, or clear…you know, the more you practice clear writing, the more clarity you’re going to get your thinking and your communication overall. And you know, and then what’s funny is that I then went on to write books and all that, so she was totally right and I was wrong, you know. And she reminds me that 10 times, like, “Remember when you insisted you were never going to be a writer, and I made you work on writing anyway, and remember how I was right?” And I’m like, “Yes, mom, thank you.”

But she did exactly the same thing that you’re describing of saying, like, okay, what’s actually going to matter? And we still did chemistry and I still remember, you know, random facts from that.

But, you know, I think my parents did a really good job of stressing those things. And they never had a requirement that I start a business or something like that, they just always encouraged it. They didn’t give us allowances and so we started a pet sitting business around the neighbors’ houses. I started a woodworking business and sold, you know, wood projects door to door to the neighbors I think probably when I was 12 or 13. And so that was…there were always these things and ways to make money and it was very much a hands-on education.

Katie: I love that. We’ve taken a similar approach with our kids, they don’t get an allowance. Our thought was always we don’t get paid to do things around the house we’re all just part of the team that lives here. But we do incentivize them to find problems and solve them because, to me, that’s a valuable life skill and also very much an entrepreneur skill. So if they notice something is broken and fix it, then we will pay for that but they have to take the initiative. And I love that seems like the same for you. You found ways to make money.

And just like in entrepreneurship, we tell them, you make money by solving problems and by helping people so find those needs and figure out how to fill them. I’m curious, I’d love to hear how you now are implementing some of these things and what you’ve changed in how you are raising and teaching your own kids.

Nathan: So I’ve got three kids now, they’re all boys. They’re eight, six, and then six months. Let’s see, things that I have kept the same would be lots of free play, unsupervised, unstructured, you know, just trying to have a lot of that. I grew up on a lot of land. I don’t have the same desire to live in the mountains, you know, 45 minutes outside of town. But we did buy four and a half acre little farm homestead that over the last couple of years we’ve making around and it’s, you know, right here at Boise, so that’s nice.

So there’s always projects. Actually, my son August who is six told me last night that he’s going to live off the land now. So he’s exclusively going to live outside, at least for…he said…What did he say? Four days and three nights. So I’m not sure where he got that level of precision from. But, you know, he was talking about how I think the list of things he’s going to eat, right, because we have a garden and everything. He’s like “I’m gonna eat blueberries and strawberries and chicken eggs.” And what else? He was like, “Peas and cucumbers and chicken eggs, and carrots.” And he kept going but chicken eggs was listed three times. So apparently, eggs are a key part of this diet that he has planned.

But, you know, he slept on the trampoline last night and he got my wife Hillary to help him cook breakfast on a camp stove. And, you know, a lot of that of just letting them kind of play and explore and it’s nice that we have this land where they can do their own things.

Now on the education side…well actually I was about to make distinction there of, like, you know, that’s the one side and then it now it’s like education. But I actually believe that that is the education, right. So many of these things that…whether we’re building or whatever else, he sees us build projects all the time. Like I have a tiny house office that I built, you know, as a fun project and so he’s always helping with that and doing those things. And he has some project that he’s building. I don’t really know what for but he’s taken, like, a bunch of bricks and he was measuring them. He’s like, “No, dad, I don’t want the 12-inch ones, I want the 14-inch ones.” I was like, “Okay.” You know, I don’t understand why but he’s learning about all these numbers and all the stuff just in this very hands-on way.

So I guess on the formal education side, we have a family member…my sister in law, runs a school that is half private school, half homeschool. And so they do two days a week in school and three days a week at home. So I think there’s a lot of those lessons that they get of, like, on all of those home days they, you know, have that autonomy of, like, hey, your homework takes as long as you let it basically, you know. And they have that freedom and all that.

Other things that we’re keeping…you know, it’s just tons of reading. We read like crazy as kids, we all would always joke…I’m curious if this was the same for you. That like the homeschoolers curse was not knowing how to pronounce words. And it’s not because we weren’t smart or, you know, had speech issues or something like that. It’s just that we read, you know, hundreds or thousands more words than we’d ever heard spoken. And so like, I had this whole vocabulary, it’s like, I’ve actually never heard this word spoken, but I try to use it in sentences, you know, not actually know how it was pronounced. Did you run into that same issue with tons of reading and that affecting your not knowing how to pronounce things?

Katie: Absolutely. And I haven’t outgrown it yet, ironically, is the fun part. So I’ve heard it said, you know, never judge those who mispronounce words because it means they learned from reading. But in the health world, I’m constantly in scientific studies and reading all the terms and then I’ll find myself like on a podcast going, “Oh, no, I have to know how to say this out loud.” And I often don’t, besides, I’m glad people, like, listeners give me a lot of grace with that kind of stuff, but absolutely same experience.

Nathan: Yeah, because you just…I mean, you read so much. I remember we would go to the library once a week and I remember fretting about maybe I don’t have enough books, is this stack going to last me a week? You know, and that’s a great problem to have. So we’re definitely keeping that. I think something that we’re changing is I didn’t play sports growing up. I don’t think that sports are, you know, a requirement by any means. But in the last like five or six years, I got into playing sports and, like, particularly soccer, and I just absolutely love it. And so that’s something that we’re doing more of. My oldest son Oliver absolutely loves soccer and, you know, all sports. They both do, but Oliver especially.

And so we’re making sure there’s plenty of time for that because that’s something that I wish was different. I think I’d enjoy soccer even more now if I had played as a kid and had that extra time. So, that’s something that we’re changing. I’m not sure…Well, one thing that we are changing…and I think this is specific to our kids is that we want them to have other adults telling them what to do. And we wanna get them out of their comfort zone a little bit more. I was super shy as a kid, both of my boys who are old enough to know whether they’re shy, you know, the ones that are older than six months old are super shy. And so I think having them in school for that two days a week…and you could solve for that with, you know, a bunch of methods of, you know, like a weekly homeschool co-op sort of thing or like all kinds of ways. You know, just this hybrid school is what we’ve chosen.

But I think having other adults telling them what to do, you know, and providing some of that structure that time around other kids has been really good. And then just providing kind of that different environment has been helpful, especially because we’re kind of home bodies, and we spend a lot of time here on our farm. So that’s sort of how we’ve optimized for it and I think that it’s a good balance for us.

Katie: Oh, my gosh, several things I wanna touch on there. First, I’ll say, I’m also technically a college dropout and I’m actually very proud of that fact. It’s funny that now, when you’re like up for certain things, and they’re looking at you as an entrepreneur, they’re like, “Oh, did you drop out of college because that would be great?” Like it looks just so funny to me.

Nathan: Yes. It matches their narrative.

Katie: Yeah, I had the similar experience on the sports aspect as well. And that is something we now encourage with our kids more, as well. And thankfully, at a lot of places, if you’re considering homeschooling or if you are homeschooling, a lot of times kids can play sports, even with a school system if they want to. There’s a lot of programs now in a lot of states that make that possible. My parents also did not really encourage sports and movement because we were so focused on the academic side. And I’ve, like you, discovered that as an adult, and taken up pole vaulting and sprinting and weightlifting and track, and it’s been the most fun thing to explore.

And you mentioned with your kids, you know, letting them explore outside and move and I’m sure they’re technically doing all these things that are exercise, but for them, it’s play. And we know based on psychology, how important that is for their vestibular development and things that are gonna serve them as adults like risk tolerance and knowing their boundaries. Like there’s a lot of crossover in movement there.

But all that to say, I’m really curious also your take on higher education in college at this point. It might have been Tim Ferriss, I forget who said it that “You could get a college education for essentially the price of $5 in late fees at a local library,” or now it’s open-sourced from many universities online, including IT. I’m curious, your take on college in the current climate, and what you will encourage your kids to do when they start hitting that age?

Nathan: Yeah. So I don’t have the same perspective on college of like, you know, go to the library and learn everything. I think the reason is that there’s….it shortchanges what you’ve actually learned from college, you know. And so many people will just say like, “Oh, you know, I didn’t learn anything.” And that’s one person’s experience, for someone else, it might be totally transformational. For me, when I went to college, I was a shy, awkward 15-year-old. Now I did two things at once, one I did a theater program separately, that was through our church. And that really helped me, like, get out of my shell and, you know, be comfortable on stage and that played a huge role. So those extracurricular activities of like theater and music and sports, I think are so, so important.

But on college, you know, all those group projects that everybody complains about, and everything else, those were so valuable for me. I had so much book knowledge and not as much of like how to navigate certain…it’s like the adult world because there’s parts of it that I was totally, like, very, very confident. But it was sort of all these, I don’t know, like more negative social dynamics or something like that.

I basically learned a ton in college, of like, what life is like and how to navigate a lot of those things that I hadn’t learned. And I probably would have learned all of that in high school over time. I was just rushing forward. One funny anecdote I had another friend who…she was two years older than me and she went to college early, she went when she was 16. And she had given me this tip of like, never tell anyone how old you are because they’ll treat you differently. Like, obviously, you look super young, when you’re 15 or 16 going to college. But the moment they know how young you are, they’ll treat you differently.

And so I learned this from her and people would say, like, how old are you? I’m like, “Oh, well guess.” And they’d be like, “Ah, you know, like, 15 would be ridiculous. And you’re clearly not 18 or 19” because, you know, I looked super young. So you’d be like, 17 and I would just say, “Oh, good guess.” And then leave it at that and then, like, never actually tell them whether or not, you know, it was a good guess, it’s wrong, but still gotta respect the guess. And so they’re little things like that of navigating social situations or things that I learned that college was really good for.

So I would still recommend college, I think college is a good default, and I would recommend pursuing it if you don’t have something else that you wanna do. You know, at that 16, 17, 18 age, if you’re clear on what you want, whether it’s entrepreneurship or, you know, pursuing the arts or something else then…and if it works outside of college, I think that’s great and I would say go for it. There are definitely scenarios, and I have a couple of siblings, who I think that they really didn’t know what they wanted. And I think that college…and they didn’t end up going to college. And I think that college would have been helpful to get them out of their comfort zone and push them to figure out what it is that they wanted. So I think it’s a great default. And I think I’ll encourage it for my kids as a default. But if they know what they want, I’d tell them to just like shortcut it and pursue that instead.

Katie: I think I’ve kind of told mine if you have a reason to go to college or a specific pursuit, then, of course, I would support that. My hope as a mom…and I won’t push this on them. But my hope is that like you and like me, they’ll have kind of a business idea or something else they’re already pursuing by that point. Because I know so many people who went to college and got a degree and still kind of didn’t know what they wanted to do. Or I would guess maybe the same for you like ended up learning skills, not in college or post-college that ended up being the things that actually became a career. I know like I taught myself to code and went back for nutrition and all these things post-college, separate of college.

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I also love that you brought up the social aspect because that is definitely one of the biggest objections I hear when it comes to the idea of homeschooling. And I’ve personally known of homeschooling students who are just anecdotal examples to kind of go against that idea that homeschool students don’t get enough social interaction. But I’m curious if that’s something you are specifically addressing with your kids? I know you touched on it a little bit, and then how you’ll do that as they get older as well?

Nathan: Yeah, so there’s a couple of things. One, if you say, like, “Oh, I’m thinking about homeschooling.” People will be like, “Oh, I can’t believe you want your kids to be socially stunted,” and that’s just ridiculous. But there is another side of it, like, if we were to break down social interactions, we would need to start putting into the categories, right? Your ability maybe to navigate peer pressure, when, you know, like, your 15-year-old friends are saying like, hey, let’s go, I don’t know, and break into the store down the street, let’s go steal this thing or whatever, right? Like, all these things that a lot of teenagers are wanting to do or suggesting.

There’s how to…you know, as a little kid, how to talk to adults, like that’s something that comes up a lot. And like if we were to break down social skills into so many things, you know, even reading the room, like having that social awareness to realize, oh, when she says this, I don’t think that’s what she means, I think she means something else. Or like noticing when something happens or any of those things.

And I think that instead of lumping it all together and saying homeschoolers don’t have social skills, we should start to break that down. Because for me, what was the case is I was great at talking to adults. And actually, every homeschooler that I’ve ever met has been really good at being clear spoken, carrying a conversation, everything, because that’s what we do. We talk to people across all age ranges, because of our siblings, our families, all the scenarios.

I had this moment where I was in maybe Shopko, I think ShopKo was the store, and I was asking my mom, “Hey, do you know where the Legos are?” And she’s like, “I don’t but that gentleman works here you can go ask him.” And you know, I was super shy, so I went, okay, all right, let’s go ask him. Like “Sir do you know where the Legos are?” And I must have been nine or something at the time. And now having an eight-year-old, I’m like, this would be ridiculous to talk to him this way. But this guy like gets down like in this exaggerated way down on the ground and he’s like, “Oh, yeah, okay, you want some Legos? Yeah, Legos would be great. Oh, that’s amazing you want that? You know, the Legos are just down there then you go around the corner.”

And I was like, looking…You know, now I’d be like, what the hell is this guy doing? You know, I didn’t have those words at the time. But I go back to my mom and was like, “What is his deal?” And she was just like, “Yeah, some people feel the need to talk to kids that way.” And it was so stark because no one had ever talked to me that way in my life. No one had ever treated me differently because I was a kid. And so, in many ways, I had great social skills because I had had so many interactions with adults and had carried on so many conversations. I had learned so much from spending time with people who were older, younger, you know, every different age range, rather than just like my batch in the factory, that is education.

But then at the other side, you know, there are lots of social skills that I didn’t know how to navigate of, you know, like certain finer points of, I don’t know, more difficult interactions. Like peer pressure, some of those other things where you’re like, “Okay, what actually is going on here?” And so anyway, I guess I would say I always break it down. And then also, you know, if you think about…for everyone who went to high school. If you think about okay, maybe 500 kids in the high school, and break down the whole range that you have across the board there of everyone’s social skills. Like, you know, some people are going to be so outgoing and just like so confident and great communicators and everything else can navigate any situation.

And some people are going to be totally awkward and distant and everything else. And like, we would expect that in school. Well, guess what, you’re gonna have the same range across homeschooling, where people’s natural personalities and the environments they grew up in and their home life and everything else is going to come out in different ways. And you’re definitely going to get some homeschoolers who are shy, awkward, and don’t know how to navigate certain situations. And you’re gonna get some who are ridiculously outgoing and so confident on stage and whatever else.

So that’s what I would say homeschooling or a lack of social exposure is not a reason to not homeschool. It’s just something that you need to build in your system so that there’s plenty of opportunities to get your kids more and more opportunities and get them in…you know, talking to adults in front of people running their businesses, you know.

Like, we have friends who homeschooled and they’ve had two daughters who I think are seven and five. And they ran a lemonade stand, you know, just in the neighborhood. And, you know, people might say like, they’re not socialized enough, I don’t know. But like whenever they didn’t have enough business, they would run over to like somebody’s house and knock on the door and, like, tell them to come buy stuff from their lemonade stand. It was like, pretty sure those girls know how to navigate social situations I think they will do just fine as homeschoolers. So, it’s just about what you put into your system and what opportunities you give them. And what challenges you put them in front of.

Katie: Definitely with you on all of that, and yeah, those girls have a head start on marketing.

Nathan: Yes, exactly. If you can learn direct sales at seven years old, like, you’re set.

Katie: Exactly. Okay, so as a homeschool parent, I don’t know about you. I have gotten calls from literally dozens of friends over the last few months who are either considering or planning to make the jump to homeschooling with everything that’s going on right now. So I’d love to get, like, super practical and kind of go through any advice or thoughts you have to anyone considering homeschooling right now. I’ve seen estimates as many as one in five families are thinking about it this year. And I know a lot of parents kind of are freaking out with the idea like, “I don’t have a background in homeschooling.” “I’m not a teacher, can I make this work?” And “How am I gonna do this and it’s gonna take so much time.”

So as a springboard into the conversation I will say, as a homeschooling mom, not to compare it to a public school timetable. I think if you add up the time you take getting kids to and from school and getting them ready to and from school and homework after school. Most people I know who make this switch actually spend less time homeschooling than getting their kids ready for regular school. But I’m curious, any practical tips, advice, encouragement, etc, you would give to parents who are trying to make that leap?

Nathan: Yeah, well, the first thing I would say is, you know, this quarantine, this pandemic is not the same as homeschooling. It’s giving people a taste of what it could be like or open these questions or all those things, but it’s not the same, we shouldn’t pretend that it’s the same. And that’s the point that I tried to make in the article that I wrote and everything else of, like, okay, there’s your taste of it, it’s not the same.

So there’s a lot of stresses that, you know, we have now depending on where in the world you’re listening from, and the current state of, you know, the quarantine and everything that you’re not gonna have going on in homeschooling. You know, like, there will be more of a system, there’ll be other things.

So if you’re thinking about it, the things that I would say, exactly what you said, of like set time expectations. I think you could do a great job homeschooling your kids in two hours a day. And if I think if you said we will only spend two hours a day on school in a formal way, I think your kids might have like a much better education than if you were like okay, class goes from 8:00 to 3:00. And so okay, we need to spend, you know, like all this time. I think you’ll do way better in two hours versus seven hours. So that’d be the first thing.

The second thing I would say is, again, what you talked about earlier, throw out the system, and go to first principles and say, okay, what outcome are we trying to create? How do we want this child to show up in the world? How do we want them to be prepared for the road that they’re going to need to walk? Because there’s a lot of that that, yep, math, geometry, chemistry, language, all of those things, they’re going to be really important. But what’s going to be more important is helping them develop habits, motivation, you know, autonomy, all of these things, letting them know what they can optimize for.

So I would focus everything on that and then once you have those values, that outcome, and sort of that framework, then start to fit in the lessons of, like, okay, they’re in this grade, they should be learning these things and do it within that. And kind of the last thing is this I think my parents did so well is make the child the one in charge and the one responsible. Your job…you are not…So in my opinion in homeschooling done well, you are not the teacher. The child is both the student…well, no, I think this is the role of the student is they’re in charge.

They are saying okay, this is what I need to work towards. They’re responsible for getting their school done for, you know, writing their papers for everything else, and your role is to help them. So, for example, we do this a lot with my son Oliver, if he’s having a really rough time on school, or if he’s, you know, acting like an eight-year-old and being rude or whatever else. Then we’ll just say, “Hey, it seems like now is not a good time, why don’t you come get me when you’re ready to do school?” Now, that actually frustrates him because he knows that the next day when he’s actually at class, he has to stay in and do his homework if it’s not done. And so he has to miss recess and sit in with his teacher.

And so we make him responsible for that. And so instead of us trying to say like, “Come on Oliver, like, you gotta get this done.” And like this whole thing of us trying to make him do it. And so we just say, “Here’s the consequence, if you don’t do it, but you’re in charge.” And I think, that plays out in a lot of ways where then the kid takes responsibility for their education and they learn, okay, I get the upside, I get the downside, guess what, that’s how the rest of life works so let’s just match that.

And then I’m responsible for learning and so I, you know, come to my parents when I need help when something doesn’t make sense when I need anything. And that mindset, one, kids can get that way earlier than you think like a six-year-old can do fantastic with that. And then two, it makes the burden a lot less on a parent who’s homeschooling, because you don’t have this mindset of, like, the kid can’t be doing school unless I’m sitting there doing it with them, which is just a crazy idea.

Katie: Yeah, I fully agree. I think for us most days, school is accomplished in about two hours, at least of just kind of focused school time versus…I feel like to your point earlier. If you wanna make a distinction, just call it formal school time because they spend the rest of the time doing all these outdoor activities or like your son building, whatever it is that he’s building, or my son…

Nathan: Who knows, I still don’t know what he’s building.

Katie: My son’s project this week is he built a foundry in our backyard to melt down aluminum so that he could use it to make his Halloween costume so he can be the Mandalorian. But I feel like they’re learning and they’re learning like, at what temperature does aluminum melt, and all of these properties that would be chemistry or various aspects of science. So they’re still learning, they’re always learning but the actual school part takes so much less time.

And I get why if someone is thinking about making the jump, it seems daunting if you’re anticipating an eight hour school day and having to divide everything up into blocks and all of that. But truly, like, what you’ve explained, is when you put the ball in their court, and you let them take ownership for it, just like an adult life, they can move at their own pace. And often, I found, at least with my kids, they’re highly motivated to want to do that quickly. And then be able to go outside and play with their friends in our neighborhood, which then solves the social aspect.

So that’s my encouragement to any parents. On the edge of that right now is that there are so many resources that were not there, I’m sure, when our parents were figuring this out for us. Because we’re close enough to the same age. I’m guessing your parents probably had to pioneer a lot of this in your state, for the most part, would you say?

Nathan: Yeah, and my parents were pretty active in the homeschooling community. My mom even… you know, it’s funny now in the age of iPhone apps and everything. She made like a memory system that she actually sold later on a different like homeschooling conventions and stuff like that. It was this folder, it’s basically the size of a sheet of paper but opened up and had all these little slots for like little business card-sized whether you’re trying to learn language or anatomy and physiology. You know, like basically all these flashcards you’re going through. And had a system built-in of like, you’d move a card through the daily section and weekly and then monthly.

And it’s super funny because now like actually, years later, when I was learning to program iPhone apps, I rebuilt the whole thing as an iPhone app. But yeah, my mom was pioneering that kind of stuff and she started a curriculum…somewhat a curriculum but she started basically a distance writing program for homeschoolers where they could all have writing assignments and books assignments, all that, but then when they wrote short stories and essays and all that, she had a publication. And I think there was only like 25 families or something. But then they’d all get featured in this publication, they just went back to the same families, it was called the Fireside.

And like a bunch of the kids were involved in laying it out in Microsoft Publisher and just this whole thing. Like, looking back, my parents did such a great job of creating those opportunities, but that also like not making too big of a deal out of it. It was just relatively simple and straightforward. And they put us in charge is that so they would say things like, you know, “Hey, make sure that you write a short story to include in the Fireside this month,” or I think maybe it’s quarterly. So yeah, my parents pioneered a lot of that stuff and now there are so many great things.

My friend Ryan Delk just launched a new startup specifically for homeschoolers called Primer. I’m excited to see that develop. He’s actually got like… One of his engineers left SpaceX to come work at Primer. And so they’re like, “Oh, well, let’s just do the stuff on model rockets, let’s do…” You know, it’s like a SpaceX engineer who’s helping you do it. So there are just so many incredible opportunities right now, like, I’ve never been more excited for the homeschool community. And then just this broader cultural shift that’s happening, of whatever stigma homeschooling had 25 years ago, it just doesn’t have anymore.

Katie: Yeah, I couldn’t agree more. I think we’re in a really amazing time for all of the problems right now there is a much wider acceptance of virtual learning and amazing tools that are developing out of the need for that right now. I’ll make sure to link to Primer in the show notes people can find it. And later this year, I’m also gonna be releasing sort of curriculum/ the entrepreneur incubator that I’ve talked about as a curriculum as well for other families to be able to use. But I’m so excited to see this more widespread acceptance of homeschooling and virtual schooling I think our kids can absolutely benefit from this.

And there are so many amazing resources already available. I will link to some of my favorites in the show notes. And if you think of it and have any favorites, I’d love to hear them and include them or if you wanna just shoot them over to me later, I can put them in the show notes as well.

Nathan: Sounds good. Yeah, I mean, the biggest thing is, I have to tell everyone as they’re looking through all of these, you know, contemplating the decision, one, know that you’re a hero for even considering it. Just for being that invest in your kids and I think it’s fantastic. But then, you know, like speaking as a listener and just thinking for you and I, we’re just case studies. It worked out really, really well for us, we’ve got successful businesses. Not to brag too much, but we’ve both got fantastic families, you know, and it’s just like, homeschooling is good.

And I think questioning all of these standard things and, you know, whether it’s education or business or all that if you can raise kids who think for themselves and question, then I don’t know, you’re gonna do really good things both for your family and for the world.

Katie: Yeah, I think that’s a very worthy goal, whether we homeschool, whether we don’t, I think all parents can unite on that front. And like you, I’m so grateful and excited for all of the business stuff and for being an entrepreneur but I think the greatest joy in my life is getting to see…like you said, we have pretty amazing families, getting to see these things with my kids and getting to help them learn. And to have them home and have more time with them and to teach them. So on that note, like as a mom, I would say I really encourage if you’re considering homeschooling it really is amazing to have that calm and to have them home and to be less rushed. There are so many benefits to that as well.

As a busy entrepreneur as well, you probably get this question relatively often, I know I do. Do you have any tips for getting it all done for balancing time, and family, and work, and all the things that end up on our plates?

Nathan: Yeah, it’s a good question. I’ll just tell you what I do and, you know, there’s nothing groundbreaking about this. But I do the Pomodoro method of just like setting a timer and focusing for 25 minutes, quitting everything. And I actually have this little dish in front of me that has two sides to it. And I’ve got 10 marbles. And every time I do a 25 minute focused session and check something off my to-do list then I just move a marble from one side to the other. So like a really good day would be like a seven marble day. But just kind of this nice, like visual reminder of like, right, I’m supposed to be focusing. So I actually have a little kitchen timer on my desk as well. And it’s a fun little reminder.

But like there’s nothing that special to productivity, it’s just really write down what’s the most important. And then set aside focus time. And, you know, like, reward yourself in small increments as you check that off. So I think kids can do well with that system, also. And we’ve done that a lot where we’re sitting down to read or something like that, “Okay, we’re gonna set a timer we’re all gonna read for…” This was when they’re younger, but for 15 minutes. And they’re like, “Okay,” and they would, like, be like, “Oh, is it time to done?” They could see the timer, and it’s still going. So just like those little examples. Deep work focus is really hard for kids, it’s hard for adults but the earlier you learn it, the better off you’ll be.

Katie: I love it, and I will…I’ve used that as well. I’ll put a link to the Pomodoro technique for anybody who’s not familiar with it. Also, is there a book or a number of books that have had a dramatic influence on your life, and if so, what are they and why?

Nathan: Okay, so I’m like turning around looking at my bookshelf behind me. “Anything You Want” by Derek Sivers, there are so many things in there. The book takes an hour to read. He built CD Baby, which was the first online retailer of independent music and sold it for like $20 million. An amazing story, great, great thinker and I love his perspective. Yeah, I think that would be the biggest one. And then an audiobook, I’m trying to remember the exact name. I’ll look it up it’s by Brené Brown. It’s basically on raising successful kids. But it’s like a three-hour listen on Audible. “The Gifts of Imperfect Parenting” that’s what it’s called. And it’s by Brené Brown and it was really good so I would definitely check out both of those.

Katie: Awesome, I will make sure those are linked in the show notes as well as a lot of the stuff that we have talked about and as well as ConvertKit, which is your company and the new one Primer so people can find those and continue learning. Where can people find you online if they wanna just stay in touch and learn from your work?

Nathan: Yeah, I’m pretty active on Twitter @Nathanbarry. Barry is spelled B-A-R-R-Y and then nathanbarry.com. Every couple of weeks, I’ve got a blog post that I put out, I dive deep on entrepreneurship, design, marketing, and occasionally homeschooling. And then I’ve got a newsletter that you could sign up for there that I put out every week on Tuesdays.

Katie: Wonderful, okay, I’ll link all of those at wellnessmama.fm. So if you are driving or exercising while you’re listening, you can find everything we’ve talked about there. Nathan, I really appreciate the time. I know just how busy you are as a dad and an entrepreneur, and I’m grateful for everything you shared today.

Nathan: Yeah, thanks so much for having me on.

Katie: And thanks as always to you for listening and sharing your most valuable asset, your time with both of us. We’re so grateful that you did. And I hope that you will join me again on the next episode of “The Wellness Mama Podcast.”

If you’re enjoying these interviews, would you please take two minutes to leave a rating or review on iTunes for me? Doing this helps more people to find the podcast, which means even more moms and families could benefit from the information. I really appreciate your time, and thanks as always for listening.

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