Part 1: Raising Curious, Courageous, Principled Rebels

A Conversation with Ben Greenfield from his book Boundless Parenting

“Your job as a parent is to be receptive, curious, and exploratory, not just for the bad stuff, but for the wins, the accomplishments, and the achievements – and break it down into molecular parts.”

Note: This interview is an abbreviated version of the chapter from Ben Greenfield’s new book, Boundless Parenting (click here to order).

Ben: Not long ago, I released an interview with Todd Kashdan, author of The Art of Insubordination: How To Dissent And Defy Effectively. During our conversation, we discussed how to gracefully be insubordinate in an era in which many people are “sheeple” who swim downstream. Todd’s book teaches you how to swim upstream, how to defy the status quo, how to assert your rights, and how to stand up for what you believe in; it’s a valuable resource for anyone who wants to be part of creating a world with more justice, creativity, and courage.

During that interview, we didn’t have enough time to talk about a particular chapter that I really dug, specifically the chapter that addresses how to raise super resilient and impactful children, and how to empower and teach them to think independently. So, I invited Todd back for a second conversation that focused on parenting. In this interview, we touch on a variety of topics, including training children in divergent thinking, reconciling different parenting styles, some of his favorite parenting resources, and much more.

So, tell me about your kids.

Todd: Chloe and Raven, my 16-year-old twins, have just entered the world of dating in their own incomprehensible way. There are about seven different steps now between being friends and dating someone, which I'm not going to go through because TikTok can offer that if you’re interested. Raven is a hardcore athlete. She plays on the high school soccer team, as well as a travel soccer team. She also made the high school volleyball team. While I’m incredibly proud of her athletic achievements, I’m even more proud of how her fitness mindset is evolving. As you know, like you, I believe in prioritizing care of mind and body. During the pandemic, Raven gravitated towards my “garage workouts” with elastic bands, dumbbells, and kettlebells. She wanted to learn everything. So, I bought her gloves and we lived in that garage. Raven wants to have an athletic Venus/Serena Williams-type body, not to be skinny. She embraces the model of women being physically fit, muscular, and agile.

Ben:  So, what she’s into is more like functional fitness?

Todd: Exactly. When Raven was four or five years old, and we would go on car trips, I would test her creative thinking with word association games. I’m a psychologist – I experiment on my kids all the time. So, I would say, “Meatball,” and then she would say, “Unicycle,” or I would say “Lightbulb,” and then she would say, “Vegetarian hamburger.” Her reaction time was so quick that I remember turning to her mom and saying, "Oh, my God! I want to figure out the associations in her brain. How did one lead to the other? You're supposed to say, ‘Spaghetti,’ when you hear, ‘Meatball.’ You're supposed to say, ‘Dark,’ when you hear, ‘Light.’" Raven is very creative, a fast processor, and extemporaneous; on the flip side, she may blurt out things, and be impulsive, but she also comes up with answers quickly in social settings, which makes for really fun interactions.

Chloe, her twin, is a more deliberative thinker. She's the analytical machine of my daughters. My father was one of the first computer engineers for Apple – back before Apple was popular and Steve Jobs served as a role model – and she reminds me of him.

Ben: Did he transfer his employee ownership stock onto you, so you're filthy rich now?

Todd: I should be, except he walked out of my family when I was two. So, it's mostly stories that I hear about him, as opposed to him actually being a part of my life. This makes for an interesting conversation about being a father when you didn't have a father figure yourself in your own youth.

Chloe is a rational thinker. She comes up with great arguments. If I try to discipline her, she might say, "Listen, dad. Here's why it doesn't make sense. Here's why you're hypocritical. Here's why it's not going to work." Of my three kids, I probably make the most mea culpas with Chloe, because she’s right more often than not. She's going to be a prosecuting attorney, a private investigator, or someone who takes down serial killers as a profiler for the FBI. Chloe used to be really into sports, but I think she got burnt out. I'm sure other parents can relate to how that can happen when your child is really good, really early. Other people, including myself, overly defined her as an incredibly exceptional athlete. Her hand-eye coordination is something I could have only dreamed of. Think of Barry Sanders, Michael Jordan, or Peter Sampras – athletes who, when they jump in the air, know where they are, even if they're doing a 360 on a soccer field. That's Chloe.

Violet, my youngest, who is 10, is the imaginative one. In certain ways, I'm parenting her a bit differently because she's the last licks on this thing. Violet is into stuffed animals. She has an entire world in her closet (which has no clothes in it!). Instead, in her closet she’ll create these mausoleums, and hotels, and large landscapes where the stuffed animals have personalities. Violet will spend more money buying them food, supplies, and furniture than she’ll spend on herself. Honestly, we’re diving into it because I'm such a big fan of training her to be as divergent of a thinker as possible. School provides nothing but convergent thinking, so I'm not going to do a premature closure on any of this imaginary play, even though most of her friends have moved on to more parallel play, sports, and outdoor activities. Violet also likes to design videos. Interestingly, Violet is incredibly perceptive about other people's emotional states. She almost has the instincts of someone who was physically and emotionally abused, where they can recognize just by the pace of a parent walking through the household whether it will be a good day or a bad day. Violet does this with everyone, so she has interpersonal intelligence that's off the charts.

Ben: One thing that you brought up with regards to your unique way of raising your girls and what you've learned from writing Insubordination is training your kids in divergent thinking. What do you mean by that and how do you pull that off?

Todd: The second part is a tough question, which is why I'm glad you have a diverse set of parents in your book. To define divergent thinking, it’s helpful to first define convergent thinking. Convergent thinking is when you have a problem or situation with a clearly defined set of possibilities or answers. There is a clear answer to the question, "What's the quadratic formula?" But it’s different if someone says to you, "Can I have breakfast? I need at least 30 grams of protein because I just read in the New York Times yesterday that this is important for someone aged 48 or older." Another answer exists. That's convergent thinking.

The divergent thinking part might start with, “Is the quadratic formula the best way to express the mathematical relationship here?” or, “What’s the best way to extract protein for optimizing the mind and body for the day?” Divergent thinking happens when you’re playing billiards, or when you're planning a party and deciding where the people and furniture should go.

Once you have an open-ended range of possibilities exploring terrain, problems, and decisions, you've entered the creative world of divergent thinking. You also move into divergent thinking as soon as you move away from conventional and orthodox approaches. A good example of that – not that we want to get stuck on cultural issues that people fight about incessantly – is when someone says, "America started with the Mayflower,” or “America started with the slave trade,” or “America started with the Constitution." Those ideas are often taught in classes, and by adult figures, as if they are convergent questions with clear answers; however, great divergent thinking can be launched just by mentioning those thoughts as mere possibilities. Divergent thinking is asking questions such as, “When we think about what America is, what are we talking about? Are we talking about a thing? Are we talking about something that's inscribed in text? Are we talking about culture? Is culture fixed?” As soon as you start exploring questions about the initial question, you enter the realm of divergent thinking.

Ben: Are there specific strategies that you use to teach divergent thinking? The reason I ask is that it seems to me – and correct me if I'm wrong – that the modern educational system largely specializes in teaching convergent thinking, cooperation, putting a square peg in a square hole, and a round peg in a round hole, with those pegs all lined up in a row. Basically, kids are taught to be good little factory workers painting with a broad brush. Obviously, there are exceptions to the rule, with several public schools or Montessori academies that stand out; however, there must be strategies for effectively training a child in divergent thinking, even if they're enrolled in a school that might specialize in a more convergent thinking-type of education.

Todd: Yes, it's very challenging when you're not homeschooling, which we aren’t. My daughters are in the public education system. I do so many things to encourage divergent thinking. One is that I walk my 10-year-old daughter to school every day (unless I am traveling for work), and I walked my 16-year-olds to school every day until high school. On 95% of their school days, during these walks, I brought up questions that helped encourage divergent thinking.

Every morning, I find something in the news to bring up to my kids, but without offering my lens of how to view that topic. At the time of this interview, 19 elementary school kids were tragically shot by an 18-year-old in Texas. When I introduced that story to my daughters – obviously very differently to the 16-year-olds than the 10-year-old – I didn't state my viewpoint; rather, I gave them space to offer their own thoughts and opinions about that event, and then I built upon what they said. When I talked about it with my 16-year-olds, they already heard about it from their friends and on TikTok. I asked them, "What was the source of that information? What did you hear that you think is true and what did you hear that you're unsure about?" It's that uncertainty piece that I play with almost every day of their lives. In this case, I asked a question with no definite answer: "What did you hear was the motivation behind the killing that happened? There’s an 18-year-old and we know nothing else about him; what are your guesses?" Since my kids are being raised by a psychologist, they brought up loneliness, bullying, and body dysmorphia, which is something that we had recently discussed. They also brought up the theory that maybe he didn’t have a good relationship with his parents, or maybe he wasn’t going to get into college.

They ended up talking about a number of different possibilities, and that led to the next question, which was, "Would those adversities, if they happened, lead him down a path of bringing a gun to school?" This is where divergent and critical thinking starts to pick up. Every morning, I have no idea where the conversation will go and I don't care. It's more about just having time with them when I'm not acting as the authority figure. We're not trying to find answers; we're just exploring really interesting topics.

Ben: I want to return to the current events piece because I think that's important. My sons subscribe to a current events publication called The Week Junior, which is a fantastic little digest of current events, specifically targeted towards adolescents. When that magazine arrives each week, I read it before giving it to them. This provides good fodder for dinner table conversations. I can say, "Hey, what do you think about what's going on in Ukraine right now? Do you think Putin made the right decision? What do you think the people of Ukraine should do? What do you think we should do to help out, if at all? Do you think we're contributing to something that you don't believe in or stand for?" I know many people say that you shouldn't look at the news because the news is negative; however, I think it is our prerogative to stay up-to-date on what's going on in the world, even if that simply means staying informed so we can figure out to help people or contribute to society in some way. Being on the same page of the current events digest with your children, in order to foster discussion, is particularly important.

Todd: I love imagining dinner conversations with your kids. One is you're giving your sons agency in the conversation as contributing members. The other is you're treating them not as the owner of a three-pound brain that will eventually turn into something that's valuable, but as the owner of a brain that’s valuable now. There won’t be a point at which you suddenly say, "Now that you've graduated high school, your opinion matters. Now that you've crossed the arbitrary threshold of 18 years of age, I will listen to your opinion.” You're starting now. What I like about this practice with your sons, which I espouse as well, has to do with one of the modern phrases that I despise the most: “Stay in your lane." I don't know if you feel the same way. Someone just said this yesterday; it seems to happen every three days with me.

Ben: I get that, too. It's always, “Stick to fitness, bro."

Todd: My response is always the same: “Where do you think creative ideas come from?”

Creative ideas come from searching for the flaws, knowing that you have biases and a psychological conflict of interest. If this is your area of expertise, and you receive a paycheck from it, what is your motivation for seeing problems or alternative solutions?

Society should want tons of people to stray outside of their lane! Here's where we get back to parenting:

If you say you should stay in your lane, what you're saying is that no kid's voice matters because they don't have a lane yet.

They're still roaming on the periphery of highways with no yellow or white lines. Kids are zigzagging, they're taking motor scooters, and they're riding their bicycles up and down hills, going through people's yards. They don't have freaking lanes! So, when you say that, you're saying students and kids don't matter; rather, only pseudo-quasi experts who have vegetable soup titles and degrees after their names should have a say. That is an absurd approach to a culture trying to evolve and improve, in terms of decision-making and eliminating dysfunctional ideas and systems.

Ben: As far as the actual development of the style of thinking that you're trying to foster in your daughters, do you rely upon any type of curriculum, books, systems, models, or resources? Do you just piece things together on your own? Do you have a set of key resources for this?

Todd: The answer is no, with an exception. After being trained as a clinical psychologist, I found one framework to be most beneficial to me – above all – and to my clients, which is acceptance and commitment therapy. In a nutshell, acceptance and commitment therapy means being in the present moment, accepting an exploration of experiences that are outside the self and within the self, and engaging in behaviors that are aligned with your values. It's a triangle: You have presence, you have exploration, and then you have commitment. That approach to psychological experiences, and that practice of being situationally aware of what behaviors will work best in a particular situation – as well as not being rigid in your thinking or behavior – is something that I've adopted for my own life, and is something that I'm training my kids in, as well. Here’s an example. One of my kids has seen a therapist, because they were having trouble with self-doubting, self-deprecating mental chatter. The voice in their head said, "I'm not good enough. I'm not attractive enough. I'm fat at a very young age." What I did with the therapist was to say, "Listen, I want them to work on this negative self-talk, but I can't be the one to do it because I don't want to play the role of therapist on top of being a dad, a coach, a friend, and everything else.”

I want my kids to understand that their thoughts are just words that their brain is constantly producing and their identity is unattached to any statement. Your brain is always talking to you, just like a friend that sometimes gives good advice and sometimes gives terrible advice. Just because your brain is attached to you doesn't mean that the statements are factual. I want my kids to have a relationship with their brain in which they can say, "Okay, that's an interesting idea. It's an interesting hypothesis that you say that I'm fat. Let me go test that. Let me ask three people," or question, “In the past week, has anybody pointed out that I'm overweight?” The answer is, “No,” to both questions. So, right now, I have less confidence in that hypothesis that I am fat. That approach fits with acceptance and commitment therapy, and it's a nice psychological tool to train my kids to use to be more tolerant of strain that arises as they're navigating their social world.

Ben: It reminds me just a little bit of something that might go hand-in-hand with mindfulness-based meditation – namely, observing your thoughts and feelings as you meditate, without judging them or trying to change them. You simply step back and pay attention to what your brain is doing, almost as though you're observing yourself in the third person. I think that mindfulness-based meditation or some form of meditation in which you're just sitting and allowing yourself to observe your thoughts without judgment is pretty important. I practice meditation every morning with my kids for about 10 minutes and then we do a repeat self-examination at the end of the day. It really helps them to get to know themselves and to be able to understand their thought patterns.

Todd: These models steal from other models. So, yes, there is overlap with mindfulness meditation. As a New Yorker my kids are like me: hyperactive, hypomanic. Traditional meditation has never worked. What works for them has worked for me. When we do activities, we absorb ourselves to such a degree that we lose our sense of self and ego. That's the form of meditation that we use. Whether it's playing soccer, lifting weights, or engaging in cardiovascular activity, this is our preferred means of meditation. I say this to emphasize the importance of everyone figuring it out for themselves. Here's a methodology that works for me that emerges when you mention mindfulness meditation. A routine and simplistic activity, whether that’s gardening, knitting, or playing a sport, is more likely to work as a form of meditation for certain people.

Ben: For my kids, it's probably art. They do a lot of painting that would qualify as that style of activity.

I would like to revisit the fact that you outsourced some of that cognitive awareness and assistance to a third party. I think that's important for a couple of reasons, including, as you noted, that you are not stepping into the role of a therapist, as a parent. In a way, it’s bringing your work home when that's your profession. Even if you don’t have the mentality of, "It takes a village to raise a child," outsourcing certain things can be highly beneficial. For example, my sons have participated in a rite of passage, which are traditionally not overseen by the father. Instead, they're led by an uncle, a tribal leader, or another man, so that the child can cut their connection with the father. They should not be dependent on the parent while they navigate a difficult scenario. That way, they are required to think for themselves, or at least not assume that their parents will always be there to help. As we all know, that’s not the case, as we grow older.

Also featured in this book, Tim Corcoran (see Chapter 9), is the wilderness survival instructor who oversaw the rite of passage for my sons. He holds a monthly mentorship call as they go through a nature awareness and self-awareness course. Sometimes, I get a little jealous as a father, listening to these long calls with my sons, when he's telling them stories and hearing their thoughts, feelings, and emotions. But then I think, "No, no, this is good that they have someone other than their parents teaching them something that goes beyond what they might learn in a traditional schooling setting." I'm not talking about the idea of outsourcing your kid’s entire education to a schooling system, which I think is a failure on the part of many parents; they get kids off to school and assume all the work is done, and that they have nothing left to do when the kids come home, aside from just hanging out with them and having fun. There's still a lot that you have to teach kids – convergent versus divergent thinking patterns being a perfect example. This willingness to have other people come on board to help to foster your child's progression towards becoming a fully grown human being is important. Still, there are parents who struggle with inviting other people into their kids’ lives, particularly when that person plays a role similar to that of a parent.

Todd: This might be one of the 20 most important parts of your book. I love that you mentioned how you sometimes feel jealous. By naming it as parents and caregivers, we can do it better.

If you were raised in the 80s, like I was, you would sometimes sleep over at a friend’s house for a week without coming home. It was a different environment. I'm not saying it was better or worse; it was just different. You spent plenty of time talking to the parents of your friends. I've encouraged my kids to talk to other parents and I talk to the parents of my kids’ friends. I say things like, "Listen, I really value that my kids are comfortable disclosing stuff to you, especially in regards to sex and relationships. I'm the only male in the house with three daughters." I communicate with some of the moms, saying, "I hope that they tell you stuff. You don't have to tell me everything that they say. I wish that they would tell me all of the things they tell you. I'm just glad you exist in their lives.” I show them a ton of gratitude and give them explicit free range to work with my kids however they want, with their styles of incentives, punishments, and interactions.

As a result, my kids regularly say, "It's like we have other moms and dads in our lives." It's so touching to me; yet, as you said, there's a level of jealousy that may sound like, "I should be able to do it all. Why would I need other parents to play this role?" But my kids need a buffer between the person who is basically responsible for their physical welfare, and then all of these experiences that are happening in their lives. They need separation. It's also good for them because they learn to communicate with other adults and that prepares them for real-world practical intelligence.

Ben: That makes sense.

Now, regarding your book, The Art of Insubordination, in preparing for and writing that book, was there anything that you learned and then specifically made a point to pass on to your daughters?

Todd: Definitely. The fun part about writing a book is that you get to unearth science that nobody's talking about. For instance, there's a guy in Greece who conducted research on the best way to get kids interested in science. He tested out whether there were benefits of sharing stories about the social difficulties and adversaries of people like Galileo or Nikola Tesla. Galileo was basically told, "Listen, this is not the way. You can't do it your way. You're under house arrest, and we're going to kill you unless you recant statements made.” For decades, Tesla and Edison would subvert each other’s work, trying to steal each other's patents and burn down each other's laboratories. That's part of the story. Then, there's Tesla's loneliness and his difficulty with friendships and romance because of a work obsession. He lacked life balance.

If you tell the stories with the psychology intact, people pay attention. The Grecian researcher found that people not only pay attention but are more interested in being a scientist when they hear stories. They realize, "Oh, this is exciting and challenging! This is like climbing Mount Kilimanjaro. This is like fighting for the civil rights of people who are being marginalized. This is an adventure. It's not just learning formulas, math, and engineering." That approach is something that I've adopted in the kids' lives.

For example, on Martin Luther King Jr. Day, I talk about the facts they don’t bring up in school. One of the fascinating things about Martin Luther King Jr. is that he had a tough marriage. He also had friendships that frayed at the seams, because there were people who wanted to take a more violent approach to the civil right movement. My kids and I have conversations about how he navigated that, and it humanizes him. He’s a flawed man who had a lot of infidelities, who had difficulties with friendships, and who made questionable decisions – and, yet, he changed the world. When you tell the story with warts and all, all of a sudden, a kid doesn't just idolize Martin Luther King Jr.; they believe that they can be like him. They realize, "Oh, someone like me who's all messed up with a weird, jagged profile of strengths and weaknesses can become a Martin Luther King Jr." That's what you really want for kids. You don't want them to idolize people; you want them to see templates of what’s possible.

Ben: Having gone through many years of child-rearing already, are there things that you do with the 10-year-old that are different from what you did with your 16-year-olds, due to your experiences with the older kids?

Todd: Yes, and my answer involves physical and emotional affection. When my kids were young and I could carry them, I was like someone from a third world country: I always had them on my back in a Bjorn. As my twins got older, I let them loose and stopped hugging them as much or tucking them in every night. Now, I tuck my 10-year-old into bed every night. I will come home from a concert early – even skipping out on an encore from an amazing band like Pearl Jam – to tuck my kid into bed. It's essential that she go to sleep knowing that she is physically and emotionally loved by me. I don't think I did that as well with my older kids.

My relationship with physical affection has been influenced by my own masculinity, along with being raised by a single mom who couldn't always provide optimally – although she did an amazing job. As a result, I got caught up in how I was brought up, as opposed to inventing how I wanted to raise my kids. Now, I’m dedicated to getting the physical affection piece right with my 10-year-old.

Ben: This is a bit of a shift, but in terms of the one-on-one time, have you decoded that? Do you have protocols for really carving out quality one-on-one time with your girls? Because you're a dad with twins, I bet it's even more difficult.

Todd: Yes, I have. The reason that I've been able to figure this out is because I'm also a twin. So, I'm a twin with twins. My dad left us when we were two. Then, I got a letter when I was about 17 years old from one of my cousins, basically saying, "Listen, you've never heard your dad's side of the story." My mom passed away when I was 13, so I was raised by my grandmother. And my grandfather died a year before my mom. As a result, I had no father figure – no male figure – in my teens, adolescent years, or beyond.

Then, when I was about 22, I got another letter, this one from my father. This letter was tragic. It was an apology for never differentiating between my twin brother and me, and never spending sufficient time with us, individually. As a result of the divorce, my father only got us for the weekend; because of that, there was so little time that he couldn't figure out how to separate time with my brother and myself. That letter – which I received long before I had my own kids – had a profound impact on me. I didn’t want to reconcile with my father but I did want to make sure that, if I ever had kids, I would spend sufficient time with them, one-on-one.

Part of my work involves public speaking around the world, and one thing that I do is take my kids with me, separately. When I gave a talk in Japan, Raven came with me and we climbed Mount Fuji. We had studied the Japanese language beforehand, to make sure that we could start conversations. We hired a guide together. We went to temples together. We woke up at 5:30 am. We did everything together. Due to our rule of no cabs unless necessary when we travel, we took only mass transportation. Raven got to experience culture shock with me. We didn’t know what to say, we weren’t sure where we were, and we didn’t know what to do all of the time – but we did it together. That one-on-one experience is the most profound moment in my relationship with Raven. I've been meaning to write an article about that trip to Mount Fuji because if I die today, I will remember that two-week period as what created our relationship today. This experience cemented it for both of us.

As for Chloe and Violet, when I travel with them individually, I learn so much about them. There's so much grumpiness, there's so much novelty, there's so much discovery of how people respond to stress and potential opportunities that you don't get in your domesticated life. I strongly encourage not just one-on-one time with kids, but literal adventures individually with them.

Ben: I almost got chills when you were talking about that letter because there’s a tiny piece of angst for me that’s always asking the question, "Gosh, are my kids going to grow up and wish…?” Their names are River and Terran. Is River going to grow up and wish he'd have more one-on-one time with me? Or is Terran going to grow up and wish he had some time away from his brother, River, to be able to express himself in a different way? I do carve out individual time, though. We go on one-on-one dates every month and I go on walks with them. At night, once a week, we do eye gazing – it's five minutes of playing a song, hands on each other's hearts, looking deep into each other's eyes, not saying anything or saying short things like, "I love you," or, "You mean so much to me." At the same time, I'm constantly asking myself if I could be doing more. Thank you for sharing how you take one-on-one vacations. It has made me think about the importance of that even more.

Part 2 of our interview is coming soon. In the meantime, access everything here:

BoundlessParentingBook.com

Extra Curiosities:

A reader sent me this absolutely gorgeous tune from a singer I never heard of. It is painful to acknowledge my loss in music, books, and art because greatness often fails to reach my attentional portal. Lissie should be famous. Let me know if you agree:

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