Raising Independent Creative Children (Unconventional Entrepreneurial Parenting Tips)
Chris Do shares his unconventional parenting philosophy for raising independent, creative children who thrive on their own terms.
Chris Do
Founder, The Futur™ · March 18, 2025
An Unforeseen Outcome
Chris Do’s oldest son is studying philosophy at Columbia University. His youngest son made six figures before he turned 18. These are not the results of a meticulously planned, Ivy-League-or-bust parenting strategy. They are the product of a radical, counterintuitive philosophy built on two simple rules and a vast expanse of freedom.
The success of his children seems, on the surface, contradictory. One pursues the life of the mind, the other the fast-paced world of digital assets. Yet both paths were forged from the same environment, one that actively rejected the norms of modern, over-involved parenting.
This is not a story about how to micromanage a child into success. It is a story about how to get out of their way. As Do reveals, “I have very firm rules for the things that matter to me and almost no rules in between.”
The foundation of his approach comes from an observation by the yogi and mystic Sadhguru, who suggests that children are born perfect. It is the intervention of adults, primarily parents, that corrupts this state. Reflecting on his own childhood as a latchkey kid of working-class immigrants in the 1970s, Do realized the lack of parental hovering was not a deficit. It was an advantage.
The long hours of unsupervised time, the absence of a curated schedule, and the freedom to be bored allowed his imagination to flourish. “This laissez-faire style of management in terms of raising me allowed me to dream, to daydream,” Do explains. “It allowed my creative child to survive into adulthood.”
As a parent and successful entrepreneur, Do faced a new challenge: how to recreate that environment of benign neglect for his own children, who were growing up with far more privilege and resources. The answer was not to replicate the poverty, but to replicate the principles.
The Two-Rule System
While many modern parents operate with a complex and ever-expanding list of rules, Do’s entire system rests on just two non-negotiables. There are, he says, only two things that truly matter.
The rules are simple, clear, and absolute:
- Rule 1: Always give people respect first. This is the cornerstone. Respect is not earned; it is the default setting. Disrespect towards anyone, from a parent to a teacher to a stranger, is a critical failure.
- Rule 2: Zero tolerance for physical violence. There are no exceptions and no justifications.
That’s it. Between these two firm guardrails lies a vast territory for exploration, mistakes, and self-discovery. This approach stands in stark contrast to what has become known as helicopter parenting, a style defined by constant hovering and micromanagement.
Do paints a vivid picture: a parent at a playground, obsessively wiping hands, checking for splinters, and literally catching their child at the bottom of the slide. While the intent is to protect, the outcome is damaging. “Our desire to protect our children actually prevents them from making good decisions later on,” he argues. By shielding them from every small bump and bruise, we rob them of the chance to learn that life involves setbacks. We prevent them from normalizing failure as a part of growth.
A psychologist at a seminar once described parenting as downloading your operating system onto your child. The real test is not how they behave when you are watching. “The real question is what will they do when you’re not around?” Do asks. Over-parenting creates compliance, not character. It teaches children to follow external commands rather than developing an internal compass.
This leads to another critical insight from that seminar about the strong-willed child. Society often encourages parents to break a child's will, to tame them like a wild animal. This is a profound mistake. That strong will, that internal conviction, is precisely what they will need later in life to resist peer pressure, to stand up for what is right, and to navigate a world that doesn't always have their best interests at heart.
“If you break that as a parent,” Do warns, “you’ll also break it when they need to use it when you’re not around.” The goal is not to shatter their will, but to guide it with a few unbreakable principles.
The Poison of Permissiveness
Living in an affluent community provided Do with a front-row seat to the consequences of a different parenting failure: the complete lack of boundaries. He observed a disturbing pattern among the children of his wealthy neighbors.
These children, he noticed, were often “poorly behaved.” They operated without boundaries, spoke in commands instead of requests, and displayed a profound lack of gratitude and respect. They treated their parents like subordinates, driving the relationship dynamic entirely.
A simple title could reveal everything. “I’m Mr. Do, I’m not Chris,” he would tell his children’s friends. “You don’t earn that right until I give you that permission.” This old-school formality was a world away from the homes where kids called their parents by their first names, blurring the lines of authority.
Do recounts a trip with another affluent family. At mealtime, the child would eat one small part of their food, discard the rest, and demand another. The parent, without hesitation, would summon the flight attendant and order a replacement meal, which would also be picked at and wasted. The entitlement, the waste, and the lack of appreciation were maddening to witness.
This behavior is a symptom of a deeper problem: an inability to delay gratification and a complete absence of meaningful limits. When these children do not get what they want, they shift into “turbo temper mode.” When faced with a simple choice, like vanilla or chocolate, they melt down, unable to decide. The parental solution is often to just buy both, compensating for indecisiveness with money and wastefulness.
The long-term consequences are severe. These children grow into adults who are self-absorbed, egotistical, and unable to function in a world that is not designed to appease them. Their social skills are stunted because they have never had to consider anyone but themselves.
“You can’t blame them for that,” Do admits. “Because if I grew up in an environment for 18 years of my life where everyone just gave me whatever I wanted...why wouldn’t I expect the entire world to do that?”
When this pattern of behavior appears in public figures, people who cannot handle their fame or wealth, Do conjectures a lack of boundaries in their upbringing. Someone, at some point, should have sat them down and told them to chill out. But no one ever did.
Winning the War, Not the Battle
At times, Do found himself forced to be that person. During a group outing, watching a child run roughshod over their parents, his internal thermometer reached its boiling point. He couldn't take it anymore.
He knelt down to the child’s level. “I don’t know if you know this, but I’m going to say this in behalf of your mom and dad,” he began. “They’ve worked really hard to provide you what you have...and the level of disrespect that I’m seeing is really hard for me to witness.”
The child, never having been spoken to like that, froze. The parent’s reaction was even more telling. “See, Johnny? That’s how Uncle Chris raises his kids,” they would say, completely abdicating their own responsibility.
Initially, Do’s own children resented these interventions. “Dad, I can’t believe you said that to them,” they’d complain. “Now no one wants to come over and play at our house.”
Do’s response was unwavering. “That’s good. Until they learn respect and boundaries and to be grateful, I don’t really want them here.”
He was willing to endure his children's temporary anger and social isolation to uphold a core value. This is the essence of his philosophy: playing the long game. So many parents, desperate to be liked by their children, make decisions to appease them in the moment. They are constantly trying to win the battle for affection. Do’s focus was always on the war: raising a functional, respectful, and self-sufficient adult.
“I will forgo the temporary loss of a battle to win the entire war,” he states. “And the war is I want to make sure that my children when they’re adults have a good set of rules and beliefs and values and know how to govern themselves.”
Years later, his children, now older and more aware, would observe similar behavior in their peers and turn to him. “Oh my God, that’s a mess,” they would say. “Dad, I’m just glad you raised us the right way.” It was an implicit apology, a validation of the entire strategy. The long game had paid off. The resentment had transformed into understanding and appreciation, a journey he explores in the context of personal branding in Ditch Networking. Build An Authentic Personal Brand Instead.
The Parent as Facilitator, Not Dictator
The alternative to hovering or appeasing is not apathy. It is facilitation. The parent’s job is not to shape the child into a preconceived mold, but to see what they gravitate towards and clear a path for them to explore it.
This means resisting the urge to live vicariously through them or have them fix your own life's regrets. “You had your shot,” Do says directly to parents. “Why inflict the same wound to your own children?”
Too often, parents push their children toward paths they themselves wish they had taken: the uneducated parent demanding a PhD, the aspiring politician pushing their child into government, the failed artist insisting on art school. This is inherited trauma, passing down a set of rigid, outdated rules, or what Do calls “dogma.” In a world changing as rapidly as ours, with AI and social media rewriting the rules of career and life, this dogma is more dangerous than ever.
Instead, the parent’s role is to be a provider of resources. When Do’s sons showed interest in things, the family supported them.
- For his son interested in drawing, they provided art supplies and helped him set up a camera to make YouTube time-lapse videos.
- For his son who loved music, they ensured he had a piano and access to tutors, encouraging him to write his own songs.
Crucially, when their interest waned, they were allowed to stop. It was never about what the parent wanted for the child; it was about what the child wanted for themselves. It’s a mindset similar to finding your own purpose, a topic Do covers in his Ikigai Workshop on turning passion into profit.
This freedom from expectation is why Do never once checked his children’s homework or looked at their report cards. He bribed them to drop out of school, not to get straight A’s. “We want them to love school for their own reasons, not because we told them to,” he explains. If they did poorly, his assumption wasn't that the child was failing, but that the school was a bad fit.
This approach baffled his cousin, who asked in amazement how he got his kids to do their homework. The answer, “I’ve never checked,” was so foreign it was almost incomprehensible. But it was the truth.
The Operator's Manual for Independence
Creating independent children requires a tactical approach. It’s not just a feeling; it’s a set of deliberate actions. Do credits his family therapist, Dr. Joan Lightfoot, with providing some of his most effective tools.
One of the most powerful concepts was that children feel safe when they know someone’s in charge. This insight rocked his world. When parents try to be friends with their children, blurring the lines of authority, it creates anxiety. The child worries, “If we are equals, who’s in charge?” This lack of a clear leader creates dysregulation and insecurity.
This is why Do embraces an authoritarian stance on things that truly matter, especially physical safety. Dr. Lightfoot gave him a specific technique for this. In a dangerous situation like a parking lot, he uses a firm “dad voice” to call his children to him. But he doesn’t stop there.
Following her advice, he would pick them up and show them the danger from his vantage point. “You see that person over there?” he would say, pointing to a car about to back up. “I bet you couldn’t have seen that down there.” He demonstrated *why* they needed to listen, proving his authority was based on superior knowledge and a desire to protect them. The result? When he used his dad voice, they listened. Immediately.
This consistency is key. He notes his wife struggled to get the same response because she gave too many instructions, diluting the importance of any single one. “I rarely give instruction,” Do says. “So when I give one, they know it’s got to be important.”
Another crucial tool was giving children the illusion of choice. Instead of open-ended, paralyzing questions like, “Where do you want to eat?” he would offer two pre-approved options: “Do you guys want Chinese or pizza?” This strategy achieves several things at once: it empowers the child to make a decision, it builds their decision-making muscle, and it ensures the outcome is acceptable to the parent. Over time, these small, low-stakes decisions build the confidence to tackle bigger ones.
This confidence was put to the test on a dangerous hike at Angel's Landing in Utah, a trail so treacherous people die on it every year. At a narrow section where they had to hold onto a chain bolted to a rock face with a sheer drop below, his older son panicked. But his younger son, Matias, kept going. Why? “Because he was borrowing on my confidence,” Do explains. “And he knows who’s in charge and he feels safe.” They made it to the top together, a core memory built on trust and clear leadership.
The Unforeseen Payoff
For a long time, Matias, the younger son, was the quiet one. He seemed less confident than his older brother. He was the one who, as a small boy, was too afraid to ask for a drink refill at a restaurant. Do worried about his indecisiveness.
But while his parents thought he was just playing video games, Matias was doing something else entirely. He was immersing himself in digital culture. He started creating digital paintings and was commissioned for NFT projects. He learned about cryptocurrency, created his own digital wallet, and became a savvy trader, even advising his high school friends on their investments.
The discovery was a shock. One day, his older brother asked, “Dad, do you know how much money Matias has? He has over $100,000.”
This was the ultimate validation of the hands-off philosophy. Had Do been a helicopter parent, he would have intervened. He would have questioned the screen time, warned against crypto “scammers,” and tried to negotiate the contracts. By staying out of it, he allowed Matias to make his own decisions and his own mistakes.
And the mistakes were as important as the successes. When the crypto market crashed, Matias’s friends lost money based on his advice. He felt a deep sense of personal responsibility. He didn't walk away. He spent months painstakingly guiding them until they were all back in the black. Once they were safe, he told them to sell. The lesson was learned. “Dad, I finally got them out of the red,” he said with a sigh of relief. “I will never do that again.”
The boy who was once afraid to ask for a refill had learned a graduate-level lesson in risk, responsibility, and ethics, not in a classroom, but in the real world. That is the power of allowing children the freedom to operate. This entrepreneurial spirit is a mindset that applies far beyond business, as explored in You're Stronger Than You Think w/ Ryan Blair.
This hands-off approach also applies to the fear of failure. After a talk with his son about a homeless person, the boy declared, “I guess I’m glad I’ll never be homeless.” Do immediately challenged him. Why not? The boy assumed he could just take over his father's business. “That’s a big assumption,” Do replied. “That’s an option for you too, if you want to.”
He isn’t sure if he would actually let his children become homeless, but he says, “they need to believe that.” The absence of a safety net forces them to own their decisions, to understand that choices have real and lasting consequences.
Stop the Generational Trauma
The ultimate job of a parent is not to create a perfect child or a flawless life. It is to stop the cycle of inherited trauma. Most parents repeat the patterns of their own upbringing, often unconsciously, even the parts they disliked.
You must become self-aware about these inherited behaviors and beliefs. The rules that governed your parents’ world likely do not apply today. The fear they operated with is not the reality your children face.
The parent who is soft when they need to be hard and hard when they need to be soft is a parent without a clear internal framework. They get upset over spilled milk but let disrespect slide. This happens when you haven't defined your non-negotiables.
Make a short list of what truly matters. Communicate it clearly. And enforce it with consistency. For everything else, let go. Your need to control robs your children of their ability to develop their own decision-making power.
Your job is to create an autonomous, independent, creative human being who is not afraid of the world because they understand how it works. They understand that every decision has a benefit and a consequence, and they are prepared to own both.
You had your shot. Let them have theirs.
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“I'm not trying to win the battle, I'm trying to win the war.”
— Chris Do
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