How to raise happy and entrepreneurial children — perspectives from a Silicon Valley CEO
Most of my friends are ambitious Type A personalities and they have all learned to successfully navigate their professional life. A curveball is thrown when children enter the picture and one has to learn a whole new set of parenting skills. This blog post shares what I have learned from raising young children through trial and error, successes and failures, and adapting my past experiences to what I now consider to be parenting best practices.
As a bit of background, I have been blessed by going through some of the best leadership training in the world. First in the Marine Corps Officer program, then the Army Special Forces, then two years at Harvard Business School, and later through mentorship programs such as the Presidential Leadership Scholars and Y Combinator.
In total, these programs provided years of training and even more years of putting leadership theories into practice while serving as a commander leading troops in combat and then as a CEO/founder of two startups (CarDash and RallyPoint).
I am now a father of a 2, 4, and 6 year old and one of my most important jobs is to be a leader within my own family. While none of my training directly prepared me for fatherhood, I certainly try to tap into my experiences to be the best father I can be.
I focus on teaching my children resourcefulness, initiative, self confidence, integrity, and resiliency. This complement’s my wife’s values and her emphasis on compassion, gratitude, and team work.
This focus has led to some incredible results in our young children and other parents have asked me to share my approach. The following are 8 tips for anybody who wishes to emphasize these values in raising happy children.
1. Never say “because I said so”
This is a conversation many parents can relate to:
Parent: “Time to brush your teeth”
Child: “Why?”
Parent: “So you don’t get cavities”
Child: “Why?”
(Tired) Parent: “Because I said so”
What conversations like the above teach our children is there is a hard limit to understanding the world and why we do things. Children can ask close to 400 questions per day, so it’s understandable that a parent loses patience and reverts to the nuclear “because I said so” option. It is nuclear because it ends the conversation and also because it kills the child’s curiosity.
If after asking “why” three times a parent always answers “because I said so” then the child is trained to end their curiosity at two levels of depth. It generally discourages them from asking “too many” questions and ultimately understanding the fundamental truths around them.
As adults most of us have have long stopped asking why things are the way they are. Many men wear a neck tie at some point, yet how many men ever stopped to ask why we wear completely useless and non-functional strips of fabric around our neck? Maybe we should wear ties, but shouldn’t we also understand why we do it?
Adults routinely do things without knowing why, mostly because other people have done it and we never bothered to question it. Other people see us do things and then they do it. We mimic each other without questioning, which creates a ripple effect on society ranging from innocuous fashion trends to disastrous economic bubbles and crashes.
Part of the reason adults have largely lost the mental muscle of curiosity is that children are implicitly, and sometimes explicitly, discouraged from asking why too many times.
So encourage your children to celebrate their curiosity. Here is the above example in our house:
Parent: “Time to brush your teeth”
Child: “Why?”
Parent: “So you don’t get cavities”
Child: “Why?”
Parent: “So your teeth are healthy”
Child: “Why?”
Parent: “So you can be overall healthy and not have any medical problems”
Child: “Why?”
Parent: “So you can be happy”
Child: “Why?”
Parent: “Because being happy is important in life”
Child: “Why?”
Parent: “Pursuing happiness is part of human nature, but why that is the case is a good question and I don’t have a great answer for you. Maybe that is something you will be able to answer for your children when you grow up.”
Child: Nods in understanding and ponders the answer.
Often a “why” eventually can’t be answered because we don’t know the answer to it. When this happens, marvel in the mystery that the child unlocked in your life and share in that curiosity with them. Other times it forces us to come face to face with our most fundamental beliefs, which can be a teaching moment for both ourselves and our children. Both are good outcomes.
Encourage your children to ask why. Don’t shut the door on their curiosity.
2. Let them solve their own problems
“Daddy, Ethan hit me!” — Sarah comes into the kitchen to tell me.
At some point in the past one of our kids hit the other and an adult must have interjected, likely admonishing the offending toddler to the great satisfaction of the whistleblower. The child who was hit has learned that if they go to their parent they can expect a reaction and a satisfying outcome, likely in the form of a time out sentenced on the offending toddler.
While each of these interactions are small in isolation, it is important that children don’t develop an instinct of going to an adult to solve every small challenge they face throughout the day. Having your smaller 4 year old brother take your lego or having your bigger 6 year old sister hit you is something our children should be able to at least try to handle themselves, even if that attempt fails and turns into a learning opportunity.
So now if one of our children comes to us with a “Daddy, my brother hit me”, my response is “Did you defend yourself? What did you do about it?”
Upon asking this question, you can see the gears turning in their head thinking “oh, I could have tried to do something about it myself.” I then try to talk through the situation and encourage her to deal with the problem directly next time. This typically includes first physically defending herself, explaining to her brother how he made her feel, and asking for an apology.
For anyone who grew up with a sibling near in age, you know this often degenerates into wrestling and one-upmanship, but I much rather have that and to cultivate an instinct of solving your own problems instead of running to someone else. Plus sometimes they actually can work it out through conversation and understanding. Learning to defend yourself physically and emotionally is pretty valuable too.
Teach them to solve their own problems, even if the solution is not as optimized as what your decades of experience can solve for them.
Caveat: Of course we want children to report to adults if something serious happens, but those should be the exceptions not the rule. It’s important those differences are explained and discussed.
3. Get back up and keep going
From the day that children learn to walk, they also learn to fall. Next time you see a child fall, pay special attention to how the caretaker reacts.
The worried parent shows immense concern on her face and rushes to pick up the child, likely just in time as the child emotionally loses it and begins crying out of control.
The deliberate parent intentionally does not pay attention to the fall and acts as though nothing happened (preferably not even looking at the child). The child will typically just get back up, look around, and keep going with no drama.
So what’s the difference between these two children? What’s happening is that the child’s emotional state reflects the parent’s emotional state. Children learn to mimic their parents for nearly everything, so a worried parent begets a worried child. A calm parent begets a calm child.
If you fall and your caretaker gives you a distraught look like a disaster just happened, a child will naturally become very concerned. Toddlers are not equipped to emotionally handle this and begin to cry. The worried parent then comes to comfort them, thereby rewarding their crying and reinforcing the cycle.
When at the park, I’ve seen many kids fall and lay crying waiting for somebody to come make them feel better. My children (usually!) get back up as though nothing happened. After all, nothing really did happen. No bones broke. No muscles were torn. You just get back up and keep going. What’s the trick? Teaching them to get back up and keep going — before they fall.
“Get back up and keep going” is something I have taught my children since before they could talk. Initially it was my motto any time they were likely to fall, and it took on a more strategic purpose. We take many falls in life. Initially it’s just falling off a bike, but later it becomes more symbolic falls like academic failures, losses in competitions, and social challenges.
My children know that if they fall they must “get back up and keep going” — if they fall during the day they proudly tell me at night “Daddy, I fell today but I got up and kept going!” We then exchange big smiles and a high five. I show more excitement and pride when they back up and keep going versus if they don’t fall at all. They’ve learned that “get back up and keep going” is what their father considers success and they are eager to succeed.
Instilling this before accidents happen is crucial. When teaching them how to ride their bike, I ask them in advance “if you fall, what will you do?” — “I’ll get back up and keep going” they tell me. I asked this every time they got on a bike for the first year. Mentally rehearsing in advance for this inevitable scenario prepared them well, like an athlete mentally preparing for what may happen in a competition.
There will be many days in my children’s lives when their failures will be much more painful than scraping a knee. Long after I’m gone, I hope an inner voice will reverberate for them “just get back up and keep going.”
4. Infuse leadership into everyday life
My favorite topic to work on with my children is leadership. From before they could talk, I introduced the concept of leadership to them.
Not finding any satisfactory books on leadership for toddlers, I wrote a little book/pamphlet called “Leaders Make The World A Better Place” featuring my three kids. The book follows their day through different scenarios; from getting dressed, to playing at the park, to eating dinner, and in each scenario a child leader helps the group make a decision and overcome obstacles. Through these vignettes I began introducing the concept of leadership to our children.
Infusing leadership concepts is not a one time training event or even a scheduled series of events. After the basic concept is introduced, it is a continuous series of many small teachings that are integrated into every day life. The following are some examples:
- Leaders tend to lead from the front. When we walk in a group, we verbally designate a leader within the family. Sometimes it’s me, sometimes it’s my wife, and often it’s one of the kids — depending on our surroundings. What’s important is that there is self-awareness that there is a leader and what the leader is doing. I ask “ok, who wants to be the leader?” and the kids maneuver their way to the front of the group and say “I want to be the leader!” To settle sibling rivalry, we often have to rotate leaders every few minutes so everyone gets a chance. This creates a great sense of self-confidence and purpose, and while this form of leadership is basic, it is building habits that forms the leader’s mind.
- The leadership directive that humans can most easily understand is “follow me” — a variation of the most instinctive and natural form of leadership “do as I do.” When one of the kids is leading our group or he wants to pull me into the back yard to show me his latest mischief, he knows the only way I will budge is if he leads me there with a “follow me” command. “Hey daddy, I want to show you something. Follow me!” And off he goes running. I oblige and reinforce his sense of leadership accomplishment. In this way, they learn that leading by example is an effective tool and it’s something they can practice with anyone anywhere.
- As with most parents, I’ve taught Sarah to look both ways when crossing the street. I also use this little interaction to put leadership training into practice. When we are biking or walking together and reach a crossing, I ask “Ok Sarah, how about you lead us across?” It gives me such great pride when she replies “Ok daddy, I’ll take the lead here.” She then gets up to the intersection, looks both ways, and tells me when it’s safe to cross. She says “It’s safe to cross. Follow me!” — While I am naturally also checking traffic to safeguard, as far as Sarah is concerned, she is the leader, evaluating traffic and directing others to follow her when she deems it safe to cross. At first this was difficult for her, but over time taking this sort of initiative has become second nature and I don’t even have to ask.
- Leaders ensure the well being of others before themselves. Leaders eat last. On a recent picnic, we had one dessert item for each member of the family. So I asked “who wants to be the dessert leader?” — instinctively all the kids raised their hands because they’ve cultivated an instinct to be in a leadership position. I selected one of the kids and handed him all the cupcakes and the conversation went like this:
- Parent: “Ok, you’re the dessert leader. Who will get dessert first?”
- Child: “Me!”
- Parent: “Really? Do leaders take care of themselves or others first?”
- Child: “Umm… others!”
- Parent: “That’s right. So who what will be the order of the dessert?”
- Child: “First Jacob, then Sarah, then Daddy, and finally me!”
- Parent: “Great job. You’re being a good leader.”
Keep in mind this child is only 4 years old and he is already learning key principles of leadership. Such a practice can and should come at every opportunity, from crossing the street to eating cup cakes. It may not seem like much, but when combined with dozens of other similar acts every day, a great deal of leadership instincts and habits are formed.
5. Establish and post your family values
Some particularly well organized families come up with family mission statements, plans, and objectives, similar as one does for a business. It helps ensure the parents are on the same page and putting one’s ideas on paper is always a good exercise to flush out priorities.
As part of this process, families may come up with the family values that they want to promote and adhere to. I think it’s important that these are posted in the house and well understood by everyone.
This doesn’t have to be a complicated exercise though. We found an off-the-shelf canvas which was already well aligned with our values, thereby saving me an arts and crafts project of creating my own.
We keep the above next to the kitchen table where the kids sit every day. While we don’t make them recite it in some militaristic fashion, I have no doubt that seeing the posted values day after day does have some influence. It’s helpful even for myself and my wife to read from time to time to re-center ourselves.
6. Let them earn their rewards
My daughter was whining that “mommy never gets me what I want” when my wife refused to buy her a stuffed animal she wanted. This felt like a trap. A response along the line of “you already have enough stuffed animals” is hardly satisfying to a young child. There is also no intellectually satisfying answer of why 3 or 7 or 20 is the magic number for stuffed animal ownership levels. Additionally, the empathetic response promoted by most parenting manuals along the line of “I understand you want another stuffed animal but we just can’t (or won’t) get one right now” is equally unsatisfying as the child may interpret that to mean mommy doesn’t care enough about her needs and wants.
As adults, we also wouldn’t like any of these reasons given to us if we wanted to acquire something, so why should we say that to our kids? It doesn’t answer the why.
Instead, I took this opportunity to inject an important life lessons and responded with “Sarah, none of us get what we just want in life. We only get what we earn.” I then went online and ordered play money and had it at the house the next day. My wife and I formalized our chore calendar for the kids and each of our kids is now rewarded $5/week in play money if they complete their chores. They can exchange their play money for real money from the Bank of Weiss when making a purchase.
Not completing chores leads to a deduction in the weekly stipend. Misbehavior can also reduce the payout. Conversely, doing extra work around the house can lead to a bonus. Just like the real world.
Some may say this is teaching children materialism too early, but I think it’s the opposite. The children already want those stuffed animals, toy cars, and robot arms. We are hardly teaching them any material desire. We are just teaching them that one has to earn what they get and forces them to re-consider if they really want it that much.
This also teaches them that getting what they want is the result of effort, and not the type of “nag mommy and daddy enough until they give in” type of effort, which is the perverse skill set most children learn to master.
Side note: I also contemplated how to come up with the pay schedule. My first thought was to do it based on age, with increased pay as one gets older assuming that one can do more complicated tasks with age. I then realized that would be teaching a quasi socialist incentive structure where tenure superseded merit. So instead the stipend is determined by every child’s ability and effort and nothing more. An incredibly important lesson to learn early in life in a land of opportunity.
7. Teach them a contact sport
Life is a contact sport, at least emotionally. For children, it’s also often physical. A child in 1st grade may be going to school with somebody nearly twice their size in 5th grade. I believe that to be self confident emotionally, one also has to be self confident physically.
For a child this means being fit, reasonably athletic, coordinated, and able to stand up for themselves.
Team sports bring the benefit of teamwork and social skills, which are important and should be integrated in the child’s life. Individual contact sports, however, further develop qualities one cannot easily attain when they are just one person on an eleven member soccer team.
Individual sports, and especially contact sports, puts the child at the center of attention and emphasizes the need for discipline, setting goals, overcoming personal challenges, and mentally mastering one’s own body.
This doesn’t mean we are raising our kids to become olympic athletes, but being athletic, coordinated, and physically self confident are characteristics I want to promote in our children.
Most pre-schools and elementary schools in the United States already emphasize team sports and team activities, given how important they are for social development and practical limitations of teacher-to-student ratios. While there are many benefits to team sports and they should be encouraged, it may be difficult for team sports to offer a child the same level of discipline and focus that one gets from an individual sport.
If there isn’t a good outlet to learn a contact sport in your area, or if the child has other needs that won’t allow it, consider any individual sport. I am just biased for a contact sport because any child can learn it whereas handing a tennis racquet to a toddler may not get you as far.
8. Give them more responsibility — and watch from afar
One area that has consistently surprised me as a father is how clever, mature, and insightful kids can be. The more I approach them with “adult logic” the more I am pleasantly surprised how much they rise to the occasion.
As a general rule of thumb, I look for ways to give my children a sense of responsibility, safeguard from afar, and see how much they accomplish.
These are not grandiose experiments, but rather every day moments which I put into action. One example is our use of a fireplace.
We have a working indoor fireplace and an outdoor fire pit that we put to use in the winter. At first, there was some concern about letting the children near the fire, but after introducing them to the safety measures needed, they showed great curiosity and responsibility. We discussed how fires work, why some things burn and some don’t, why a little bit of blowing on fire creates stronger fires while a lot of blowing can put it out. We discussed how to arrange the wood and how kindling works. After showing them how to light fire with a lighter, we moved on to using a magnesium and flint sparker to ignite our fires. They absorbed and understood this remarkably well.
The above pictures may scare some parents, but that need not be the case. When properly introduced, and with proper supervision, kids can step up in gradual responsibility.
Once the kids understood how fires worked, I always put one in charge. Of course I was still there to watch, but the child “in charge” felt responsible and would repeat the importance of fire discipline to the others.
Whether supervising a fireplace, a younger sibling, or a setting a dinner table — try putting your child in charge and safeguard from afar. Just remember to do it in small steps if this is new to them!
Happiness is a frame of mind
Neither bigger kitchens, nor newer cars, nor fancy vacations bring lasting happiness. They may all bring temporary joy, but that joy is quickly metabolized and the mind will need an even bigger joy to feel the same way again. Happiness comes from living in the present loving what you have and who you are.
Whatever situation you find yourself in, strive to be happy with the present.
We should all be grateful for the gifts we have — in the moment — to enjoy.
