“The Days are Long, but the Years are Short”

Parenting four kids through a pandemic, divorce and much more

⚠️ This post is private so please don't share it on social media

Nothing encapsulates parenting quite like the title of this post, which is a quote from Gretchen Rubin. Especially so when you have three kids. Make that four, with a nephew we’re jointly raising as a sibling. Throw in a global pandemic, a divorce, several venture-backed startups, a nine-person multi-generational household, and I’ve got some stories to tell, along with some hard-earned advice on parenting young kids — much of it in the camp of “what not to do,” along with a bit of what’s worked really well which I've codified into my "Five Rules from Appa" below.

I'll start with what’s worked well since that’s the shorter list. But first, some background.

I’ve got one older daughter, Devina, along with two younger boys, Darián and Dilán. (See what we did with the names there? My name also starts with “D.” Cute, huh?) My nephew Zen rounds out the final tally: One girl and three boys, all under the age of 10 with my youngest just out of diapers, which means I’ll almost certainly be writing another blog post in a decade because the hard part hasn’t even started yet.

I’m a startup CEO in Silicon Valley. Anyone who’s done a venture-backed startup knows that effectively counts as another kid since startups ask for your undivided attention, too.

And just to make it clear that I don’t have it all figured out, there’s the matter of my divorce that I haven’t really announced to the world yet. More on that later in blog post “Part 2” of what hasn’t worked so well.

Let’s dip our toes into the shallow end of the pool.

Parenting Four Kids, Part 1: What’s Worked Well

I love being a dad. I always thought that I would, even though I started relatively late. I was 38 when my daughter was born. I also love having a troop of kids. My “Parenting Operating System” lends itself to allowing my children to run wild in stores such that I get disapproving stares from the other patrons and I’m often approached by the store manager. And yet, in some ways, I’m quite strict with my kids.

I’d describe my parenting style as a mix of encouraging curiosity by pushing social norms and boundaries while maniacally enforcing a small number of important rules.

So here's my "Parenting OS" – Appa's Five Parenting Rules:

Rule #1: Experiences start with yes. Make yourself justify no.

If you only pick up one thing from this post, let this be it. Appa's golden parenting rule.

Often as parents we tell our kids “no.” Don’t touch that. Don’t go there. Don’t say that. We follow them around to make sure they don’t break something, or draw on that wall, spill that food, or fall on that crack. We are worried and protective.

But what are we protecting them from? In our attempt to be responsible parents we are protecting them from having new experiences. And discovering the world, the richness of how it works, and how they can fit into it is the very essence of childhood. I see parents all around me shielding their kids from having experiences that could teach them a new skill, a new boundary, even a valuable life lesson.

I always start with yes when it comes to my kids having an experience. When I’m faced with a yes/no decision, my first question to myself is “What’s the worst that could happen?”

If there’s a real & present danger to the child or the surroundings, then my next question is “How can I ameliorate the danger so I can stay at a “yes”?

This might mean I put those glass bottles up on the countertop so the kids can’t knock them over. But I always attempt not to just say “no, you can’t go over there.”

Even if there’s some level of risk to the child, I’ll likely still let them explore on a much longer leash than other parents I see give their kids because I’m weighing the risk with the value of the new experience for my child.

This is why my kids get to run around in stores, play in the clothes racks, and try things on, often giggling the entire time. What’s the worst that can happen? Nobody’s going to die, and if they make a mess, it’s a great learning opportunity for the kids to also have the experience of picking up after themselves so they can be more responsible in their fun next time.

Repeat this 1,000 times over many years, and I firmly believe you’ll end up with adventurous, curious, and responsible kids as they grow up.

Another reason parents often say “no” is because it’s often just easier than saying “yes”.

I vividly remember pulling up to a gas station when my daughter was about a year old. She wanted to pump gas with me. It would’ve been so easy for me to say no. I’d have to take her out of her car seat just for a few minutes, then go through the reverse process of getting her put back in. Plus, the pump is dirty — I’d have to wash her hands. So many reasons to say no.

But I have this life rule, and I couldn’t justify a “no,” so I pulled her out, had her punch the buttons on the gas pump, and showed her how the gas nozzle worked. She was fascinated and proud to have helped me “feed the car”, and that moment really reinforced why I have this rule.

Corollaries to this rule:

• When eating, I have my kids try tasting everything at least once. No exceptions. I find that kids who are picky eaters are often that way because they get to dictate the limited palate of food put in front of them. If my kids try it and they don’t like it, they don’t have to eat more than a bite. But they always try a bite of whatever flavors are at the dinner table.
• And related to that: If they don’t like what’s being served at mealtime, they can make themselves something else, but they’re responsible for cooking it, and for cleanup. My kids like to translate this into “you get what you get, and you don’t get upset.”

Rule #2: I can’t is not in our vocabulary

With new experiences come plenty of challenges, and it’s easy for kids to say they can’t do something — often before even trying to do it. I don’t let them say that. What they can say is “I don’t know if I can do it, but I’ll try.” I always have them try. They often surprise themselves with abilities they didn’t know they had. And if they try but fail, I’ll show them how to do it; often with us doing it together.

Corollaries to this rule:

• Whenever possible, don’t do it for them. (See rule #1: Starting with “yes” means the kids are the ones having the experiences, even if it’s easier for you to just do it for them instead.) What I often see is a kid asking for something, like “Can I have a glass of water?” And the parent gets it for them. But in our household, we’ve put stepstools in the kitchen and a water jug at kids’ height so they can get their own glasses of water. Similarly, in restaurants, if they want something (say, a condiment like ketchup), I have them ask the server for it. My three-year-old, who loves drinking the thimble-sized half-and-half containers, has become a pro at asking for those by the bowl-full.
• And in teaching my kids to have these interactions, we always practice saying “please” and “thank you” to those helping them.

Rule #3: A “no” stays a “no”

This is a big one. I see parents often giving in to kids if the kids are persistent enough, and this creates a pretty strong incentive for kids to double down on their influence campaigns and for parents to throw their hands up in the air and eventually give in — often causing conflict between the parents in the process. I’m very firm in sidestepping this dynamic entirely: When I tell the kids “no,” it stays as a “no” unless I independently decide otherwise, no matter how much pressure the kids apply. This means if I say “no” to buying something in a store (and I usually do), that will never turn into a “yes” if the kids keep asking.

Corollaries to this rule:

• Parents maintain a united front. Even if I disagree with the way mom is parenting, I always try to have a united front with the kids and then discuss it later. Kids have a knack for exposing deeply rooted differences in parenting philosophies among the adults, and as the kids get older, those parenting gaps will become leveraged as the kids learn to push boundaries.
• Enforce consequences. I define the difference between a “consequence” and a “punishment” to be that a child has advance notice of a consequence. I tell the kids “If you do [x] then [y] will happen,” and I enforce that. For example: I told my kids one night that if they got ready for bed quickly enough, they could listen to a bedtime podcast. However, they took their time getting ready, playing and dilly-dallying, and so after a while, I told them they’d have to go straight to bed and we could try again the next night. They objected loudly, but the “no” stayed a “no,” and in the process, I was enforcing the consequence I’d warned them about.

Rule #4: All for one, and one for all

I teach my kids that we’re all in it together. This means they share everything — no toy or thing in the house “belongs” to any one child. They also share experiences (to the extent possible based on the age range), and they face the consequences together as well. If one child takes too long to get ready for bed, like in the example above, none of them get to listen to the bedtime podcast. This approach really solidifies that we are a family unit and that they are all siblings that have to look after each other.

Corollaries to this rule:

• Untangling conflict: With younger kids, conflict usually happens over some physical item, like a toy. I always have the kids face each other and put the item in question down in front of them — nobody gets to “hold” the item that’s causing the conflict. They have to work through the conflict and make a plan together about who gets the item first and for how long before they can pick it back up.
• Ask before interrupting: When I’m talking to an adult, and one of my kids interrupts, I tell them that I’m having a conversation with the other adult and if they need to interrupt, they can ask for permission. When they ask for permission to interrupt, I’ll gauge how urgent the request is. Nine times out of ten, I’ll tell them, “let me finish this conversation first.” I’ll look for the first available break in the conversation flow with the adult and always come back to the child. This teaches them to observe and understand that other conversations are happening and how to handle them. It’s also a valuable life skill for them to learn with each other.

Rule #5: Share your feelings: “What was the impact on you?”

I encourage my kids to share the impact on them when a sibling does something to upset them, instead of letting them get alway with the “it’s all your fault” or “look what you did” tendencies kids typically have. I’ve seen my nine-year-old daughter grit her teeth and say to a younger brother “I get so frustrated when you do [xyz]” and I smile inside, knowing that her learning to express her feelings is a step towards her learning Clean Communication as she gets older.

Clean Communication is not just for kids. Here's a PDF for adults to use too. We've even made it one of our core values at Storytell.

That’s pretty much it for my “Parenting OS” — a simple, tight set of five rules that I really work to live by consistently and which create the space for my kids to have rich experiences loaded with learnings and life lessons to craft a curious, independent, adventurous, loving and respectful approach to life.

Corollary to "Appa's 5 Rules":

• Tell your kids you love them often. Sometimes it helps to remember that although the days are long, the years are short, and by the time they leave the house, you’ll have spent the vast majority of the time you’ll ever spend with them throughout their entire lives. So give them that extra snuggle at night when you’re putting them to bed.

A few more “pro-tips” that aren’t rules exactly, but I highly recommend:

• HUGE pro-tip for getting your kids to open up and talk to you: If you've ever asked your kids How did school go today? and gotten a fine, dad type of response, this tip is for you:
  • Ask them specific – not general – questions. It's incredible how well this works. Instead of asking "how did school go today?" ask questions like:
    • Who walked backward in school today?
    • Who did something with the color yellow today?
    • Who high-fived someone today?
• Who farted in class today?
• For older kids: Who heard some gossip today?
• Whatever the age-appropriate specific questions are – try those. The more specific the better. You'll be amazed by how they brighten up and open up with fun and engaging answers.
• Baby sign language: If you do this starting several months in, by the time your baby is 6-8 months old, they’ll be starting to sign things they won’t be able to verbalize for another 6-12 months. It’s helpful for all involved that your baby can tell you when they are tired, want water, want a bath, etc.
• Speak with your kids only in a second language: This requires a lot of commitment because it has to be an “all or nothing” approach if you want it to stick. If you only sometimes speak with your kids in a second language, they’ll default to their primary language as they start to interact with the world. I only speak in Spanish with my kids, which often means I have to teach them vocabulary sentence by sentence multiple times every day, especially when they’re younger. If you’re ready to sign up for that level of commitment, you’ll appreciate having put the work in when it starts to pay off, but it’ll take years of uncompromising effort.
• Digital devices are for “creating,” not just “consuming”: My kids’ screen time is tightly regulated for “consuming” activities like watching a show (which they also have to do in Spanish). But if they are “creating” with the device (taking photos, learning to draw, playing chess, etc), I’m much more liberal with how much time they can spend on it.
• Be an Adventure dad: I love creating as many unique experiences for my kids as I can. More on that in my #Vanlife resource.

Lastly, to preface "Part 2: What didn’t work out so well", which I’ll write in a future post: I formulated much of this “Parenting OS” over almost 20 years of partnership with my ex-wife Sue. In some ways, our parenting styles are very aligned, and in some ways, they aren’t, but what I can say for sure is that I’ve never doubted her dedication to our kids, and without her influence, I know that my parenting style wouldn’t be as well formed as it is today.