A white background with a few lines on it

Raising Curious Kids: Why I Always Answer ‘Why?’ (Even When It’s Annoying)

AJ Oberlender • December 9, 2024

How answering endless “whys” can nurture curiosity, critical thinking, and lifelong learning in your kids.

A little girl is thinking with her hand on her chin.

Parenting means living in a constant stream of questions. “Why is the sky blue?” “Why do we need socks?” “Why can’t I have candy for breakfast?” (To be fair, an excellent question.) If you’ve ever faced an inquisitive toddler, you know how quickly those ‘whys’ can pile up. But in my house, there’s a rule: no matter how tired I am—or how ridiculous the question may seem—I always answer.


Why? Because every “why” is a gateway to curiosity, critical thinking, and learning. And because of something I learned while working at Apple: the phrase “I don’t know, let’s find out.”


Lessons from Apple and Endless Toddler Questions


At Apple, one of the biggest takeaways wasn’t just about technology or customer service. It was the power of admitting when you don’t know something—and using that moment as a starting point for discovery. I brought that philosophy home, and it’s become a cornerstone of how I parent. When Yael asks me a tough question (like why some birds don’t fly), my response is, “I don’t know, let’s find out.” We grab a book, hop online, or just start brainstorming together.


This simple shift teaches her that not knowing isn’t a failure—it’s an invitation to explore. That curiosity? It’s like a muscle. The more she exercises it, the stronger it gets. And I’m her first personal trainer in this gym of endless questions.


Flipping the Script: “Because” Isn’t an Answer


One of my favorite strategies for handling Yael’s avalanche of “whys” is flipping the question back on her. I’ll ask, “What do you think?” or “Why do you think that happens?” At first, this was just a way to buy myself time when I had no idea what to say. But over time, it’s become something bigger: a way to show her that because isn’t the end of the story—it’s the beginning.


Apparently, it stuck. One day, Mazi (my wife) tried to wrap up one of Yael’s spiraling questions with a casual “because.” Yael shot back, “Mommy, that’s not an answer. That’s the beginning of an answer.” I mean, come on—that’s parenting gold.


Moments like that remind me why I lean into these questions, even when I’m running on fumes. When I teach her that answers aren’t just handed to you, but something you actively seek, I’m helping her build a mindset she can carry through life.


Curiosity is Exhausting—But Totally Worth It


Let’s be real: there are times when answering “why” for the hundredth time before breakfast makes me want to run out the door. Between raising two kids (shoutout to my newborn, Diana, for those sleepless nights) and managing work, the mental energy it takes to keep up with Yael’s questions can be… a lot.


But here’s the thing: fostering curiosity is one of the best gifts we can give our kids. Studies show that curious children grow into better problem solvers, stronger communicators, and more empathetic adults. And while I may not always have the patience in the moment, I remind myself: every question she asks is shaping her future.


Tips for Tackling the Toddler Inquisition


If you’re living in the world of endless “whys,” here’s what works for me:

  1. Use “I Don’t Know, Let’s Find Out”: It’s okay not to have all the answers. Show them how to research and problem-solve together.
  2. Flip the Question: When you ask them what they think, it encourages creativity—and gives you a breather.
  3. Set Limits (Gently): Sometimes, a quick, “Let’s save that one for later” can help manage the flow without shutting them down.
  4. Keep Answers Simple: You don’t need a dissertation on aerodynamics to explain why planes fly. Give them just enough to spark their curiosity.


Raising Problem Solvers, One “Why” at a Time


As someone who balances fatherhood, work at DoorLoop, and my branding business, I’ve realized that answering “why” isn’t just about parenting—it’s about leadership. Whether at home or in business, the willingness to ask questions, admit you don’t know, and dig for answers is a superpower. It’s what drives innovation, builds trust, and keeps us connected.


So yeah, it’s exhausting to answer every “why.” But I’ll keep doing it, because every question is a chance to teach my kids that learning never stops—and that because is just the beginning.


Have a favorite “why” moment with your kids? Drop it in the comments—I’d love to hear how you’re fostering curiosity in your home!

A woman is sitting on a desk in a lotus position with headphones on.
By AJ Oberlender July 23, 2025
Discover why authentic personal branding beats AI-generated content every time. Learn the 70/30 rule for using AI tools while keeping your unique voice and personality that connects with your audience.
A man with a beard and glasses is smiling in front of a pink background.
By AJ Oberlender July 13, 2025
A web designer's honest experiment with AI website builders. Discover what AI gets right, where it fails spectacularly, and why human creativity still matters in web design. Plus, why the "human in the loop" approach might be the future.
A woman is standing behind a counter in a restaurant holding a computer monitor.
By AJ Oberlender July 5, 2025
Discover how hospitality-inspired employee treatment delivers 300% ROI and 40% less turnover. From Ritz-Carlton secrets to Southwest Airlines success, learn the VIP strategies transforming workplace culture and employee engagement.
A man is holding a baby and two little girls on a sidewalk.
By AJ Oberlender June 27, 2025
Raising bold, compassionate, and fearless kids in today's world. A personal reflection on teaching my daughters the true meaning of chutzpah - not just being pushy, but having the audacity to care and the courage to make things better.
A little girl is sitting on a boat in front of a dolphins banner.
By AJ Oberlender June 17, 2025
Discover why sports fans spend 306% more than regular customers and how businesses like Apple, Netflix, and Patagonia are creating fanatic-level brand loyalty. Learn the psychology and strategies behind building devoted brand communities.
By AJ Oberlender June 12, 2025
Discover how the ancient Shema prayer became our secret weapon for meaningful bedtime connection. A Miami dad's guide to blending spirituality and modern parenting for better sleep and stronger family bonds.
A man wearing glasses and a hat is standing with his arms crossed.
By AJ Oberlender May 26, 2025
Discover the Story-Driven Contrast Method to build an authentic personal brand that cuts through the noise. Real strategies for entrepreneurs who refuse to sound like everyone else.
A close up of a dollar bill 's eye.
By AJ Oberlender May 22, 2025
Stop hiding behind generic marketing speak. Learn how to reverse engineer your best client wins into a compelling value proposition that actually converts browsers into buyers.
A row of buildings lit up at night with palm trees in front of them.
By AJ Oberlender May 13, 2025
Exploring the vibrant culture that inspires creativity and hustle. From Brickell to Little Havana, discover how Miami's unique energy creates the perfect storm for innovation and breakthrough thinking.
A collage of pictures shows a man holding a child
By AJ Oberlender May 5, 2025
A tribute to my dad, Brian Oberlender—VP, mentor, and morning coffee buddy. Lessons in grit, failure, and why being human is stronger than being a hero.
Show More