My real learning journey didn’t start in school — it started after.

In most of my school classes, I coasted through, completing the work without much effort, just enough to pass. I just wasn't interested in what the teachers had to say.

But the spark came later — when I started asking my own questions. That’s when learning became alive, personal, and connected to who I wanted to become.

And if there’s one truth I’ve discovered, it’s this: curiosity is the gateway. You don’t stumble into passion or purpose by waiting for lightning to strike. You uncover them by asking better questions.

That’s why I love the 100 Questions Exercise from How to Think Like Leonardo da Vinci. It’s simple, uncomfortable, and powerful — and it might just change the way you see yourself.

How It Works

Grab a notebook (yes, pen and paper works best) and carve out 20–30 minutes. Then:

1. Write 100 questions in one sitting.

• Don’t censor yourself.
• Don’t worry about grammar or repeating ideas.
• Just let curiosity flow.

2. Look for themes.

• After you’ve hit 100, go back and scan your list. What patterns show up? Do your questions orbit around energy? Relationships? Purpose? Work? Fun?

3. Pick your Top 10.

• These are the ones that make your chest tighten, your heart leap, or your mind start racing. Rank them 1–10.

4. Live with them.

• Carry one question into your day, reflect in your Awareness Check-Ins, or journal about them. Sometimes the right question shifts more than the right answer.

Why It Matters

Most of our days run on installed habits — the automatic patterns of drift. That’s fine when they’re aligned. But when drift runs the show, we forget to ask why we’re doing what we’re doing.

Questions cut through the autopilot. They raise awareness, shift prediction scores, and open up new options. And when you consistently ask bigger, deeper questions, you create the conditions for curiosity → passion → purpose to emerge.

My Experience

When I did this exercise, my hand cramped around question 60 and my brain wanted to quit. But pushing through is where the gold is. Around question 80–100, the “surface stuff” drops away and deeper themes start to emerge.

Here are a few of the questions I wrote:

• How can I get people to install 1,000,000 habits?
• Why am I so obsessed with habits?
• How can I raise my energy without defaulting to sugar or caffeine?
• How can I be a good father, husband, and friend?
• What legacy do I want to leave for my daughters?
• How can I build a top 100 app?
• What is happiness — and what does it mean to me?
• What is stopping me from achieving my goals?
• How can I live without regret?
• Who do I want to become?

Looking back, I saw clear clusters:

• Purpose & Legacy — mission, meaning, contribution, the 1,000,000 habit goal.
• Health & Longevity — energy, sleep, anxiety, living to 100.
• Family & Relationships — presence, support, being the dad/husband/friend I want to be.
• Work & Creativity — building apps, writing, community growth.
• Inner Growth — happiness, mindfulness, meaning of life, enlightenment.

Those themes showed me what I was really wrestling with — and gave me a roadmap for which habits to install next.

What You’ll Discover

When you sit down to write, here’s what to expect:

• The Resistance: Your hand will cramp. Your brain will want to quit. Push through. The best questions often come after the wall.
• The Themes: You’ll start noticing clusters — health, money, work, relationships, purpose, growth. Those patterns are your deeper longings speaking up.
• The Roadmap: Once you see the themes, you’ll know where to place your attention. You’ll know which habits matter most.

My Challenge to You

Do the 100 Questions Exercise this week.

• Don’t overthink it.
• Write fast.
• Push past the resistance.

Then, share one or two of your surprising questions (or themes) in the Habits HQ community. Sometimes the most powerful question is the one you didn’t know you needed to ask.

Because curiosity leads to passion. Passion leads to purpose. And it all starts with the questions you dare to write down.