Raise your learning ceiling by asking 100 better questions today

Medium - Requires some preparation Recommended

You sit down with a warm mug that’s already cooling, open a blank page, and write the first question that pops up. It feels basic, even silly. Then another arrives, and another, until the page starts to fill in clumps—work, health, money, meaning. Your phone buzzes, but you let it ride. At question thirty, you notice a pattern: you keep asking about energy. Why it dips, how to protect it, what fuels it. You might be wrong about the cause, but the theme is loud.

At fifty, you stop reaching for perfect questions. Quantity loosens you up. “How do I reduce meetings by 30%?” sits next to “What music makes me write faster?” and “Who is a quiet mentor I’m overlooking?” The mix is the point. Your brain loves novelty plus relevance, and when you let curiosity off leash, it delivers both. A memory flashes: last Tuesday, you solved a thorny task in twenty minutes after a short walk. That’s a clue.

By the time you hit one hundred, the page looks like a topographic map of your life. You circle energy, time, and creative output. You star the question, “What’s one 30‑minute daily ritual that would change everything this month?” The answer won’t come by thinking harder. It will come from testing. So you choose tonight’s micro‑experiment: a 20‑minute Spanish video with 10 minutes of mimicry, because learning lights you up.

Seven days later, you flip back through your sprint and notice your questions are sharper. You ask more how and what, less why me. You’ve shipped two experiments and collected real data. Curiosity turned a foggy concern into a concrete plan. That is the quiet magic: unanswered questions become maps when you put them on paper and commit to testing.

This practice draws on the psychology of question‑storming, growth mindset, and deliberate practice. Questions focus attention, attention drives learning, and small tests create feedback loops. By batching many questions and then selecting a few to test, you harness divergent and convergent thinking in one sitting, which accelerates insight and behavior change.

Grab your notebook and set a 25‑minute timer. Push out 100 questions without judging them and let repeats happen, because repeats point to themes. When time’s up, cluster similar questions and star the top ten that matter most right now. Pick one and design a 30‑minute micro‑experiment you can run tonight, like trying a new study method or a different bedtime routine. Put a weekly review on your calendar to add five new questions and one new test, so your curiosity keeps evolving from ink on a page into evidence in your day. Give it a try tonight.

What You'll Achieve

Shift from vague worry to focused exploration, feel more engaged and energized, and produce measurable progress through weekly experiments that answer your most important questions.

Run a 100‑question curiosity sprint

1

Set a 25‑minute timer

Open a notebook and promise yourself zero judgment. Your job is quantity, not quality. This time box lowers pressure and gets you moving.

2

Write 100 questions nonstop

Mix life, work, and wonder. Include tiny questions (What energizes me at 3 p.m.?) and big ones (What is my purpose?). Rephrase repeats—they reveal themes.

3

Cluster and star your top ten

Circle recurring ideas, then choose ten that feel most alive. Put a star by the one you want to explore this week.

4

Schedule one micro‑experiment

Pick a top question and design a 30‑minute test. Example: If asking “How can I learn Spanish faster?”, try a 20‑minute immersion video plus a 10‑minute mimic session tonight.

5

Review weekly

Each week, add five new questions and one new experiment. Watch how the themes evolve and sharpen.

Reflection Questions

  • Which questions keep repeating across different parts of my life?
  • What 30‑minute test could turn my top question into data?
  • When during the week am I most naturally curious? How can I protect that time?
  • What did last week’s experiment actually change?
  • Who can be a sounding board for my next sprint?

Personalization Tips

  • Career: If you’re stuck on growth, list 100 ways your role could add value beyond your job description and pilot one tiny idea with a teammate.
  • Health: Ask 100 questions about sleep and test one variable (light, caffeine timing, wind‑down ritual) for three nights.
  • Parenting: Co‑create 25 questions with your child before a museum visit, then hunt answers together.
How to Think Like Leonardo da Vinci: Seven Steps to Genius Every Day
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How to Think Like Leonardo da Vinci: Seven Steps to Genius Every Day

Michael J. Gelb 1998
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