To Live a Better Life, Ask Better Questions.

Higher-level questions yield a higher-level life.

Artwork by my sister, Kate Faldin.

I’ve heard this before.

In truth, I think it was Tim Ferriss’s book — The Tribe of Mentors — that had this idea. I even used it as the starting point for my first-ever media project, assembling entrepreneurs and asking them questions about life, business, and the meaning of education.

Yet, I’ve never internalized it. Perhaps I was just too young and inexperienced and didn’t have anything to reflect on. It’s not like I have lots to reflect on today — I am still young and inexperienced by all means and standards.

But I realized that I got stuck asking myself the wrong questions.

You live, work, and keep asking yourself the same questions you were 3–4 years ago. That’s called stagnation.

Let me give you an example. For as long as I can remember, I wanted to build a company. It started when I was 10. I lived in Silicon Valley and dreamed of having a company and changing the world, and be like Steve Jobs — my ultimate hero.

When I came of age and dropped out of college, the only question I kept asking myself was ‘How do I set up a business that makes money?’ — as in, makes a living. After several trials and errors, I managed to set up a…