To Live a Better Life, Ask Better Questions.

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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 small agency business where I rented out my time but that brought me enough money to live on and pay the rent.

These days, I have jobs and projects that pay the bills. There’s no need for me to go and build a company that makes a living renting out my timebecause that’s what I am doing already. Yet, almost by inertia, I keep asking myself the same questions as I was 3–4 years ago when that was all that mattered.

What I realized is that by asking myself the wrong questions, I get the wrong answers. I really don’t want to build the type of businesses that make a living (e.g., agency) because they seem small and artificial. It’s not relevant to me anymore. As a result, the answers that I get disappoint me and I don’t move forward.

What I really always wanted was to build a large-scale project or organization. It is something that makes long-term wealth, not merely a living (reminds me of Naval Ravikant who preached: seek wealth, not money or status.). And because I have projects that pay the bills, I have the luxury of asking myself questions of a higher level.

So the question I should be asking myself is, ‘In the next 5 years, how do I set up a process of building long-term wealth?’ Businesses are vehicles for building wealth. Wealth means freedom from having to work. Wealth means equity. Wealth creation means a lot of things that require a change in mindset. The businesses that make a living are not the businesses I want to build.

Higher-level questions yield higher-level answers and, as a result, a higher-level life.

We may often get stuck (mentally) on where we were several years ago. Even though we’ve changed — physically, financially, otherwise — our minds still keep thinking in old terms. That’s what we’re used to, and that’s where we’re comfortable.

Yet the key is to force yourself and upgrade the questions. Seek better (and new!) answers. And use them to upgrade your life.

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