One of the most important lessons I’ve learned from reading books, interviewing smart people, and having conversations with my mentors is that questions are more important than answers.

But that goes against everything you learn in school where you’re rewarded for the quality of your answers.

However, that’s not what you should judge a person on. Instead, look at the quality of a person’s questions, like Voltaire famously said:

“Judge a man by his questions rather than his answers.”

And one of my friends who’s a consultant at one of the big three management consultancies, once told me that, “my job is to be ignorant.” He was referring to Peter Drucker, arguably one of the greatest management consultants of all time, who said:

“My greatest strength as a consultant is to be ignorant and ask a few questions.”

The right question at the right time can spark the right answer that changes your life. Not just first date questions, I’ve experienced that myself over the last few years.

And I’ve formed a habit of asking myself questions all the time. In this article, I want to share 15 questions across four areas that have the potential to change everything about what you do. Let’s get started.

Life In General

Let’s start with a few yes/no questions to assess how you feel. Like all the questions in this article, I answer them in my journal. I have simply made a note in my note-taking app with these 21 questions.

A few times a month, I open the note and look at the questions (I have added the note to my shortcuts in Evernote so I’m frequently reminded by the questions). I randomly answer a few at a time. I challenge you to use it in the same way. But you can also answer everything chronologically if you prefer.

1. Am I happy?
2. Am I grateful?
3. Do I like my job?
4. Do I feel good?
5. Do I spend enough time on my education?

The reason why these quick questions are important is that you want to adjust your strategy if you answer no to any one of them.

Often, we go through life unhappy, ungrateful, and feeling bad for way too long. If something is wrong in your life, acknowledge it quickly, and then find a solution.

These questions are not only about yourself. When you’re happy and in a good mood, you can lift the spirits of the people in your life. That’s why I focus on fixing my own happiness first. Otherwise, you can’t make your spouse, family, or others happy.

See those first five questions as a quick assessment. Be honest. There’s no one to impress. Think about how you feel.

Recently I read a comment from someone who said that people who think about themselves are selfish — and that we get a selfish world if everyone behaves that way. That’s a very limited and ignorant perspective.

When you take care of yourself and make sure you’re happy, you’ll have a good life. You won’t be jealous of others. You’ll smile every day. And most importantly, you’ll have the resources and time to help others.

That’s how the world works. Success breeds success. Misery breeds misery.


Let’s move to an important area of our lives. You spend most of your waking hours at work. So it’s crucial that you get satisfaction from it.

In fact, doing work that you enjoy is more important than “hygiene” factors like income, job safety, resources, location, etc. It’s one of the lessons I’ve learned from Clayton Christensen’s book, How Will You Measure Your Life?

That’s why I regularly ask myself:

6. What new things am I learning? This is the most important thing for me. When I learn, I feel like I’m moving forward. When I’m moving forward, I feel good.

7. Where is my career going? You need a vision. If you don’t have one — create one.

8. How meaningful is my work? I want to feel satisfied with my work at the end of the day.

9. What can I do that I’m currently not doing? I’m always looking for things to do around the office and at home. That’s how you learn new things.

10. How can I get better at what I do? When you get better at what you do, you can make a bigger impact and solve bigger problems. That gives you more satisfaction. And also more income.


As an entrepreneur, I need to take care of my business. Without it, there will be no income and no money to pay our team.

Sure, you can raise capital or take out a loan. But I believe that you should always be able to make money as a business.

It’s simple: If your business doesn’t generate money, it’s not a business — it’s a hobby.

To make sure we generate income, we ask:

11. What is the biggest pain point that our clients/customers have? We only solve actual problems that other people or businesses have.

12. What is the ideal solution in the eyes of our clients/customers? Give people what they truly want.

13. How can we give away more value without charging more? Over-deliver.

14. Where can we reach our potential clients/customers? Go where your audience is instead of trying it the other way around.

15. How can we decrease our costs? We always operate our business with low costs. We negotiate prices of everything — even simple things like office supplies. That’s better for us and our customers.