The 21 Most Important Questions Of Your Life

21 questions

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. 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 21 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?
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.


All the above things sound great on paper, right? But they are nothing without execution. You and I both know that.

But there’s still a difference between how effective we are. That comes down to one thing: How GOOD are you at executing?

These questions can help you to figure that out:

16. What’s my #1 priority right now?

17. How can I achieve my #1 priority faster? It’s not about being impatient. It’s about pushing yourself to think of creative ways to get faster results.

18. What tasks should I stop doing? We all waste time. Identify those tasks and stop doing them.

19. What tasks am I procrastinating? Use the time you’re saving by answering the previous question for this. We all avoid important tasks — things that we should be doing. Things that we avoid.

20. What questions am I not asking myself? There are a lot of things in the universe that we don’t know that we don’t know. So always try to look for the unknown. Keep an open mind.

There are a lot of questions that I’m not asking myself. That’s why I will keep questioning everything — all the time.

One thing I do know is that life has more meaning when you give more. That’s why I want to close with this:

21. How can I help one person today?

A simple gesture is enough. Give your family member a call. Cheer your friend up. Start by helping the people in your life. And then ask them to pay it forward.

You see, it all starts with questions. Just don’t be surprised if you receive everything you ask for like Maya Angelou once said:

“Ask for what you want and be prepared to get it!”



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  1. Great STUFF…👍
    Keep up the AWESOME advice…
    I learn something every time I read ANY of your article’s…

  2. Been reading your articles/newsletter for a while now, have to say this is one of the best, I am going to start using some of these. Thank you and keep it going !

  3. have to agree, this is like saying that 1st grade questions should be asked 24/7. maybe, until youre older, then you can stop. some of these questions are lame and useless, but I guess D has to fill his “blogs” with words so he gets his ad money…… try living a good life and see what questions come up – answer those.

  4. I am a school counselor and work with juniors and seniors as they start to focus on life goals. This is a wonderful summary of some great life wisdom! Thanks for writing it up and publishing!

  5. Wow… as always I see those who know it all chime in with ridicule and negative comments. I’m referring to those claiming how stupid the questions seemed to them and or the questions were for children or beginners if you will. These persons you’ll notice fit the simpleton mold; they condem most things using ridicule as their point because they inherently have to prove they know or understand more than everyone else. We all know these types, their way is always the better way the smarter way except you never hear them talk in detail or specifics exactly what that way is! Again, their focal point is driven by their subconscience which provides nothing positive or educational it’s just the simple focus put on tearing down something and never specifically adding any substance or proven productive methods or even at least suggestions or examples of what works better or even produces results of any type to substantiate and back up their ridicule and negativity. For example if these questions we’re surpassed long ago and ones infinite wisdom is so vast now why is it that the focal point of their statement is on the questions value being trivial and basic yet with all this experience and wisdom their excercising to judge it seems that the ability to support this opinion with facts or examples of what is more important or to use their train of thought, what are the grown up questions we should be asking ourselves? You’ll notice these traits are consistent with these people; rather than the focal point being put on the questions that all this experience and wisdom theyre eluding to they want you to believe you should be asking, but never state what they are and certainly why they should be the ones asked they’ll only go as far as to tear down the positive with negative. You’ll not hear anything positive and or well founded to replace or support their comments and negative judgement because they haven’t anything to add beneficial that doesn’t open themselves up to be scrutinized because they’ll run the risk of failure and that will expose their whole game. These question are solid. They’re intended in my understanding to keep oneself learning, always in flux educating ourselves to what’s important to and for us. They’re not to take notes and fourse feed others some recited cookie cutter formula if bullshit to mold others, they’re for one to use to grow as much as you want to in ways that work for you and importantly to educate yourself on what doesn’t work for you so that you can live a life that’s conducive to YOU being happy and helpful to others not the reverse like the sad “know it alls” who commented on these questions from a miserable exsistance they call their life. I’ve expressed my thoughts enough here, YOU be your own judge here; questions that will strengthen your foundation in life based on and for you and what works for you, which equates to happy and helping others or know it all and ridicule the world on how stupid they are and be miserable with nothing constructive and positive to add to life… This choice we all make every day and it’s not hard to know which choice a persons made if you listen to what they say and what it is they’re asking – in fact it’s so clear which choice they’ve made in life a first grader can tell the difference, just ask them!

  6. Doug here.I liked your thoughts you put into writing. Good job !!!!!