The older I get, the more time I spend – as a percentage of each day- on crafting better questions. In my experience, going from 1x to 10x, from 10x to 100x, and from 100x to ( when Lady luck really smiles) 1000 x returns in various areas has been a product of better questions.” Tim Ferris

Albert grunted.  ‘Do you know what happens to lads who ask to many questions?  ‘

Mort thought for a moment.

‘No,’ he said eventually, ‘what?’

There was a silence.

Then Albert straightened up and said, ‘Damned if I know.

Probably they get answers, and serve’em right.'”

— Terry Pratchett, Mort

My life’s mission right now is to dissect and investigate the routines, habits, and characteristics of successful and happy people, and through countless hours of studying books, documentaries, and interviewing high achievers in person, I was able to identify some of the commonalities among them.

Clinical psychology always fascinated me, especially mood disorders, or in much more casual terms, unhappiness.

I constantly try to find patterns, habits, rituals, and strategies that lead to happiness and stay away from habits that will lead to unhappiness eventually.  So, I asked myself what the difference between a happy and successful person, and a person who suffers from depression, for example, is?

One glaring thing I have found was that successful people ask themselves different questions.  Instead of asking “why me”, they ask themselves “how can I use this problem to get stronger”, for example.  They all seem to possess the habit of asking good questions.

One of the differences between happy and unhappy people lies in the quality of the questions that they ask themselves.

If you ask yourself the right kind of questions, every situation becomes a growing experience, and you will find yourself constantly in learning mode.

And for me, I feel most happy if I get better if I grow because, for me, growth equals happiness.  This is why I created this website, to constantly improve and change for the better, and to share my findings with the world.

How Do You Get Better?

I only know of one way to get better; to learn.

But how do you learn?

In my mind, there were only two possible ways of learning:

  1. Try to find the solution by yourself.
  2. Find people who already have the answer to what you are looking for and ask them.

Being the lazy bastard that I am, the decision was utterly easy for me.  Option B it was.

When I was working in a psychiatric facility, I investigated the problems of people and the causes of their unhappiness, and one of my personal takeaways was that people’s problems are not as unique as you might think.  With that realisation in mind, my own problems became less special, and I started to look for patterns, habits, and rituals that one should avoid at all cost.  A recipe for unhappiness, so to speak.

I thought that there have to be people who have struggled with the same demons as I, and who have successfully mastered their problems.  My answer to this problem was to surround myself with a network of mentors.

Very early in my childhood, my mother gave me very demanding and sophisticated books to read.  While other kids my age were playing with Pokémon cards, I was reading Nietzsche, Shakespeare, and Viktor Frankl.

Later in my life, I discovered that she did this to instil a mental framework of mentors in my brain.

For me, reading was taking advice from the greatest minds in history.  Advice that was bitterly needed, because I was failing on every level imaginable.

When I was a teenager, and I struggled with self-pity, she gave me a book by Nelson Mandela.  When I wanted to become better at basketball, she gave me a book by Michael Jordan.  When I had problems with a woman and loved, my mom gave me books from Shakespeare, and so on.

To me, all those authors became like guides and teachers for me.  If I was in a quarrel, I asked myself, for example, “What would Michael Jordan do right now?”

But books also have their limits.  I needed to ask real questions and get answers from real people.

This was when I decided that I needed to find mentors, and ask them how they became successful or happy, or muscular, or spiritually enlighted.

But what do you do if you find them?  How would you dissect their knowledge?  How do you ask better questions?  How do you interview them?

To learn how to ask questions, I investigated the best psychotherapists, journalists, and interviewers in the world.  From James Lipton to David Letterman, to Tim Ferris.  If you are interested in asking yourself and others better questions, then stay with me here.

Who Is Tim Ferris

Tim Ferris is a bestselling American author, entrepreneur, and self-proclaimed “human guinea pig”.  He is most famous for his self-help books.  You might have heard of his book, “The 4- Hour Workweek”.  But what he is most famous for is his Podcast, “The Tim Ferris Show”, which has over 80 million downloads.  In his podcast, Tim interviews world experts and masters of any field imaginable.  Guests like Peter Diamandis, Arnold Schwarzenegger, Jamie Fox, Dave Asprey, and other incredible high achievers.  What has this to do with questions?

The older I get, the more time I spend – as a percentage of each day on crafting better questions.  In my experience, going from 1 x to 10 x, from 10 x to 100x and from 100x to 1000x returns in various areas has been a product of better questions.  “Tim Ferris

It is Tim’s mission to decode human greatness.  He interviews high achievers of any kind to find emulatable commonalities among the top 1%ers of the world.  He does so by asking questions.  Coming from a psychological background, listening to his podcast was a true game-changer for me.  For me, interesting people are case studies, and up to this point, I only knew about case studies that were in the unsuccessful part of the spectrum.  Tim gave me 280 amazing human brains to dissect, and he did so by asking them questions.  His questions were so good that he was called the “Oprah of Audio”.  If you have not checked him out, stop reading this article right now, and check out his blog.  Click here to see his blog.

How To Ask Questions Like Tim Ferris

In the following short video, Tim gives tips on how to ask questions better.

Here Are His 5 Bullet Points

The Question Has To Be Answered Quickly

If you are dealing with highly successful people, time matters to them.  If your question cannot be answered quickly, change it.  Questions like, “How can I be successful” are terrible.  They do not have the capacity to be your personal life coach.

Build Up From Easy Questions

It is important not to start right off the bat with the most difficult questions.  Most of the time, the first part of the interview is like warming up before the game.  A show that is very famous for its high-quality questions is inside the actor’s studio with James Lipton.

In this show, James interviews the most successful actors in front of young aspiring actors to deconstruct their greatness.  It is a great show, you should binge it.  Guest include Sir Ben Kingsley, Tom Hanks, Al Pacino, Robert DeNiro, Brad Pitt, Robin Williams, and many many more.  At the end of the show, James asks every guest the same questions.  Let us see how they are structured.  The questionnaire was originally used by Bernard Pivot, who many people consider the greatest talk show host ever.

  1. What is your favourite word?
  2. What is your least favourite word?
  3. What turns you on creatively, spiritually, or emotionally?
  4. What turns you off?
  5. What is your favourite curse word?
  6. What sound or noise do you love?
  7. What sound or noise do you hate?
  8. What profession, other than your own, would you like to attempt?
  9. What profession would you not like to do?
  10. If Heaven exists, what would you like to hear God say when you arrive at the Pearly Gates?

As you can see, James starts by asking very easy questions that are quick to answer.  In the end, the questions become really complex and philosophical.  If you want to ask those important questions, you have to build up to them.

Give Examples

Very often, the guys that you interview will not have a quick answer when they are fishing for words, it is important to help them and give them an example.

Let us see how Tim does this in his new book, Tribe of Mentors.

A question from his book, Tribe of Mentors: What is one of the most worthwhile investments you’ve ever made?  Then he gives examples (could be an investment of money, time, energy, etc.).

Remember, these are some tough questions to answer, and if you do not want to experience awkward silence all the time, it is important to help.

Do Not Ask Questions Google Could Answer

If you want to interview someone, you have the intention in mind that you want to acquire some sort of knowledge or information that, in your opinion, will help you and add value to others.  It is only logical that you first do your homework and see if the person has answered the same question in the past.  Again, if you are interviewing highly successful people, you do not want to waste their time or yours.

Do Not Ask Broad Questions

Your questions should be as specific as possible.

Questions like “How do I get rich?” are horrible questions.  A better question would be: “What three things/resources would you give to a young entrepreneur who is struggling with getting stuff done?”.  Or ask, “If you could give advice to your 30-year-old self, what would the advice be?”

How To Ask Yourself Better Questions – 3 Personal Take-Aways

The older I get, the more time I spend – as a percentage of each day- on crafting better questions.  In my experience, going from 1x to 10x, from 10x to 100x, and from 100x to ( when Lady luck really smiles) 1000 x returns in various areas has been a product of better questions.” Tim Ferris

1. Before Asking Others, Your Frist Need To Ask The Questions Yourself.

There is a part of Tim’s new book, Tribe of Mentors that really struck me.  It deals with questions you should ask yourself.  It is not enough to ask other people question; first, you need to ask and define the questions for yourself.  If they cannot be answered, then you go out and ask experts.  Many people are aiming for mentors just because it is the thing right now, but you should define first what kind of problems you have and what kind of questions you cannot answer by yourself or via google.

If I had only one hour to save the world, I would spend fifty-five minutes defining the problem, and only five minutes finding the solution “.  Albert Einstein

If you want to have a major breakthrough, and you want your career to really take off, if you want to become the 2.0 version of yourself, you first have to define how that vision, that breakthrough, that career, that 2.0, that next level will look like for you personally.  One of the questions that Tim asks that helps here is:

“When you think of the word successful, what Person comes to mind?” Tim Ferris

If you want to read the full article on asking yourself good questions from Tim himself, click here.

2. Ask Specific Questions

Whether you ask yourself or an expert a question, your question should be as specific as possible.  Let us say you have the dream of becoming rich.  The questions of how do I become rich is not a good question because it is too vague.  Rather, ask yourself what kind of person do I have to become, to become financially independent.  Be specific about your goals, and determine what being financially independent is for you.  What exact income do you need to become financially independent?  Write the amount down to the penny, and now ask yourself, what three actions can I do today to get closer to this goal.

Life punishes the vague wish and rewards the specific ask”.  Tim Ferris

3. Why Make it Hard When You Can Make it Easy

Since I was little, I was always a grinder.  My special superpower is that I can work longer hours than everybody I know.  For example, when I played basketball, my way of getting better was just to put in double the hours that everybody else on the team was putting in.  And it worked, to this day I am still known as a gym rat, which is a term for a basketball player who is always in the gym constantly working on their game.

I was working harder, not smarter.  One of the side effects of working too hard, and not smart, is that at a certain point, you link pain to what was originally pleasure for you.  I started playing basketball because it was my passion, and I loved every second of it.  But, after some years of sickening work in the gym, basketball was more pain then it was fun.  I was missing out on a lot of things, and I suffered socially and educationally.  It got so bad that I needed to stop playing for a while.  Remember, our brain does everything to avoid pain, and everything to get pleasure.  Click here to read my article about conditioning.

To this day, I feel that if I have not completely burned the candle from two sides, I was not working hard enough.  Tim Ferris asked himself the same thing.  One question from him changed my approach.

What Would this look like if it was easy?”

What if my unending-working-hard-in-the-salt-mines approach was not the way to go?  I began to link fun and easiness to my obsession towards work and progress.  I was at first, fearing that I would lose my edge, that I will not be able to grind as long or heavy if I would be completely happy and easy while working, but the opposite happens, I could work even more because being happy while working actually helps with procrastination.  Why should you avoid, for example, learning if it was fun?  Why should you skip a workout if it was easy and hilarious?  So, you should ask yourself from time to time:

Am I Making this Harder than it Needs to Be?

For example, I love learning languages, and it is one of my personal goals to become fluent in 3 new languages every 6 months.  One of my takeaways from this is to make things that were hard before easier.  When I started playing basketball, I did not even consider it sports.  I could play all day and would never consider it a workout.  I wanted to transfer this approach to learning languages.

For example, I am learning Japanese and Spanish right now.  Instead of only memorising the vocabulary in a loveless cold way, I started watching my favourite anime “one-piece” with Japanese dub and Spanish sub.  With this method, for example, I have some quality time for myself and learn 2 languages at the same time.


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Here is some homework for you. It's your turn now!
  1. Define your three biggest problems in your life. What problems do you need to solve for your health, career, or happiness to really take off?
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  3. If you could only work 2 hours a week on your projects, what would you focus on?
  4. Imagine you have an interview with an all-knowing wizard, and you could ask him anything, what three questions would you ask him?
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