These 20 Questions Will Improve Your Self-Awareness

Self-awareness is currently one of the sexiest words in entrepreneurship, happiness, productivity, or anything that has to do with personal growth.

Almost every entrepreneur or thought leader says that self-awareness is one of the keys to personal success. While that may be true — it’s by no means a new concept.

Greek philosopher Aristotle, who lived between 384–322 BC, once said:

“Knowing yourself is the beginning of all wisdom.”

We get it, self-awareness (or knowing yourself) is important. But I’ve learned that it’s also one of the most difficult things that you can master in life.

Benjamin Franklin put it best:

“There are three things extremely hard: steel, a diamond, and to know one’s self.”

Unfortunately, there’s no such thing as a universal answer to self-awareness. Everybody is different, and the only person that can teach you self-awareness is you.

Becoming More Self-Aware

We know that self-awareness is important, but how do you develop it? And, what’s the use?

One school of thought goes like this: Just live long enough and do a lot of stuff—eventually you will know yourself.

Alright, but what if that takes 60 years? I’m not impatient and I have no trouble waiting. But that approach is just too passive for me.

And I think you can accelerate the process of developing self-awareness by examining yourself consciously.

Let me tell you how I’ve gone about knowing myself better and how I use it in my daily life.

I started by answering these 20 questions:

If you want to try this method, I would answer these questions with the first answer that pops up in your mind. As you can see, these practical questions.

Please don’t start a discussion about how you should interpret these questions. If you do that, we will be still at it in 8o years from now.

The truth is that everyone interprets these questions in a different way. And that’s exactly the point.

For example: What things do I value in life? My answer is time, family, well-being. What was your answer? You see, there are no right or wrong answers.

Also, I’m a practical person and don’t like woo-woo questions like: “Who am I? What’s the meaning of life?” You are what you repeatedly do, and you decide what meaning you give to life.

“Now what?”

Well, your initial answers to these questions are not that important. It’s impossible to give yourself the right answers, so don’t worry about getting things right.

Especially difficult questions like: “What am I bad at?”

What’s more important is to practice your thinking muscle with those questions—just give an answer (don’t say “I don’t know”).

Now comes the most important part: Use that information to improve your life. You do that by reasoning.

Aristotle called it ‘logos’ (different from the Stoic definition of logos).

Historian Paul Rahe explained Aristotle’s definition of logos best:

For Aristotle, is something more refined than the capacity to make private feelings public: it enables the human being to perform as no other animal can; it makes it possible for him to perceive and make clear to others through reasoned discourse the difference between what is advantageous and what is harmful, between what is just and what is unjust, and between what is good and what is evil.

To me, self-awareness is (1) the ability to translate your feelings into words and (2) to give it meaning.

You’re trying to uncover about yourself which things are advantageous and which things are harmful.

“And then what?”

Double down on the advantageous stuff and start eliminating the harmful stuff (as far as possible).

  • Do more things that make you happy.
  • Do more things that you’re good at.
  • Avoid things that make you unhappy.
  • Avoid things that you’re bad at.

That’s it. That’s knowing yourself.

One thing: Don’t take this process literally. For example, relationships can make you both happy and sad.

That doesn’t mean you should avoid relationships altogether. But rather avoid the things that make your relationships bad—things like selfishness, lying, lack of empathy, etc.

“But how do you practice logos/reasoning?”

Here are some ideas:

  • Read philosophy. If you don’t know where to start I recommend reading The Story Of Philosophy by Will Durant.
  • Become neutral in discussions with people. Don’t just try to prove a point. Always try to reason from different points of view.
  • Journal, and follow through on your thoughts. Always ask yourself why? For example: John made me mad. Why? Because he lied. Why? Because he didn’t want to upset me. Why? Because he cares about me. Conclusion: John is an idiot who should learn that lying is not helpful.
  • Talk. Talk. Talk. With friends, colleagues, mentors, coaches. Just by vocalizing your feelings, you discover new things about yourself. Especially when you talk to people who ask questions that make you think.

There you go. That’s my process for self-awareness. Introspection is difficult because you must be honest with yourself. And most of us prefer to lie because the truth is scary.

But since I’ve practiced self-awareness consciously, my life has improved massively. Knowing yourself makes living easier.

Will this exact process work for you? I don’t know, but what I do know is that this could be a start. And that’s all you need to become more self-aware.

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