20 Questions Everyone Should Ask Themselves

Chiselled on a column at the Temple of Apollo reads the well-known aphorism Know thyself. This ancient bit of ancient wisdom is still relevant today.

Self-examination is an effective way of shining light on your own patterns of thought and behavior. It is one of the most direct ways in which we can begin to peer into our own minds. This is precious time when we take a step back and look at ourselves as if we were another individual. Asking questions is a way of doing that, because it can reveal useful insights we can use to live in alignment with ourselves.

The path to self-knowledge is winding and tough, scattered with resistance and setbacks. However hard, the price of not doing it is even greater. Your ego might get hurt and your pride might suffer a few blows, but it’s all in the name of truth and wisdom.

I’ve compiled a list of questions I think we should come back to regularly to get to know ourselves better. You may not like the answer to some of these, but the goal is blunt honesty. There’s nothing to be gained by deceiving ourselves. Think of this exercise as a “life audit”.

Grab a (digital) pen and paper and let’s begin.

Attention & Energy

Attention is one of your most prized possessions. Where you choose to focus it will directly shape how the world looks like to you. Being intentional with where our attention and energy go can influence the quality of our lives.

  • What have I worked on during the past week?
  • Is there a mismatch between the importance of the activity/subject and the attention I give it?
  • Am I energized or dulled out by most of my projects?


Our motivation falls into two categories: intrinsic and extrinsic. Although it’s more rewarding to engage in activities that are inherently valuable for themselves, it’s totally natural to have extrinsic desires that drive us (sometimes that’s the only way to get through a dull job). It’s helpful to take a step back and reassess the motives behind your actions. Take a look at your attitude towards your job, relationships and hobbies. For each, ask the following:

  • What is my main drive?
  • What am I hoping to get out of it?


Values are the lighthouses of our character. They show us the way when we’re swimming in uncertain waters. Failing to align our values with our goals will lead to psychological distress and a deterioration of our well-being.

  • Are my actions and my values aligned?
  • Do my actions match the ideal I want to live up to?

Guiding Principles

Think of your guiding principles as short wisdom-packed phrases, which you turn to when you’re faced with challenging situations. They are informed by our values and can offer guidance on how to approach life. You perhaps already live by some, but are not aware of it.
One of mine is Socrates’ famous maxim, “The unexamined life is not worth living.”

  • What are 5 guiding principles you can identify that have informed your actions lately?
  • Should any of them be questioned?
  • Can you think of others that you can add to the list?
    (If you don’t have any set of principles guiding you now, I suggest you try to compile a list of phrases and quotes that can be used as reminders of how to think, act and be in the world.)

Information diet

Just like you (hopefully) pay attention to the food you put in your body, you need to apply the same considerations to the diet of your mind. Reflect on the news, articles, videos, podcasts and books you’re consuming. Are they nourishing you? Do they provide value or just empty “calories”?

  • How would I rate the quality of the information I consume?
  • What about quantity? Is it too much?
  • Have I locked myself into an echo-chamber where none of my beliefs are challenged?
  • How do I feel after each piece of information? What can this tell me about its quality?


When we’re left to our own devices, we tend to use our… devices.
How we spend our leisure is one of the most deeply personal and individual decisions we make. Choosing what to do when we can do anything is a reflection of who you are as a person. It’s how you honor your authentic self.

  • How am I spending my free time?
  • Do I use my free time as an avenue of learning and playing, or do I simply resort to low-value activities (like mindless-consumption)?


Almost all of us can point to a project or an idea that we’re yet to act on, even though we’re excited about it and our heart start beating a bit faster when thinking about it. Whenever a goal stretches us as people, it’s normal to feel hesitant and let overthinking get the better of you. But that shouldn’t stop you from at least giving it a chance.

  • What have I been postponing?
  • Why have I postponed it?
  • What needs to be done in order for me to take the first step?


The quality of the people around us infuses almost every aspect of our existence. Thinking about how we can nurture and appreciate the ones close to us will give us tremendous happiness.

  • Who can I message this week to catch up?
  • Can I reach out to someone to ask if they might need any help?
  • What is one small gesture I can do to brighten someone’s day?

Your sentence

In Drive: The Surprising Truth About What Motivates Us, Daniel Pink talks about finding your sentence, which is a short statement that encapsulates your life’s purpose.

I am using it a bit differently here. While he talks about an overarching life purpose, we can zoom in and consider just the current slice of our life. This can be the present year or only a few months. Usually, we’re always working on something, trying to figure something out or learning a new skill, so it can be helpful to put it into context and get clear on exactly what our sentence is for the time being. It’s totally fine for this to change.

  • What is my sentence (right now)?


Leave a Reply

Your email address will not be published. Required fields are marked *