20 Questions You Should Ask Yourself Every Day, Week, Month, Year

7 min readOct 26, 2020

I’ve recently finished this 90-day journal.

It was an amazing journey and I highly recommend it.

In this post I’ll discussed the insights I have gained and how I’ve changed.

I will summarize with 20 questions you can ask yourself daily, weekly or monthly and yearly to keep you growing as a person.


If you plan to go through this mini-course (which I highly recommend),
do not read any further. It’s much better to learn these lessons YOURSELF.

Now if you’re still here, let’s cover the important lessons learnt in this book.

Photo by Estée Janssens on Unsplash


Most of us have a vague idea of self-improvement.

We read articles & books randomly. Whenever we feel like it.

We might not remember what we have learnt. We get an aha! moment and move on.

One key lesson I have learnt is to prioritize your growth.

How To Start Prioritizing Growth

  1. Setting specific time to work on personal growth
  2. Doing it in a systematic way
  3. Incorporate it as a habit as part of your routine

Instead of retaining 10% of information that we read randomly. It’s better we have a process that allows us to retain, reflect and incorporate into our daily lives.

Which leads us to our next point.

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You need to commit to personal growth.

If you don’t commit, someday you will lose the motivation.

You’ll forget the reason you started.

You’ll get swept away by the thousands of little unimportant distractions that make up part of modern life.

Here’s what I realized about commitment:
You have to be okay with failing.

I wasn’t perfect the whole 90 days.

Somedays I just simply wrote, “I don’t know.”

Why? Because it’s much better than losing momentum and pondering the answer over days.

Perfection really is the enemy of progress.

How to practice commitment:

  • Be patient
  • Focus on small daily victories
  • Fight the desire for perfection
  • Keep the end in mind
  • Know that you will make mistakes someday, prepare for it
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Ask Yourself Good Questions

One special thing about this book is that it asks hard hitting questions that causes you to reflect or think deeply.

Regardless whether you plan to follow the book or not. It’s good to have a series of probing questions to check on yourself.

Asking yourself good questions:

  1. Helps you see what you’re doing unconsciously
  2. Helps you see blindspots in your life
  3. Helps you realize some things that are not normal
  4. Helps you understand yourself more
  5. Helps you identify limiting beliefs
  6. Helps you listen to your own self-talk
  7. Helps you keep yourself accountable
  8. Helps you identify excuses you make to yourself

Read on to the end and I’ll provide a list of questions that you can ask yourself today.

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Focus On Your Potential

By shifting away from thinking such as:

‘What can I do?’
‘What am I allowed to do?’
‘What should I do?’

Into a much more powerful:

What do I have the potential to do?’

There previous 3 questions are weak because they consider reality as is.

By considering our potential we can transcend the immediate conditions of our reality and look at what is possible.

This gives us a sense of freedom. We are not limited by there here and now.

We start operating in the realm of possibility.

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Design Your Environment

I am a strong believer of you are the result of the 5 people you spend the most time with. I’m blessed to surrounded by good and positive friends now. In the past, I couldn’t say the same.

We must pay attention to our environment and actively seek company of people who encourage our personal growth.

But we can’t only take from our environment, we must also actively contribute to the people around us. So we can all grow together.

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Developing Character

If you met yourself now, can you trust yourself?

This question start me on a journey to look deeply into negative perceptions that might have been ingrained in me a long time ago.

To develop good character we must not only ask what is wrong with our behaviour, but why do we behave in this way?

There is a big difference between solving the symptom vs solving the cause.

By understand how we develop certain negative traits, we can then understand why we behave in negative ways.

Paying more attention to your character is a step that everybody can take today.

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Trade Offs

“If you want something you’ve never had, you have to do something you’ve never done”

No matter what our definition of success is. It’s not going to be easy.

We have to trade something to reach a significant level of success.

We might have to trade comfort.
Trade our social life.
Trade our time spent mindlessly on our phone.
Trade negativity.

Sometimes we even have to trade the things we enjoy today, so that we can get the things we want tomorrow.

“We must all suffer from one of two pains: the pain of discipline or the pain of regret. The difference is discipline weighs ounces while regret weighs tons.”

— Jim Rohn

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Settling For Average

We often feel it’s easier to live in ‘the land of the okay’.

That means we settle for averageness and mediocrity.

We never stretch and challenge ourselves towards our goals.

We stay in our comfort zone and believe we can take the easy way in life.

This settling will come back to haunt us one day.

20 Questions You Should Ask Yourself Every Day, Week, Month, Year

  1. What do I truly have the potential to do?
  2. What are my priorities in life?
  3. How committed you are to your goals?
  4. Have a been consistent in reaching toward my goals?
  5. What excuses do I make that prevent me from reaching my goals?
  6. What are my strengths and weaknesses?
  7. Do I have values? What are my values?
  8. What direction is my life heading to? Am I truly satisfied with this direction? If not, how can I change it?
  9. What gives you satisfaction?
  10. Is personal growth important to you? If so, are you measuring it?
  11. Is your current environment helping you or harming you?
  12. How can you add value to your environment?
  13. Are you happy with yourself? If not, how can you change this?
  14. How often do you reflect on yourself?
  15. Have you been putting off things that you know you should do?
  16. Have you been settling for just average?
  17. What are you willing to trade to reach the success that you want?
  18. Are you a curious person? How can you develop this curiosity?
  19. What would you do if you had no limitations?
  20. Looking back at your life, what has worked to keep you on the path to growth and what did not work?

Write down all your answers on a piece of paper. It will be helpful to keep it somewhere visible to remind you of your journey.

What has changed?

Learning lessons in this book are useless if I don’t take action on any of them.


After completing that book I found myself more know how to be more consistent.

This is a major breakthrough for me.

Most of my life I would just do things based on my feelings.

Days when I feel good, I would work. Days where I didn’t I wouldn’t.

There was no benefit of momentum.

By developing a routine, which led me to be more consistent, I finally broke free from this negative chain.

By being more consistent in turn made me more productive. I have set times to work instead of working whenever the opportunity presents itself.


The period of my life when I started jumpstart was a directionless one.

I felt really lost and didn’t know what to do.

For the first time in my life I was financially stable & emotional needs met. I didn’t know what to strive for.

In the middle of jumpstart I finally figured out my goal.

That is to strive for excellence in everything I do.

It won’t be easy but it will be worth it.


Before jumpstart, I did not think about my character. I just thought that it is what it is.

Jumpstart helped me to take a good hard look at myself. My values, principles, and integrity.

I realized that I needed a lot of help.

Thus began my journey studying philosophy and psychology so that I could be my own therapist. This was not a conscious journey. I genuinely enjoyed reading out of curiosity. But little did I know the things I read helped me so much. Especially my learnings on Emptiness.

I worried less about impressing people.
I worried less about comparing myself with others.
I learnt to practice non-attachment.
I’m learning to understand impermanence,
and so much more.

This helped me begin the cleansing process in my mind. Clearing the years of accumulated toxic.


I’m now beginning the other courses in this series. Excited to look back and see how I have changed in other areas of my life.