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101 Questions to Ask Yourself in Life

“The key to wisdom is knowing all the right questions.” – John Simone

What questions do you ask yourself every day?


Believe it or not, the kind of questions you ask determine the kind of life you lead. That’s because your questions trigger its own set of answers, which lead to certain emotions, which then lead to certain actions (or inactions), followed by results. If you ask yourself limiting questions, you’ll get limited results. If you ask yourself mind-opening, forwarding questions, you’ll gain a lot more out of them.

Some people like to ask questions like “Why am I so unlucky?”, “What if I had done this earlier?” and “Why am I always in such a situation?”. Because these questions are backward looking, the answers you get with them are naturally disempowering. On the other hand, questions like “What can I learn from this experience?”, “What can I do differently move forward?” and “What am I grateful for?” are empowering. They provoke you and get you thinking, putting you on the path to a better life.

If you’re someone who normally doesn’t self-reflect, you might be stumped by questions. However, this is perfectly normal. I remember when I was a primary school student, the teacher asked us how we would describe ourselves. The question got me stumped, because I had never thought much about it. It took me some time to find some meaningful adjectives to describe myself, but even then they didn’t seem right. That was one of the starting points of my self-exploration journey. Somewhere along the way, I became a big fan of introspection, enjoying the process of self-reflecting and thinking over questions.

Today, I believe questions are a key to self-awareness and personal growth. In my 1-1 coaching sessions, I enable my clients to discover the answers to their goals/questions by asking them the right questions. It’d be easy if I just tell my coachees what they “should” do and what they “should not” do. But that’s not the point. It’s about empowering my clients to discover themselves through asking the right guiding questions, catered to their situation and their profiles. The right questions will help them untangle the blockages in them and connect with their inner self.

It doesn’t matter if you get stumped in the beginning, or if you don’t know the answers to the questions at first. Our minds are boundless. Just because you don’t get an answer immediately, it doesn’t mean there are no answers. The answers are there — it’s just that your mind is too foggy since you’ve not consulted it before. The more you ask, the clearer your mind will be, and the more ready you’ll be to receive the answers.

Here are 101 important questions for your self-reflection, by yours truly. Many are questions that I ask my 1-1 clients during our coaching sessions to help them uncover their inner self. These questions will help you focus on what’s important to you and what you want. They are not meant to be answered all at one shot — they are to be reflected duly over time, as part of your growth journey. Pick out a few questions to reflect on today, then bookmark and check back a week later to think over the others. Check back regularly to reflect on the questions.

Remember, there is no one final answer. It’s a continuous discovery process. Your answers to the questions today will be different from your answers one month, three months, six months, and one year down the road. Add these important questions to your weekly review sessions. This is a highly important article for your growth journey.


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