7 Biggest Questions To Ask of Your Life

In my journey toward a better life and career, great life questions have played an important role. Oftentimes I’ve journaled these questions, other times I’ve just pondered them while taking a walk.

Hi, I'm Michael

I started this blog to help people find their path in life—from finding your passion to just getting a better job. Read my story here.

Questions are powerful. They cause us to think, to reveal, to discover, and most importantly, we do all this ourselves. Answers on the other hand are often told to us from the outside, from advice-givers. And this often concludes our thinking and causes us to stop searching.

As Kapil Gupta has said “Questions create your path, answers end it."

In my journey toward a better life and career, great life questions have played an important role. Oftentimes I’ve journaled these questions, other times I’ve just pondered them while taking a walk.

Regardless, they’ve helped me make a lot of breakthroughs in my life. A good question not only puts you into a different mindset, but gets your brain spinning with new ideas. 

What would you do, that if upon doing it, you knew the universe would respond positively?

Sometimes we’re unwilling to admit to ourselves we want something because we don’t think it’s possible to acquire. To quote Sir Ernest Hall, “our ambitions drop to the level at which we can find just enough confidence to achieve them.”  

Or maybe we don’t take action because we’re afraid of losing our current situation, or afraid of what others might say. 

Either way, this is unfortunate not only because we never try, but also because we get confused about what we want. We begin to play it safe, then slowly but surely, we forget what our real desires were in the first place.

This question is my version of “What would you try if failure was unlikely?” I like my version because I feel like it draws more ideas from the mind. This is because the possibility that the universe will respond positively makes us more inspired.

I recommend answering this by listing out all the ideas that come to mind. From there you might find your next endeavor.

Based on my actions only, what is it that I value?

You’ve probably asked yourself “What is it that I value?”. Maybe you’ve said things like balance, autonomy, or friendship. But what we say can be a lot different than what we do. When asked a question, we often default to the answer that sounds good.

A good way to reveal what values you embody is to base the answer off your actions. 

Imagine that for a week there were a bunch of security cameras around you in your day-to-day that would be later reviewed by five random people. What would they observe? What do you think their impression of you would be? What would they say you value based solely on your actions?

From here, you can decide if these desires will lead you to the life you want.

You can also dive into why you exhibit these values. For example, a person playing video games ten hours a day may seem like they value video games. But it might actually be the comradery they feel playing with teammates with a shared goal. From here, they can find other things that also fulfill this need, if they so choose.

How have I been complicit in creating the conditions in my life I say I don’t want?

This is one of my favorite questions. I heard it from Jerry Colonna who wrote a book called Reboot.

I like it because this question turns the focus on ourselves and how we play a hand in our situation. 

Also, the words “I say I don’t want” are key. Often we might say we don’t want something, but deep down we may reap some benefit from it. I might say I don’t like my job, but why do I stay? What comfort does it provide? 

The example here should be taken with a grain of salt. The question should not be causing an individual to up and quit right away, but to more clearly see why they stay. It’s a question that makes things more clear.

It is also important to not turn it into a blame session. You may be responsible, but this doesn’t mean there needs to be guilt or shame. You simply need to see the reality of the situation.

If I didn’t already have this, how much would I work to get it?

It’s easy to try to maintain what you currently have without really considering if you even want it in the first place. 

In the simplest example, you can ask this question of an article of clothing you have: “How much would I pay for these jeans if I didn’t already have them?” If the answer is “not much”, maybe it’s time to throw them out.

How about the job you currently have? How hard would you work to acquire that job if you didn’t already have it? Would you take classes to learn how to do what you are currently doing?

You can use this question for lots of things—work, relationships, the city you live in. You can even do this with a book you’re reading. Maybe you’re trying to finish it simply because you’re half-way into it. 

If you knew what you know now at the half-way point of the book, would you still pick it up and start at page one?

Who could I be?

A question people often ask is “Who am I?”, but this is only addressing our current state. Who you are currently may not be who you want to be. If this is the case, it may be due to not being intentional about who you want to be. Or it could be due to simply going with the flow of modern-day life and becoming like everyone else. There’s nothing intrinsically wrong with being like everyone else, but what are the chances you share the same desires?

A better and more exciting question is “Who could I be?”

Who could you be if you really tried? If you started taking your gifts, time, and energy seriously? What would happen if you started taking care of yourself like someone you care about? What if instead of joking your flaws away you took them seriously? 

Who would you become in three years?

Who are you resentful of?

Resentment is rarely discussed. Maybe it’s because to admit that you are resentful of someone would be such a shameful thing to do in public that we won’t admit it to ourselves even behind closed doors.

But this emotion holds a lot of information. Whenever I notice myself being resentful or envious, which takes some practice, it's probably related to something I desire.

In the past I found myself resentful of content creators and influencers. This made me realize that I also had something I wanted to express online, and that not doing it was causing inner turmoil. So I knew I couldn’t ignore it, which motivated me to start this blog.

What people do you find yourself criticizing? 

What positions are people in where you find yourself viewing it as inferior? It’s possible this is because it’s truly divorced from your values, but it could also be a defense mechanism. You may not want to see that you have that desire within you. 

In the end, you want to figure out why that resentment is there.

How is this the best thing that ever happened to me?

When something we don’t want happens, our natural reaction is to deny it, push it away, or simply lament. But we all know from the movies that the challenges the main character faces end up playing an important part in their story. 

This question helps you make the connection between a “negative” event and your story.

Let me give you a small example. Last year I got a pinched nerve in my neck. I could barely look to my left and I had to take a month off from any sort of exercise. Seems like a bad situation all round right?

But how is that pinched nerve the best thing that ever happened to me? Well, it forced me to think about my posture in my day-to-day life, and the ergonomics of my work space. It also made me more cognizant of how important my form is during a workout. In fact, after that pinched nerve I’ve completely changed my workout regimen to something more geared towards long-term health, rather than just vanity.

So that pinched nerve was actually a great thing because it made me correct a lot of things about my physical health.

If the thing that occurs is particularly rough, it’s okay to feel that disappointment and spend some time processing a negative event. We need rest. If you lose your job, take a week for yourself. 

But when you’re ready, posing the question “How is this the best thing that ever happened to me?” will help you process the event and make it a part of your story rather than an unwelcome disruption.


I hope these questions can help you like they did me. My philosophy is that an individual has to see something with their own eyes in order to begin to change and grow. This is where questions play such an important role.

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