The Right Questions to Ask Yourself
Take self-reflection to the next level with these questions

Every morning, I’m hunched on my blue loveseat with a pen and a bullet journal, scribbling ferociously until the sun comes up. This lets me unclutter my brain and unload any negativity that I had collected the previous day. At the beginning of my journaling journey, I wrote about how I was feeling, why I was feeling that way, and what I can do to cope better.
What I’ve found over the years is that I need to ask myself the right questions when journaling. These questions should challenge my current thinking, and remove any self-imposed limitations. If I fail to question myself in this manner, I don’t reap the optimal benefits of this inward-looking act.
Self-reflection is an essential ingredient of a well-lived life. Some tools for self-reflection are journaling, therapy, meditation, prayer, and the like. Irrespective of the method you use, the benefits of sitting still, looking inward honestly, and asking the right questions need not be recollected here.
Here are some questions you can ask yourself when you're self-reflecting using your preferred method. Questions are organized into different situations. This is simply a starting point. Please feel free to adapt these as you see fit.
When you’re feeling stuck
What’s stopping me from moving?
We all feel stuck at times and generally, it’s because of an innate fear or longtime assumption. When you inspect all your fears without any self-judgment and bring them to the forefront of your conscious mind, fears can’t hide anymore. This question is helpful because the first step of getting unstuck and tackling fears head-on is to identify what they are.

When I was starting off as a freelance writer, I kept pushing back on cold-emailing clients to offer my writing services because I needed more writing samples. But when I stopped and asked myself whether this was really true, I was able to see that I had enough samples to start off with and that only my fear of rejection was keeping me from moving forward.
What’s the tiniest thing I can try to get unstuck?
Now that you have a handle on your fears, let’s try to devise one task that you can try to get unstuck. This act needs to be small and doable. Don’t aim for the stars here. For example, if you’re stuck with writing and are unable to get yourself to write daily, ask yourself whether you can start by writing 100 words or 10 sentences daily.
When thinking about this step, have an experimental mindset. Know that this task may or may not work, and you may need to try out a few such steps to strike gold on getting unstuck.
What can I be thankful for?
I truly believe gratitude is the greatest healer of all. When you’re stuck, start small on gratitude and list three things you are thankful for each morning or night or both. And you will see your life turn around much faster than you thought possible.
The key is not to rattle off things; you need to feel the gratitude. Close your eyes and thank life for all the little-big things you have received despite whatever you’re going through now.
When I was dealing with a severe breakup and questioning my existence on earth, I turned to my gratitude journal. Nothing much was happening in my life at that time and my gratitude list included supposedly basic things like watching the sunset, a Netflix series I resonated with, and tea. Within a few days, my zest for life came back rushing and I began to realize that life had so much meaning still left.
About those relationships
Am I happy in this relationship?
I’m well aware that this may sound like a selfish, individualistic question to ask yourself. But tell me, apart from your happiness and peace what else will matter on your deathbed? Your life is not a self-sacrificing fest after all.
Relationships with loved ones are supposed to make you happy, at least most of the time. Even if you get into the occasional thundering argument, you should genuinely feel like your partner loves and respects you through it all. It’s important to not get confused between wanting them to love you and them truly loving you.

Have I tried my best to make it better?
If your answer to the question above is mostly no, then have you tried to work this through with your partner? Do they know what makes you unhappy? You have to make your needs known because no other individual can read your mind, especially when everyone has a lot going on in their own lives.
In my personal relationships, I try to discuss issues at least three times so I give a fair hearing to the other party. But if I have tried to remedy a situation and nothing has worked, it’s time to leave. It’s no one’s fault, it may just boil down to incompatibility.
Why am I not able to leave?
This is a loaded question no doubt. But if you’re not happy and you've tried your best to arrive at a compromise, then you know that leaving is the only other option.
If you’re unable to do this, ask yourself why. Is there something in this relationship that fulfills your other needs apart from happiness and love? It could be security, financing, status, biological ties, or your kids, and if fulfilling these needs are more important to your value system, that’s perfectly alright. But knowing this and accepting this will set you up for contentment and keep you from expecting the relationship to get better.
When success seems elusive
Am I doing everything I can to attain my goal?
We normally take the conventional route to success and don’t like to stray from it. But sometimes, off the beaten path lies gems of vibrant milestones. So it’s important to look at other routes often.
Our brains are such skilled idea-generators if we only let them. Spend some time brainstorming ideas for your life, venture, or side hustle, and you will be surprised as to how many additional things you could be doing to get closer to your goals. You will come up with many unconventional ideas if you challenge yourself often.
What is not working for me?
It is critical to understand what’s not working for you. When deciding on what’s not working, you need to differentiate on what’s truly not working vs. what takes longer to demonstrate results.
When you understand what is not working, you can then dive into why it’s not working. Then you can come up with steps to make the required changes. Sometimes, certain actions may even need to be discontinued to cut losses and move on.

Am I making decisions from a place of fear or lack?
Often, I find myself making decisions from a place of fear or lack. I have not enrolled in certain writing programs because “it’s too expensive,” or departed from relationships until too late because “I may never find someone else.”
When I questioned myself and started challenging my limiting beliefs, I realized that if I save what I spend on takeouts for two months, I’ll be saving enough to buy that writing program that would further my writing manifold. I also understood that there are billions in this world and it was illogical for me to think that I may never find someone else.
We live with so many limiting beliefs that have been fed into our subconscious by society, especially when our psych was forming as kids. When we don’t question these beliefs, we make decisions expecting the worse to happen. Thus, this becomes a self-fulfilling prophecy that reinforces these beliefs. By challenging these limits, you are breaking the cycle for good.
What is the worst that can happen?
It is always helpful to understand the worst-case scenario as it clarifies the least desirable situation and brings it to life vs. having vague, unformed ideas around what could go wrong. When you know the beast, you can think of ways to keep it at bay.
One of my biggest fears of taking the plunge to freelance was becoming dirt-poor and not being able to pay my mortgage. When I asked myself to visualize the worst case, I found that I may have to downgrade my living arrangement and maybe stay in a dirty room in a rotten part of Toronto. But, then I thought is it that bad to live in such conditions if I get to do what I love for a living? Can I not do a retail job to take the pressure off freelancing? So many ways to soften the blow.
Is there someone I need to get help from?
There’s always someone who’s done what you want to do in the way you want it done. Actively seek out those mentors and learn from them. On the flip side, be available and helpful to mentees when they seek your guidance later on.

Make a list of all possible mentors and then categorize what each person can teach you. It can be someone famous, a friend, someone from your professional network, a family member, or someone you find through Googling. Although you can meet some of these people one-on-one and recruit them to be your advocate, you can learn from famous mentors merely by reading their autobiographies and following them on social media.
You can attain your goals on your own too. But it will take eons and who has that kind of time to kill?
About those naysayers
Do they have what you are aiming for?
Finally, about those naysayers, who are too big a proportion of today’s society. These people are everywhere, telling us this can’t be done and that will take ages. They can even be well-intending friends or family.
When someone belittles your ambitions, the first question to ask is do they have what you want. In other words, are they a reliable narrator? If not, irrespective of how close they are to you, their opinion is worth nothing. They are simply not qualified to advise on something they know nothing about.
In some instances, they may have tried to do what you want to do and given up too soon. You can learn from their experience as a cautionary tale. But even then, you should not be limiting yourself based on their projections on you as they are not your ideal mentors.
In conclusion, observing your life as an external party and asking the right questions can take you places. Your beliefs and outlook will change and along with them, so will your life. When you see life in a different light, all those cracks will slowly start mending. And this is what I want for you.
I hope these questions will help you reverse some of your ruts just like they have helped me reverse mine. Thank you for reading.