Self-improvement | Philosophy
The 5 Most Powerful Questions You Should Obsess Over if You Want to Live a Fulfilling Life
They take minutes to answer but impact your entire life

Socrates once said that the unexamined life is not worth living.
If we take that quote to heart, then a life abundant with self-reflection and introspection is worth living.
I’ve been asking myself a plethora of questions for the past few years to uncover who I am and what’s important.
Out of those, here are the five best questions I still obsess over.
1. When are you going to start demanding the best of yourself?
This quote, attributed to Epictetus, calls for you to stop putting off being a good person.
Instead, as the Stoics would say: stop thinking about being a good person and just be one.
By saying you’ll improve tomorrow or next month, you’re admitting that you’re comfortable being insufferable, willingly shameless and letting other people/things have power over you.
If it is worth doing — if you’re worth improving — focus on it now.

You may leave life at any moment, Marcus Aurelius repeated to himself, philosopher and former emperor of Rome. Let that determine what you do, say and think.
Time is fleeting and the end of life appears to greet you at a distance. But that distance will only ever decrease.
Will you fill that space with purpose and passion or continue to put things off until it’s too late?
2. What would you pursue if success was guaranteed?
Most people are terrified of failure.
Me included.
Doing something new and taking the risk to dedicate effort to it — even though it could be a complete waste of time— is severely uncomfortable, no matter who you are.
Plus, imagine what everyone else will think of you. How scary!
Pair this with perfectionism, being too prideful to look like a beginner and all the other little insecurities you have, and voilà! You’ve built a molehill so big it’s become a mountain.
Lots of people think the fear of failure is a problem.
It’s not. It’s giving in to the fear of failure. Every single person is scared of looking like a wombat. Everybody feels resistance at first.
The people who succeed feel that fear and do it anyway.
This is the framework they use to start doing the tough shit:
- They ask: what would I give my energy and time towards if I knew that success was inevitable? This helps you gauge what is important.
- Then, create a bias for action: will I let the belief that I might be viewed as a failure by someone else be the sole reason why I live forever below my potential and die with all the regrets of things I didn’t do?
The more biased you feel towards taking action the easier it will be.
For example, instead of seeing failure as a win-or-lose situation, see it as a win-or-learn situation, creating an outcome that can only benefit you.
Thinking of success as inevitable prevents you from choosing superficial comfort. It forces you to be aware of what’s important.
Then you can stop dancing around it and expect the best from yourself.
3. What do you want out of life?
Have you ever stopped and asked: what am I aiming at/for?
If you go through life without defining what you want or who you wish to become then it will be defined for you.
If you aim at nothing, you’ll hit it every time
~ Zig Ziglar
This ties in closely with imagining what you’d do if success was guaranteed. Instead, this optimises for joy and fulfilment.
Just because you can be successful at something doesn’t mean you should be.
What do you want in the future?
- A loving family?
- A job you look forward to every morning?
- A smooth life without stress?
- A cabin in the middle of nowhere away from everyone else?
Do you want it in 1 year, 5 years or 20 years?
And why? The more potent and tangible your sense of why, the more likely you are to act for that outcome.
Now you need to align your current actions with your future desires.
4. How would your future self want you to act?
Short-term gratification is the most slept-on villain.
It’s easy to see and say what you want to do. But actions speak louder than words, and most people have their dreams swept under the rug by vices and distractions.
The solution? Delay gratification by embracing hard work and pain to better yourself in the future.

By thinking about how you tomorrow, next week, month or year would have wanted you to act right now, you’ll be more prepared to take the appropriate actions aligned with your desired future.
And there’s an easy way to see if you’re on track:
- Think: what future do I really want?
- And: what future do I really not want?
- Then: if I keep acting as I do, which future is more likely to become true?
Thinking of both ends of the spectrum can help put into perspective your current trajectory; it will create a sense of urgency to get your shit together.
Sometimes a sense of urgency is all you need.
5. Are you living true to yourself?
This question is a subtle guidepost.
One that predicts whether or not you’ll die with agonising regret.
So… no biggie.
In a study done among people who were dying, the most common regret among them was:
[not having the] courage to live a life true to myself, not the life others expected of me.
Real quick, do some internal recon, situational analysis, introspection, or whatever you want to call it, and ask: am I doing this for me? Or am I doing it for what people expect of me?
It’s time to live life on your terms.
Conclusion
Well, now you have something new to obsess over (if my ability to create this article is good enough!).
Writing this was annoying, scary and uncomfortable. I felt like procrastinating for hours or watching a film instead. But, spoiler alert, I didn’t. I just did it anyway. Aren’t I amazing?
Epictetus said that reading something once isn’t enough for it to make a real impact — we’ll forget it in a few days.
Instead, you should “take your thoughts, write them, read them aloud, talk to yourself and others about them”. This will help you remember what you learn and take it seriously.
So in that case, you should comment, share and talk about this article plus the questions it talks about often (pretty cool marketing strategy as well).
I hope you enjoyed it. Be true to yourself.
Woah, check it out! Another amazing article:






