Deep Questions to Ask: Philosophers and How They Wrestled with These Questions

If you’re a wisdom seeker, chances are you’re always on the lookout for new deep questions to ask. 

After all, there’s nothing like a good deep question to get your brain cells firing and to get you thinking about life, the universe, and everything. 

But where do you find these deep questions? And once you’ve found them, how do you go about answering them?

Fortunately, you’re not the first person to ask these types of questions. Throughout history, there have been many famous philosophers and thinkers who have wrestled with the same deep questions that you’re now grappling with.

 In this blog post, we’ll take a look at some of these famous philosophers and how they approached these deep questions. Maybe their answers will give you some clues as to how you can answer some of your own deep questions.

Deep Question #1: What is the meaning of life?

Every human being has asked themselves at some point in their life, “What is the meaning of life?”

It is a question that has been debated by philosophers for centuries, and one that is still very relevant today. Let’s take a look at how the great philosopher Aristotle answered this question. 

Aristotle was born in 384 BC in the city of Stagira in Macedonia. His father was a doctor who served the Macedonian king Amyntas III, and Aristotle was brought up with an appreciation for medicine and science. 

He later studied at Plato’s Academy in Athens, where he became friends with another young student named Alexander (who would later become known as Alexander the Great). After leaving the Academy, Aristotle traveled to Asia Minor and Lesbos before returning to Macedonia, where he became the tutor of Alexander. 

It was during his time teaching Alexander that Aristotle began to seriously ponder the question of what the meaning of life might be. 

He knew that it was a question that had been debated by philosophers for centuries, but he felt that he could add something new to the discussion. 

So, Aristotle set out to find an answer that was both logical and satisfying. 

Aristotle’s Definition of Happiness

Aristotle began his quest for the meaning of life by looking at the concept of happiness. He reasoned that if humans are rational beings, then it stands to reason that our lives must have a purpose or goal. 

Furthermore, he believed that this purpose is always to attain some good. But what is this “good” that we are striving for? Aristotle concluded that the “good” or ultimate purpose for humanity is Eudaimonia. 

Eudaimonia is often translated as “happiness,” but it is important to note that Aristotle’s conception of happiness is quite different from the way most modern people understand the word. 

For Aristotle, Eudaimonia is not a transient feeling or emotion; rather, it is a long-term condition that results from living a virtuous life. So, how does one achieve Eudaimonia? 

According to Aristotle, there are two main components: 

  1. using reason well
  2. engaging in virtuous action. 

Using Reason Well

Aristotle believed that humans are unique among all other forms of life in the entire world because we have the ability to reason on a deeper level. This ability sets us apart from animals and gives us great potential for growth and development. 

To realize our full potential as human beings, Aristotle argued that we must use our reason well. This means constantly striving to gain knowledge, asking personal questions, and understanding about both ourselves and the world around us. 

Engaging in Virtuous Action

The second component of achieving Eudaimonia is engaging in virtuous action. Virtue, for Aristotle, refers to excellence or goodness – doing what we ought to do (as opposed to vice or badness – doing what we ought not to do). 

The key here is moral virtue – action done not out of fear of punishment or hope of reward, but because it is intrinsically good or worthwhile. So living a virtuous life means acting in accordance with moral virtue – doing things because they are good in themselves, not just because they lead to some other goal such as wealth or pleasure. 

In conclusion, we can see that Aristotle’s quest for the meaning of life led him to the important lesson that our ultimate purpose as human beings is to achieve Eudaimonia – a long-term condition resulting from living a virtuous life characterized by using reason well and engaging in virtuous action. 

Although this may not be the answer everyone is looking for, it provides a logical and satisfying explanation for why we exist and what we should strive for in our lives.

Deep Question #2: What is the nature of reality? 

Another deep question that has puzzled philosophers for centuries is what is the nature of reality? Is what we see and experience in our everyday lives really all there is? Or is there something more to reality than meets the eye? 

The 20th-century philosopher Ludwig Wittgenstein grappled with this question and came to the conclusion that “the limits of my language mean the limits of my world.” 

In other words, our understanding of reality is limited by our ability to understand and communicate it. 

But how did Wittgenstein come to this conclusion? Here are some examples of how Wittgenstein personally wrestled with this question in his own life. 

Ludwig Wittgenstein was a 20th-century philosopher who was deeply troubled by the question of reality. He wrestled with this question throughout his life, both in his personal life and in his professional work. 

Wittgenstein was known for being a very private man, and he did not share his innermost thoughts with many people. However, those closest to him knew that he was constantly grappling with big questions about life, death, and the nature of reality. 

One famous story about Wittgenstein illustrates this struggle perfectly. 

Wittgenstein was once sitting on a beach with a friend, looking out at the ocean. 

His friend asked him what he was thinking about, and Wittgenstein replied, “I am wondering if I am really here, or if I am just dreaming.” This story perfectly encapsulates Wittgenstein’s struggle to come to grips with the nature of reality. 

Wittgenstein’s belief that our understanding of reality is limited by our ability to understand and communicate it. He came to this conclusion after years of struggling with the question of whether or not what we see and experience in our everyday lives is really all there is. 

Wittgenstein realized that we can only understand and explain reality through language. And because language is limited, so is our understanding of reality. 

This might sound like a negative conclusion, but Wittgenstein actually saw it as a positive thing. He believed that the fact that we can never fully understand reality is what makes life interesting and meaningful. 

If we could understand everything about reality, then life would be boring and predictable. But because we can only glimpse at reality through the lens of language, we are constantly discovering new things about it. 

Deep Question #3: How should we live our lives? 

How we choose to live our lives is ultimately up to us. But that doesn’t stop us from wondering whether we are living our lives in the right way. 

The ancient Chinese philosopher Confucius wrestled with this question and came up with his own set of guidelines for how to live a good life. He said that we should “Do unto others as you would have them do unto you” and “Love your neighbor as yourself.” Doesn’t that sound familiar to what Jesus said as well?

But how did Confucius come to this conclusion? Here are some examples of how Confucius personally wrestled with this question in his own life. 

As a young man, Confucius was appointed to a minor government post. However, he soon became disillusioned with the corruption he saw around him. He resigned from his position and began traveling around China, teaching people about morality and ethics. 

During his travels, he met a man named Lao Tzu who was so impressed with Confucius’ wisdom that he gave him a copy of the Tao Te Ching, a book that would have a profound influence on him. 

Confucius eventually settled down and started a school where he taught his philosophy to students from all over China. His teachings became so popular that the Emperor invited him to court to advise him on how to run the country. 

However, not everyone agreed with Confucianism. There were many debates between Confucians and other schools of thought, such as Mohism and Legalism. In the end, Confucianism prevailed and had a lasting impact on Chinese culture. 

Overall, Confucius believed that we should treat others with kindness and compassion and always strive to improve ourselves. His philosophy has endured for centuries and continues to be relevant today. As we grapple with our own deep questions about how we should live our lives, it is worth considering what Confucius has to say on the matter.

Deep Questions to Ask – Conclusion

These are just a few of the many deep questions that philosophers have asked throughout history. As you can see, there are no easy answers to these types of questions. 

But that doesn’t mean they’re not worth asking. In fact, it’s often through asking these difficult questions and staring your biggest fear in the face is important. 

For more related information, please read this Pick The Brain article “Ancient Philosophy and Modern Personal Development”.

In this way we can gain a greater understanding of ourselves and the world around us. So don’t be afraid to ask those tough questions—you never know what kind of insights you might glean from doing so.

Jared Levenson is a blogger at Eating Enlightenment. A former Zen Monk and Intuitive Eating Counselor, Jared blogs about mindfulness and journaling to treat binge and emotional eating.


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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