“The unexamined life is not worth living.” — Socrates
How often do you reflect on your life?
We often think of philosophy as something esoteric and impractical. However, it doesn’t have to be that way. Thinking like a philosopher doesn’t mean asking never-ending questions or setting up intellectual traps.
The word “philosophy” literally means the love of wisdom — it’s about getting more involved with the world. To better understand how we act and think.
Wisdom distinguishes great leaders from the rest. If knowledge is information, wisdom is acting upon that knowledge. We can gain a lifetime of knowledge, yet never extract any wisdom out of it.
You don’t need to become a philosopher to think like one — you need to be a lover of wisdom.
1. Go Slow to Go Fast
Our world is driven by speed. We feel forced to keep pace with things because we fear missing out. But, if we are always in a rush, we are more prone to making mistakes and losing perspective.
Thinking like a philosopher requires to create space for reflection.
To be fast in making decisions, you must slow down — make time for contemplation.
As Christian Madsbjerg, author of the Moment of Clarity said, “Every sentence should be on trial for its existence.”
By taking more time when reading or writing, you train your mind to slow down. You clarify your thinking. Instead of moving from one thing to another, you try to understand what’s underneath something — what’s driving our behavior.
Wise leaders slow down their minds — they observe things from a distance. Making wise decisions requires balancing urgency and rigor.
Ancient philosophers and Buddhists monks ‘booked’ a considerable amount of time for self-reflection, learning, and meditation. Make space to pause and reflect, not just to do things.
2. Focus on What’s Essential
We associate more with better. The more you do and the more you have, the better person you become. Unfortunately, this endless race to do and achieve more and more drives confusion and frustration. When everything is important, we can’t separate what matters from what doesn’t.
As Marcus Aurelius said, “If you seek tranquillity, do less.”
The Roman emperor and philosopher didn’t say do nothing, but less. He invited us to focus on what’ essential. He called it the double satisfaction:
“to do less, better.”
That’s the premise behind the book Essentialism by Greg McKeown: get only the right things done. It’s not about getting less done or about getting more done in less time. Essentialism is challenging the assumption of ‘we can have it all’ and ‘we have to do everything.’ You focus on the pursuit of ‘the right thing, in the right way, at the right time.’
Roman philosopher Seneca was amazed by how people were so protective of their property, money, and possessions, yet careless about their most precious asset: their time.
Life is never short if we know how to use it.
As Seneca wrote, “It is not that we have a short time to live, but that we waste a lot of it.”
3. Think in Shades of Grey
Seeing the world in black and white terms gets us stuck. In the US, there’s a strong debate currently going on around capitalism. Those who highlight any flaw from the system, are immediately labeled as “socialists” — you are either in or out.
Thinking in shades of grey is about learning, not taking positions — we stop seeing opposing concepts as enemies.
Integrative thinking is the capacity to hold two diametrically opposing ideas in our head and reconcile them for a problem at hand.
Buddhists refer to this as the “middle way” — it’s not an average of two concepts, but not seeing them as opposites. We shift from duality to integration. Rather than seeing materialism and spiritualism, for example, as exclusive things, we embrace both — we realize they are two sides of the same coin.
As Robert Wesley Miller wrote, “When you are at the top you only see shadows and when you’re at the bottom you are blinded by the light, but from the middle everything is pleasing… day and night.”
Wise people embrace nuance and diverse perspectives.
4. Spot the Weakness in an Argument
The words we don’t challenge become true.
The purpose of philosophy is not to find an error, but to avoid acting based on false assumptions.
We are usually prone to various cognitive biases. The confirmation bias, for example, is our tendency to look for and to recall evidence that confirms, but not that disconfirms, our beliefs and hypotheses.
As Daniel Dennett said, “The word ‘surely’ is as good as a blinking light locating a weak point in the argument.”
The philosopher shares a quick trick that may save you much time and effort. When reading a whitepaper, look for “surely” in the document, and check each occurrence. Most of the times, it marks the edge when the author states a ‘truism’ without offering sufficient reason or evidence — s/he hopes the reader will quickly agree. If the author were really sure, s/he wouldn’t need the word “surely.”
Thinking like a philosopher means not taking things for granted.
Logical fallacies are arguments that fail to make sense scientifically — though they can often make an emotional appeal, they do not prove the underlying claims. Proof by example is a fallacy that uses one or more cases to suggest a general rule. For instance, when you observe people from a particular group doing something and then assume everyone who belongs to that group acts the same way.
5. Be Intellectually Humble
Most leaders tend to overestimate how much they know. They don’t make wrong decisions because of a lack of facts but of low self-awareness.
That’s the problem of celebrating intellectual brilliance — we reward certainty, and condemn doubts. Being right, then, matters more than finding the correct answer.
As Bertrand Rusell wrote, “The whole problem with the world is that fools and fanatics are always so certain of themselves, and wiser people so full of doubts.”
Intellectual Humility is about recognizing that the things you believe in might, in fact, be wrong. It’s an invitation to ‘empty your cup,’ so you can fill it up with new knowledge.
Practice being obsessively curious. Challenge everything — especially what you believe is right. Leave the door open for better solutions, rather than sticking to your answer. Intellectual humility is letting go of certainty.
As Edgar Schein explains in his book Humble Inquiry, being intellectually humble requires accepting that, in many aspects, our status is inferior to others — they know or can do something we can’t.
Being wise requires acknowledging when you become temporarily dependent on other people’s knowledge or expertise.
6. Knock Down Your Own Ideas
We all tend to fall in love with our own ideas — especially, our most recent ones.
To spot the weakness in other people’s arguments, we must practice challenging our own first. That’s exactly what Christian Madsbjerg suggests by saying that you must “knock down your own ideas.”
As a philosopher who consults Fortune 500 companies, Madsbjerg spends a lot of time observing things that don’t make sense. He believes the corporate world is absurd. Companies invest in silly things but then cut down others that are vital to their community.
“When you have an idea about something, the first thing you do is try and kill it. You try to empty a gun into the head of your own idea. The first inclination of a philosopher is to be as rough on your own idea as possible,” Madsbjerg explains.
We usually try to defend or sell our ideas. What if we treat them as rough as possible? Challenge yourself: What would be the opposing view? If they stand up to that test, then they are worth pursuing.
7. Consider Alternative Possibilities
Most of the times, we can’t find the real solution because we’re not looking for it. The congruence bias completely dominates our minds; we can’t even realize there are alternative theories.
Systematically considering alternative possibilities — common to both philosophical and scientific thinking — is an effective way to overcome this bias. Practice generating various explanations for each observation.
By creating alternative possibilities, we pursue the best possible answer, not the one that comes up first. When you have options, you can make a more educated decision. Isaac Newton used the term ‘crucial experiment’ to refer to decisive tests between rival hypothesis.
As Plato said, “Opinion is the medium between knowledge and ignorance.”
To arrive at the truth, generate multiple hypotheses and methodically evaluate how they fair against reason and observation.
Evaluating alternative possibilities is a useful tool for wiser thinking.
8. There’s No Right Thing
Certainty is the enemy of wisdom. The ‘right answer’ is a stop, not the final destination. Seeking wisdom is a never-ending journey.
“Of all the words yet spoken, none comes quite as far as wisdom, which is the action of the mind beyond all things that must be said.” — Heraclitus
Alan Hájek, a professor of philosophy at the Australian National University in Canberra, has an excellent exploration of what he calls philosophical heuristic. Several of his tools involve questioning assumptions in how we ask a question.
For example, asking what the right thing to do is presupposes that there is a single right thing to do. That could be the case occasionally. However, ‘right’ has many senses — it could be what is rational or what is moral, etc. Also, there can be multiple actions that could be equally good.
Moral superiority is another righteousness trap, as I wrote here. We think our beliefs — religion, political affiliation, etc. — are superior to other people’s. Rather than trying to have a civilized argument with someone with different beliefs, we try to impose our views. We believe our morality is superior — it becomes the right thing to do.
Thinking like a philosopher is understanding that there’s not just one single right answer.
9. Balance Ethics and Pragmatism
Being a lover of wisdom requires acting with a purpose.
We often hear people having to decide between acting according to morality or pragmatism — like if one thing excludes the other.
Wise leaders make decisions that are both ethically sound and pragmatic. As the authors of From Smart to Wise explain, wise leaders, align their actions with their purpose, act boldly yet prudently, and are sensitive to the context. They maintain their composure, rely on their intuition, and act with integrity.
Practice examining people’s ruling principles — even those of the wise, as Marcus Aurelius suggests on Meditations. We must understand what people avoid, but also what they pursue.
The authors cite how Microsoft’s Bill Gates stepped down from his CEO role and created the Bill & Melinda Gates Foundation. He started using his wealth, smartness and leadership skills for the greater good. Today he is no longer seen as a polarising figure, but as a wise one tackling global problems such as the lack of universal education and infectious diseases.
There’s never a perfect day to get started — choose today.
As Marcus Aurelius wrote, “This is what you deserve. You could be good today. But instead, you choose tomorrow.”
Are You Making Progress?
We spend our entires lives being a lover of wisdom. But, how can we determine if we are making progress?
Seneca came up with a simple approach. He believed that accepting oneself is the first step to be more open to accepting other people and their views. The Roman philosopher believed that a person who is a friend to themselves is an aid to all humankind.
Isn’t that the most important purpose of being wise?
As Seneca wrote, “What progress, you ask, have I made? I have begun to be a friend to myself.”