In our last post, I laid out a map of the timeless skills that help us grow. I promised we’d start with Critical Thinking, and for good reason.
Today, you can scroll through three contradictory takes on the same issue before breakfast. One calls it progress, one calls it corruption, the third insists it’s satire. The only thing they share is certainty.
In this environment, the ability to pause, think for ourselves, and make sound judgments isn’t just a nice-to-have; it’s essential for our work, our decisions, and our peace of mind.
But what does "critical thinking" actually mean? It’s not about being negative or criticising everything. It’s the skill of looking at a situation, questioning the assumptions, and making a decision you can stand behind. It’s about trading reaction for reflection.
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Why Is This So Hard?
Let's be honest: thinking slowly and deliberately is hard work. Our brains are wired to take shortcuts, to follow the crowd, and to seek out information that confirms what we already believe. Social media algorithms feed us more of what we like, creating echo chambers that make it feel like our view is the only view.
Breaking out of this requires conscious effort. It means choosing the harder path of questioning over the easy path of accepting.
The Three Habits of a Critical Thinker
We can break this skill down into three core habits.
1 - Spot the Hidden Assumptions First
Every statement, proposal, or belief is built on a foundation of assumptions. You read a confident Slack message and assume someone has all the facts, but they might just be echoing the last thing they heard. The first step is to learn to see these hidden layers by asking: What must be true for this to be true?
For example, if a colleague says, "We need to launch this feature by next month to beat our competitors," the statement rests on several assumptions:
That we know what our competitors are launching.
That beating them to market is the most important factor for success.
That launching by next month is actually possible without sacrificing quality.
Asking the question reveals the shaky ground an idea might be standing on.
2 - Question the Evidence
Once we see the assumptions, we need to look at the evidence supporting them. This is where we become detectives. We ask: Where did this information come from? Is the source credible? Is this a fact, an opinion, or an interpretation? Answering these questions helps us assign a "confidence score" to the information. If it’s an unsourced opinion, we give it less weight. If it’s a well-sourced fact, we give it more. This isn't about dismissing information, but about understanding its quality before we decide to build our own conclusions on it.
3 - Argue Against Yourself
A critical thinker doesn't just look for flaws in one argument; they actively seek out others. This is often the hardest habit to build because it means pushing against our own ego. To practice this, take your preferred conclusion and actively try to prove it wrong. For example, you might reject a product idea because it reminds you of one that failed. The exercise is to ask, "What if I'm wrong?" and then genuinely search for evidence that supports the new idea. Has the market changed? Is the technology better now? The goal isn't to abandon your original position, but to test it. If you can't find a strong counter-argument, your initial idea is likely solid. If you do find one, you can refine your original idea to account for it. This leads to more resilient, well-thought-out decisions.
How to Build This Skill: Three Practical Exercises
Like any skill, critical thinking is built through practice. Here are three simple exercises you can start using today.
The "Intellectual Steel Man"
Instead of creating a "straw man" (a weak version of an opponent's argument), do the opposite. To practice this, take an argument you disagree with and follow these steps:
Find the strongest advocate: Seek out the most intelligent and persuasive source for the opposing view.
Summarise their best points: Listen without judgment and write down their core reasoning and evidence.
Find the positive intent: Try to understand the value they are trying to uphold. Are they prioritising long-term trust over short-term sales?
Articulate their argument: State their position back, perhaps even more clearly than they did.
Only then should you form your response. This forces you to engage with the strongest version of their idea, which strengthens your own thinking.
The "Decision Journal"
This practice trains you to see the flaws in your own thinking over time. When you have to make a significant decision, don't just make it. Grab a notebook and follow these steps:
Capture the context: Note the date and the situation. What decision do you need to make?
State your reasoning: Write down what you decided and, most importantly, why. What assumptions are you making? What evidence are you relying on?
Define expectations: What do you expect to happen as a result of this decision?
Schedule a review: Set a calendar reminder for 1, 3, or 6 months in the future to review this entry.
Reflect on the outcome: When the reminder comes up, look back. Were you right? Were you wrong? What can you learn from the outcome?
Practice the "5 Whys"
This is a simple technique to get to the root of a problem. When faced with an issue, ask "Why?" five times. For example: "The project is behind schedule."
Why? Because a key task took longer than expected.
Why? Because we didn't have the right data.
Why? Because we didn't ask the right department for it.
Why? Because we didn't know who to ask.
Why? Because we didn't have a clear communication plan at the start.
The initial problem (delay) is just a symptom. The root problem is a lack of planning.
A Quick Word on Common Pitfalls
As we start using these tools, it's easy to run into a few common traps. Here’s how to navigate them:
Analysis Paralysis: The goal of critical thinking isn't to think forever; it's to make better decisions. If you find yourself endlessly researching without acting, give yourself a deadline. Say, "I will gather information for one hour, and then I will make a decision." It's often better to make a good decision now than a perfect decision next week.
Sounding Like a Critic: When working in a team, frame your questions with curiosity, not confrontation. Instead of saying, "That will never work," try asking, "Have we considered what might happen if X goes wrong?" or "That's an interesting point. Could you walk me through the evidence you found most compelling?" This turns a potential conflict into a collaborative exploration.
Skepticism vs. Cynicism: A healthy skeptic questions assumptions to find the truth. A cynic assumes bad intent and dismisses ideas without investigation. The first opens up possibilities; the second shuts them down. Always aim to be a constructive skeptic.
Critical thinking isn't an academic exercise. It's a practical tool for navigating a complex world with clarity and confidence. Each time you pause to question instead of react, you widen your view. Not everything deserves your agreement. Not everything deserves your outrage. But it all deserves your attention if you want to think for yourself.
Next time, we’ll explore the second thinking tool: Creativity & Original Ideation. We'll look at how to generate new ideas, even when you don't feel "talented" enough.
What’s your take on today’s topic? Did I miss something, did something resonate?
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very powerful question: Where did this information come from?
This is incredible. It covers so many of the wonderful and challenging angles that come with thinking. This is beautifully written.