February 3, 2024




The Most Powerful Paradoxes of Life

At a glance

Today’s Fast Summary:

  • Paradoxes are self-contradictory statements that, when analyzed, reveal important truths. The purpose of a paradox is to provoke original thought.

  • Being pulled in two directions creates tension, but understanding and probing paradoxes yields power. 

  • In this newsletter, I’ll cover 21 of the most powerful paradoxes.

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The Most Powerful Paradoxes of Life

Life is full of paradoxes. 

CEOs seek to maximize revenue whilst minimizing costs. Doctors want to prescribe medications with maximum benefit to the patient with few side effects. These are just a few examples. 

Paradoxes are self-contradictory statements that, when analyzed, reveal important truths. The purpose of a paradox is to provoke original thought. 

Paradoxes push us to think outside our comfort bubble and hone in on the insights below the surface. 

Being pulled in two directions creates tension, but understanding and probing paradoxes yields ingenuity, flexibility, and productivity. Paradoxes are good for problem-solving and conscious thought.  

The following are 21 of the most powerful paradoxes I’ve come across.  Understand them, and unlock a trove of insights.

21 of The Most Powerful Paradoxes I’ve Found

1. The Resistance Paradox

We face challenges and obstacles daily. Some are larger than others. 

It’s normal to feel resistance toward these struggles. But this resistance is instinctual. 

When we accept resistance, resistance disappears. When we accept our challenges, we’re able to start solving them.

When we face the fire, the fire can be extinguished.

Our resistance is an opportunity or an ever-growing thorn in our side.

2. The Failure Paradox

The more you’re prepared to fail, the more likely you are to succeed. 

Failure beats stagnation, as failure breeds learning. Learning breeds insights, and insights breed advantages that lead to success.

The faster you fail, the faster you’ll succeed.

Take J. K. Rowling for example. The author of the Harry Potter series faced unemployment and poverty when she wrote the 1st book. It was rejected by multiple publishers. 

But her series has become one of the most commercially successful franchises in history. In failure, she found success. 

3. The Helping Paradox

The more you need help with something, the less others want to give it to you. 

The less you need help, the easier it is to get. 

For example, a college professor is likely to provide an extension to a strong pupil. Mentors spend time nurturing thriving mentees. 

People want to help those who have first helped themselves—or who display the appearance of self-sufficiency.

4. The Icarus Paradox

“Success breeds complacency. Complacency breeds failure. Only the paranoid survive.” - Andy Grove

The bird that flew too close to the sun burned. Downfalls are triggered by the very elements that led to success.

Hubris is the antithesis of success. To avoid failure, remember what bred your achievements.

5. The Service Recovery Paradox

“Never let a good crisis go to waste.” - Winston Churchill

Successfully fixing an issue with a product or service can lead to higher customer satisfaction than if no problem were to occur at all. 

You’re more likely to praise a restaurant if they took an undercooked steak back and comped it than you would if it had been cooked correctly. 

Trust is built quickly in compromising situations.

6. The Hegel Paradox

“We can learn from history, but we can also deceive ourselves when we selectively take evidence from the past to justify what we have already made up our minds to do.” -Margaret MacMillan

We learn from history that we do not learn from history.

Conscious self-reflection is a rare commodity. Objectively reflect on your past or you’re bound to repeat it. 

7. The Friendship Paradox

On average, most people have fewer friends than their friends have.

People with more friends are more likely to be one of your friends.

In reality, it's a contradiction because most people believe they have more friends than their friends have.

Cultivating a diverse set of friends yields happiness and wisdom. 

8. The Knowledge Paradox 

The more you know, the less you can clearly explain. 

This is why experts in certain fields have a difficult time explaining concepts to beginners. It’s among the reasons why individuals don’t share potentially beneficial knowledge with others. 

This is also referred to as the curse of knowledge. 

Our inability to explain familiar concepts is a form of cognitive bias wherein experts often overestimate the ability of novices.

9. The Easterlin Paradox

At a point in time happiness varies directly with income, but over time happiness doesn’t continue growing as income grows.

In other words, you think making more money will make you happier, but you’re wrong.

  1. The Business Dad Paradox

Technology has allowed us to become more efficient in our work.

Increased efficiency means more of the most precious commodity: time. 

But time for what, exactly? Usually, to do more work.

Credit to @annehelen and @cwarzel for this paradox. 

  1. The Abundance Paradox

The average quality of information is decreasing over time. But the highest quality stuff gets better and better.

Abundance is bad for the 'median' consumer, but simultaneously good for the 'conscious, discerning' consumer who filters out noise.

Food inequality in Western countries is an example of this. 

  1. The Man in the Car Paradox

No one is impressed with your possessions as much as you are.

You think you want an expensive car or a fancy watch. In reality, what you want is respect and admiration from other people.

Don't have the mistaken belief that expensive stuff provides validation.

  1. The Choice Paradox

The more choices you have, the less happy you are with your final choice. More choices create more opportunity costs and thoughts of, "I wonder if...?"

Remember that there are infinite ways to achieve a goal, embrace the one you've chosen.

Decomplication and the Stop Doing framework are powerful ways to overcome the Choice Paradox. 

  1. The Approval Paradox

Imagine you're at a party. While you’re there, you meet two people. 

One is very eager to please those around them. They constantly seek others’ validation and try to fit in.

The other is calm, collected, and seemingly authentic. They’re not afraid to voice dissenting opinions. 

Which person would you be more drawn to? 

Most likely, the second person. Their authenticity and self-confidence are appealing, whilst the other person’s approval-seeking behaviour is offputting and annoying. 

The more you want someone's approval, the harder it is to get it.

Approval-seeking is a sign of insecurity and neediness, both unattractive traits.

  1. The Unanimity Paradox 

Under ancient Jewish law, if a suspect was found guilty by all judges, they were acquitted.

Too much agreement implies a systematic error in judgment.

Beware of unanimous agreement, it might mean a bad decision is being made. 

  1. The Knowing Paradox

The more you admit you don’t know, the more you will know.

It’s the curiosity and humility to admit you don’t know that allows you to ask the questions that lead to knowing.

A willingness to look dumb in the moment makes you smarter tomorrow.

The key is to ask more questions than you answer.

  1. The Scarcity Paradox

The more available something is, the less we want it. What’s scarce is deemed valuable, what’s abundant is deemed worthless.

In reality, utility doesn’t always follow scarcity. Abundant pleasures can be our most valuable pleasures—and vice versa.

  1. The Change Paradox

“Yesterday I was clever, so I wanted to change the world. Today I am wise, so I am changing myself.” - Rumi

We want others to change, but we’re unwilling to change ourselves.

Forget it. 

We can’t change others, we can only change ourselves.

  1. The Vulnerability Paradox

“Vulnerability is the currency of human connection.” - Brene Brown

We believe showing our whole selves will scare others away when in reality it draws them closer.

Expose yourself to those you trust. Develop deeper connections with others. Foster belonging in the process. 

The ability to be vulnerable in a world of status games is a superpower. 

  1. The Attention Paradox

Not paying attention to something is paying attention. We resist temptation through deliberate consciousness.

To cut distractions, act consciously, not impulsively.

  1. The Happiness Paradox

The more you search for happiness, the more it eludes you. If you want to be happy, stop thinking about trying to be happy so much.

Happiness is a natural state that occurs when you accept ‘what is’ and don't desire anything else.

Notes on Paradoxes

Two realities can exist concurrently with one another. Understanding this is paramount to success. 

Leverage these counter-intuitive statements to provide yourself a sense of peace and improve problem-solving. 

Consider this quote by author Brennan Manning, “When I get honest, I admit I am a bundle of paradoxes.”

Examine a few of the paradoxes presented in this newsletter and apply them to your life. Seek a more profound understanding of who and why you are. Write your answers down as you go. 

  1. The Failure Paradox. 

    a. Consider the last time you failed. Think about the context and stakes. Write out what happened. 

    b. Why did you fail? Be as objective as possible. 

    c. Did you prepare for the failure? Rationalize how you prepared to fail, or why you didn’t. 

    d. In retrospect, how could you have prepared to fail? Would that have led to success? Consider only concrete steps.

  1. The Hegel Paradox. Use the same scenario/situation as you did in the last question.

    a. Reflect on the components, reasons, and mindsets contributing to your failure. Write these down.

    b. What could you have done to mitigate these? Consider only concrete reasons.

    c. Objectively think about how you could’ve done things differently. Employ a bird’s eye perspective.

  1. The Approval Paradox

    a. According to the definition in the newsletter, do you engage in the approval paradox? 

    b. Consider the last time you engaged in the approval paradox. What was the context? What did you do? 

    c. Why did you seek others approval? Carefully reflect on your motivations. 

    d. What was the outcome? Were your efforts fruitful? 

  1. The Change Paradox

    a. When was the last time you engaged in the change paradox? Consider a situation/context in which you wished for another person or thing to change. 

    b. Why did you want them to change? Reflect on this deeply. 

    c. How could you have potentially changed yourself or your approach in this scenario? What would’ve been the outcome? 

Reflect on the role of these paradoxes in your life. Leverage them to your advantage.


I’d love to hear from you:

  • Which paradoxes do you fall victim to? 

  • Do you have a paradox-oriented mindset? 

  • How can you leverage these to solve problems?

Tweet at me (@_alexbrogan) or respond to this email — I’ll try to respond to everyone.

Have a wonderful Saturday, all.

Until next time,


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