On Paradoxes that occur in Life
More than a Dozen powerful paradoxes on money, growth, careers, business, and life
Life is full of paradoxes. Once you become aware of them, you will find yourself empowered to use them to your advantage.
Paradox: a seemingly absurd or self-contradictory statement or proposition that when investigated or explained may prove to be well founded or true.
From a young age, we are pressured to view the world using ‘‘common’’ sense (or what the majority agree on as consensus) — when in reality it is anything but. Many of life’s most important truths appear contradictory or convoluted on the surface.
Observe and contemplate long enough and you’ll realize this truth:
Life is full of paradoxes.
They are everywhere around you. They have the potential to confuse…or to empower.
Once you become aware of these paradoxes—once you truly internalize them—you will find serenity from a chaotic or turbulent world.
To get you started on this journey, unfortunately you would probably have to have something (bad) happen to you, like it did to me.
Sometimes it’s a dread taking medicine because it tastes so bitter, but the patient needs it.
Steve Jobs: It was awful tasting medicine, but I guess the patient needed it.
When these perplexing events happen within our lives; you are of course free to ignore them and continue life as usual, or you may feel a stirring need inside to answer the call.
Like Alice (in Wonderland); you may choose to venture down the rabbit hole into strange lands. This is the beginning of the archetypal descent into the unknown depths of life; into the hidden unconscious aspects of oneself which lie outside the matrix or consensus reality that we have become habituated to.
Humans have an age-old tendency to want to simplify. To reduce things to black and white. Good and evil. When in reality... nothing is simple. Everything has... texture. Nuance.
But thinking is incredibly difficult. It is a lot of work just to peel back the layers. So the majority of the time, we will take the easy way out. And judge.
To the uninitiated, our mind simply does not possess the capacity for this sort of nuance. To understand the world from both sides of the same coin.
They see villains and heroes, that is all.
Wisdom is having the ability to hold two opposing thoughts at the same time and not crumble under its weight.
Observe nature and you will notice that she holds up pretty well on her own without needing a central authority or gods to govern (like a central bank or government) to dictate what one might need to do or not.
What is this special glue that holds reality together?
Something you might describe as energy between all things, a tension, a balance, that binds the universe together.
Well, let’s find out…
Sprezzatura (“Studied Carelessness”)
Italians love to use this word to describe how they dress so elegantly.
It's like embracing imperfection, and in so doing, pulling it off. When pulled off expertly, sprezzatura is what you get when you put a lot of thought into your clothing, but it doesn't appear that you did so.
However, you have to put in a lot of effort to make something appear effortless!
Effortless, elegant performances are often the result of many iterations & gritty practice. Simple yet complex.
In simple terms: Sprezzatura is earned effortlessness.
Or what can be described as the Paradox of Effort.
Once you internalize the concept of the Paradox of Effort, you'll see it all around you.
Picasso in the Market
There is a famous tale of Picasso's interaction with a woman in a market.
Picasso was walking through the market one day when a woman approached him. She pulled out a piece of paper and said, “Mr. Picasso, I am a fan of your work. Please, could you do a little drawing for me?”
Picasso smiled and quickly drew a small, but beautiful piece of art on the paper. He handed it back to her. “That will be one million dollars.”
“But Mr. Picasso,” the woman protested, “It only took you thirty seconds to draw this little masterpiece.”
“My good woman,” Picasso smiled, “It took me thirty years to draw that masterpiece in thirty seconds.”
The ease and effortlessness of his drawing performance masked the years or input that led to that moment.
It is also the reason why the top 1% command such high salaries while also working less.
In Sports
The elegance of elite athletes is another perfect example.
Roger Federer and Lionel Messi are masters of the Paradox of Effort. Their movement, speed & agility almost looks effortless. You don’t see them in the rest. They are simply in a category of their own.
Good athletes have learned to turn on max intensity and go all out. Once in a generation athletes have internalized the effortless paradox.
Their skills are largely unconscious and so appear to us to be effortless.
Here’s another great example of this: Lionel Messi.
He is often seen walking around on the pitch—almost appearing lazy—a fact that many commentators have noted.
But the reality is that this approach is essential to his incredible success.
He is the best in the world at identifying the leveraged moments where his inputs will be amplified. During these moments, he goes 100%. Outside of these moments, not so much.
When a situation calls for low intensity, they execute at low intensity. When a situation calls for high intensity, they execute at high intensity.
Striving Less Generates More Success. A wu-wei mindset promotes effortless action and non-striving flow states. He is great at identifying leveraged opportunities and execute in bursts.
You can read more on it here:
When you enter any new arena, first learn to identify the points of leverage in the system. Once you identify them, focus all of your intensity on those points. If you aren't in one of them, rest.
A thing to note though, is that if any of us ever do this, we would be mocked for not putting in enough effort.
In Nature
One final (and perhaps favorite) example: the Chinese bamboo tree.
It doesn’t break through the ground for 5 years, but once it breaks through, it can grow up to 100 feet in 5 weeks.
The growth appears effortless, but is the result of years of effort below the surface.
So from a young age while we are taught to view the world as black and white; many of life’s most ‘‘break-truths’’ appear contradictory on the surface.
The Money Paradox
Ever heard of the saying ‘‘you have to spend money to make money.’’
Every successful investor & builder has stories of the invaluable lessons learned from a terrible loss in their career. Sometimes you have to pay a price to learn.
Put skin in the game. Scared money don't make money!
The Persuasion Paradox
Have you noticed that the most argumentative people rarely persuade anyone of…well…anything?
The most persuasive people don’t argue—they observe, listen, and ask questions. They know when to stay silent and when to speak up.
“Wise men speak because they have something to say; Fools speak because they have to say something” - Plato
Speaking less increases the weight of your words.
Persuasion is an art that requires a paintbrush, not a sledgehammer.
Friday Night Lights (the movie) has a famous scene where a notoriously quiet player gives a riveting speech that turns around a game. He rarely spoke up, so when he did, it hit. Hard. If you want to be heard, talk less. You’ll find more power in your words.
“We have two ears and one mouth so that we can listen twice as much as we speak.” — Epictetus
If you want your words and ideas to be heard, start by talking less and listening more. You’ll find more power in your words.
Talk less to be heard more.
Slow Down to Speed Up
Want to speed up? Try slowing down. Slowing down gives you the time to be deliberate with your actions. You can focus, gather energy, and deploy your resources more efficiently. It allows you to focus on leverage and ROI. Move slow to move fast.
The Growth Paradox
Growth takes a much longer time coming than you think, and then it happens much faster than you ever would have thought.
Growth happens gradually, then suddenly.
When you realize this, you start to do things differently—apply effort appropriately, stay the course, and let compounding work its magic.
Learn More to Know Less
The wisdom paradox - the more you learn, the more you are exposed to the immense unknown. This should be empowering, not frightening.
“The more I learn, the more I realize how much I don't know.” - Albert Einstein
Embrace lifelong learning.
The News Paradox
The more news you consume, the less well-informed you are.
Taleb calls it the noise bottleneck: As you consume more data, the noise to signal ratio increases, so you end up knowing less about what is actually going on.
Want to know more about the world? Turn off the news.
The Looking Paradox
You may have to stop looking in order to find what you are looking for.
Have you noticed that when you are looking for something, you rarely find it?
Stop looking—what you’re looking for may just find you.
Applies to love, business, investing, or life...
Shrink to Grow
Growth is never linear. In order to grow, sometimes you need to shrink. Shedding deadweight may feel like a step back, but it is a necessity for long-term growth. This principle applies to your career, startup, or life. One step back for two steps forward.
Remember Alice had to shrink in order to ‘‘Grow’’.
Fail More to Succeed More
We fear failure, so most of us play it safe to avoid it. But our greatest moments of growth often stem directly from our greatest failures. Don’t fear failure, just learn to fail smart and fast. Fail more - you’ll learn, adapt, and grow.
Take On Less, Accomplish More
Success doesn’t come from taking on everything that comes your way. It comes from focus - deep, disciplined focus on the tasks that really matter. Say yes to what matters, say no to what doesn’t. Protect your time. It is a gift to be cherished.
Memento Mori
A favorite of Stoic philosophy, it is a reminder of the certainty and inescapability of death. It is not intended to be morbid or dark; rather, to clarify, illuminate, and inspire. You must know your death in order to truly live your life.
Ones attachment in life, accumulating ‘‘material stuff’’ would require you (at a later point in life) to learn to let it ALL go. Because we can’t bring our attachments to our afterlife. The things you own ends up owning You!
Everybody want to go to heaven, but nobody wants to die to get there. ‘‘Everybody wants to be free, but only death can set one free.’’ To be truly free, one must breakthrough the barriers of the physical.
The Only Constant is Change
Entropy is reality. The world is in a continuous state of change. It’s the one thing you can always count on - the only constant. Embrace it - be dynamic, be adaptable.
“When you are finished changing, you are finished.” - Benjamin Franklin
The Icarus Paradox
It is a classic tale of Greek mythology.
Icarus crafted wings out of feathers and beeswax to escape an island. He began to fly—the wings working wonders. But he quickly became blinded by his own engineering prowess and flew too close to the sun, which caused the beeswax to melt and sent him plummeting to his death.
What makes you successful can lead to your downfall.
An incumbent achieves success with one thing, but overconfidence blinds them to coming disruption. Beware!
More Choices, Less Satisfaction
We assume a positive linear relationship between choice and satisfaction. But is this wrong? “Choice paralysis” is a very real phenomenon. The relationship between choice and satisfaction is much more nuanced than you’ve been led to believe.
Face Your Fears
If something scares you, you should probably go do it. Fears, when avoided, become limiters on our growth and life. Make a habit of getting closer to your fears. Then take the leap (metaphorically!) - you may just find growth on the other side.
The Hamlet Paradox
"I must be cruel only to be kind." — Hamlet
In Hamlet, the protagonist is forced to take a seemingly cruel action in order to prevent a much larger harm.
Life is so complex. The long-term righteous course may be the one that appears short-term anything but.
Get Vulnerable to Become Strong
The stigma of vulnerability has been broken. It’s ok to admit we aren’t ok. Strength comes from opening up to our vulnerabilities - embracing them, owning them, and growing through them. Want to get strong? Get vulnerable first.
Nothing is Certain
“The only certainty is that nothing is certain.” - Pliny the Elder
Uncertainty and randomness are features, not bugs. Embrace them.
“It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.” Mark Twain
The Control Paradox
More controlling, less control.
We have all seen or experienced this as children, partners, or parents. The most controlling often end up with the least control.
Humans are wired for independence—any attempts to counter this will be met with resistance.
Concluding Thoughts
Life is full of paradoxes.
They are everywhere around you. Don’t let them cloud your path.
Internalize them—use them to your advantage.
I hope this post helps you do just that…