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Today at a Glance:
A paradox is defined as a seemingly absurd or self-contradictory statement or proposition that when investigated or explained may prove to be well founded or true.
Life is full of paradoxes. Once you become aware of them, you will find yourself empowered to use them to your advantage.
Paradoxes of Life
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 as linear and logical—when in reality it is anything but. Many of life’s most important truths appear contradictory or convoluted on the surface.
Look around long enough and you’ll realize the ultimate truth:
Life is full of paradoxes.
They are everywhere around you. They have the potential to confuse…or empower.
Once you become aware of these paradoxes—once you truly internalize them—you will find yourself empowered to use them to your advantage.
To get you started on this journey, here are 20+ powerful paradoxes of life…
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.
Argue less, persuade more.
Persuasion is an art that requires a paintbrush, not a sledgehammer.
The Effort Paradox
Sprezzatura is an Italian word meaning “studied carelessness”—it encapsulates the effortful art of appearing effortless.
You have to put in more effort to make something appear effortless.
Effortless, elegant performances are often the result of a large volume of effortful, gritty practice.
Watch videos of Roger Federer playing tennis in his prime. There is a certain nonchalance to his actions on the court, but this nonchalance was the earned result of endless hours of studied, careful, meticulous practice.
Small things become big things. Simple is not simple.
The Wisdom Paradox
“The more I learn, the more I realize how much I don't know.” — Albert Einstein
The more you learn, the more you are exposed to the immense unknown.
This should be empowering, not frightening. Embrace your own ignorance. Embrace lifelong learning.
The Productivity Paradox
Parkinson's Law says that work expands to fill the time available for its completion.
Work longer, get less done.
When you establish fixed hours to your work, you find unproductive ways to fill it.
Modern work culture is a remnant of the Industrial Age. It encourages long periods of steady, monotonous work unsuited for the Information Age.
To do truly great, creative work, you have to be a lion. Sprint when inspired. Rest. Repeat.
The Money Paradox
You have to lose money in order 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 to learn.
Put skin in the game. Scared money don't make money!
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.
The Failure Paradox
You have to fail more to succeed more.
Our greatest moments of growth often stem directly from our greatest failures.
Don’t fear failure, just learn to fail smart and fast.
After all, getting punched in the face—a few times, but not too many—builds a strong jaw.
The Say No Paradox
Take on less, accomplish more.
Success doesn’t come from taking on everything that comes your way. It comes from focus—deep focus on the tasks that really matter.
Say yes to what matters, say no to what doesn’t. Protect your time as a gift to be cherished.
The Speed Paradox
You have to slow down to speed up.
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, not effort.
Move slow to move fast.
The Death Paradox
You must know your death in order to truly live your life.
Memento Mori is a Stoic reminder of the certainty and inescapability of death. It is not intended to be morbid; rather, to clarify, illuminate, and inspire.
Death is inevitable. Live while you're alive.
The Fear Paradox
The thing we fear the most is often the thing we need the most.
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 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 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!
The Shrinking Paradox
In order to grow, sometimes you need to shrink.
Growth is never linear. Shedding deadweight may feel like a step back, but it is a necessity for long-term growth.
One step back, two steps forward is a recipe for consistent, long-term success.
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...
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.
The Tony Robbins Paradox
In investing, the willingness to admit you have no competitive advantage can be the ultimate competitive advantage.
Strong self-awareness breeds high-quality decision-making. Foolish self-confidence breeds nothing of use.
Be self-aware—act accordingly.
The Talking Paradox
“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.
The Connectedness Paradox
More connectedness, less connected.
We're constantly connected—bombarded by notifications and dopamine hits. But while we have more connectedness, we feel less connected.
Put down the phone. Look someone in the eye. Have a conversation. Breathe.
The Taleb Surgeon Paradox
Looking the part is sometimes the worst indicator of competency.
The one who doesn’t look the part has had to overcome much more to achieve its status than the one from central casting.
If forced to choose, choose the one that doesn’t look the part.
The Constant Change Paradox
“When you are finished changing, you are finished.” — Benjamin Franklin
The only constant in life is change. Entropy is reality. It’s the one thing you can always count on—the only constant.
Embrace it—be dynamic, be adaptable.
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.
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…
Where It Happens Podcast
Episode 2: The NSFW Framework & the Magic of Community-Product Fit with Amanda Goetz
Special thanks to our sponsors for providing us with the support to bring this episode to life.
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That does it for today’s newsletter. If you’re celebrating…Happy Thanksgiving!
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