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LEADERSHIP

“[I’ve missed out on] so many deals

I can't even count, but I don't regret

any of them. My success put[s] me

in a position to evaluate the deals I

mistakenly passed on. Things have

turned out ok despite my misses.”

First of all, let’s clear the air on this

one: “ok” is an understatement

But what is fascinating about

Cuban is the idea of living with

“no regrets” regarding his business

decisions.

It permeates popular culture. Tattoos

across the chests of young

men and comments made by

celebrities, artists, politicians,

and anyone with a voice in

the public all center around

the idea that no matter

how events play out or

what decisions are made,

there are no regrets. Even if

things seem to go badly, most

people who prescribe to a “no

regrets” mentality argue that

it’s a positive moment—a learning

experience.

Is it really, truly possible to live a life of no regrets? Sure, it’s

possible—if you have the right mentality for it. But

crafting that mindset is no easy feat, especially for

people in places of wealth and power. Notorious

B.I.G. makes it pretty clear: mo’ money,

mo’ problems.

Take our fictional hero/billionaire Stark.

His fortune continually provides

him ample opportunities to make

decisions—and robots—that he

ends up deeply regretting. But

it’s not the money that is the root

of the problem for him, nor is it

a valid reason for anyone in a

position of wealth or power.

The real-life examples are scarier.

The

Enron

leaders, the “too-

big-to-fail” CEOs of banks

on the

precipice of the Great Recession,

and top brass at the car companies

who lied about emissions to the

public all have one thing in common: a

terrifying lack of transparency that led to

huge, regretful decisions.

“[I’VE MISSED OUT ON]

SO MANY DEALS I CAN'T EVEN COUNT,

BUT I DON'T REGRET ANY OF THEM.

MY SUCCESS PUT[S] ME IN A POSITION

TO EVALUATE THE DEALS

I MISTAKENLY PASSED ON.

THINGS HAVE TURNED OUT OK

DESPITE MY MISSES.”

“THERE IS NO SHORTAG

OF FEEDBACK ON SOCIAL ME

WHILE THERE IS A LOT O

FILTERING OF NOISE,

ALL IT TAKES IS ONE NUGG

OF KNOWLEDGE FOR ME

TO BENEFIT.”