AN

INTRODUCTION
TO STOICISM
D ay 6 : P re m e d i ta tio
M al o rum : T h e Sto i c Art of
Neg at i ve V i su a l i zation

D A I L Y S T O I C . C O M
 CEO calls her staff into the conference
A room on the eve of the launch of a major
new initiative. They file in and take their seats around
the table. She calls the meeting to attention and begins,
“I have bad news. The project has failed spectacularly.
What went wrong?”
The team is perplexed: What?! But we haven’t even
launched yet…!
I know it seems strange and maybe even
counterproductive to demand that employees think
negatively instead of optimistically, but in business
circles today, everyone from startups to Fortune 500
companies and the Harvard Business Review are doing

DA I LYSTO I C .C O M 1
this exact exercise. In a direct response to optimistic,
feel-good thinking, these leaders are encouraging their
employees to think negatively.
The technique that the CEO above was using
was designed by psychologist Gary Klein. It’s called
a premortem. In a premortem, a project manager must
envision what could go wrong—what will go wrong—in
advance, before starting. Why? Far too many ambitious
undertakings fail for preventable reasons. Far too many
people don’t have a backup plan because they refuse to
consider that something might not go exactly as they
wish.
In fact, I think more companies need a Chief
Dissent Officer, someone to shoot down the bad ideas
that our blind spots and naive optimism too often
obscure. They can catch us when we are puffed up with
visions of our own greatness and preordained success.
Remember Netflix’s aborted attempt to split into
two separate companies? Or when Google Wave was
marketed as “the next Gmail,” only to be shut down in
a little over a year? If only these great companies had
stopped to envision the possible travails that awaited
them, they might have been able to prevent them.
No one has ever understood this better than former
heavyweight champion Mike Tyson, who, reflecting on
the collapse of his fortune and fame, told a reporter, “If
you’re not humble, life will visit humbleness upon you.”

2 DA I LYSTO I C .C O M
 The practice goes back much further than just
psychology though. It dates back many thousands
of years, in fact—to the great Stoic philosophers like
Marcus Aurelius, Epictetus and Seneca. And they
had an even better name for it: premeditatio malorum
(premeditation of evils).
A writer like Seneca would begin by reviewing or
rehearsing his plans, say, to take a trip. And then, in his
head (or in writing), he would go over the things that
could go wrong or prevent it from happening—a storm
could arise, the captain could fall ill, the ship could be
attacked by pirates.
“Nothing happens to the wise man against his
expectation,” he wrote to a friend. “. . . nor do all things
turn out for him as he wished but as he reckoned—and
above all he reckoned that something could block his
plans.”
By doing this exercise, Seneca was always prepared
for disruption and always working that disruption into
his plans. He was fitted for defeat or victory. And let’s
be honest, a pleasant surprise is a lot better than an
unpleasant one.
In a case where nothing could be done, the Stoics
would use it as an important practice to do something
the rest of us too often fail to do—manage expectations.
Because sometimes the only answer to “What if?” is, “It
will suck but we’ll be okay.”

DA I LYSTO I C .C O M 3
 We often learn the hard way that our world is
ruled by external factors. We don’t always get what is
rightfully ours, even if we’ve earned it. Not everything
is as clean and straightforward as the games they play
in business school. Psychologically, we must prepare
ourselves for this to happen.
If it comes as a constant surprise each and every
time something unexpected occurs, you’re not only
going to be miserable whenever you attempt something
big, you’re going to have a much harder time accepting
it and moving on to attempts two, three, and four. The
only guarantee, ever, is that things could go wrong. The
only thing we can use to mitigate this is anticipation,
because the only variable we control completely is
ourselves.
The world might call you a pessimist. Who cares?
It’s far better to seem like a downer than to be blindsided
or caught off guard.
If we have prepared ourselves for the obstacles
that are inevitably on their way, we can rest assured that
it’s other people who have not. In other words, this bad
luck is actually a chance for us to make up some time.
We become like runners who train on hills or at altitude
so they can beat racers who expected the course would
be flat.
Anticipation doesn’t magically make things easier,
of course. But we are more prepared for them to be as
hard as they need to be, as hard as they actually are.
4 DA I LYSTO I C .C O M
 You know what’s better than building things
up in your imagination? Building things up in real
life. Of course, it’s a lot more fun to build things up
in your imagination than it is to tear them down. But
what purpose does that serve? It only sets you up for
disappointment. Chimeras are like bandages—they
hurt when torn away.
With anticipation, we have time to raise defenses,
or even avoid them entirely. We’re ready to be driven off
course because we’ve plotted a way back. We can resist
going to pieces if things didn’t go as planned. With
anticipation, we can endure.
We are prepared for failure and ready for success.
P.S. Check out our premeditatio malorum medallion in
the Daily Stoic Store.

DA I LYSTO I C .C O M 5