In our own time, there are web pages, courses, seminars, experts and an entire industry devoted to “positive thinking,” to the happy and the feel-good. Perhaps this is because there’s such an avid market of people who want to feel better about themselves at any cost. Within the maelstrom of self-improvement books appearing every season, Ryan Holiday is an interesting author. This is not only because he’s managed to stay on the bestseller list, but because he’s done so by revitalizing a practical, ancient philosophy that has little to do with the “positivity” of our own time: that of the Stoic philosophers.

In books such as Ego Is The Enemy and The Obstacle Is The Way, Holiday reviews stories, concepts, and quotes from philosophers like Epictetus, Seneca (in a wonderful treatise on dealing with anger) or Marcus Aurelius, all of whom practiced the art of what we’d today call “negative visualization.” That is, take note of everything that can go wrong with your plans and anticipate it.

The famous logic of “Murphy’s law,” (“anything that can go wrong, will”) was anticipated by the Stoics as a reverse engineering tool in which we go from a worst possible scenario back to a state prior to any action at all. In other words, if your goal is to take a road trip, try to review and prevent everything that could slow you down. In reality, we’re never able to be 100% certain that nothing wayward will happen, but at least we can be prepared for some eventualities by keeping an open mind.

In Latin, the practice of negative visualization was called praemeditatio malorum, that is, to think beforehand about the bad. It serves both to remind you to put a spare tire in the trunk or for NASA astronauts to take account of unexpected factors outside of Earth’s atmosphere. “Nothing happens to the wise man against his expectation,” Seneca wrote to a friend, adding that, “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.”

To meditate beforehand on future evils is not an exercise in pessimism, but one of reason. A good attitude may help us to enjoy life once we get to the beach on our hypothetical road trip, but a mental overhaul of what might prevent us from arriving better prepares us to deal with the obstacles we don’t yet know.

If all goes well, you’ll have nothing to worry about. If everything goes wrong, you were prepared in advance to deal with the adversity. It’s not so much a question of “thinking everything will go wrong,” as it is an exercise of imagination such that reality – in its own mysterious way – surprises us with good things and never catches us with our guard down.

In our own time, there are web pages, courses, seminars, experts and an entire industry devoted to “positive thinking,” to the happy and the feel-good. Perhaps this is because there’s such an avid market of people who want to feel better about themselves at any cost. Within the maelstrom of self-improvement books appearing every season, Ryan Holiday is an interesting author. This is not only because he’s managed to stay on the bestseller list, but because he’s done so by revitalizing a practical, ancient philosophy that has little to do with the “positivity” of our own time: that of the Stoic philosophers.

In books such as Ego Is The Enemy and The Obstacle Is The Way, Holiday reviews stories, concepts, and quotes from philosophers like Epictetus, Seneca (in a wonderful treatise on dealing with anger) or Marcus Aurelius, all of whom practiced the art of what we’d today call “negative visualization.” That is, take note of everything that can go wrong with your plans and anticipate it.

The famous logic of “Murphy’s law,” (“anything that can go wrong, will”) was anticipated by the Stoics as a reverse engineering tool in which we go from a worst possible scenario back to a state prior to any action at all. In other words, if your goal is to take a road trip, try to review and prevent everything that could slow you down. In reality, we’re never able to be 100% certain that nothing wayward will happen, but at least we can be prepared for some eventualities by keeping an open mind.

In Latin, the practice of negative visualization was called praemeditatio malorum, that is, to think beforehand about the bad. It serves both to remind you to put a spare tire in the trunk or for NASA astronauts to take account of unexpected factors outside of Earth’s atmosphere. “Nothing happens to the wise man against his expectation,” Seneca wrote to a friend, adding that, “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.”

To meditate beforehand on future evils is not an exercise in pessimism, but one of reason. A good attitude may help us to enjoy life once we get to the beach on our hypothetical road trip, but a mental overhaul of what might prevent us from arriving better prepares us to deal with the obstacles we don’t yet know.

If all goes well, you’ll have nothing to worry about. If everything goes wrong, you were prepared in advance to deal with the adversity. It’s not so much a question of “thinking everything will go wrong,” as it is an exercise of imagination such that reality – in its own mysterious way – surprises us with good things and never catches us with our guard down.