US Highway 50

In ancient Greece and Rome, many prominent thinkers subscribed to a philosophy called Stoicism.1 We’ll talk generally about borrowing ideas from Stoicism in an upcoming post, but today, I’d like to share a simple Stoic thought exercise that can make it a little easier to bounce back from hardship.

I first encountered this thought exercise a few years ago in the writings of the Roman philosopher Seneca, and it’s become a favorite of mine. It’s simple, easy to do, and as timely today as it was 2,000 years ago.

The exercise is called premeditatio malorum, or premeditation of evils.

A useful technique with a scary name

“Premeditation of evils” simply means taking a moment to think through everything that could go wrong with a particular plan. This may sound like a huge downer, but it’s actually calming. Let’s look at an example.

Say you’re starting a side business which you hope will become your full-time job in a couple of years. You’re excited, and you’re sure you’ll be wildly successful. In the back of your mind, though, you know that 80% of businesses fail in the first year.

You decide to perform a premeditation of evils, and you make a list of all the things that could go wrong.

  1. You could misjudge demand for your product or service.
  2. Your product or service could be priced too high. Or too low.
  3. You market research could be off.
  4. You could simply burn out.

In making this list, maybe you realize that you haven’t done enough market research. You’re really not sure what kind of person is likely to be your customer, and you especially don’t know what websites they frequent or how to get their attention.

You decide to delay launching your business for two months while you shore up your knowledge of the market, and in doing so, you increase your likelihood of success.

Crucially, you also prepare yourself mentally for the possibility that even with perfect preparation, this might not work (as Seth Godin likes to say). Would it really be that bad? Would your life fall apart? Probably not. So how would you recover?

We need to think about these things.

Two benefits of this process

Regularly engaging in premeditation of evils delivers two main benefits.

First, as we’ve seen, it forces us to consider outcomes that are unpleasant but fairly likely.

To use another example, let’s say you’re planning a road trip from Maine to San Francisco, and your car has 175,000 miles on it. Your car will probably make the trip. But there’s also a reasonable chance that a vehicle with that many miles will break down on a road trip that long, and it’s best to think about what you’d do in that situation. Doing a premeditation of evils might therefore influence your plans, as you decide to avoid U.S. Highway 50, the “loneliest road in America” (pictured above).

Or maybe you want to drive Highway 50, so you rent a car.

Second, it prepares us for hardship in general.

Not all problems can be predicted, and we need to be prepared for unlikely tragedies, like the sudden loss of a healthy family member. Most of us tend to assume everything will go according to plan, even though our own life experience shows otherwise. Regularly taking a few moments to ask ourselves “What would I do in a worst-case scenario?” may be sobering, but when life doesn’t go according to plan (and when does it?), such thinking pays off.

photo by Jonathan Berman


  1. For more on Stoicism, check out author Ryan Holiday’s great blog Daily Stoic. Here’s a good post to start with.. Or dive right in and read Marcus Aurelius’ Meditations (I recommend Gregory Hays’ translation). ↩︎