Sometimes The Obstacle Isn’t The Way

You don’t have to accept it.

Jessica Wildfire
7 min readSep 14, 2021


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The Roman emperor Augustus had a slave for everything. He even had a slave to fan him while he slept at night. If you were a Roman citizen, your life was pretty great. If you were a slave, it wasn’t.

I’ve always had a little bit of a problem with stoicism.

That problem is history.

Sure, the Romans gave us philosophy. They also kind of stole it from Greece, like they appropriated most of Greek culture after conquering them and completely destroying the city of Corinth (as an example) in 146 B.C. As my historian friends remind me:

Be careful when you borrow ideas from the Romans.
They’re not your friends.

If you ever traveled back in time to meet a real Roman, they would’ve considered you subhuman, inferior.

The Romans conquered a huge part of the world and enslaved its population. Centuries later, Europe paid it forward by doing exactly the same thing to virtually every other civilization. So if we’re going to give them credit for stoicism and aqueducts, let’s not forget the imperialism we also inherited. They taught us that, too.

I’ve always been conflicted about books like Ryan Holiday’s The Obstacle Is The Way, which has inspired hundreds (maybe thousands) of articles and blog posts about stoicism. Sure, it’s important to get a handle on the things you can and can’t control in your life. Our egos often do get in the way, and we can definitely sabotage our own happiness. A mindset that embraces resilience and problem-solving can take you a long way.

You can learn how to turn obstacles into opportunities.

Of course, if your obstacle was a Roman legion, you were kinda screwed. It strikes me as ironic that the guys who tell us to reach for the stars were the same ones who would murder you and your family, and burn your city to the ground, if you ever tried to stand up to them.

It bothers me.

Roman glory depended on slaves.

The Roman empire was built by slaves.

Your chances of winding up as a slave in Rome were about one in three. There were lots of ways to fall into…