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If there’s one thing the Stoics like Seneca, Marcus Aurelius, and Epictetus knew how to do, it’s navigating adversity. So I thought it’d be a great time to bust out my copy of “The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph,” by Ryan Holiday.

I’m always blown away by people who thrive in the face of adversity and so inspired by companies founded during the most uncertain of times (i.e., Proctor & Gamble during the Great Panic of 1837, Revlon during the Great Depression, and LinkedIn in 2002 after the post-dot-com bubble). 

These people are not immune to the fear, confusion, helplessness, and depression that crises bring. Yet, they managed to thrive not despite, but because of the challenges they faced.   

Stoicism sheds some light on how we can do the same.

Here are three of my most significant takeaways from Holiday’s, “The Obstacle Is the Way” I hope you’ll find inspiring.  


Perception is everything.

“There is no good or bad without us; there is only perception. There is the event itself, and the story we tell ourselves about what it means.” Ryan Holiday.

This is the most critical concept in the book. How you perceive a situation will determine how you feel about it. How you feel will affect how you decide to act.

We know this is a universal truth. If I perceive a situation to be hopeless, I feel helpless. When I feel helpless, what productive actions do I take? None.

Conversely, if I perceive a situation to be difficult, but I decide to find even a small way to make it better, I feel empowered. When I feel empowered, I take productive action.

Perception is everything.

Pro Tip:  In the book, Holiday covers many ways to manage perspective, including the idea of bringing objectivity to your perceptions. Objectivity requires practice, but one approach I found valuable is to take the “you” out of the perception. Pretend you are advising someone else on the problem. What are all the ways someone might solve this challenge?

Recognize Your Power

“Focusing exclusively on what is in our power magnifies and enhances our power.”  Ryan Holiday

We can’t control the circumstances. We can’t argue with reality either. Well, we can, but we lose every time. Being upset with and even enraged by our situation is human, but it’s not helpful. It’s a passive activity that changes nothing and only wears us down.

Here’s what we can control:

  • Our thoughts
  • Our perspectives
  • Our attitude
  • Our creativity
  • Our emotions
  • Our effort
  • Our determination
  • How we spend our time
  • What we feed our mind

This is where we find our power.

It’s supposed to be hard.

Yes, it’s supposed to be hard, and that doesn’t mean you are doing it wrong. Just keep going.

“You will fail. Failure is teaching us something. It’s teaching us what isn’t the way.” Ryan Holiday

I love this idea. Any exceptional achievement will not be easy. We understand that intellectually, yet for some reason, when we eventually run up against that obstacle, we are a bit surprised. We internalize it and think:

  • I must be doing it wrong.
  • It’s too hard.
  • Someone else wouldn’t have this problem.
  • I must not be good enough, smart enough, etc.

The Stoics teach us we are doing it exactly right.

They encourage us to expect things to go wrong by practicing a technique called premeditatio malorum (premeditation of evils). We would recognize this as a project premortem.  The Stoics recommend we ready ourselves for the challenges and adversity we’ll inevitably encounter by anticipating all the things that could go wrong. What are the obstacles we could experience, and what would we do about them?

I’ve created an excellent Project Premortem PDF tool you can download for free below.

Download my Project Premortem Tool


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These three lessons are potent ideas to embrace right now. Thinking positively about a terrible situation doesn’t work for me. The Stoics teach us that people who thrive in the face of hardship don’t do so through happy thoughts. Instead, they shift their perspective to see things more objectively; focus on what they can control to make the bad situation better; expect to get their asses kicked, and, most importantly, always persist.

Now that does work for me.

Stay safe and be well.

“In the meantime, cling tooth and nail to the following rule: not to give in to adversity, not to trust prosperity, and always take full note of fortune’s habit of behaving just as she pleases.” —SENECA