5 Lessons Learned from “The Obstacle Is The Way”


This post was originally published on the FCR blog on June 3, 2016. Click here to read the original.

Ok, I’ve heard of hacking used in many different contexts like computer hacking, hacking at roots to get a stump out of the ground, and growth hacking (though I’m not sure what that one actually means). In the book, The Obstacle Is The Way, Ryan Holiday introduced me to a new sort of hacking: Life Hacking. Essentially life hacking is all about changing our approach to the inevitable obstacles in life and responding to them in such a way that they become an advantage.

The book is packed with examples of people who succeeded because of the way they responded to adversity. I’d like to share the five insights that I did the most underlining on in my read.

1. Controlling Our Emotions

Holiday warns that inability to deal with our emotions can lead to panic and cause us to make mistakes. He tells of Astronaut John Glenn training himself to keep his heart rate under one hundred beats per minute so he’d be prepared to keep his cool in those stressful situations in space.

We know that emotional intelligence is important and I’ve certainly regretted some of my actions where I wasn’t in control of my emotions. Here’s the point from Holiday that I found particularly insightful:

If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion. Or, quite possibly a destructive one.

Are emotions natural and normal? Yes. But they can also be unhelpful and destructive.

2. Altering Our Perspective

When you can break apart something, or look at it from some new angle, it loses its power over you.

Holiday shares a story about George Clooney who early in his career was getting rejected at auditions. He was disappointed and typically resorted to blaming others for not giving him a chance. Clooney eventually changed his perspective and rather than waiting for someone to have mercy on him and give him a shot, approached it with the mindset of showing producers what special ability and value he brought to the table. Projecting this attitude made all of the difference and the rest is history for George Clooney.

3. Finding The Opportunity

There is good in everything, if only we look for it. – Laura Ingalls Wilder

In World War II, rather than opting for a long, costly war, the German army employed their Blitzkrieg strategy. This all out offensive was designed to intimidate, deflate, and overwhelm the enemy. Holiday tells us that in the face of this, General Eisenhower mandated that his military leaders maintain an upbeat and cheery demeanor when they met together. By doing so, they realized that the Germans sought to intimidate and were ultimately defeated by the Allies.

4. Do What Works

This is easily my favorite story in the book. Two American fruit companies were battling for a valuable piece of land in South America. The only problem was that two different local individuals believed they owned the land. While one fruit company geared up for a legal battle to settle the dispute, the other paid both parties full price for the land. While it cost double, they beat their competition and ultimately succeeded. Holiday’s point is that:

Sometimes you do it this way. Sometimes that way. Not deploying the tactics you learned in school but adapting them to fit each and every situation. Any way that works – that’s the motto.

How often do we only see one way to achieve a goal?

5. Meditate On Our Mortality

In probably the most sobering insight from the book, Holiday encourages us to consider our own mortality. He points out that, “we may not say it, but deep down we act and behave like we’re invincible.” By considering our death, it helps us focus on what really matters and what we want to accomplish with our lives. This really takes Stephen Covey’s “begin with the end in mind” to a new level for me. He leaves us with this statement:

If something is in our control, it’s worth every ounce of our efforts and energy. Death is not one of those things – it is not in our control how long we will live or what will come and takes us from life.

I’ve merely scratched the surface here of a very insightful book. If you’ve read The Obstacle Is The Way, what insights stood out to you? If you haven’t read it, do so and then come back with your insights.


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