The Stoic Challenge - William B. Irvine

The Stoic Challenge - William B. Irvine

Video Book Summary

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Book Summary Notes

The Stoic Challenge

“This book is an exercise in what might be thought of as twenty-first-century Stoicism. In these pages, I have fused the advice given by the first-century Stoic philosophers with the research done by late twentieth-century psychologists."

"Some in academia will resent me for meddling with classical Stoicism in this manner. They think of Stoicism the way they think of a priceless ancient relic—as something to be kept in a hermetically sealed case, to be seen but not touched.

"By contrast, I treat Stoicism as a tool that, although in need of sharpening because of the passage of time, is not only still useful but can have a profoundly beneficial impact on modern lives."

"I begin by describing the sorts of setbacks to which we are susceptible and the ways in which we typically respond to them. Although many people become frustrated, angry, anxious, or even despondent, others take setbacks in their stride. How do they do it?"

"I then explore the psychology of setbacks: why do they affect us emotionally the way they do? I go on to show how, instead of thinking of setbacks merely as unfortunate experiences, we can reframe them as tests of our resilience and ingenuity. Doing this can have a profound impact on how we respond to them. Instead of experiencing a mixture of anger and anxiety, we might be surprised to discover that we are rising enthusiastically to the challenge presented by a setback."

"And finally I show how using the Stoic test strategy, besides helping our days go better, can help us have a good life—and when it comes time to make our exit from this world, a good death.”

Creating your own personal Stoic Toolbelt!

William notes here that he views Stoicism as a tool that we can sharpen to have a profound impact on our lives.. 

This is something I think that can't be overlooked..  

What can these tools help us do?

Look at life as precious and motivate yourself to live it to the fullest

Understand that every hardship in our lives is a test that if passed makes us stronger

Among many many other things which we'll explore in the summary

Have situations really changed that much?

Most of the things we deal with on a monthly, weekly and daily basis are much the same as when the original Stoics walked the earth..  

They struggled with things like procrastination, anger, grief, guilt and all sorts of negative emotional states!

So why should we listen to them..  

Well the Stoics had an amazing way of not only clearly articulating a problem.  (Making it easy to identify in our own lives). 

But also doing an amazing job at creating easy to implement practical exercises to help us think about the things we encounter in life.

Why we shouldn't just listen!

The exercises we're going to talk about today are extremely powerful..  If used!

That means you're going to need a piece of paper, a mind map and the pause button to journal and contemplate!


Setback Stories

“Setback stories like those related above leave me with curiously mixed emotions. On hearing them, I might be moved to tears, but at the same time, I might feel ashamed for myself for taking so much of my life for granted." 

"In the course of going about my daily business, I might experience a minor setback, like discovering that all the parking spaces close to the grocery store have been taken. Oh, great! I might think, only to recall that in walking the few more steps that I was complaining about, I was living the life that Stephen Hawking or Jean-Dominique Bauby could only dream of. Shame on me!"

"Although setback stories can sadden and shame us, they can also be enormously uplifting. In them, we encounter ordinary people who have experienced setbacks vastly more challenging than any we are likely to experience, and who, instead of wallowing in self-pity, responded with courage and intelligence. They thereby transformed what could have been personal tragedy into personal triumph.”

Putting setbacks into perspective.. 

Welcome to our first tool!

  • Life is full of setbacks; not getting the promotion, failing in business or cheating on your health regimen..
  • These things are baked into the system!  They are going to happen no matter what.  We can't control this.

What can we control?  How we respond.

  • The Stoics were big believers in the space between stimulus and response..  
  • “Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.” - Viktor Frankl (who was inspired in part by the Stoics).
  • They believed in short that it wasn't what happened to use that mattered but how we responded.

What was the last 'setback' you've had?

  • Did you paying attention to how you thought about it?  (That's the first step by the way).  
  • Where I to guess I would say that you (like most of us) beat yourself up, got upset or angry about the setback. 
  • Actually..  It's likely that you have created a cycle of setbacks because of your response to one setback a long time ago.  (Something very common in coaching clients). 
  • Pay attention next time..  Make some space between that stimulus and response.

How might we respond better next time?

Let's talk about one of my business coaching clients..  And a 'setback' that he had! 

Earlier this week I had a coaching call with one of my clients trying to build an online business!

Things had been going great after our last call and I was excited to see how he had implemented our plan.

When I show up to the call I can see the look on his face..  Something went wrong with our plan!  And he was taking it hard. 

The sales message he sent out didn't work!  Not even one response..  He was ready to quit.  

Rather than indulge his misery or come up with a new plan.  (Something the old me would have done).  

I decided our best course of action was Google.  

For the next 30 minutes we research how the best businesses in history started with a string of failures..  

Then we looked at how they responded to those failures and bounced back stronger.. 

This didn't help him with his sales problem.  But it allowed him to play the game for another day.  Opened his mind to creative actions.  Probably the two most important things in business.  

How about you?  We already know what your last setback was..  But let's think about your most common ones. 

Make a list of common setbacks that happen to you.  

Then research on YouTube, Google and Documentaries for people who have gone through similar situations and made it through.

Keep that list close..  Because another setback is right around the corner!  Pull it out then. 


“We explored what might be called the resilience continuum. At one end we find resilient individuals. When they encounter a setback, they bounce back quickly—or better still, they don’t get upset by the setback, meaning they have nothing to bounce back from. They come off looking strong and even heroic. At the other end of the continuum we find fragile individuals. On being set back, they become flustered, angry, or even despondent. As a result, they tend to be unhappy, and their friends and relatives may pity them rather than admire them.”

"A resilient person will refuse to play the role of victim. To play this role is to invite pity, and she doesn’t regard herself as a pitiful being. She is strong and capable. She may not be able to control whether she is a target of injustice, but she has considerable control over how she responds to being targeted. She can let it ruin her day and possibly her life, or she can respond to it bravely, remaining upbeat while she looks for workarounds to the obstacles that people have wrongly placed in her path.”

 “Consider how different our world would be if Nelson Mandela and Mahatma Gandhi had played the role of victim. Suppose, more precisely, that they had been raised to think it was emotionally risky to deal with setbacks on their own and that at any rate, they shouldn’t have to deal with them. Under such circumstances, they probably wouldn’t have responded to the injustices they experienced as bravely as they did. They might instead have made an appointment with a therapist for advice on how best to cope with their situation, or they might have restricted their efforts to writing heartfelt letters to elected officials.”

What role are you playing?  Victim or hero (you choose).

This is another great tool coming out of the book..

Something difficult happening in your life?  Take some time to reflect.  What role am I playing right now?

  • Victim
  • Blaming outside people or circumstances
  • Giving up or giving in
  • Cultivating fragility
  • Hero
  • Looking for a way to grow
  • Identifying the positives
  • Cultivating resilience

People who are successful are resilient!  But they might not have started that way..  

  • The great thing about resilience in my eyes is that it's a skill a tool that you can learn to use! 
  • If today you're hurt by every setback you can take small steps to move towards a more resilient mindset. 

The Alter Ego - Exercise

  • This is an exercise I use with coaching clients to help them get into a resilient frame of mind:
  • Step One: Ask the identifying question.  What role am I playing right now? Victim or Hero. 
  • Step Two: Imagine.  What does your superhero self look like?  How would they react?
  • Step Three: Take a deep breathe.  Work to embody that superhero-self.  Then take the next right action. 

Stoic Test

“The Stoics weren’t anti-emotion; indeed, they placed a high value on positive emotions, including delight, joy, and a sense of awe. They knew that without these emotions, ours would be a gray existence—and probably pointless as well. At the same time, though, they were intent on reducing the number of negative emotions they experienced, including frustration, anger, grief, and disappointment."

"This is why they came up with what I am calling the Stoic test strategy. To employ it, we assume that setbacks we experience are not simply underserved tribulations but tests of our ingenuity and resilience, administered by imaginary Stoic gods. To pass these tests, we must not only come up with effective workarounds to setbacks but must also, while doing so, avoid the onset of negative emotions."

"By treating a setback as a Stoic test, we take our subconscious mind out of the setback-response loop. More precisely, we preclude it from suggesting a finger-pointing explanation for a setback, an explanation that assumes that someone else is taking advantage of us or abusing us. This prevents the activation of our emotions, which not only dramatically lowers the personal cost of being set back but also improves our chances of dealing with the setback in a thoughtful manner.”

The Stoics were not (as many think) emotionless beings intent only on personal improvement.. 

William points out here that the Stoics placed a high value on positive emotions.

  • In fact most of the tools and exercises we are going over here today are really just ways of moving from or through negative emotions..  
  • Leaving more room in your life for the positive ones like delight, joy and awe. 

Dealing with something difficult?  Try using the 'Stoic Test' mental framework.. 

  • Say something like 'The Stoic gods are testing me here.  This is a great chance to prove how strong I am getting.  Let's do this!'
  • This is another great tool to help you cultivate resilience in your life..  

It's not about how many times you get knocked down but how many you get back up.. 

  • Actually..  This Stoic Test could be turned into a Stoic Game!  
  • How quickly can I change my Mental Framework from that of a victim to that of a hero?
  • Which tool works best for you?  Setback Stories, Alter Ego or The Stoic Test!  


“The ancient Stoic philosophers were way ahead of these psychologists and businessmen. They employed the anchoring phenomenon not to sell shirts but to have a more fulfilling life." 

"In particular, they would periodically make a point of imagining ways in which their lives could be worse. This might sound like a recipe for a miserable existence, but was in fact quite the opposite. By thinking about how things could be worse, they effectively sank an anchor into their subconscious minds (not that they thought in these psychological terms)."

"The presence of the anchor affected how they subsequently felt about their current situation. Instead of comparing it to the superior situations they routinely found themselves dreaming of, they compared it to the inferior situations they imagined and thereupon concluded that things weren’t so bad."

"This process, now known as negative visualization, is one of the most remarkable psychological instruments in the Stoic tool kit. It is important to realize that in advising us to negatively visualize, the Stoics weren’t advocating that we dwell on how things could be worse; that would indeed be a recipe for misery. Instead, what we should do is periodically have flickering thoughts about how our lives and circumstances could be worse.”

'Things could always be worse' is a cliche for a reason..

The reason is because it's actually a very powerful re-framing tool! 

  • We as humans have a tendency to over-dramatize everything in our lives..  Especially the bad things.
  • This exercise can help you when you're stuck in that state!  The key here is to get true perspective. 

Asking yourself 'How could things be worse?' is a great way to step outside your problems and into reality.. 

  • Didn't get that promotion?  At least you weren't fired!
  • Have to wait in line?  At least you can stand. 
  • Lose your job?  At least you can look for another. 

I really like this Stoic exercise!  But I think Jocko Willink takes it to another level in his latest book. 

  • Jocko has a one word reframe that is incredible when things are going 'wrong' for you.  Good.
  • Didn't get the promotion?  Good now you have more time to practice your skills! 
  • Have to wait in line?  Good now is a chance to practice a meditation!
  • Lose your job?  Good now you have time to find a better one. 
  • This quick re-frame is very powerful for when you're wallowing in your own self-pity!  Try it out.

Lazy Bill

“A spectator at a regatta would naturally think that I am rowing against the other rowers."

"From my Stoic point of view, though, the other rowers are my teammates in a much more important undertaking: my battle against Lazy Bill. I have nothing against winning a race, in the conventional sense of the word, by rowing faster than the other boats that have entered. What really matters to me, though, is that I soundly defeat Lazy Bill."

"I am probably not alone in having a lazy self lurking within me; indeed, it is conceivable that you, dear reader, have one as well. In the coming days, be on the lookout for this being, and when it appears, don’t simply capitulate, but consider your options. Experiment with ignoring or even reprimanding it. Ask yourself whether you really want this lowly creature, who has never accomplished anything worthy of note, running your life.”

We are all only competing against one person..  The worst (laziest) version of ourselves.

William tells us to be on the lookout for this lazy self.

  • They will be the one sleeping in, not dedicated or even the one self-sabotaging..  
  • Indeed this lazy self has probably ruined countless things in your life already..

Ray Dalio says that we all have two people inside of us! 

  • One is our highest self and one our lowest self.  (same concept). 
  • So we need to be mindful that when we're creating plans or serving other people we're talking to two (invisible beings). 
  • Therefore we need to set our plans in a way that accounts for that lower version of ourselves and other people getting in the way.  
  • This has been instrumental in my coaching practice.  Whenever two people get together there are always four people in the room. 

Finally I want to leave you with this..  Life is all about closing the gaps!  Which gaps?

  • First we need to close the gap between stimulus and response.  How are we responding to our environment, circumstances and events?
  • Second we need to close the gap between who our highest self could be and who we are actually being.  Staying mindful of our lower (lazy) self wanting to drag us down and instead move towards our higher self.  
  • This happens moment to moment to moment day in and day out.  (Hint: We'll never be perfect our aim is just to get a little closer). 
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