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Updated: June 25, 2021


The Stockdale Paradox

A key concept for success in business and life

The Stockdale Paradox – James StockdaleThe Stockdale Paradox is a concept coined by author Jim Collins in the book Good to Great.

In this article you will learn:

  • What the Stockdale Paradox is and who it’s named after.
  • An example of a $20 billion company that embodies the paradox.
  • How understanding the paradox can help you succeed with your online business.

Let’s get started.

The Stockdale Paradox

The Stockdale Paradox is named after Admiral Jim Stockdale, who was a United States military officer held captive for eight years during the Vietnam War.

Stockdale was tortured more than twenty times by his captors, and never had much reason to believe he would survive the prison camp and someday get to return home and see his wife again.

And yet, as Stockdale revealed in Good to Great, he never lost faith during his ordeal:

“I never doubted not only that I would get out, but also that I would prevail in the end and turn the experience into the defining event of my life, which, in retrospect, I would not trade.”

Then comes the paradox.

While Stockdale had remarkable faith in the unknowable, he noted that it was always the most optimistic of his prison mates who failed to make it out of there alive.

“They were the ones who said, ‘We’re going to be out by Christmas.’ And Christmas would come, and Christmas would go. Then they’d say, ‘We’re going to be out by Easter.’ And Easter would come, and Easter would go. And then Thanksgiving, and then it would be Christmas again. And they died of a broken heart.”

What the optimists failed to do was confront the reality of their situation.

They preferred the ostrich approach, sticking their heads in the sand and hoping for the difficulties to go away.

That self-delusion might have made it easier on them in the short-term, but when they were eventually forced to face reality, it had become too much and they couldn’t handle it.

Stockdale approached adversity with a very different mindset: he accepted the reality of his situation.

The Stockdale Paradox – James Stockdale receiving the Medal of Honor
Above: James Stockdale – namesake of The Stockdale Paradox – receiving the Medal of Honor

Stockdale knew he was in hell, but, rather than bury his head in the sand, he stepped up and did everything he could to lift the morale and prolong the lives of his fellow prisoners.

  • He created a tapping code so they could communicate with each other. 1
  • He developed a milestone system that helped them deal with torture.
  • And he sent intelligence information to his wife, hidden in the seemingly innocent letters he wrote.

Author Jim Collins and his team observed a similar mindset in the good-to-great companies. They labeled it the Stockdale Paradox and described it like so:

You must retain faith that you will prevail in the end, regardless of the difficulties.

AND at the same time…

You must confront the most brutal facts of your current reality, whatever they might be.

A $20 billion company that embodies the Stockdale Paradox

Stripe logoThat company is Stripe, the online payments powerhouse that disrupted an entire industry.

A former engineering manager for Stripe notes that optimism has long been a “top-level value” for the company:

When you’re trying to transform the global payments system with a staff of 200 people, a) things are constantly on fire and b) there are lots of good reasons to believe you’ll fail. Stripe’s optimism meant not letting those negative thoughts drag down the team.

Optimism was the emotional equivalent of free money. It was thus highly beneficial for Stripe to adopt this as a top-level value.

But, as we’ve learned, optimism alone won’t get you very far.

To embody the Stockdale Paradox, you must also confront the brutal facts of your reality.

In the early days of Stripe, reality was brutal indeed.

The renowned Paul Graham touches on the complexity of the problem the company was trying to solve:

Though the idea of fixing payments was right there in plain sight, [most startups] never saw it, because their unconscious mind shrank from the complications involved. You’d have to make deals with banks. How do you do that? Plus you’re moving money, so you’re going to have to deal with fraud, and people trying to break into your servers. Plus there are probably all sorts of regulations to comply with.

Stripe founders John and Patrick Collison were both in their early 20’s when they started Stripe, and admit that the work was extremely difficult early on:

“It has taken a ton of work and there’s a good reason that no one has done this before.”

John Collison, co-founder of Stripe
Above: John Collison, co-founder of Stripe (image credit: Web Summit on Flickr)

Technology writer Ashlee Vance notes that the company continues to fight tough battles despite being well established at this point:

Stripe is in a vicious universe dominated by banks and credit card companies and larded with regulations.

Stripe’s willingness to confront those brutal realities, combined with their relentless optimism, surely plays no small part in their success.

Applying the Stockdale Paradox to your online business

For me, the Stockdale Paradox boils down to a delicate balance of faith and honesty.

  • Have faith: never doubt that you can achieve your business goals, no matter how lofty they may be and no matter how many critics and naysayers you may have.

But at the same time…

  • Be honest: always take honest stock of your current situation. Don’t lie to yourself for fear of short-term embarrassment or discomfort, because such deception will only come back to bite you.

Living the first half of this paradox is relatively easy, since optimism really isn’t that hard. You just choose to believe that it will all turn out for the best, and everything that happens is a means to that end.

But optimism on its own can be a dangerous thing:

There’s no difference between a pessimist who says, “Oh, it’s hopeless, so don’t bother doing anything,” and an optimist who says, “Don’t bother doing anything, it’s going to turn out fine anyway.” Either way, nothing happens.

– Yvon Chouinard, founder of Patagonia, Inc.

So you need to embrace the second half of the Stockdale Paradox to really make strides with your online business.

You must combine that optimism with brutal honesty and a willingness to take action.

Now of course, nobody likes admitting that their product or service sucks, that they don’t have time to work on their business, or that their skills simply aren’t up to scratch.

But admitting such truths is an absolute necessity if you want to grow and improve your business.

It might feel like you’re taking a few steps backward by doing so, but you can view that retreat as the pull-back on a sling shot: you’re just setting yourself up to make significant progress down the road.

Stockdale and You

How have you applied the Stockdale Paradox in your own life?

Let me know in the comments below.

I’m especially interested to hear examples related to building an online business.

You might also enjoy…

About The Author
Niall Doherty – Founder and Lead Editor of eBiz Facts Born and raised in Ireland, Niall has been making a living from his laptop since quitting his office job in 2010. He's fond of basketball, once spent 44 months traveling around the world without flying, and has been featured in such publications as The Irish Times and Huffington Post. Read more...

36 thoughts on “The Stockdale Paradox”

  1. Neil, I love Admiral Stockdale, too, and the book Good to Great. In fact, I was so impressed with his story that I wrote about the Admiral and the Stockdale Paradox in my book “Take the Quantum Leap into Abundance: A guide to the good life.” His philosophy has kept me going through the tough times. I loved your article. -c.w. pickett

  2. Good evening, Mr. Doherty. I found your article today while searching for information about the Stockdale Paradox, which also I heard about only a couple of days back. I had no idea what this paradox was about and most certainly was not expecting to read my thoughts from another person! I don’t plan anything. I prefer to go with the flow adapting to the situation and changing it when I can. What I tell my colleagues (and in a previous life, my students) is to always expect the worst but do their best. Thanks for the introduction to Admiral Stockdale!

  3. It’s just mind blowing! I can’t respond with intelligence after reading that! It’s so unfamiliar I’m today’s world. It’s such a rare quality that heroes like this possess. It absolutely wants to make be a better human. How can we ever repay people like this for what they’ve done!? Thank you Admiral Stockdale

  4. Hi Niall,

    I also recently came to know about this book from Jim Collins through a friend. At first I was a bit apprehensive, as it appeared ‘far from my bed’. While my friend was reading ‘Good to Great’, I was reading a philosophical book about the benefit of doubt and how philosophy can enrich your day-to-day life. We then switched books and found out how overlapping these two books were – eventhough their subjects don’t seem to have much in common. A lot of the themes from ‘Good to Great’ have a great effect on my daily life now – a truly marvellous book; not only for companies, but also on a personal level.

  5. Niall,

    Good for you setting yourself some challenges to push your boundaries. I think it is something that everyone should try.

    A while back I was frustrated with the progress I was making with my career. I knew I needed inspiration to change so I spent time analysing people I knew that were successful in some way. Although these people came from different backgrounds, and had different opportunities, I began to realise that they had similar traits. They were doers, they didn’t make excuses, they had a goal in mind and were determined to achieve it by any means necessary.

    As soon as I began to not only have faith, but really focus on achieving my goals my career and personal life began to see huge improvements. I think this is a similar approach to Stockdale, having a positive mental outlook and setting realistic goals that challenge me to be the best I can be.

    In the past 5 years I have become a better person by applying this philosophy to my life.

    I think that is what makes the difference.

    There are two types of people, those that dream, and those that do. The sooner you begin to understand that most opportunities are created, and not chance, the sooner you will see doors open, relationships formed, and careers advance.

    I heard a quote that I try to pass on to others

    “The world needs dreamers and the world needs doers. But above all, the world needs dreamers who do”

    By combining our goals, and realistically assessing our circumstances, we can all achieve more in most aspects of our life.

    • Chris,
      I read the article and was reading through the comments and wanted to let you know that I agree with you. You say you have applied this philosophy to your life for the past 5 years and as a result, you have become a better person. Right now I am in the same situation that you were in 5 years ago. I am having some personal problems, and all my life I have been told I just need to believe and I just need to be optimistic and stay hopeful. I am in my 30s and ever since high school, I have been waiting for my personal problems to go away. I thought just the passage of time will take care of my problems. Not so.

      And Mr. Doherty, thanks for this article, from the bottom of my heart. It really solves a major piece of the puzzle in my life.

  6. The term “optimist”, apart from being somewhat euphemistic, is really but a “misno_mer’ciful” in reference to Stockdale’s prisonmates who didn’t survive their ordeal at *the hands of their captors*. Another way of looking at their predicament is that, in reality[something of which they were evidently sorely lacking], even though it took quite some time before they eventually succumbed, all they did was *play into the hands of their captors*[sound familiar?]. Apart from accentuating it, all they really did was merely prolong their agony[more later]. We’ve all seen cowboy movies where two gunslingers face each other off and the one who is “on-the-prod” usually goads the other to “make his play”[ie, go for his gun]. If the one of them who isn’t “on-the-prod” decides that he won’t play into the hands of the gunslinger who IS “on-the-prod”, by going for his gun first, an action into which he’s being goaded, then chances are that he’ll survive the ordeal, especially if there are witnesses. We must be ever mindful about errantly labelling persons as being “optimists” when they clearly are not, because if we begin with an false premise then we, just like Stockdale’s prisonmates, won’t “succeed”, which is just another word for “survive”. I wonder just how many[if any] of Stockdale’s prisonmates knew of the following little gem for anyone who feels that they’re locked-in for the duration. Here it is: “Stone walls do not a prison make…nor iron bars a cage!” If you think that they do, then they will, but only for you if you’re the only person who thinks so. Here’s another little gem that you can tell someone who may have been in the depths of depression and they’re wondering why they are crying all the time. It’s best told to them after you youself have had a good cry about something, then you can give it to them straight from the horse’s mouth, having learnt from it yourself. Here it is: “Perhaps my tears are the prism that I need to find the rainbow that is me”. Whilst it may be somewhat scientific…it ain’t exactly rocket sci_”ence’inte”. Lock up..err..look up the military meaning of “enceinte”. Knowingly prolonging agony is exactly the same as the situation that faced many persons at sea during both World Wars when they had to abandon their ship. Their problem lay in the fact that their life jackets would not remain buoyant indefintely, and would eventually become waterlogged, so they would then, after having suffered hypothermia for ages, eventually meet Davy Jones in his locker, in not first taken by sharks. If they knew that help wasn’t on the way then their life jackets were only going to prolong their agony, so many never even bothered to “put them on”. If you “put yourself on”, then all you are doing is not accepting reality for that which it actually is[sound familiar?]!

    Getting back to errantly labelling someone as being an “optimist” when they’re not, to label these “psuedo-optimists” as being such veritably “begs the question”, which means that you are “assuming something that is yet to be proven”. Don’t ever confuse “begs the question” with “raises the question”, as they are two entirely different concepts. Like I said, be very careful with those labels lest you make a rod for your own b_ack’nowledgement, and the backs of others too…and they’re very likely to get their backs up in the process! My late father[2/11th Battn, A.I.F.] survived three and a half years as a prisoner of war at the hands of his German captors, having been taken prisoner on the island of Crete in 1941. He was interned in several stalags in Europe, “very proximate” to some of the infamous concentration camps where millions of men, women and children were gassed in confined spaces then cremated. He too did many of the same things that Jim Stockdale did in keeping morale at a pragmatically realistic level, and along with many of his mates, survived, else I’d not be here posting this comment!

    A true “optimist” will always *make* the most of a prevailing situation and never *fake* the most[or any] of it. There is a decided distinction…and it’s merely predicated on his/her sole decision!

  7. Interesting concept. A good old quote also came through my mind while I was reading this post, saying you should always “Hope for the best while expecting the worst.”

    Optimism isn’t as simple as it sounds at first. Well, the first part you’ve explained is, but you have to be careful not to fall into the trap of thinking that simply by being optimistic all of your problems will just simply go away.

    I have experienced that myself a lot of times 🙂

  8. Hi, there! This is Taewoong, Seoul Korea. I happened to know about Stockdale paradox while searching wonderful idea to share with my friends. I’ve been in charge of my own English conversation club since 1997 and that is why I need to have a lot of wonderful and inspiring issues to talk about.
    Thanks to this smart world with all kinds of smart devices and gadgets, I just wanted to know further on that paradox I mention above. I should say this is all about chances linking different ppl with different thinking. It is great to know about your wonderful journey with great courage anyway. Good luck Neil!

  9. This is similar to the concept of being a Rational Optimist. Rational optimists believe that they can and will make progress by pursing a bold, but sensible, approach. While they hold an optimistic view of life, they recognise that optimism is NOT necessarily the opposite of pessimism. It is not the idealistic belief (or hope) that things will get better simply because they want them to.

    Instead, rational optimism is a balanced understanding of the whole system of which they are part. It is recognition of both strength and weakness; an interest in building the best as well as repairing the worst; and a concern for finding self fulfillment as well as serving the community. Rational optimists are realists, but their defining point of difference is that they don’t give up on themselves.

    Hope this is helpful.


  10. So, the Stockdale paradox is just making Kierkegaard’s final movement of the absurd in true faith. Acknowledging the reality of a situation/giving in to infinite resignment/still believing truly things will work out in the grand scheme based on faith of it happening.

  11. niall,

    i hadn’t heard this before. so many big truths i find are wrapped up in an acceptance and employment of paradox. people often talk about finding balance, but i have found that idea to be lacking. in the continuum of optimistic/realistic, i do not want to be partially optimistic and partially realistic. i don’t want to compromise either side by working toward some kind of middle ground. i want to be able to hold both of these things in their entirety. i want to be completely optimistic – to fully believe in the favorable outcome; and completely realistic – to fully see the situation as it now is. in this way i am neither clouded in my bare-realities assessment of the situation by some kind of rosy hopefulness; nor am i deterred in my positive belief by nagging doubt.

    it’s a tricky position to hold, but it is possible.

    and your image of the slingshot reminded me of this quote from georges bataille, ‘it is necessary to recoil, but it is necessary to leap. and perhaps one only recoils in order to leap better.’

    thanks for the great post!

  12. Thanks Niall,

    I’m always interested in anything to do with personal growth. Along these same lines of how one can transcend the most horrific situations, I consider Victor Frankl to be a hero. There are others.

    Applying this Stockdale Paradox to myself, my first thoughts are that this process is quite elementary, but a second look causes me to realize that I often fit the optimist who couldn’t see the reality of a situation category. I sometimes have what could be described as an unrealistic optimism, kinda like the person on the titanic believing all would be well as the ship stands vertical and submerges. So, I do always maintain an optimistic view, but not always with a realistic view of the situation.

    I will say that the latest challenge in my life is by far the most difficult ever…’s a serious unexpected health crisis that completely changes all of my hopes and dreams permanently. I made it about 10 years fighting hard with my usual optimistic view, and evolving through all 5 stages of grief before reaching acceptance. One thing different this time was that I wasn’t denying the reality of my situation….. rather the facts of my situation were not known. No one knew why I was so sick or that it was permanent. Kind of hard to accept an unclear situation like that. But I have now. Like a great doctor told me…..You must re-write the script. Another line that I really like is, “We must transcend that which hold us”.

    I have gained some insight reading your post. Thank you.

    • Thank you, Carly! I can only imagine what it must be like to have a serious health problem. I’ve been very lucky all my life, never having to deal with anything like that. It sounds like you’re tackling it with a great attitude though. I wish you all the best.

    • I’m sorry, Carly, about what is happening to you with your health. I know what it is like to have all your hopes and dreams changed permanently. I hope when you are finished reading this you are encouraged and hope is returned to you. The list goes on and on of the things I’ve had to overcome in my life including divorce to a man I loved more than my own life and then of late, breast cancer so bad that I could see the tumor that just showed up all of a sudden. I had to have chemo to shrink the tumor down before they would even operate and then several doses radiation. Seems I’ve been gone from life for the last 4 years and when I came back everything was different. It’s been hard to catch up. The treatments that fixed me also made me very sick and destroyed my immune system, energy and other things in my body. I have lost everything, except my family, since I was not able to work during my illness. Currently I still do not have a job, car or money. My wonderful young kids have been supporting me and doing without to take care of me to this day. I feel grateful but awful to put them through this so long and not be on my feet. They can’t go on with their lives and dreams because of me but they do not complain and refuse to make me feel bad about it. To add to it all , right before my diagnosis my first and only grandbaby was born, but stopped developing at all and actually went backwards in his development at 15 mos. He was diagnosed with Autism, which we believe, after much research, was a result of required booster injections he received. He has been through a ton of therapy and goes to a wonderful preschool for special needs kids that has brought him a long way. He is 4 now and still is not potty trained, does not talk and only eats about 4 or 5 foods. He, however, is a good communicator and is trying some sign language. He is my breath and life and I love and accept how ever he is going to be in life. My kids and he are what has held me together through all of this. I know you can not change your situation, Carly, and it is devastating to the way you envisioned your life, but if you can find something that brings you immense joy, like my grandbaby does me, that will make all the difference in the world. When I have my grandbaby. I spend time with him noticing all the wonderful and special things about him even his disability. It is part of what I love about him and takes me away from what makes me sad in my own life. One little hug and kiss from him makes all my trouble melt away. Believe me I know it is sad to have to change or lose your dreams but keeping an open mind about coming up with new dream in life that can bring you great joy and peace in disappointing and trying times in life. I do hope you will hang in there and find your new dream and joy. Know you are not alone out here.

    • It could be possible that your medical condition does not need to be permanent.
      Many times, the parameters of other medical systems(example;Chinese traditional medicine)may lead to a different solution.
      Acceptance is another way to not do anything.
      If you will act, life will change.
      Someone should talk to me!

  13. I guess this is much like the approach I’ve always tried to take (and often taught at motivational seminars) of ‘expecting the best but preparing for the worst’.

  14. Thanks, Kevin. I agree about the three circles. Those resonated with me, too, and I actually wrote a blog post related to them a while back: Finding your life purpose.

    • Thanks for writing this, I was just looking for management lessons in this Good to Great book and leant this life lesson with Stockdale Paradox. Unemployment is not war situation but yes it’s equally depressing and difficult for survival of candidates. This paradox is big hope for them.

      • Hi Roseland. Should be working, yes. Otherwise you wouldn’t have been able to post your comment, no?

        Which link in particular are you having trouble with?

  15. Good for you. Good to great I have read and reread every year. It is my own Personal Development book and something I enjoy. I’m happy to see that I am not the only one. For me the three circles, passionate, economic denominator, and best in the world at are key

    • Hi there boys and girls… I just happened onto this site and wanted to say hello. Dad was a pretty amazing guy and would have been pleased to read these comments on the ‘paradox’ side of things. Interestingly enough, when Jim Collins came to actually writing the chapter about the paradox (around 2001 or 2?) he wanted to be in touch with Dad so he could get it as right as he could. ((Jim Collins is not only a brilliant author – but a gentleman and a good friend. He has always gone out of his way to include our family in the process of portraying Dad’s experience – a rarity in our world – a man of authentic integrity.)) Well anyway, at that point Dad had been pretty well taken over by dementia… Mom told Jim when he called and Jim said, “What should I do?” She said, “Call Jimmy – he’ll get it as close as anyone else can.” And so, on a Saturday morning with Dad’s papers splayed in front of me – Jim and I talked for two hours (a privilege and an honor). We talked about a lot of things but focused, of course, on the presentation of Dad’s ideas. Jim helped convey Dad’s experience in a more ‘modern’ perspective – for use in our ‘regular’ world – not exclusively a prison monologue… Really useful, actually. The paradox comes up time and again as one piece of the wisdom you glean when enduring such treatment. Dad was one of four prisoners who spent over four years in solitary. THAT will give you the time and motivation to assess life’s real value – and sort the precious from the dross.
      One prison correction. Dad did not invent or come up with the tap code. It is called the quadratic alphabet and it became the life blood of communication among the imprisoned. But here’s the thing – NO ONE was taught that code in survival school (weekend workups of what prison could feel like). Uniquely, while taking the survival school classroom lecture/Q&A, an Air Force pilot named Smitty Harris approached the speaker and was asking a question or two when (almost suddenly) the speaker started to describe this ‘tap code’ that’s been used for a long time in American (and other) domestic prisons allowing the inmates to communicate. Smitty left with the description and a diagram of the code and, according to Smitty, promptly pretty much forgot about it – until he’d been in Heartbreak for about ten days. (Heartbreak was an ominous portion of the main prison given over to isolation, brutality, and a fierce ‘shakedown.’) So there you have it. About 500 men imprisoned over an eight year span and communicating by tapping on the walls – in a code one of them had learned BY ACCIDENT. If you ever have a chance, read the first 25 pages of the book “Darkness at Noon” published over 70 years ago – and there you’ll see it memorialized – as Rubashov, a newly accused prisoner, alludes to the almost constant quiet tapping sound that travelled through the plumbing in his cellblock. Even the Cyrillic alphabet could be put in a logical 5 by 5 box allowing even the most isolated political prisoners to converse and stay up to speed on expectations or orders.
      Thanks for thinking enough of Dad to include this material. He would be surprised and thrilled that people still appreciate his ideas.
      LAST THING: The Naval War College in Newport, RI still teaches the course Dad and Joe Brennan conceived and taught to young leadership officers called “The Foundations of Moral Obligation.” Dad was named president of the college in the seventies and decided he HAD to find a way to convey many of the choices and quandaries he had faced in prison to younger, ambitious military officers. The seminar remains over-enrolled to this day. JS2


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