The Art of the Fail

Note: For readers especially pressed for time, key takeaways, action steps, and additional resources for this post are provided at the end.

This post is about the ways in which learning to navigate failure is one of the central secrets to leading a successful, fulfilling life in the adult world. But before diving into the post—which features five surprising and powerful lessons about failure—we first need to begin with a little candor, a little honesty, and come clean about the role of failure in everyday adult life.

On any given morning, the average adult wakes, and at that moment, engages in a quick gratitude exercise: yes! I made it. I am alive another day. Building on that enthusiasm, the adult might have had a revelation that occurred during his or her sleep, maybe some good idea for how to handle a work challenge. This day, they thinks, is really starting to look promising.

The adult makes it all the way to the kitchen. And it is then—just 15 minutes into the day—that things start going south. Someone used the last coffee filter without mentioning it! The adult is going to have use a paper towel as a temporary filter. Coffee grounds will get through. And paper towel chemicals. Not good.

As they wait for the coffee to brew, try to shake off the annoyance about the filters (seriously, how hard is it to communicate that we are out of filters!?!), get back to the good feeling they had upon waking, the adult notices it. Something has gone terribly wrong with the cat. Or maybe it was the dog.

Some creature has been ill, apparently throwing up and battling diarrhea simultaneously, while running from room to room. The house is a Jackson Pollack painting of pet fluids. This will take hours to clean and there is no guarantee it will all come out.

It is at this point that the adult contemplates grabbing their purse or wallet, walking out the door, and just driving. Never looking back. The adult will assume a new identity. And start fresh. Take a do over. Starting a new life, knowing what they know now, they will live life right.

This is adulthood. We have all been there. Most of us reading this post on our second or third identity. We can be honest here. This is a safe space. It happens. No judgment.

Yes, there’s some hyperbole in all that, but you know what I mean. Coffee filters. Pet issues. Failing to sign kids up for the popular summer programs before they were all filled up. Fail, fail, fail. The list goes on and on.

In adulthood, we don’t get particularly far into any given day before we start racking up the misfires and the falling-shorts and by day’s end, for most of us, the to-dos that didn’t get crossed off far outnumber the ones that did.

For adults, failure is water and we are fish swimming in it, actually oblivious to how everpresent it is (to borrow the central metaphor of the great David Foster Wallace commencement speech, This is Water).

Which is one reason we adults typically don’t school our kids in the role of failure early on in life. A part of us doesn’t realize how central it is, it is so pervasive.

And then to extent we do think about failure, our focus is usually on shielding our kids from this ever present reality, just as our parents did.

A friend has a particularly vivid example of how effectively adults can hide this reality. He discovered the truth when he was in his late twenties and was nostalgically telling a group of friends about a favorite beach camping trip his family took when he was a kid.

His older sister, who was listening to him tell the story, incredulously interrupted him: “We weren’t camping, dummy. We were homeless. Didn’t you notice, Mom and dad were gone during the day? They were trying to get jobs.”

There are lots of well-founded reasons why parents work to shield kids from failure, including the admirable desire to ensure kids feel safe as they develop. We know that the research emphasizes the importance of a feeling safety and scurity to child development.

But hiding failure is also a result of the superstitious side of parents.

We worry. A lot. We worry that if our kids are in any way exposed to failing, they might end up as failures. They could catch failure. And we could end up the parent with the adult kid living in out in the garage in their thirties, surviving on cans of Chef Boyardee, while spending years trying to finish the application to their tattoo art college safety school.

Whatever the reasons that we keep failure on the down low, the degree to which we do is a something to reconsider, as navigating and knowing how to leverage failure really is one of central keys to an effective and meaningful life.

This fact has been backed up and illustrated by some of the most popular non-fiction books over the last several decades, which have managed to radically transform how we understand the instrumental role failure can and should have in our lives.

The following five lessons, which feature some of the powerful lessons related to failure, provide a great foundation for pre-adults, as well as any adults who might be looking to get unstuck.

Lesson 1 - Failure and the growth mindset

It is difficult to adequately express the difference Carol Dweck and her 2006 bestseller Mindsets made in how we view failure. Dweck, as has been referenced multiple times in my posts, wrote about her research into the existence of fixed and growth mindsets in people, and how those differences impact the ability of people to learn and grow.

This insight is, thankfully, now often taught in school. Kids today learn about growth mindsets and how believing that you can learn and improve (i.e., have a growth mindset) is in part a determining factor the degree to which you develop and thrive in life.

In hindsight, it actually seems obvious, something that we should have all grasped. And you almost have to be an adult of a certain age, and have had a mindset that leaned fixed back in the day, to fully appreciate the impact that Dweck’s work has had on our perception of failure.

Because back in the day—ridiculous as this seems—if you were bad at something—a failure—well, that was just it. It was the end of the line. It often didn’t occur that it could be otherwise.

Tom Bilyeu, successful entrepreneur turned life effectiveness guru, illustrates this fact by describing being on a basketball team as a kid and being terrible at the game. His response to his terribleness was to put all of his energy into avoiding being put in the game or, when he was put in, into avoiding getting the ball.

He marvels that it actually didn’t enter his mind that, if he put in some time and practice, he would improve. That obvious fact didn’t enter his mind. He was a complete failure at it and the best option was to focus on minimizing the damage.

He is not the only one. This was common, as I can attest. I handled trumpet playing in elementary school the same way. I seemed to have no knack for it, but instead of trying to do something about it, like practice, I resorted to feigned illness on days when I might have to play alone in front of the class.

My wife, who grew up studying dance, had a similar experience. While she had clear strengths in dance (connecting with the music and moving expressively), she struggled when it came to the more technical dance skills and her response was the same, that this failure was unfortunately just the way things were.

This was life back then, pre-Dweck. If you had a fixed mindset and weren’t a natural at something, failure was failure. End of the line. Millions of kids putting all of their pluck and creative energy into avoiding the thing they were seemingly failing at, rather than trying to improve.

But now we know. We know of the brain’s inherent plasticity. We know that, thanks to myelination and the other mental wiring processes, our brains are designed to constantly learning new information and acquire new skills, as long as we don’t doom ourselves with the belief that we can’t do something, that we are failures.

Presumably, our kids already know this, have ideally talked growth mindsets and related topics in school, but if they haven’t, isn’t this lesson is the place to start? And you might be able to illustrate it with some good farcical tales of the ways many of us back in the day went out of ways to remain failures, not even understanding there was another way.

Lesson 2 - Failure and iteration

After Dweck’s 2006 transformation of how we understand failure, the next two most seismic advances came shortly after, first with Malcom Gladwell’s Outliers, published in 2008, followed by Eric Ries’s The Lean Startup, published in 2011. Both of the books address different aspects of how success is accomplished through iteration and versioning.

Gladwell’s bestseller most famously shone a spotlight on the research of Anders Ericson and gave rise to the notion of the 10,000 hour rule—the idea that achieving mastery of a skill, such as chess, is achieved through a process that involves thousands and thousands of hours of deliberate practice.

Deliberate practice is a key component of the concept, one that is often overlooked. Those 10,000 hours must be filled with disciplined, targeted practice that includes feedback from a coach, teacher, or other expert, and practice that is focused on improving areas of one’s performance that most requires further improvement.

10,000 hours—that catchy figure really took off in the public imagination, though many would argue that, in reality, 10,000 is the minimum for performance mastery in many areas. So, depending on your pursuit, we might actually be talking a 15,000 hour rule or 20,000 hour rule.

In respect to our subject of failure, Anders Erickson was implying that: to succeed at a high level, we should get ready for 9,999 hours of falling short, which for many can feel like failure. For those without a calculator handy, that is the equivalent of ust under five years of a full-time job—during which time you have to continually accept that you are not yet there.

Is it clear what a radical shift in thinking this is? Instead of responding to failure by hiding, we are now talking about willingly embracing some degree of failure for years and years. And that, we now see, is just how getting good works.

The Lean Startup also introduced a term that would take on a life of its own. The book popularized the concept of MVP, or minimally viable product (a term actually first coined in 2001 by Frank Robinson), which is one many readers will be familiar with (all of us who have worked for organizations that develop software).

MVP, which originated in the Lean methodology for software development, takes it as a given that, because software products can iterate and improve relatively rapidly (unlike hard goods like a new refrigerator or car), it can make more sense to not try to build all the bells and whistles a product could have before launching it out into the market.

Product developers working with MVP need to understand what is most important to the market, what is minimally viable, and then get the product out there and continue making improvements, especially in response to user feedback from the real world users, as well as the product team’s overall vision and strategic product roadmap.

The notion of launching something that is minimally viable to product developers of earlier generations and the world hard goods would have been nightmarish, but software developers should make peace with making the perfect product in exchange for tapping into the powerful process of incremental progress through iteration and versioning.

This notion of MVP is a compelling way to go through life. We ourselves are continually versioning, continually iterating. Version 1.0 of you couldn’t hold its head up (what is less minimally viable than a human baby?). The more you put your current version out into the world, and seek some feedback, the more advanced and more appealing will be the version of you a few years from now.

As both 10,000 hours and MVP illustrate, for much of life there is a middle ground between starting something and success, and that middle ground is likely filled with a great deal of hard work, along with masses of humbling feedback, all of which, for those not armed the proper mindset and understanding of the concepts, likely seem a just a lot like failure.

Lesson 3 - Failure is the way

The next enlightening insight about failure is one that many readers may have have figured out the hard way after many years of living.

You look back at moments of success in life (however you define that), or at moments of feeling deep fulfillment, and you may notice a paradox—our best highs often followed some of our most maddening lows.

Quod obstat viae fit via. These are the words of Marcus Aurelius from back in the year 170 to explain this phenomenon. Stated in English: The impediment to action advances action; what stands in the way becomes the way.

This paradoxical notion that the way to life’s highs is often through its lows is, Aurelius was pointing out, not a coincidence. It is not our imagination. Going through the difficulties—setbacks and obstacles and failure—are actually what often make our successes and moments of fulfillment possible.

For one very simple example from my own life, the simple fact of having to earn a living and provide for my family led to plunging into work I may not have always felt passionate about, and may have involved working for the occasional deranged boss, and firing at least one drunk employee, along with enduring many battles with Sunday blues, lots of strategizing on how to overcome my weaknesses, and so on. Along the way, I surely fantasized about a lotto ticket coming through or coming into an inheritance from a distant industrialist relative whose existence I was unaware of so that I could be done with all the struggle.

And yet I have to admit that I am forever indebted for the personal development that resulted from the challenges of that work, much as that is not what I was thinking about during all the struggle.

Ryan Holiday popularized this notion in 2013 with the publication of The Obstacle is the Way. The book went on to be a smash best-seller and made Holiday a darling of pro football coaches, rappers, CEOs, and many other high performers, many of whom had also learned this lesson through their own struggles and were glad someone finally gave it a label.

True as the obstacle is the way may be, it is not necessarily fun to learn. We are not masochists. It would be more appealing if the Latin translated to: the way to succeed in life, especially in the face of challenges, is to call in sick, eat a pizza and a pint ice cream for lunch, and take a great nap.

That is not the case. But at least with Holiday’s book, and the resurgence in the popularity of Stoic thinking it inspired, it is easier to embrace this truth and explain it to others: the challenges and failures and setbacks we encountered fueled our deeper resolve, inspired more creative thinking, increased our strength, taught us valuable lessons about how life works, and on and on.

Holiday’s book uses great stories from history and famous figures to not only put forward the central idea that the obstacle is the way, but it also provides tools and concepts for increasing one’s ability to embrace this reality and better take on the obstacles. His method centers around three themes: perception, action, and will.

For those of us who are parents, though, I don’t think we need to coach our kids, we don’t need to get them into the weeds of enhancing their ability to leverage quod obstat viae fit via their lives.

Simply introducing them to the central paradox upfront will go a long way toward understanding that the difficult and possibly failure fraught path will paradoxically be the way to the big payoffs and good feelings, and in many ways may actually be what makes them possible.

Super annoying, but also super true.

Lesson 4 - Failure and accountability

You would think that would be it. That that was all the good news on failure and the positive role it can play in our lives popularized in the last twenty years. But you would be wrong.

And this next insight, like the obstacle is the way, is initially offputting, given that it involves adopting a mindset close to: everything that goes wrong, especially failure, is all my fault.

This is, to say the least, not our preferred mindset as humans. Especially for our young people. If you would like an especially vivid illustration of this, I encourage you to fly to Minnesota some winter evening and join me in watching a youth hockey game, which is how I spend most nights in the winter.

On such a night, one of the teams will, sadly, lose, and you and I will position ourselves so that we are able to hear the kids on the losing team as they walk with their parents to their cars. The kids will be explaining to their parents how the referees on this particular night were particularly bad and biased toward the other team.

Or it may be that no one else on their team was passing except for them. Or the evening’s dominant excuse may be that their coach made some particularly unfair decisions in terms of who played which position. The specifics will vary, but you get the idea.

What you will not hear kids saying is: that loss is on me. My bad. It was my fault. I know that if I just practiced harder, trained more, and studied strategy more intensely, I would be able play at a higher level and would have easily tipped the scales in a way that would have resulted in us winning that game. Seriously, my bad.

But that is in fact the truth. The games are typically close, and if any one of the kids on either team had fully accepted responsibility for the outcomes of games, and in so doing had significantly increased their effort (both in training and once on the ice), they could have made the difference.

Wayne Gretzky understood this about his hockey games. Mia Hamm knew this about her soccer matches. Kobe brought this commitment to the basketball court. None of the kids we would watch play hockey may be as naturally gifted as those famous names, but they are all talented enough to up their effort in way that would be difference making.

Former Navy SEAL Jocko Willink, in his 2015 book Extreme Ownership, was one of a number of authors to popularize the mindset in recent years. In the book, he vividly recounts a tragedy involving his platoon mistakenly fighting another SEAL platoon and resulting in the death of a fellow SEAL.

It was in analyzing the tragedy in the aftermath from the perspective that, no matter who had done what, Willink, as one of the leaders, was ultimately accountable, that he realized he could truly learn all there was to glean from the experience, which in turn, he acknowledges, saved his career.

(One emphatic note to make about this mindset, which is hopefully obvious but is nonetheless important to state clearly, is that there are situations in life when considering oneself as ultimately accountable is not at all helpful, and even likely damaging, as in the case when individuals have been victimized.)

Taking an aggressive stance regarding our accountability in the face of failure, or any disappointment, is, as any who have tried it, a revelation (marriage, as it happens, is particularly rife with opportunities that benefit from the mindset, much as minds might want to suggest spouses may be to blame for mishaps.)

Stepping back, taking the long view on how, in hindsight, we had opportunities to take steps, communicate with others, perform actions that would alleviated failure—there may be no greater tool for accelerating personal development—sort of like Carol Dweck’s growth mindset on HGH.

Lesson 5 - The one true failure

Humans have accomplished many impressive things, especially in comparison to the rest of the animal kingdom here on Earth. The list usually starts with making our way to the moon. Skyscrapers are up there too (that Bhurj Khalifa in Dubai!). And, of course, making it through your child’s school play without checking your phone more than that one time is worth of accolades.

So many amazing accomplishments. What is even more mind blowing is to consider all that we haven’t accomplished due the other way we stand out among the planet’s creatures: our outstanding gift for giving up and quitting.

For every set of Wright brothers who miraculously, not only didn’t give up, but didn’t die in their quest to make flying machines, there are a thousand sets of other brothers and sisters with astounding ideas for invention, but who, after discussing the idea and getting excited, somehow didn’t follow through.

Maybe a kid got sick and had to be attended to. Maybe things got crazy at work. Possibly, some new shiny thing came along and they got distracted—a neighbor got one of those new fangled bikes with the giant front tire and they decided to start racing those. And that great idea they were so excited about was set aside.

This is how failure happens. Real failure happens when we give up. When we quit. All of those other efforts when we see things through, when we give it our all, but perhaps don’t get the outcome we had hoped, that is all opportunity for self satisfaction (I gave it my all) and learning (here’s what I will do differently next time). But quitting offers none of that.

It really is haunting imagine what the world would be like if humans were all able to follow through on all our good ideas. This really might be a Shangri-La. At a minimum, James Clear, author of the great Atomic Habits, would not have sold 10 million books to would-be readers who are once more struggling to start doing something they know is good for them. Ten million copies!

And what is so nefarious and naughty about quitting is the fact that it is so sneaking. So often, it does seem to be the issue at work, or with family, or any other arguably valid rationalization for why we are giving up. Tom Bilyeu refers to this as our psychological immune system—this ability to quit without confronting the reality of what are doing.

We humans celebrate those who triumph over all the odds. Ernest Shackleton, along with his Endurance crew, are the patron saints of perseverance for the way they survived a shipwreck during their Antarctic expedition, eventually getting every member of the crew home alive. Meanwhile, we human’s harbor humanity’s dirty secret: we are prone to throwing in the towel.

At least I am, if I am honest. Looking back over decades of living, seeking out all the instances of not following through, often for reasons that seemed incredibly valid, the scale of ideas, projects, personal initiatives that went by the wayside—it is chilling moment at the end of Raiders of the Lost Ark when we see the scale of the warehouse in which the Ark is being stored.

This psychological immune system is one of the great secret tragedies of human existence. The good news is that if you really get this in your mind, really appreciate it, it can become almost entertaining to watch the psychological immune system kick in, to hear the voices suggesting all the creative ideas for why you should stop with what you were trying to do.

(I will spare you the chorus of voices telling me at this very moment what a bad idea this post his and how important it is that I start on my taxes now and a handful of other valid reasons for stopping.)

Our kids should know that it is okay to quit, but for their sake, for all that they may accomplish in their lives, they should understand that when it comes to quitting, we want to face what we are doing. Own up to it and welcome the sting, the better to avoid this sort of stealth failing in the future.

They should also know that this tendency is of humans to abort our missions is also a bit of a dark secret of the successful and high achievers in life. Not quitting is often all it takes to skip the front of the line in life. Simply learn to not to give into this sneaky form of real failure and you are on your way to being one of life’s high performers.

Concluding in the frontier of competence

Five lessons in failure—aren’t those kind of amazing, powerful lessons? Especially when compared to the primitive lack of understanding of failure most of us were gifted with when we were kids.

I know that we adults are wired to protect our kids, and the pain of failure is high on the list of our psyche’s scary things, but given the power of the ideas above, it would be a disservice to not to at least make some introductions. Kids, meet great failure insights. Failure insights, meet the kids.

These are many other complementary lessons we could explore, including Simon Sinek’s famous lesson about the importance of finding your why in life, which makes all the difference for weathering failure and obstacles.. There lessons around the importance of enjoying the journey of life, instead of believing that the attainment of any particular goal will bring peace.

Perhaps the best complementary lesson is one a friend recently shared with his child after she turned in assignment he knew she had put a lot of time and energy into. He encouraged her to—before receiving any feedback from the teacher—to understand that the satisfaction she felt about working so well on the assignment was one of the secrets to fulfillment in life. Savor that feeling.

Plenty of such lessons to cover, as parents and in future blog posts, but first to wrap up the current exploration of failure.

I am a big f-ck up. Pardon the language, but that is the only word that does it justice—a huge, olympic level f-ck up. To whit, as I type this, I am in an office so strewn with papers, books, laundry and dog toys in a way that screams: dangerous shut in. And I realized yesterday that my driver’s license expired months ago. And I am once more hurrying to get a post out, knowing there will be errors.

And yet, I have also, if am being honest, accomplished far more interesting and fulfilling things in my life than I even imagined for myself in my more optimistic moments as a youth, with plans to accomplish lots more before the end. So, world-class f-up and pleasantly accomplished. I am guessing most of us can view our life through both of these lenses. This is the dichotomy of life.

At some point in the last year the phrase ‘frontier of competence’ popped into my mind as I have been thinking about failing. In the same way that the outer edge of the universe is continually expanding, our personal competence—all we understand and are capable of—can be constantly extending out further, spreading into new realms, transforming who we are in the process.

But for that to happen, we need to be actively inhabiting and working on the outer edge, our frontier of competence. Our expansion is, unfortunately, not propelled by the momentum of some early big bang, but by our willingness to push into new areas and learn and practice and attempt, despite all of the discomfort that lives out there on that frontier, with failing being a leading source.

A dream of a parent (one of many) is that our kids manage to navigate life in such a way, and have the requisite good fortune, that they are able to spend a good amount of time out there on their frontier of competence, bravely expanding who they can be amidst all the challenges that come with it, and reaping the reward of satisfaction and fulfillment that can come with such an adventure.

But that is presumably a ways down the line. As a start, we can help our kids, and ourselves, in life by understanding that failing, while admittedly at times unpleasant, is both inescapable and a surprisingly essential, powerful tool for navigating life. And now matter what, avoid no moving forward due to some fear of failing, because failing is absolutely a given.

Best not not to tell them to what an extent failure is the water of adult life—the whole business about how we barely make it to through a first coffee before everything goes sideways. That lesson they can learn on their own in their own good time. Thanks to the five lessons above, they will hopefully have a better chance of having some great momentum before things get really complicated.

Take-aways, caveats, details, fine print

The ability to navigate failure, to learn its lessons and embrace the fear that it can cause, is a core strength for reliably leading a successful and fulfilling life as an adult. This includes dealing with the reality that failure, for adults with jobs and families, becomes a constant of daily life that we almost lose the ability to see.

At the same time, for a variety of reasons, we adults are inclined to overly shield our kids from failure, including the many positive lessons for making the most of it—lessons that have been the subject of some of the most popular non-fiction books over the last several decades. The lessons covered in the post above include:

• Lesson 1 - Failure and the growth mindset. It is almost impossible to appreciate the extent to which those of us with a fixed mindset accepted failure or being bad at things years ago, back before Carol Dweck’s work on the growth mindset. Understanding failure in relation to the natural plasticity of our brains and the difference made by a growth mindset is the place to begin building a positive understanding of failure.

• Lesson 2 - Failure and iteration. The next lesson on failure has to do with learning how practice and iteration involve the often long process of progressing toward toward a desired end state (such as mastering a skill or producing a great product), with lots of stops along the way that may seem like failure. To get where we want to go means making peace with these in-between states.

• Lesson 3 - Failure is the way. The positive news about failure gets even more extreme with the Stoic notion: the obstacle is the way, a concept that has been well popularized by Ryan Holiday. This Stoic concept points to a reality many of us eventually understand only later in life—that it is often all of moments that we might have assumed were things we would like to do without—obstacles, setbacks, stinging sense of failure—that turn out to be what made our eventual moments of success possible.

• Lesson 4 - Failure and accountability. There is still one more great foundational lesson in making the most of failure to share, though this is for many the hardest to embrace. The natural tendency of humans in life is to deflect accountability. It is not my fault. The purest example is how kids process a loss in team sports. It was the ref, etc. The mindset that is most productive though is the opposite: it is all my fault. As soothing as it can be to see the fault for failure in others, aggressively finding the ways we could change outcomes in the future is a superpower (note: not to be applied in cases of truly being victimized).

• Lesson 5 - The one true failure. What seems like failure in life is typically an opportunity to learn, to experiment, to pat ourselves on the back for trying hard. That said, there is an epidemic of a sort of stealth failure that is always lurking and we must be on the look out for, which is quitting, particularly the version that happens without our conscious awareness, when we rationalize our way out of a project or goal. Or simply get distracted. Simply not quitting may be one of life’s most effective strategies for achieving greatness.

If we are able to make peace with feelings of failure, and lean into obstacles and setbacks, we can function out on the edge of our competence, and in so doing, be continually expanding ourselves. The experience calls to mind the edge of our ever expanding universe. But only we can cause our own expansion. To be in this place in life is a privilege on many levels, and one that for parents is among the greatest gifts we can wish for our kids.

Bonus Lesson - We evolved to get in over our heads and flirt with failure

This next lesson was cut from the original piece, but I am adding it as a sort of director’s cut.

The lesson has to do with the reality that we may just we wired to get into these situations where we are flirting with failure. It comes Thinking, Fast and Slow, the 2011 best-seller written by the Nobel prize winning psychologist Daniel Kahneman. The book popularized years of research Kahneman and his partner Amos Tversky did to reveal surprising fallacies and biases of human thinking.

One of the insights covered was the planning fallacy, which is the optimistic bias that we humans have when we are planning future tasks and projects. As the fallacy reveals, we can’t seem but to view the likely timeline for our future work in the rosiest light, even if we have had past experiences that have shown us the reality of all that can go wrong with what we are taking on.

Kahneman details that the factor we are often off by is often large, and he chronicles his firsthand experience of mis-estimating how long a project he and others were working on by years. Boston’s famed construction mishap, known as the Big Dig, is also often given as example of the absurd levels by which we can be off in our estimating.

The lesson I draw from this is not exactly to point out that we are apparently wired for some failure due to mental biases (though that is not a bad lesson). Instead, I have my own own theory, as a non-Nobel prize winner for why this happens and what it means for how we and our kids should view failure.

It just may be that, from an evolutionary point of view, being overly optimistic about the projects we delve into had a survival advantage over our ancestors who may have been far more realistic about what they got involved in.

We are the descendants of the early homo sapiens who kept getting in over their heads, thinking that the canoe ride to Australia would take a day or so, only to realize how wrong we were at the point that it was too late to get out, and thus we had to resort to ingenuity, hard work, and luck to bring the effort to a successful conclusion.

This is what we humans do. We paint ourselves into corners. We burn the ships and can’t get back. And then we curse ourselves for our stupidity while trying to devise a scheme for pulling a rabbit out of a hat.

To hear vivid evidence of how this plays out for entrepreneurs, listen to How I Built This. Again and again, you hear stories of the most successful entrepreneurs revealing that they didn’t know what they were getting into, didn’t realize that how much they were putting on the line or how long it would take, and that they had no choice but to go forward.

Good to know, per Kahneman, it is almost impossible for us all to not take on challenges that we only belated realize were are headed toward some level of failure by design. That sinking feeling we all get in life may the result of a kind of mental defect, but it is also our gift, offset by our potential devise creative solutions and to persevere.