“There are two kinds of failure. The first comes from never trying out your ideas because you are afraid, or because you are waiting for the perfect time. This kind of failure you can never learn from, and such timidity will destroy you. The second kind comes from a bold and venturesome spirit. If you fail in this way, the hit that you take to your reputation is greatly outweighed by what you learn. Repeated failure will toughen your spirit and show you with absolute clarity how things must be done.”
Robert Greene (1959 – )
Failing is one of my favorite things to do. My students always think I’m crazy for believing this. I haven’t always had a great relationship with failure and still to this day there are times when I wish she was never around, but failure is our most honest teacher and a natural part of learning.
Somewhere along the way, humans decided that failing is bad and wrong. We teach our youth to avoid failure at all costs, that failure is the antithesis of success, or failure makes you feel terrible and that is why we should avoid it!
All of that is hot garbage.
Failure is honest. Failure is accurate. Failure teaches us lessons that we are less likely to forget. Failure is power.
When my students attempt active recall questions, I’ve noticed an interesting phenomena – when they miss things they are less likely to miss a similar type of question later. I’ve even found this true for myself too. When I was studying for the MCAT, I would do practice questions with multiple parts. I had an easier time remembering the parts I got wrong and the parts I initially got right, I ended up getting wrong later! It’s almost like I needed to fail to remember.
I’ve read somewhere (I’ve spent days trying to find the source but alas, I failed) that people are 7 times more sensitive to negative stimuli than positive stimuli. Which makes sense because we tend to remember our critiques more than our praises. But that had me thinking-
Why are we more sensitive to negativity than positivity?
I believe it’s an evolutionary process. We are walking through unknown territory and we experience something negative, we learn quickly to adapt and survive. Whereas, if we experience something positive, the stakes aren’t as high so we don’t learn as fast.
Failure feelings like a threat. Like a real threat. To our brains, failing our self administered tasks is like having our hand touch a hot stove. We learn quickly not to do that thing anymore.
“Failure had better be an option, because whether or not you consider it an option, it’s going to happen! If you go through life with the philosophy that “failure is not an option,” then you’ll never have any good opportunities to learn.”
Jeff Olson (1958 – )
When we fail at something, the probability that we will fail in the same way is pretty small. So in a sense, everytime we fail we get better. We learn what not to do, which is a lot more useful than we like to acknowledge.
What excellent feat has occurred without failure? When we watch professionals play sports or politicians give speeches, we don’t see the hours of failure that have happened in the background. Just because we see the shiny finished product, doesn’t mean that they were always that way. In fact, if you ask them, I’m sure every single successful person will tell you that they have failed more times than they succeeded.

The Unveiling
“Mistakes and failures are precisely your means of education. They tell you about your own inadequacies. It is hard to find out such things from people, as they are often political with their praise and criticisms. Your failures also permit you to see the flaws of your ideas, which are only revealed in the execution of them.”
Robert Greene (1959 – )
I believe desirable progress is based off two things:
- Identifying what needs to improve.
- Acquiring the skills or knowledge required to improve.
Failing reveals to us exactly what needs to get better. The rest is education and deliberate practice. Failing is half the battle. Whenever we’re learning something new, we fail in all sorts of ways, but how we fail is an insight into how we succeed. It’s like trying to complete a maze; it’s not very likely that we are going to get to the exit without hitting a dead end. Once we hit the dead end, we try a different route, and if we hit another dead end we try another route until we reach the exit. We cannot discover what to do without discovering what not to do.
“Would you like me to give you the formula for success? It’s quite simple, really. Double your rate of failure.… You’re thinking of failure as the enemy of success. But it isn’t at all. You can be discouraged by failure—or you can learn from it. So go ahead and make mistakes. Make all you can. Because, remember that’s where you’ll find success. On the other side of failure.”
Thomas Watson (1874 – 1956)
In order to accept failure gracefully and learn as much as we can, we must detach our identities from our successes or failures. When we fail, we are not failures, we simply did not take the actions necessary for the desired outcome to manifest. By the same token, when we succeed, we are not successes, we simply took the actions necessary for the desired outcomes to come into being. Failure and success is simply the difference between executing necessary actions and not executing necessary actions.
Our failures are stepping stones to mastery and temporary defeats.
“Every adversity, every failure, every heartache carries with it the seed of an equal or greater benefit.”
Napoleon Hill (1883 – 1970)
Defeat is not realized until we stop getting up. We decide when we are defeated, no one else does. Whenever I’ve failed in the past, I can always find an exact moment when I admitted defeat. There is always a singular moment in time when I decide that I had enough of whatever challenge is in front of me. When I admit defeat, I stop learning because I stop finding my inadequacies. Failure is what shines the light on what needs to be improved.
Circumambulation
“I began to understand that the goal of psychic development is the self. There is no linear evolution; there is only a circumambulation of the self. Uniform development exists, at most, at the beginning; later, everything points toward the centre. This insight gave me stability, and gradually my inner peace returned.”
Carl Jung (1875 – 1961)
Circumambulation – the act of moving around an idol – in this case the idol is our maximally developed selves, also known as the Jungian conception of the self. The Self is different for each person, which makes sense to me because no one has the same genetic make up. It’s almost like The Self is a metaphysical representation of our biological dispositions.
I find the idea of circumambulation to be pivotal in understanding the power of failure. Circumambulation of the self is the idea that all of the smaller skills we develop ourselves in is actually apart of a bigger, centrifugal development. Each of these skills is obtained by traveling, so to speak, to all of the far corners of our minds. The Self is our maximally developed selves potentialized in the future and circumambulation is our journey of manifesting this self into actuality.
It’s kind of like this – we develop a bunch of smaller skills, and at first this feels like a linear progression, but as we go through life we start to see the skills pointing towards an ideal.

Learning about circumambulation freed me up in so many different ways because I was worried that I had too many different interests and developing myself in too many different things will prevent me from manifesting my Jungian Self. The best example of this was when I was repressing my love for music because I felt like it didn’t fit with the skills I needed for medicine. Now that I see it is the culmination of all of these skills that will bring about my best self, I feel free to pursue all of my interests wholeheartedly.
Jordan Peterson beautifully outlines the circumambulation of the self and how it relates to failure in the video below.
Jordan Peterson always says the fool is the precursor to the hero and I believe that makes a lot of sense because the one who is willing to make mistakes ends up learning the most, and learning is what’s necessary to save everyone from the malevolent forces of chaos. We see it all the time in movies. The main character is usually seriously flawed but grows over time and that’s where the richness of the story lies. Ash is the worst Pokemon training of all time, but that’s what gives the story room to breathe. The same case is true with us – we are flawed beings, but our admission of our flaws and the strive to improve these imperfections is what embodies our life with meaning.
Robert Greene also references circumambulation in his book, Mastery, but not explicitly. Robert talks about all children having inclinations. These inclinations are strong unexplainable interests that a child develops early on in life. As they get older, they tend to ignore these inclinations and pretend like they aren’t important. Greene suggests adults to do deep reflection to revivify that lost child within them and lean into their inclinations for that is where people will find the skills necessary to be their best. I believe the skills we need to manifest the Jungian Self are found in developing our inclinations.
When we try something new, we are usually very bad at it, but over time we get better. At first it may seem like these things are disconnected by as long as we are developing our inclinations (as defined by Greene) then we will see that all of our development aims towards a central ideal.
Course Correction
“Knock me down nine times but I get up ten, bitch.”
Cardi B (1992 – )
As mentioned earlier, we are only defeated once we stay down but sometimes our failures may throw us off course. Sometimes when we’re knocked down, it takes some time to reorient ourselves again. When we fail, we have to take stock of where we are in relation to our goals. We can’t simply get back up and start moving again. We want to get back up, get back on the right path, then start moving again. We have to consider course correction when we fail. We did not succeed for a reason and it’s important to figure out why and how we move forward without experiencing that specific failure again.
The power of course correction is really laid out in the Apollo mission to the moon-
“On its way to landing astronauts safely on the surface of the moon, the miracle of modern engineering that was an Apollo rocket was actually on course only 2 to 3 percent of the time. Which means that for at least 97 percent of the time it took to get from the Earth to the moon, it was off course. In a journey of nearly a quarter of a million miles, the vehicle was actually on track for only 7,500 miles. Or to put it another way, for every half-hour the ship was in flight, it was on course for less than one minute. And it reached the moon—safely—and returned to tell the tale.”
Jeff Olson (1958 – )
Most of the time the rocket was off course, but that didn’t matter because they still made it to their destination with continuous course correction. It doesn’t matter how often we fail, as long as we are constantly trying to get back on track. The astronauts on the Apollo rocket didn’t think “Oh no we’re off course now! It’s too late! It’s all screwed up! I can’t believe we let this get off course! Let’s just quit!” They simply acknowledged the failure and readjusted their actions accordingly and by doing that enough, they ended up on the moon!
We can see the same thing happen with sports too! Kobe Bryant had a terrible first season of basketball. When he first started, Kobe was horrendous but after he failed he took a step back and figured out exactly what he needed to work on to get his game better. He course corrected and developed The Mamba Mentality, which I think is one of the most powerful perspectives to take on.
Failure doesn’t have to be something that we desperately try to avoid. It teaches us what we need to improve and offers us opportunity to grow. Coupled with ideas like the Circumambulation of the Self and Course Correction, failure can be seen as an exciting phenomena of life. Many of my students think I’m insane for loving failure, but am I really?