Featured Essays

Why Success Is So Confusing

I've been thinking a lot about success recently, for various reasons that I'll elaborate on later, and I have begun to discover that I don't really know anything about it.

In some cases, success can be very straight forward. I envy animals in the way that their lives are just so simple:


However, when it comes to us humans, things are not so straight forwards, and I believe that being in the advantageous position of living in the twenty-first century, with the feeling of limitless possibilities and being in the top 1% of the world by income - I earn more than $32,000 per year - means that I have too much choice on what to do, and so I end up doing less than I would if I had less choice.

I've written before about the brilliant question that was posed by Sun Tzu:

"Can you imagine what I would do if I could do all I can?"

And the answer is now clear:



I simply cannot imagine what I would do if I did all I can. There is simply too much.

From the outside, it may appear that I have achieved a measure of success, especially if this success is measured against what we traditionally measure success in: *which is the collection of money and material goods. *

I live in a beautiful apartment right in the centre of town, and it costs significantly more each month that the average person in town earns during the same time period.


I have a company that employees a couple of dozen people and we do enjoyable work, even if there is the occassional stressful moment.


However, my ascension in the last four years, from a broke twenty-two year old, to paying salaries for more than twenty people each month, has made me wonder:

Am I successful?

I don't feel successful, and that is probably because I don't attach much value to things like money and fancy apartments, and that I feel that now I have less time for the things that I enjoy doing, such as reading, writing, and going for long walks, and I spend more on work that I would like.

I want to make sure that I don't look back on my life when I am older and realize that I mis-lived, and that I was chasing the wrong things, but at the same time I want make sure that I am building a good future for myself.

In fact, one could actually argue that perhaps one should not be chasing for anything, at all.

Shakespeare put it well,

“To be, or not to be: that is the question: Whether ’tis nobler in the mind to suffer the slings and arrows of outrageous fortune, or to take arms against a sea of troubles … ”

and Hunter S. Thompson made this observation from the Shakespeare quote:

And indeed, that IS the question: whether to float with the tide, or to swim for a goal. It is a choice we must all make consciously or unconsciously at one time in our lives. So few people understand this! Think of any decision you’ve ever made which had a bearing on your future: I may be wrong, but I don’t see how it could have been anything but a choice however indirect— between the two things I’ve mentioned: the floating or the swimming.
But why not float if you have no goal? That is another question. It is unquestionably better to enjoy the floating than to swim in uncertainty. So how does a man find a goal? Not a castle in the stars, but a real and tangible thing. How can a man be sure he’s not after the “big rock candy mountain,” the enticing sugar-candy goal that has little taste and no substance?

So should we float or should we swim for the goal of success? Well, before we make that decision, we need to ensure that we actually understand what success is.

The Difficulty of Defining Success

The reasons that success is confusing, because it is so damn difficult to define, and I cannot really settle for the dictionary definitions:

  1. The favorable outcome of something attempted
  2. An action, performance, etc., that is characterized by success
  3. A person or thing that is successful
  4. The attainment of wealth, fame, etc.

I think we all understand definition number one and two (duh!) and want to become definition number three, so what about definition number four?

Well, that’s the one I want to explore right now. It is kinda easy to show that while the attainment of wealth and fame may be one of the prime motivators of humans (in fact, I start to question why I write these essays...perhaps not so deep down I want to be admired?).

He who dies with the most toys wins.


The above quote by the extravagant promoter of capitalism and publisher of Forbes Magazine, Malcom Forbes, is often thought of summing up the whole ethos of the 1980s, the “decade of indulgence”. Personally, I think that it is just as suited to describe the mindset of vast swathes of the population today.

This mindset, which focuses on the acquisition of money and material goods, has actually been around for several centuries. The whole idea has sprung from the so-called fact that to be successful means becoming rich and owning lots of stuff. As a society, we place a huge amount of weight on external and almost completely neglect internal qualities which are not so obvious.

I think a more accurate saying would be something along the lines of:

He who dies with the most toys is, nonetheless, still dead.


Why do we equate vast wealth with success and happiness? My guess is that it has something to do with the fact that we are under the impression that we live in a Meritocracy, a society which hands out rewards based on how capable and deserving you are.

So, the theory goes, one goes to school, studies hard, qualifies to go to a good university and then lands a great job, earns lots of money and satisfaction and that’s that.

Conversely, if you don’t study, work hard and the rest of it, you will end up on benefits, universally despised and you will lack the money to buy the things that make you happy.

For the first time in history, people get what they deserve. Surely there couldn’t be any fairer way for society to work?

I guess not, if you agree on the definition of success and that money and material possessions will lead to satisfaction and happiness.

But again, is life satisfaction and happiness equal to success?

Ah, the rabbit whole gets deeper...


Mark Twain went as far as to say:

Whenever you find yourself on the side of the majority, it is time to pause and reflect.


With this in mind, let’s discuss the two main types of success that you can aim to achieve:

  1. External success - This is where you decide to play the game set by society, and if you play by the rules and play well, you are rewarded with admiration, attention, and recognition.
  2. Internal success - This is the type which you get to define yourself. It can, quite literally, be anything.

We will deal with internal success in the last phase of this essay, as it is essentially the solution to being successful without destroying yourself or falling into one of the many traps that you can fall into when you chase success.

The main difference between internal and external success is that internal success has the possibility of being unchanging and long-lasting, while external success changes often, and is far more susceptive to Hedonic Adaptation.

And that’s interesting thing about the so-called external success, is that it’s not a static thing, but a moving target. If we think in historical terms, we can see how the definition of external success has changed across time and cultures:

A 15th century British explorer and entrepreneur would have been deemed successful if he managed to play the Atlantic Triangular Slave Trade to the best of his abilities, and generate the largest profits for each trip, taking manufactured goods to West Africa, and exchange them for capture black slaves, who would in turn be transported to the Caribbean or American Colonies, and exchanged for cash crops, which would then be transported back to Britain, where then the cycle would again begin. Of course, this would be a highly deplorable practice these days, which would land you with several life sentences for kidnapping, murder, rape, and forced labour. However, we cannot ignore that much of London and Liverpool were built on the back of this trade, and the human cost was incredible, and comparable to the Holocaust, and Africa to this day is still recovering from the European colonizations.

So let's dig deeper into this whole wealth and fame idea, and let's see what we can come up with.

Let’s go a little further back in time, and imagine that we’re a Samurai in 15th century Japan. Success would be something completely different, and we would be judged based on the poetry (“Haikus”) that we wrote, and the respect and honor that we gave the right people in society. If we became disgraced and then committed Seppuku, a form of ritual suicide by disembowelment, that would be viewed a success, or at least without shame. Wikipedia summarizes it nicely:

The first recorded act of seppuku was performed by Minamoto no Yorimasa during the Battle of Uji in the year 1180. Seppuku was used by warriors to avoid falling into enemy hands, and to attenuate shame and avoid possible torture. Samurai could also be ordered by their daimyō (feudal lords) to carry out seppuku. Later, disgraced warriors were sometimes allowed to carry out seppuku rather than be executed in the normal manner. The most common form of seppuku for men was composed of the cutting of the abdomen, and when the samurai was finished, he stretched out his neck for an assistant to sever his spinal cord by cutting halfway into the neck. Since the main point of the act was to restore or protect one's honor as a warrior, the condemned should not be decapitated completely; instead left with a small part of the throat or neck still attached. This way the head could, both metaphorically and literally, rest in its owner's hands. Those who did not belong to the samurai caste were never ordered or expected to carry out seppuku. Samurai generally could carry out the act only with permission.

If we go back even further, and in many parts of the world at different times, just being overweight was a sign of success, as it showed that you were able to overindulge, when famine hung over the heads of the vast majority of the population. And now, the opposite is true. More people are dying because of eating too much than too little, and being overweight is something that is frowned upon.

I hope that this gives you a glimpse into how external success changes in different times and different cultures, and how it may be foolish to seek external validation of success.

However, let’s now go right ahead and tackle the two main current forms of external success: fame and money.

The Problems With Chasing Fame and Recognition

In some ways, there is a strong argument for saying that anything that has been done in human history is because humans wants recognition from their fellow human beings.

William Irvine, in his book A Guide To The Good Life, makes the following assertion:

One of the things people mistakenly pursue is fame. The fame in question comes in varying degrees. Some want to be known around the world. Some seek not world fame, but regional or local fame. Those who don’t actively pursue even local fame nevertheless seek popularity within their social circle or recognition in their chosen profession. And almost everyone seeks the admiration of friends and neighbors. They are convinced that gaining fame (in some very broad sense of the word) will make them happy. They fail to realize that fame, whether it involves world renown or merely the admiration of their neighbors, comes at a price.

The main issue with chasing fame and recognition is that you’re chasing the external type of success, the one that is defined by society, and if fame and recognition are a means to an end (let's say, happiness), then it is not a very good strategy to store your happiness in other people’s heads. This means that your are subjected to their whims and fancies, and that you are not able to be truly free, as you will always need to consider other people’s opinions before you take action, lest you do something that is not deemed appropriate and then suffer the social consequences.

“I have often wondered how it is that every man loves himself more than all the rest of men, but yet sets less value on his own opinions of himself than on the opinions of others.” Marcus Aurelius

Think about this rather trivial example. If a famous sports star goes to a coffee shop or takes a walk, he will be assaulted by fans, and will not be able to enjoy the experience as much, as he will always be interrupted. On the other hand, I am a completely unknown person, and so I will not be recognized, and I will be able to sit at a coffee shop for hours reading a book, and nobody will disturb me.

There is always a price to pay for whichever choices you make.

The Awesomeness (and Dangers) of Money

Money, at first sight, appears to be a really awesome thing. It’s a piece of paper that kinda tells everyone around you that somehow, the theory goes, you’ve been clever enough or have worked hard enough that society now owns you a debt, and you can cash in that debt at any time you want.

When you think about money in that way, it really is quite insane. So if you’ve got $1,000 in the bank, society owes you $1,000 of value, and you essentially have complete freedom on how to spend it.

And if we believe that success is about getting the things that you want in life, and that almost anything is available to be purchased with money. You can buy somewhere to live, you can travel, you can entertain yourself, you can buy drugs, healthcare, sex, you can attempt have someone killed, in some places, you may even be able to buy an election and gain power.

Essentially, money gives you options and freedom, and options and freedom are often seen as very positive things.


Unfortunately, humans are built in quite a strange way, due to evolution. We are trying to run modern software (21st century thinking), on ancient hardware that is not quite up to the task.

This is where our ugly friend Hedonic Adaptation rears its head. If written about this countless of times, and that is because it is one of the major forces at work in the world. Essentially, regardless of how happy you are, you will soon grow bored by everything you have, and you will want a great quantity and variety of whatever you have now. I’ll modestly quote myself, as usual:

The concept of Hedonic Adaptation is simple: no matter what happens, we will always return to our baseline level of inner happiness. So not only will you need to spend your entire life buying good and services, but you will need to buy ever-increasing amounts of them and you still will eventually return to the same level of happiness as you had when you started this whole cycle. The problem is that eventually you either run out of money or health. It’s perfectly possible to “fry” your brain’s reward circuitry with too much stimulation and then you might find that nothing you can buy gives you that “hit” that you requires to stay happy. This is exactly what happens to long-term drug addicts.

So it doesn’t really matter how much money you make, because you will eventually end up in one of two situations:

  1. Either you find a way to spend it all, or you crave things that are still out of your (ever expanding) economic reach, and so you are essentially where you are now, wanting more money.
  2. Or, you decide to go the other way and not grow your lifestyle and spending, which actually means you don’t really need much money at all, and so why bother going to all the effort to acquire more and more money, and make it such an important thing in the first place?

A Gentler Approach to Success

If we bring up the definition of success one more time:

  1. The favorable outcome of something attempted
  2. An action, performance, etc., that is characterized by success
  3. A person or thing that is successful
  4. The attainment of wealth, fame, etc.

Obviously the first point is desirable. Nobody starts something without some internal hope that it will be successful, and this is a tool that is at our disposal to ensure that we create the right type of success, the type that does not cost more to achieve than it brings back to ourselves or society.

The best advice that I can give based on the conclusion drawn while I’ve studied success are the following:

  • Handle money correctly.
  • Define success internally, not externally.

Handle Money Correctly

We know that rates of depression are the highest they have ever been, especially in economically developed countries, and we know that society’s definition of success is the accumulation of large amounts of wealth, fame, and power.

We’ve already discussed the perils of this, and it’s not wise to ignore the fact that chasing fame and money is like trying to hold water in your hands.

Peter Thiel, in his book Zero to One, discusses how in companies, money can either be important, or it can be everything. I think the same can be applied on the individual level.

I prefer to see money as a side-effect of whatever that I am doing, and not as the main motivational factor, as there are more important things in life.

And, excuse the cliche, there are also things that money can’t buy.

There have been studies that have shown that after a certain amount of income, the correlation between happiness or life satisfaction and wealth stops. So, you can keep earning more and more, and you’ll be essentially just as happy as you were before.

The key is to be smart about this, earn enough money to make sure that money is not important, and I don’t mean this in the way that you can spend whatever you want without ever checking the bill. I mean, ensure that you can pay for whatever basics you require to live and thrive, with the occasional luxury thrown in, and ensure that you have some money left over in case of any emergency, and that is good enough.

If you have a little money stashed away, remember that this means that society owes you a debt, and that is a much better and more comfortable position and the other way around.

Define Success Internally

I’ve discussed this before in How To Never Fail, and it is worth repeating again. We are actually very lucky if we are able to set our own internal goals and definitions of success, because we can set up ourselves to win. While this may, at first sight, appear to be a cheap phycological trick that should only be employed by losers who can’t hack the competition in the real world, I believe it is actually the opposite.

I believe it’s those who do chase after the external definitions of success that are falling for the cheap phycological trick, in the case of the dopamine hit they receive each time they hit one of their goals, only to find that it is a short lasting sensation, and that you need more and more every time to get that psychological boost, and, in the end, you ask yourself what is it all for?

The idea here is to take control of the definition of success, and define so that you're already successful.

This is the flip side of Negative Visualisation (see here).

It not only makes bad things appear better, but it can also make you realize that right now, you're probably living the dream life from someone else's point of view. After all, almost everyone you can think of could be having a worse existence, and so the fact that the worst case scenario is not happening is already a success in itself. Essentially, this is the time honoured advice to "appreciate what you already have", and many of the greatest minds across the centuries agree that this is the best path towards living a good life, to flourishing.

I'll leave you with one final quote:

"Success consists of going from failure to failure without loss of enthusiasm." Winston Churchill