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Why Achieving More Wont Make You Happier (And What Will)

Imagine, waking up tomorrow morning and there beside you, as you wipe your eyes and wonder about what’s ahead in the day to come…

You notice a lamp on your bedside table, with a sticky note saying “rub me” on it.

So without much hesitation, you say, “why not” to yourself, and then POOF.

The genie is hovering above you, and sounding just like Robin Williams says, “Your wish is my command”.

You muster up a response in your sleep-dazed state, and as you begin to spurt out a clever question, the genie interrupts you… “And, I’m the cool kinda genie. You can have as many wishes as you want”.


What would you do if you could have anything you want..?


Well, I’m sure that both you and I would have all the incredible experiences and fulfill all our wishes. 

Just like having an endless bank account, and going down the ‘supermarket aisle of life’ that offers all the experiences, you can dream of… we would be scooting down the “pleasure aisle”, with both arms out piling into our shopping trolley all the experiences we want. 

Sexual fantasies played out with whoever you wanted… and then, with them all at once. 

Parties, festivals, and weekend benders that even the rowdiest of rock stars couldn’t keep up with.

You sit on the throne of Hedonism, happily telling yourself that you achieving, succeeding, and attaining all your desires is the best way to live your life.

And we could go on like that for a long time…


But as I would think… the second scoop of choc-mint ice cream is never as good as the first.

We would become a little tired and bored of it. 

As let’s be honest. Even the most pleasurable experiences can get boring.  We need to change it up. 

So after becoming bored and tired of the pleasure aisle… we would say “what about an adventure tonight?”

We then go on a conquest of rescuing princesses from dragons, fighting monsters, and playing the role of every action hero we can think of.


But even then after a while, we would need more thrills. After all, when we know we can have all we want, by the snap of our fingers, the thrill and pleasure of it all isn’t lasting.

So for a second come back from the daydream with your cool genie, and answer this with me…


Would you be happy if you could fulfill all your desires?


Now, as you think about your answer, let me share one more story with you (and this one is true).

I woke up not that long ago, not to a genie, but my own stressed and anxious mind. I had been ruminating all night over problems with my business, marriage, money, children, and more…

For years I had been tiredly working, building my business, feeling like I was chewing glass in the pursuit of success. And I could feel I was paying the price with my health, relationships, and sanity.

All of these feelings were “normal” in so much of the entrepreneurial world I was surrounded by. But all these compromises were feeling out of alignment with what felt right, at best. And completely wrong at worst.

As I walked downstairs in the dark, to hopefully not wake my wife with my constant tossing and turning in bed, I found myself having two problems. 

The first was having the problem I was stressing about.

Then I found another thought behind it…

I was frustrated because I didn’t want to have to deal with this problem. 

“The problem of having problems” was what I thought to myself, as it felt like a greased-up slippery slide of anxiety was awaiting me.


Does this sound familiar?


You’re a smart, ambitious, highly capable person.

You’re here reading this because for the very least you’re wanting to solve a problem.

And like so many entrepreneurs and business owners I’ve talked to there is at the root the want to achieve desires.


You might be saying to yourself…


When I sell my business, I’m going to be happy.

When I get to $10 million, I’m going to have made it.

Or some variations of when you achieve X, you will feel Y.

(All of which I have said to myself at some point)


However, I can confidently say…

You can’t out-earn a lack of fulfillment.

You can’t travel away that gnawing sense in your gut that you’re on the wrong path.

You cant buy enough expensive toys to fill a hole that was made for love.

If you are wanting to fulfill all your desires, you’re wanting to be able to get rid of all your problems.

You’re indulging in the fantasy of one day being in a state where you have no more problems to deal with.

So as I sat there in the dark it came to me that “Are we not all striving and working so hard to be able to solve all of our problems, and so much of this is in the hope and idea that once we solve this next problem then I’m going to be happy.”


The method in which we’re all (and yes I’m including you reading this) using to try to be happy, to have no more problems, is by achieving things.

Right now… Name one achievement that you set out for, that brought you everlasting happiness?!


I can’t name one either.


So why then do you continue to think that achieving more, attaining the next goal, or getting the success you’ve craved for so long, will be any different?


It was truthfully answering this very question that has transformed my life. 

See I was the guy that said…

Once I earn $100,000 a year, I’ll be happy. 

Then it was once I make $100,000 a month I would have made it. 

But when I said to myself, “once I get to $1 million a month, then I will have made it.” 

I knew I was on a stairway to nowhere.

“Make what?” is what I tried to make sense of to myself. The destination that I was heading for at that point had finally shifted.

This constant pursuit of more is a race to the horizon. 

The horizon will never come. It’s always a moving target with the consequence of inevitable frustration. 


It was about 2 years ago, that I had the goal of building and selling my coaching company. Which I thought I wanted to do because of two reasons.

Firstly, I wanted the story to tell the world and myself that I was “good enough” because I was able to build and sell a company.

But also I wanted to achieve a certain level of financial freedom that comes from selling a multi-million dollar business.

Thankfully I was able to sell the business, and achieve financial freedom, but more importantly, it was the epiphany that I had in the final month of exiting the business when everything is still in limbo. And I felt like I was living on a knife edge, knowing that this milestone was so close, but also what if it all came crashing down?!

This is the way I currently think about it — Desperately trying to control all of my circumstances in the hope of “If I get everything the way I want it, then I will finally be at peace”.

All of this is rooted in thinking…

“I feel good… if the circumstances are good.”

“I feel bad… if the circumstances are bad.”


This leads to one of the major problems of this way of thinking, which is that then you must control your circumstances to feel good. 

Santideva answered this beautifully by saying ‘We can try to cover the world with leather, or we can wear a pair of sandals.

The happiness, peace, and joy that you’re longing for, are always set in the future, in the “one-day” mentality, that one day you will have achieved all of your desires, and have in your possession all those things that bring you that sense of success.

The day before I sold my business and was fully excited, I deleted myself out of slack, asana, the CRM, and every tool and software that had me tied to the business.

I woke up on Saturday, October 1st, 2022 to no team members asking me questions, no reporting for me to look over, no notifications pulling at my attention, and no projects for me to work on.

The silence was deafening.

And it was in this void where I finally questioned “success” and how we measure ourselves and the things we do, in hopes to achieve our goals.

Things such as freedom, money, impact, etc don’t land with me anymore when it comes to “success”.  Or especially the much-regurgitated phrase, “do what I want, when I want, where I want, and with whom I want.”

As success is just a word to point at if we got the result or outcome we intended. 

I’ve found it more useful to know what’s the best action. And for that, I use this phrase. 


“The true value of an action is not measured by whether it’s successful or not. But by the motivation behind it.”


We can’t control the circumstances of the world. 

But we do have the control of training our hearts and mind. 

In layman’s terms, it’s the story or meaning that we are creating, for whatever that is happening that we can control.

When we take back responsibility for the narrative that we are creating for our life, we now open up to re-writing it. Creating a new meaning by perceiving it differently.

Naval Ravikant, for whom I see a leading modern-day philosopher and thought leader said, “Desire is a contract that you make with yourself to be unhappy until you get what you want”.

This then leads me to think… The more objects you find desirable and the more you desire them the more incomplete you are as a person, which entails nothing but suffering.

The image of what Hinduism, Buddhism, and Taoism see as Preta, or the “hungry ghosts” come to mind to me here.  These are the beings that have tiny mouths, and large stomachs.  That has an insatiable thirst or hunger. Constant and never-ending suffering is inevitable when in this state because you’re craving for more will always overpower whatever it is you do, have, or achieve.

I was the hungry ghost. 

I had a tiny mouth and gigantic stomach.

I was the one that had the insatiable thirst for more.

I was the one that ticked the boxes of success and yet found myself with depression and anxiety.

Earning more money, achieving more, and working harder felt like I was just drinking seawater in the hopes of quenching my thirst… but all it did was accelerate the thirst for more.


Just like you and the genie at the start of this essay, let’s imagine you’re a lucky person, you have all the desirable things you want, and your circumstances and resources are perfect.  Hence you should be happy, right?!  

Well looking back to Saturday 1st October, I woke up as usual and got straight into the morning ritual that I had engrained in myself over the years.  After meditating and journaling I went for my morning walk followed by a sauna and ice bath.

Sitting in the sun at around 7:30 am, still shivering from the ice bath I realized that everything had changed, but nothing has changed.  This paradox of achieving a huge milestone could now easily sit inside my head as I understood that you and I are wanting to be happier, more peaceful, and have a greater sense of meaning in our lives.

Once I have chalked up a few wins, and wiser from the scars that life and entrepreneurship deal our way, it’s easy to start thinking that we’re so smart in how we go about everything, thinking we’re so talented in how we achieve, and thinking we’re so superior in our results compared to others… All of this continues to dig the grave deeper and deeper in our belief that we need to strive for more.

And when playing that game we’re at the mercy of the outside world. On one hand, I was extremely grateful for how I was able to build and then sell the business.  But being honest with myself, there were an immeasurable number of happenings that I had no control over that led up to that event taking place.

This is when I asked myself when trying not to shiver; “Isn’t this insane that I’ve been trying to be happier and more at peace, by relying on things I don’t control?!”

Now suppose you’re stuck in a bad circumstance. It does not matter how you describe your situation but let us, for the argument’s sake, say that your circumstances are as bad as possible. For example, we have more than anecdotal evidence that a person who suffers from a medical condition called locked-in syndrome may report personal happiness.

Locked-in syndrome is a rare and serious neurological disorder that happens when a part of your brainstem is damaged, usually from a stroke. People with LiS have total paralysis but still, have consciousness and normal cognitive abilities.

He can only move his eyes and now he is instructed to move his eyes in a certain direction to communicate if he is happy; he reports happiness.

This is when I had to sit down and get real with myself to then understand “well, what is happiness?”

And so far I lean on what was published in 1940, when only in his mid-twenties, Alan Watts declares in one of his class works, “Happiness is a sense of harmony, completion, and wholeness.”

Watts with this pithy pointing out of happiness gives me a sense of direction on this, but I had to go back further to around 300 BC to learn from the Greek Philosopher, Epicurus.  

Epicurus agreed with other philosophers about happiness being our ultimate human pursuit, but he suggested something very different from what others had proposed in terms of how that might look in our decision-making and behaviors.

Many philosophers suggested that experiencing pleasure and happiness meant allowing yourself to indulge and enjoy things to excess. Epicurus, on the other hand, suggested that pleasure was found in simple living.

There are three states Epicurus considered to constitute happiness… Tranquility, freedom from fear, and absence of bodily pain.

To experience tranquility, Epicurus suggested that we could seek knowledge of how the world works and limit our desires.  For him, the pleasure was to be obtained through things such as: Living a virtuous life, knowledge, friendship, community, and living with temperance and moderation.


And this is where I found Epicurus an easy bridge for me to embrace Stoic philosophy. As the Stoics thought all you needed to be happy was to be virtuous.

Christopher Gill explains stoic virtue by saying “Virtue is a form or expertise or skill, knowledge how to live well in every way, a form of knowledge that shapes the whole personality and life”

Then also in one of my favorite stoic writings, Letters from a Stoic, Seneca says — “A good character is the only guarantee of everlasting, carefree happiness.”

And this is where I found that the dots started to connect for me, and I had been living with the want of being happy all wrong.

Simply put, to live virtuously, we are striving to become the best versions of ourselves.  And to do this, we start by taking ownership of ourselves and the state of our lives.


“There is only one way to happiness and that is to cease worrying about things which are beyond the power of our will,” says Epictetus.  

You can’t control if you’re going to get a genie tomorrow morning. 

You can’t control if your partner wakes up next to you tomorrow and says they want a divorce.

You can’t control if your 4-month-old baby projectile vomits all over you.

But you can control how you act and respond.


And finally, this is where I started to find myself being more content and satisfied in my life, all thanks to letting go of outside desires, and focusing on what is in my control: my thoughts and beliefs. 

Let’s take me as an example.

I can’t control if Lauren, my wife, wakes up tomorrow morning and wants a divorce.  Sick and tired of me doing a half-assed job cleaning up the dishes, or stretching naked in the garden in the afternoons.  It’s all her choice and her choice alone.

Now that doesn’t take any of my power away. I can certainly (and should) control how loving, affectionate, compassionate and thoughtful I am to Lauren in our marriage. I can certainly do a better job doing the dishes, or put on some budgie smugglers for my 4 pm in the garden Yoga sessions.

The Stoics argue that the only two things that we have absolute control over are our thoughts and actions. Inevitably, things will happen in life that we can’t control, but it’s our perceptions of events followed by how we respond to them that makes these things good or bad. 

So shouldn’t we accept that there is good and bad in life and that wanting to only have good, is a completely unnatural, irrational, and childish way to live life?!

This is where I found for myself a sense of solace in the teaching of Taoism, which has some similarities to Stoicism.  One is what the Stoics called the Logos, and what Taoism calls the Yin and Yang. Gives us the idea of a providence beyond opposites.

Just like hide and seek. 

Without seeking, we wouldn’t know what is hiding. 

We can’t have darkness, without light.

We can’t have sound, without silence.

We can’t have highs, without lows. 

We can’t have lows, without highs. 

We can’t have here, without there. 

Because if you didn’t know where there was, you wouldn’t know where here is. 

They always go together. 

They are two of the same thing. 

We need the good and the bad. 

Without bad. We wouldn’t know what is good. 


The realization that the natural flow of life has both good and bad, got me to then see that the word “happiness” that you, I, and our modern culture use today doesn’t fit the feeling or sense I am ultimately looking for.

This is when I can only speak for myself, but with many investigations of the past 2-3 years, it’s been the word “equanimity” that is the feeling, the sense, the emotion that gives me what I’m looking for.

The ancient Stoics had a word for this: apatheia.

It’s the kind of calm equanimity that comes with the absence of irrational or extreme emotions.” writes Ryan Holiday, one of my favorite writers on Stoicism.

Apatheia points to the calm equanimity that comes when you’re not being toyed around with irrational or extreme emotions. Whereby much of the common confusion is that Stoics are a bunch of robotic, emotionless bodies.  It’s not about the loss of feeling altogether, just the loss of the harmful, unhelpful kind.

The chasing of happiness through the desire and attaining of earning more money, being in better physical shape, and ultimately being of higher status does not and will not give you or me that sense of apatheia, equanimity, or lasting fulfillment.


Because it’s the doing that makes us more fulfilled, not the having.

The buyer of my business in our first negotiation said to me; “You can make millions more if you hang onto this for longer”.

I knew his words were true, but the price of me having to run that business for long, and not move on to what else I wanted to experience, is the reason I sold knowing I was leaving millions of dollars on the table.

At that moment negotiating the sale of the business I knew I had a fork in the road.  And it was this thought that made me follow through…

“I don’t want to make more. I wanted to be more”.

As Forrest Gump said, “There’s only so much money a man needs, the rest is just for showing off.” 

Now don’t think too morally of me by saying this, it’s been over 18 months of psychotherapy for me to come to this knowledge.  As the truth is I had lived my entire life thinking money was going to solve all my problems.  Being an only child to teenage parents I saw firsthand my parent’s sacrifice and work hard to be able to provide for me.  Knowing that we didn’t have a lot of money growing up, instilled in my lust and desire to never have money problems again.


Luckily, I had my first  ‘aha moment’ in my early 20’s as a personal trainer in Sydney.

Peter was an uber-successful marketer, and also a practicing Buddhist, which thankfully was also my client. He must have seen in me something good, but also a tiresome, overly ambitious young dude that was running in the wrong direction, and moments away from making life-altering mistakes.

It was the day Peter came and picked me up out of the front of the gym in his Bently.  Whilst I was picking at my salad too overwhelmed with what he was sharing with me to have any sort of appetite.  I had the first taste that it was very possible to have wealth, and yet, not be attached to it.

And this is when my fascination with Buddhist philosophy started.  As he and his partner James also gifted me a book; Ego, Attachment and Liberation by Thubten Yeshe.

Since then I was able to start joining the dots to understand that how we perceive the world and use the resources in our environment are determined by what’s in our hearts. Is it greed or a wish to help others?

Now if you were like me when I first started out wanting to learn from the ancient wisdom traditions, this can start to sound a bit esoteric, and hard to grasp and use in your day-to-day living.

And this is where the rubber meets the road for me…

Where hedonic happiness is seeking pleasure for self.  It can easily lead to greed. There is a pendulum or tension between altruism and narcissism here which is a part of the spiritual realization of happiness.

It was the Greek philosopher Aristotle that brought us the “golden mean”, which aims for moderation or a striving for balance between extremes. Which is very much like Buddha’s “middle path” teachings.

According to Aristotle, Happiness exists in the rational exercise of the soul’s conformity with virtues such as courage, justice, temperance, benevolence, and prudence.  Similarly, Buddhism aims not to eradicate all feelings but to liberate them from its attachment to false values. 


So does living our lives wanting to have no more problems make sense?

Do we think it’s natural to never have hard or challenging times in life?

Does it sound reasonable that through a constant striving for achievement you’re going to attain ever-lasting happiness?

For me, I can confidently say no to all of those.


Rather than clenching with all my might, desperately try to hold onto the hope that everything will work out exactly the way I want it.

I can relax back to one of Joseph Goldstein’s teachings; “whatever has the nature to arise will also pass away”.

Because when I finally started to understand this pithy remark, it pointed to the glaringly obvious state that is, everything changes.

Every dollar you earn, every achievement you attain, every moment in your life is going to change and pass away. And rather than trying to cling to everything, even more, we can relax and let it happen, as it will whether you want it to or not.

So to answer, is the man or woman that can fulfill all his desires really happy?

I am now left with a spaciousness, more relaxed, less neck-clenching sensation.


The goal of being able to fulfill all my desires…

The destination of having all the money, power, and achievements…

The intention of no longer having problems in my life…

These are not things I wish for.

Instead, I lean into the belief that we are personally responsible for our happiness, and it’s up to each of us to create happiness through our thoughts and actions.

Rather than sacrificing the little precious time we have in this life chasing after things we don’t have.  We can, and likely should spend at least some of our time and attention wanting what we already have.

And instead of running away from the reality that life will be hard at times, adversity will come our way, we can embrace it and make the most of it. Dare I say, even enjoy it.


Walking down the stairs in the dark that night had me realize I had a problem with having problems. And that I had a never-ending thirst to achieve and strive. None of those we’re smart or rational ideas to live by… but so many of us do.

So now I hope that both you and I can lean into what Anthony De Mello said, feeling the strong foundation that gives us more ease and peace…

“Everything is in a mess. And all is well.”