Why External Success Didn’t Buy Me Happiness —but the freedom to find it.

Attachment. It’s the one thing that human beings crave above all else.

We want to feel important, connected, cared for, and loved.

From the moment we enter the world as infants, we are — hopefully — adorned with nothing but love, at least for a while.

We are — hopefully — given everything we need.

Our every cry is tended to, our every demand is fulfilled.

But then something happens.

Perhaps it’s around the age of two or three.

Perhaps we do something that isn’t so warmly received. Perhaps our mother is having a rough day and takes out her frustrations on us. Or perhaps we’re just being ‘little shits’ and told that we must finish our greens or we won’t get any dessert.

At this point, we learn a valuable life lesson.

We learn that we must trade our authenticity for love and attachment. If we want love, we must behave a certain way or we are unlikely to get it.

From this point on, we seek validation, an assurance that we are “enough” not from within, but from without — from people, from material possessions, from status and rewards, and it comes at the expense of our higher authentic Self.

My Story

While many infants, at least in developed countries, can expect nothing but unconditional love as infants, this wasn’t exactly the case with me.

It wasn’t because my mother was heartless — to the contrary, but she was heartbroken. Just four weeks before my birth, she had lost her 13-year-old son and my brother, to leukemia.

Infant experiences are fundamental to adult behavior, so I asked her what her relationship with me was like at the time. She confided that my physical needs were met but my emotional needs weren’t.

Her loving energy was absent, and she regularly broke down into tears and fits of hysterics, mourning her recent and devastating loss.

It is understandable and not something that I would ever hold against her — she was doing her best — but it does go a long way to explaining my life-long quest for external validation, my life-long quest to prove that I am “enough”, despite a deeply ingrained fear that I am not.

Seeking Validation

Like most first-generation kids of immigrants to a western country, I was sold the story that if I study hard, get good grades, find a good job, buy some property, and meet a nice girl, then I’ll be happy.

So I did that.

I did well at school and earned two college degrees.

In my 20s, I scored gigs at venerable institutions like EY, KPMG, and Macquarie Bank. After almost a decade in various corporate roles, I found myself comfortably miserable and quit.

In my 30s, I pursued entrepreneurship. My first foray into business was a two-year-long failure, but my second act became a seven-figure business within 15 months of launching.

It was named one of Australia’s fastest-growing new companies by the Australian Financial Review in 2018, and it earned me a comfortable lifestyle.

It gave me the freedom to write several books, and the money to buy several properties.

Attracting beautiful women became easier.

Oh…and I also drove a Tesla.

As far as external validation goes, I was doing just fine!

So why was I still miserable?

External Validation is Fleeting

The reality is that no amount of external validation is forever satisfying.

We always want a larger salary, a nicer house, a better zip code, a faster car, a more fulfilling job, a hotter girlfriend or partner.

External validation might make us feel good for a moment, but we quickly recede to a baseline level of happiness — which, as it turns out in my case, wasn’t all that happy.

This is the nature of the arrival fallacy and part of the reason why many world-famous musicians, athletes, and actors also suffer from depression and are never actually satisfied or at peace.

We might think that a new job, or a new residence, or a new partner, might make us happy, but what we might need more than anything is a new mindset.

Validators can also be taken away from us tomorrow, and so they leave us vulnerable to changes in circumstance.

If I was going to be happy, or at peace, then I would need to look inwards.

Searching for the Truth

After enduring Melbourne’s draconian lockdown measures, a complicated four-year-long romantic relationship that ended in a breakup, and a challenging business environment, I became increasingly familiar with my bedroom floor and the fetal position.

I had reached what many have called before me, the dark night of my soul.

It’s this dark night that usually precedes a revolution in the mind — a spiritual awakening towards a different way of thinking and navigating the world, and hopefully, towards greater enlightenment and inner peace.

So it was as domestic borders opened up in Australia that I booked a one-way ticket to the scenic coastal shire of Byron Bay.

The purpose wasn’t to leave my problems behind and sip green smoothies every day, but to spend some time surfing, doing yoga, spending time in nature, and most importantly, reflecting on my life — a privilege I am grateful for and something that starting a modestly successful business gave me the freedom to do.

As Naval Ravikant tweeted, “the reason to win the game is so that you can be free of it”.

I would spend many a morning hunched over a notebook, whether it was by the beach or a cafe, madly transferring thoughts from my mind to the page.

After much soul-searching, reading of books by the likes of Jiddu Krishnamurti, talking to people, and just sitting with myself, filling an entire notebook with reflections became easy. It was almost as if it was writing itself and my hand was just an agent.

So What Did I learn?

While almost impossible, I’ve distilled said notebook into 21 of my key learnings and behavioral commitments below.

For high-achievers who find that happiness or inner peace doesn’t exactly correlate with income, and are searching for answers, some of these might provide a reason for pause.

1. Surrender to negative emotions.

Don’t suppress or escape them. Watch them without judgment, and their energy (and countless possible thought associations) fades away.

Feelings and negative emotions are few — fear, sadness, anxiety, grief, anger — but thoughts are infinite. Typically, uncomfortable feelings can trigger a vicious thought cycle.

As human beings, we tend to try and suppress or escape our emotions through activities like drink, entertainment, sex, exercise, and the like, but these are just band-aid solutions that create more suppressed negative energy.

Surprisingly, when you just let the negative emotion be, watch it, sit with it, love it, without judgment, without attaching thoughts to it, it typically discharges in what seems to be moments, and countless potential thoughts don’t come to fruition.

The more you do this, the better you relate with negative emotions, the less negative energy is pent up inside you, the fewer downwards thought cycles you endure, and the more positive your disposition.

As they say, the only way out is through.

2. Love yourself unconditionally.

When you do this, you no longer base your self-worth and mood on fleeting external factors and open yourself up to be your most authentic self.

Doing so flips our need for external validation on its head. When we truly believe and show ourselves that we are enough, we stop acting out of fear and start acting out of love regardless of external circumstances.

We do things because they make us happy, not because they temporarily validate us.

3. Choose compassion over judgment.

I’ve often judged people, and it was typically to make myself feel better about myself — it was usually because deep down, I didn’t think I was enough. But with self-love, this disposition towards judgment dissolves.

Not only that, but by reminding yourself that people are doing their best with the biology and upbringing they were given and that you would be the same as them if you walked the same road, you’re left with nothing but understanding and empathy.

I’ve found that navigating the world in this way makes its edges a lot softer, and gives each day a much lighter feeling.

4. Choose gratitude and forgiveness over anger.

As the saying goes, anger is like drinking poison and hoping it will hurt the other person. Anger doesn’t hurt anybody but you, and it colors your world with all the wrong colors.

It is so much easier to choose gratitude, forgiveness, and compassion over anger — it is representative of a higher state of being.

5. Look for the positive.

Every emotion thought, or feeling has a positive and negative interpretation.

It is the nature of yin and yang.

6. Commit 100% or quit.

No matter what you’re pursuing, if you’re in, be all in.

As psychologist Barry Schwartz wrote in the Paradox of Choice, maximizers are never happy for long. But satisficers — who truly commit even to a so-called sub-optimal decision, are much happier in the long run.

7. Don’t be passive, be active in a positive way.

Being self-loving doesn’t give you a license to become a couch potato and do nothing with your life.

On the contrary, surrendering to negative emotions and truly loving yourself opens up your most authentic path and gives you the freedom to live a more aligned and consciously active life with truly meaningful relationships and meaningful work.

8. You can’t truly love someone unless you love yourself first.

Romantic relationships have been a source of self-validation throughout my life because deep down there was a sense of lacking.

However, such relationships say nothing about the other person and everything about me. They were about ‘completing’ me, in Jerry Macguire fashion, rather than truly loving the other person.

Such relationships are based on dependency, attachment, a cure for boredom and loneliness, and self-validation.

They are not based on love.

Only with truly being content in one’s own skin can we truly love another.

9. Don’t identify with thoughts and feelings.

You are not your thoughts or feelings — they are simply appearances in consciousness, no different from sounds, sights, and bodily sensations.

10. Love beats fear.

Lead with love.

11. Tame your magpies.

Don’t run or look away — they will swoop.

By staring negative emotions in the eye, they lose their power.

12. The humble can’t be humbled.

Being humble doesn’t mean being unworthy, but it does mean you are at one with others, open to new experiences because you’re leading with genuine self-esteem instead of a fearful ego and don’t mind sucking at something.

While I was in Byron Bay, I took several yoga classes. During one class, the instructor laughed at a pose I was awkwardly trying to pull off. The old me would’ve gotten inside his head for the rest of the class, and never stepped back into the studio.

The new me — leading with love and humility — laughed along with her and enthusiastically came back to that same class the very next day, and got better.

13. Stop comparing yourself and your situation with others.

Comparison is the thief of joy, and the grass is rarely, if ever, greener on the other side.

Be grateful for what you do have, and if you must compare yourself, compare yourself to people who would literally kill to be in your position.

14. You are responsible for your own happiness.

You get to wake up and decide how you will respond to external stimuli and negative emotions each day.

The problem and solution aren’t outside of yourself, they’re always within you.

15. Commit daily to being at peace.

It is a choice.

16. Accept ‘what is’ instead of perpetually seeking what ‘should be’.

What ‘should be’ is typically a programmed script that societal conditioning and upbringing have given you.

Throw out the script.

17. Let go of attachment to desire.

The Buddha said that attachment to desire (tanha) is the root of all suffering, then letting go of it renders suffering powerless.

I learned that one can still become something while truly being in the moment and accepting where they are on that journey (Becoming), but that it is more about consciously choosing which journey to take.

When we stop being unconscious victims of desire and love ourselves fully, we might find that the journey and pursuits we’re on don’t make any more sense.

18. Optimise for private wins over public wins.

It’s not what people can see but what people can’t see that matters most.

19. Pursue people, work, and ideas that align with your true self.

When you love yourself unconditionally, it creates space for your true path to open up instead of pursuing things purely for validation and ego inflation.

20. Embrace oneness.

Human beings are all one.

We all suffer.

We all strive.

We are all doing our best.

Instead of seeing yourself as a separate human being, see yourself as part of the whole and the world’s people as your brothers and sisters.

21. Nothing is good nor bad. It just is.

People aren’t good or bad; they’re loved or hurt.


Practices I’ve Incorporated

Final Thoughts

Since I returned to Melbourne, I have been making a concerted effort to re-wire my brain, stare negative emotions in the eye, show myself true self-love, and essentially embrace the above-mentioned behaviors.

It has left me feeling more content, lighter, and relating to the world and people in a much more positive, open, and loving way. It has left me with more inner peace, regardless of what goes on around me.

That being said, this is a journey. While I don’t expect to ever truly ‘arrive’ at enlightenment, by practicing every single day, I know I can live a much more intentional and authentic life, and that my friends, is perhaps the greatest gift of all.