The happiness of pursuit


Ask any human what they want, and they’ll answer “to be happy”. Happiness classes are among the most popular courses at Yale, Harvard and Berkeley (though at Stanford, it’s “Touchy Feely, aka “Interpersonal dynamics”).

However, if we dig deeper into what “happy” means, we are stumped. Why is that? Why is the most critical state of being we wish for so hard to define, recognise, elicit, and maintain?

Devoting your life to something you haven’t understood seems paradoxical, yet very common. Why? The answer is a mix of confused thinking, mimetic desire, human naivety and overcomplication.

If you’re after the TL;DR, here goes:

Happiness is the exercise of one’s vital abilities along the lines of excellence in a life that affords them scope.” Aristotle

If you are interested in further clarity, below I present the main pitfalls of striving for happiness, offer some definitions and mental models, and weave in a few contradictions so that we can all learn to beware of people bearing absolutes.

The sixth element

“Happiness is a direction, not a place.”  Sydney J. Harris.

The ingredients of happiness are not particularly controversial, and most would agree that they present a combination of the factors below, with different weights for our preferences:

  1. To be part of something larger than ourselves
  2. To be paid attention to
  3. To be listened to
  4. To be respected
  5. To be safe and loved
  6.  To matter and achieve meaning

Building on this, psychologist Abraham Maslow introduced some hierarchy to those needs in the 1943 paper “A Theory of Human Motivation”, featuring the famous pyramid of human needs we’ve all seen.

It turns out, however, that this wasn’t his latest thinking, which he updated before he died in the 1970s. In his later years, he added a new apex to the pyramid: self-transcendence, the game’s final level. 

Having worked on our emotional needs and achieving our potential, Maslow realised that we needed to transcend perceiving ourselves as individuals and instead as an integral part of the broader universe to develop the shared priorities that allow humankind to survive as a species. We can only reach the pyramid’s pinnacle if we’ve worked through its base and middle layers.

Hold that thought.


Source: Wikipedia


The pyramid’s third dimension

So far, it would seem that the algebra of happiness is simply an ingredient vs recipe problem: We know what’s needed; we just need to know the dosage and the sequencing. Unfortunately, there’s a dimension missing: perspective.

This part of our analytical framework lets us down the most often: we confuse the internal and external perspectives on happiness. I’ll skip the standard comment on how social media fuels this, but suffice it to say that the gap between those two perspectives has been growing since the Stoics.

The external perspective stipulates that worldly happiness is a reward from our evolutionary program. Get praise, money, drugs, sex, unicorn status, magazine cover. It busies the mind with craving and anxiety and is an easily observable external proxy for happiness. I am not suggesting that it is in any way wrong or inferior, as this would directly contradict hip-hop cultural values, for instance. It is, however, a more volatile notion of happiness as ever-changing external factors drive it.

Internal happiness is the reward for being in flow. Create, meditate, love, and play. These activities clear the mind and leave us in peace. Internal happiness is a more stable version but much more challenging to define, observe, and post on Instagram. Nevertheless, we can work on it and define it in our terms.

The fancier way psychology defines these core types of happiness is Hedonic: achieved through pleasure, enjoyment, and satisfaction, and Eudaimonic, achieved through meaning, purpose, and authenticity. Manslow’s framework tends towards the eudaimonic definition, and popular culture overweights the hedonic aspects of this.

Sahil Bloom has a thoughtful note on the topic that highlights that we need to find a balance between these necessary definitions of happiness by controlling the speed of our hedonic treadmill by embracing short-term, earned pleasures but focusing on building a life grounded in our long-term values and purpose. A meaningful life requires us to transcend our biology towards a more spiritual focus, but that’s not easy.

But wait…

There is a fourth dimension: time. It is important to understand that the happiness process is a dynamic set of choices about prioritising as our own needs evolve. The ever-eloquent James Clear writes that we’ll never find one answer to what makes us happy, and we should come to terms with this by acknowledging our needs at each stage of our journey. 

Common misconceptions and traps

We are notoriously good at telling ourselves stories that are simply not true. In our innate pursuit of happiness, we assume it’s what we want. Yet evolutionary psychologists could argue that we are wired for status, not happiness, as natural selection only cares about survival. The resulting common pitfalls and self-deceit can get in the way of joy through self-sabotage, which we deal with next.

Overcoming the Arrival Fallacy

“The fundamental delusion: There is something out there that will make me happy and fulfilled forever”. Naval

The arrival fallacy is the first obstacle to overcome in our pursuit of happiness. It was introduced by the behavioural scientist Tal Ben-Shahar to describe the common illusion that once we attain our goal/target/destination, we will achieve lasting happiness and fulfilment. But this simply is not true, as we are wired to always want more as a result of the evolution of the human species, which was characterised by scarcity.

The simple fact that there is no “there” is fundamental to understanding this trap. Any objective setting that starts with “I’ll be happy when X happens” is the purest exemplification of the arrival fallacy, and it is innate to each of us. Brad Stulberg puts it bluntly: “The future is a hoax. When your plans mature, you will still be living for some other future beyond.”

The reality is that we are planning for a future which we’ll never be able to enjoy, as the notion of sitting back with complete contentment and saying, “Now, I’ve arrived!” will never transpire. It has not happened for the most successful, famous, intelligent or influential people, and it won’t work for us.  Understanding how to be alive and happy now rather than in some uncertain future has resulted in the paradox we don’t know what we want and need; we confuse measurements and by-products of happiness with our actual goals, and wherever we are, the goalpost is always 10 yards down the field.

This pitfall is best exemplified in the Gold Medal fallacy. In his memoir From the Outside, the NBA basketball superstar Ray Allen wrote that after winning his first NBA championship, “As the days wore on, there was a part of me that felt empty… I had always believed that when you win a championship, you’re transported to some new, exalted place. I realised that you are the same person you were before and that if you are not content with what you are, a championship or any accomplishment isn’t going to change that.”

Gold medals, promotions, recognition, and best-seller lists are all worthy and essential achievements that will define the arcs of our lives. But if we’re not enough without them, we’ll never be enough with them.

The Butterfly paradox

“Happiness is like a butterfly; the more you chase it, the more it will evade you, but if you notice the other things around you, it will gently come and sit on your shoulder.” Henry David Thoreau

Arthur Brooks says happiness is not a feeling; feelings are evidence of happiness. The happiness state ensues after we cycle through the right (for us) conditions, and this sequencing trips up many of us, making happiness difficult to pursue. Happiness tends to ensue rather than exist as something to pursue.

The stoics had an insight into how to handle this sequencing problem with the happiness state, which will be a recurring theme in this note. “True happiness,” Seneca said, “is to enjoy the present without anxious dependence upon the future.

The realisation that happiness, like much of life, only exists in the present moment is core to the journey of holding on to a happy state. Despite its fleeting nature, we can make it a permanent part of our lives without holding on to it. It is attainable and wonderful.

This leads us to the essence of the butterfly paradox:  happiness is what you seek, but you can’t go out there seeking it. If you say, “My goal is to be happy,” then research shows you are more likely to achieve the opposite. In essence, the pursuit of happiness above all else overvalues it, creating an expectation of permanent happiness, and the correspondent disappointment results in unhappiness. Therefore, seeking happiness as a main priority is likely to be a self-defeating pursuit.

Tal Ben-Shahar, who teaches the Harvard class, explains the fallacy of pursuing happiness this way: “You cannot look directly at the sun, but you can absorb its rays.”

Taking the metaphor further, happiness is like an orgasm. If you think about it too much, it goes away. Practising gratitude and receiving gratitude is an exciting insight into orchestrating happiness—aim to make someone else happy, and you might get some as a side effect. Sometimes, you must stop looking to find what you’re looking for.

Deferred Happiness Syndrome

“The fool, with all his other faults, has this also—he is always getting ready to live.” Seneca

Marie-Louise von Franz talks about “the provisional life”, which is the  strange feeling that one is not yet in real life. “For the time being, one is doing this or that… [but] there is always the fantasy that sometime in the future the real thing will come about.” The deferred happiness syndrome is a particularly nasty derivative of the Arrival fallacy: it not only assumes that there is a point in time in which we enter the happy phase with the attending rainbows and unicorns, but it also suggests that we must defer the pleasures of life in the pursuit of arranging the chess pieces in the correct manner to reach nirvana.

“The common feeling that your life has not begun, that your present reality is a mere prelude to some idyllic future. This idyll is a mirage that’ll fade as you approach, revealing that the prelude you rushed through was, in fact, the one to your death.” Gurwinder Bhogal

The DFS fallacy is one that I’m particularly prone to, and to mitigate it, I keep reminding myself of this Seneca quote:

“Putting things off is the biggest waste of life: it snatches away each day as it comes and denies us the present by promising the future. Expectancy is the greatest obstacle to living, which hangs upon tomorrow and loses today. You are arranging what lies in Fortune’s control and abandoning what lies in yours. What are you looking at? To what goal are you straining? The whole future lies in uncertainty: live immediately.Seneca

Mental models for happiness and meaning

“Nobody wants to believe happiness is a choice because that puts responsibility in their hands. It’s the same reason people self-pity: to delay action, to make an outcry to the universe, as though the more they state how bad things are, the more likely it is that someone else will change them.” Brianna Wiest

The algebra of happiness

Many will contend that happiness is more poetry than math and it is not a solvable equation. Dissatisfaction is an inherent part of human nature and is necessary for creating growth and thriving. Nevertheless, there is one simple, direct lever we can manipulate to move our happiness gauge: expectations. I have found this definition to be helpful:

Happiness is reality minus expectations. Or what you have divided by what you want to indicate the exponential impact of our wants on our happiness. Pick one.

We will only be happy if our perception of where we find ourselves exceeds what we expect. Therefore, the lower we can set our expectations, the higher the surface of happy moments we can experience. I am not suggesting we should practice the total absence of desire, although that’s a possible path we will discuss later.

The power of expectations is difficult to overstate. Expectations destroy happiness—whether in our relationships, our personal growth, or our work. Expectations are why many people are so unhappy today, even in a world with so much abundance.

Trade expectation for appreciation. Tony Robbins

Naval’s happiness practice

Desire is a contract with yourself to be unhappy until you get what you want. Naval

Naval Ravikant is one of the clearest thinkers of our age. We can apply his insights to most areas of personal and professional life. His working definition is that happiness is when nothing is missing from our lives, the absence of desire, and the complete acceptance of the significance of the self.

His central insight is that happiness is a skill that can be learned, and like fitness, it’s a matter of reps and consistency. He explains that nothing external can bring lasting happiness and that a wiser path is to focus on quieting down the mind and body enough to experience a deep sense of inner joy and peace—an idea that has been around since the time of the Buddha.

How does one hone that skill? Naval outlines these considerations:

  1. Train your mind to stay in the present, a philosophy shared with Eckhart Tolle. Happiness is in the mind, which is as malleable as the body. However, the brain is wired to spend as little time as possible in the present, alternating between worrying about the future and regretting the past. 
  2. Navigate to the absence of desire rather than the achievement of pleasure. You know you have arrived when you have no urge to feel differently or want to change your state.
  3. Embrace “cosmic insignificance.” The universe doesn’t conform to our desires, and we need to understand that our ego makes us unhappy. Life is just the way it is, and accepting that brings peace. We don’t always get what we want, but sometimes what is happening is for the best. The sooner we can accept it as reality, the sooner we can adapt to it and find peace.

Equally crucial in Naval’s framework is what happiness is not: success, envy and anxiety.

  1. Happiness is not success. We all encounter hedonic adaptation: we quickly get used to anything.  Happiness is separate from your external situation.”The idea that you will change the outside world to bring you peace, everlasting joy, and happiness is a delusion.”
  2. Envy is the destroyer of happiness. It is a poison that can eat you alive if you let it follow you around. “If you’re not willing to do a wholesale, 24/7, 100 per cent swap with who that person is, then there is no point in being jealous.”
  3. Happiness is less anxiety. Anxiety is a series of running thoughts, the constant chattering of the mind. How Naval combats anxiety: “Would I rather have this thought right now, or would I rather have my peace?”


“At a party given by a billionaire on Shelter Island, Kurt Vonnegut informs his pal, Joseph Heller, that their host, a hedge fund manager, had made more money in a single day than Heller had earned from his wildly popular novel Catch-22 over its whole history. Heller responds, “Yes, but I have something he will never have … enough.”  From the Psychology of Money by Morgan Housel

If we just leave our instincts unexamined, we’ll never feel like we have enough. Why? Years and years of evolutionary wiring. For most of human history, we didn’t have enough, which means we’re neurologically primed to always look for more, with the goalposts of “enoughness” always moving.

A miscalibrated gauge of “enoughness” directly impacts our happiness every day. If the comparison to others is the thief of joy, the socially and evolutionarily induced quest for more distracts us from the beauty of enough in the now.

A further problem is needing to know where enough is and pulling back. The larger the surface area of what we require to be happy, the more energy and attention we must expend maintaining it. Going from one set of things to more sets of things doesn’t expand the attention expenditure linearly but exponentially.

Being thoughtful about scaling our attention footprint is a superpower that few harness well. Most of the happy people I know, especially wealthy ones, are very protective of their footprint and try to be very thoughtful about how they scale and optimise it so that the things they own don’t end up owning them. There is a lesson for all of us—maximising enjoyment and satisfaction in life requires a small surface area—but not too small, as the opposite of happiness is not unhappiness—it is emptiness.

No hoarding, little squirrel

If “enoughness” involves thinking about where and how to expand our footprint, Oliver Burkeman has a mental model for making the most of the footprint we’ve already built.

We have already discussed the benefits of fully immersing ourselves in the beauty and uniqueness of each moment, which rings true but is very hard. Managing the urgency to catch, extend, or prolong experience is to accept the transience of life, which is complicated for mortals.

A mental model that makes it a little bit easier for our brains to process the acceptance of our finitude is the “no hoarding” cognitive model of happiness. Practising releasing the mental and emotional grip on experiences, whether good or bad, helps us eliminate the “clenching” or “grasping” that prevents us from fully experiencing life. Meditation can be a tool to help reduce this tendency, but you already know that.

This builds on the insight of being present, which is a common thread in pretty much any form of life advice, but with a specific twist: Recognize and embrace the fleeting nature of experiences. Life’s moments are for living, not for hoarding or turning into a collection of achievements or a larger plan of how life should be.

Finally, we need to understand that the sadness associated with the end of a beautiful moment adds depth to the experience rather than detracting from it. This poignancy can enhance our appreciation of life’s fleeting beauty. We can’t get anything out of life, and there is no little pocket that we can tuck this in outside of life. Let’s stop trying to be squirrels. A squirrel spends so much of its life amassing the acorns that it may forget to enjoy them. 

Don’t keep your cheeks dry.

Our biggest problem is we think we’re not supposed to have any. Tony Robbins

This framework builds on the concept that we need depth and variety of experiences to recognise life’s beautiful moments rather than a bias for unending positivity.

Yale professor Laure Santos highlights how societal norms of happiness have become synonymous with only positive emotions, all the time, which she calls “the toxic positivity spectrum.” This shifting of our natural emotional centre makes us think that feeling sad, angry, or scared means that something’s gone wrong and we haven’t made the happiness Instagrammable journey right. 

We need to step back from this. Sometimes, feeling sad, frustrated, or scared is normal and valuable. This can help us learn to appreciate the happy moments, as it balances our hedonic adjustment and normalises the scales of our emotional palette.

I am not suggesting that we need to seek pain or surround ourselves with unhappy people proactively. Instead, I am suggesting that the downs of life make the ups unique, and there’s no “right” path to happiness that avoids the valleys just to scale peaks. Training our emotional muscles to have a wider operating range will teach us to be more resilient to brutal moments, which builds character. It is a necessary ingredient for a fulfilling life. I believe that this is what “the salt of life” really means – the ability to know sweetness by knowing its antecedent, saltiness. The insight here is to realise that instead of always trying to be happy. We need to effortlessly interpret events in a way that doesn’t make us lose our inner peace.

The happiness of pursuit

Becoming feels better than being. The trajectory is more important than position. Chris Williamson

The happiness of pursuit model ties together happiness, success, and meaning in a way that rings true to those who understand that the real price of something is how much of life, i.e., time, you dedicate to it.

I feel that this model resonates with me as a life strategy. Our hormones are wired for short-term pleasure, joy, or elation over long-term feelings of contentment, satisfaction, and happiness. We have over-indexed on short-term rewards, which is how we seek the variable reward highs of screens, sugary drinks, and social recognition in the form of thumbs up. The resulting monomaniacal focus on pleasure can lead to addiction-like unhappiness as we seek more and more of it.

Daniel Kahneman contends that pleasure and satisfaction are distinct. Pleasure, often confused with happiness,  is a momentary experience that arises spontaneously and is fleeting. Meanwhile, satisfaction is a long-term feeling, accumulating over time and based on building the kind of life you admire.

Lest you think I’ve gone off the deep end of the woo-woo scale, let’s bring it back to chemistry and physics. If dopamine is about the pursuit of short-term reward, serotonin can be thought of as the happiness of pursuit. There is no destination, just the beginning of the next journey. Human happiness comes from progress, not achieving. Yet, our minds often tell us to believe the exact opposite – we want to have run a marathon, not actually run a marathon.

The practical route to the happiness of pursuit is to reframe “I have to” to “I get to”, be it for driving kids to school, being of service to someone or, as I once read, trying to get Sisyphus to enjoy pushing the rock up the mountain. That’s a bit of a stretch, but the point stands – he had no choice, but he might as well enjoy it.

The tweetable truth here is that life is about experiencing things for which we will later experience nostalgia. In the heat of the moment, it’s hard to tell which experience is worthy of nostalgia. We can only connect those dots backwards.

You cannot have something valuable and essential in your life without some sense of sacrifice for it. It’s just human nature. When we experience pleasure without sacrifice, it is meaningless and, therefore, valueless. 

Finding Meaning: a motto

“The meaning of life is to find your gift. The purpose of life is to give it away.” –Pablo Picasso

 The fundamental tragedy of intelligent humans is that we are meaning-making machines. We try to find meaning in all we do, therefore assuming that life has meaning. It does not.

This is not a flippant assertion; it’s just math. The absurdity of the idea that 100 years or so in the context of 13.8 billion years worth of unguided events puts it into perspective. This is why cosmic insignificance therapy is so relieving –  it disabuses us of the notion that the universe has a purpose for us. It does not.

But that’s not a cynical or nihilistic proposition; it’s romantic. The sensible thing to do with our existence is to fill it with uniquely human experiences and learn about as much as we can about as much as we can. This makes it very exciting as we chart a path that’s uniquely ours, free of the burden of having to make it meaningful before we are dead.

Moreover, “purpose” cannot be a universal value; if it is the same for all of us, it will turn into a competition for one goal, as money has repeatedly indicated.

However, there is a time-tested formula for finding meaning and purpose that is uniquely ours. It maps to the three stages of life: Discover, Develop, and Gift. 


 The world will ask you who you are, and if you don’t know, the world will tell you.”  Carl Jung

 In the discovery phase, the objective is to experience everything we possibly can, to understand as much of the human condition as we can squeeze into one lifetime and feel the complex range of emotions that come with being human. The resulting evolution of the soul means we understand more about what it means to be human.


True hell is when the person you are meets the person you could have been. Douglas Murray

 The second phase of life is when we temporarily forget that happiness and achievement are independent variables. We hone the skills and knowledge to be helpful to ourselves and others, mixing all the life Pokemon we have collected into a recipe that makes us truly unique. This is the phase of life where we learn that our most significant liability is to impress people who couldn’t care less about us and relentlessly pursue personal improvement. We know how to love, be worthy of love, and be loved.


“Treasure is measured in units of love.” Above & Beyond

In the giving phase of our lives, fulfillment is found through connection to something more significant than the self. Love has taught us how to mirror and magnify each other’s light, and we find joy in serving others or being useful, as Arnold put it. This strengthens the only thing that really matters: our connection with others. It ensures that we maintain a social fabric around us that helps us feel relevant, needed, and of service to others.

Leo Tolstoy said, “Joy can only be real if people look upon their life as a service and have a definite object in life outside themselves and their happiness.” True contentment arises from self-transcendence, service, and deep relationships, rather than chasing personal achievements alone”. This is what Maslow discovered in the final stages of his work on happiness – that one day when there are no more laters as all the nows have passed, the only footprints that matter are the ones we left in the gardens of our loved ones.

 “And when nobody wakes you up in the mornings, and when nobody waits for you at night, and when you can do whatever you want. What do you call it, freedom or loneliness?”  Charles Bukowski

Reading list

Epilogue: We never keep to the present.

We anticipate the future as if we find it too slow in coming and are trying to hurry it up, or we recall the past as if to stay in its too rapid flight.

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