Mortgaging Happiness to Dreams

How I learned to stop aspiring to be happy and be happy now.

Badge of Honour

I’ve always been a dreamer. I don’t remember a time when I didn’t have the ambition to emigrate — I wanted to escape the confines of my hometown and home country and forge a new life in the bright, optimistic, and adventure-filled American west. And from the first moments that I can recall considering what I wanted to do with my life, beyond the few days or weeks ahead, I knew that I wanted to sidestep the world of corporate nine-to-fives. I set my sights on forging a career that I enjoyed, where every day was different and no one could tell me what to do, or what not to do.

I held those ambitions high as a teenager, I wasn’t content to accept anything less for my future. Whenever the question of happiness was raised, my answer was simple — Of course, I wasn’t happy, I wouldn’t be happy until I realised my ambitions. I was convinced that I couldn’t be happy until I got out of that town and country.

I pitied those around me following a paint-by-numbers path to corporate mediocrity and the adults in my life who settled into boring office jobs. That was a capitulation to ‘the machine’ that I knew would doom each and every one of them to a sub-par existence of stress and misery. Anyone who claimed to be happy with such an existence was a victim of the system designed to chew them up — the battery people of The Matrix. Ambition was everything to me then, the most valuable asset any person could have. I held my dissatisfaction as a badge of honour, proof of my dedication to something higher.

Photo by Arūnas Naujokas on Unsplash

Cosmic cruelty

As I grew older and my pre-frontal cortex starting to get its shit together, my outlook began to shift. The ambitions stayed firmly stuck but the reality of realising them came up against the challenges of adult life. I was forced to make compromises.

I found myself not pitying the person who settled for mediocrity but envying them. They were the ones fortunate to be happy with what they could easily reach, whilst I couldn’t dream of such contentment. Suddenly my big dreams felt like a curse, I would have to fight through all kinds of challenges to shape a life that could deliver lasting happiness, whilst others could reach out and grab it without an ounce of struggle. I’d correct my similarly ambitious friends when they disparaged others for ‘selling themselves short’ — I’d argue that if those people were content with the life they were building, they were better off than the rest of us. I began to realise that the most fortunate person in the world might just be the one who needs the least to be happy. But I wasn’t that person.

I battled with the thought that billions of people around the world were in worse circumstances than me. Why couldn’t I be content when I lived in relative luxury? I looked to the wealthy and famous for an answer. If happiness were tied to what we do and don’t have, our status, wealth, and freedom to go where we want and do what we want, how could anyone with great wealth and freedom be unhappy? How could a high-achieving musician or actor be miserable? How could a person born into great wealth ever come close to discontent?

I figured that happiness could not be absolute, it must be relative to one’s starting point. It couldn’t be about ticking a set of universal boxes but about rising beyond your circumstances. A person born into wealth couldn’t be expected to discover happiness in the same way that a person born into poverty would. Each would find their version of happiness in rising beyond their starting point. What one needs to be happy is dictated by cosmic circumstance, and ambition is the tool for realising it.

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Mortgaging Happiness to dreams

“Nothing is enough for the man to whom enough is too little”


I hadn’t ever questioned my understanding of how ambition and happiness connect. There was a faulty assumption beneath it all that doomed every mental model I had. That faulty assumption is the end to every fairytale we grow up with in western culture: Happily Ever After.

What does it mean, Happily ever after? It means after this event, this achievement or acquisition, happiness endures into eternity. It paints a picture of happiness as a videogame, with levels and completion percentages — once you dispatch the big boss or hit the top score, you’re all set.

It’s so ingrained in our culture that we shape our lives around it. We imagine that once we’re married, we’ll discover enduring happiness. Once we have children or get that promotion, once we reach world number one, win the Superbowl, or get tenure. Your list of achievements is the yardstick of meaning and contentment. The resumé is king. We spend our lives satisfying wanting in the understanding that eventually, those checkboxes will deliver us to the promised land.

But we don’t have to look far into our own experiences to see the flaws in that worldview. We’ve all achieved things that we set out to do or acquired material possessions we desperately wanted, yet we don’t get progressively happier. We don’t level up each time, we reset and discover new things that we want. It’s called hedonic adaptation and it goes both ways. We have an overwhelming tendency to return to a stable level of happiness after major positive or negative events or acquisitions. Lottery winners don’t tend to be significantly happier once their new reality sets in. Victims of catastrophic accidents can be similarly happy after their accidents as they were before. Olympic gold medallists suffer from depression and aimlessness after conquering the competition and world-famous artists battle depression.

Happiness is not relative to ones starting point as I believed as a young man. Realised ambitions won’t rescue anyone from the threat of dissatisfaction. And in attaching our happiness to future goals, we condemn ourselves to a kind of purgatory where the quality of our lived experience is defined by the gap between where we are and where we want to be. Many will never get there and so never discover what it is to be truly contented. And for those that do make their dreams come true, they quickly discover a new normal that fails to live up to expectations.

We need not mortgage our happiness to future goals. I had held on to the idea that the ingredients of my own happiness cocktail were determined by my circumstances and I had a choice to either satisfy my niche goals or make my peace with discontent. As it turns out, there are absolutes when it comes to happiness and wellbeing and they aren’t attached to the intricacies of modern life or our skewed cultural priorities. Philosophers throughout recorded history have told us that we can overcome the relentless pull of desire and discover happiness in the here and now. And science is beginning to verify those ideas.

Our ancestors had far less than we have today. A middle-class home in Europe or the USA today has luxury and material wealth a Roman emperor could hardly fathom. Yet our ancestors were likely no less happy than we are. That’s because happiness isn’t tethered to the complexities of modern life but the simplest, most ancient, and constant aspects of being human. Our evolved mechanisms for wellbeing don’t recognise designer brands or sports cars, they don’t see the difference between this or that job title. Our innate machinery thrives on meaningful, loving relationships, flow states, mindfulness and good health. A regular reflection on everything you’re grateful for has a bigger impact on happiness than a shopping spree.

The ancient Stoics encouraged us to learn to want what we already have. They saw that eudaemonia (human flourishing) isn’t found by changing our circumstances but by changing how we respond to them, in cultivating character and living in harmony with our highest values.

“Very little is needed to make a happy life; it is all within yourself in your way of thinking.” Marcus Aurelius

There is no ‘Happily ever after’. Happiness and wellbeing demand constant work, just like health and fitness or any skill we can develop. But that work is quite simple and for many of us, it’s constantly available. Happiness need not be defined by the gap between where we are today and where we want to be. No goal, however grand, can deliver the kind of happiness we expect if we never learn how to appreciate what we have. If we forever chase the end of the rainbow, we’ll never appreciate its beauty from where we stand.

“I undertook to conquer myself rather than fortune, and to alter my desires rather than change the order of the world, and accustom myself to believe that nothing is entirely in our own power except our own thoughts… Here, I think, is the secret of those ancient philosophers who were able to free themselves from the tyranny of fortune, or, despite suffering and poverty, to rival the gods in Happiness”

Rene Descartes

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Rainbow Chasing

Were my instincts about ambition wrong all along, should we abandon it altogether? No. Ambition does have an important place in the landscape of happiness. When we have something to strive towards, we open the door to challenge and in turn, progress. And progress, however minor, plays a big part in wellbeing. The small victories along the way are exactly what make a journey worthwhile, regardless of the final outcome.

Mountaineers don’t climb because they are certain they’ll reach the summit, if they were, it probably wouldn’t appeal at all. They climb for the challenge and flow states that come with it. They climb for the awe and beauty of the experience and the rewards of each move upwards. If they reach the summit, they look to the horizon for a new challenge. And if they don’t, the climb doesn’t disappear from memory as if it never happened, it becomes a formative, meaningful experience to reflect on. The point of the task isn’t the summit, it’s the potential for progress.

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Where ambition runs off the rails is when it leads us to neglect and abandon happiness in the here and now. When we pin our happiness to the end goal and pursue it with blind abandon, never stopping to take a look around and enjoy the journey, we undermine the mission altogether. Neglected health, ruined relationships, and compromised values are a perfect recipe for the unhappy hero — the depressed superstar, the drug-addicted millionaire. And ultimately, no superficial reward will remedy the misery of those experiences.

I was drawn down this path by a career that promised to grant me that escape in the American West that I’d always wanted. It was the closest I’d ever come to a tangible opportunity at grabbing that dream. But the job itself, the culture of the industry, and the way it distorted my lifestyle were all heavy compromises. Regardless, I kept pushing on blindly until my opportunities were suddenly derailed by circumstance. Only then did I stop to take it all in and notice all the ways I was undermining my wellbeing and compromising my values. I was throwing away today’s happiness in pursuit of a ‘happily ever after’. I’d been on a moving train to nowhere and now I had the choice to get off and choose my own direction. I did.

That’s not to say I don’t still dream of the American west, I do. But suddenly I appreciate the beauty of the world outside my window. And if I find a new path to that ultimate goal, it’ll be lined with meaningful experiences, loving relationships, and deep gratitude for it all. If the summit never comes, the climb will have been worth it regardless.

We should see the gold at the end of the rainbow as a reason for a meaningful journey. By all means, chase it, but keep your eyes up the whole time, revel in its beauty and everything you can be grateful for along the way. In the end, you might find yourself so distracted by the joy of the experience itself that the gold need never be more than just an idea.