Chasing Dreams \\ on self-sabotage, nearly quitting Housemanship and seeking my ‘Personal Legend’

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Chasing Dreams is a multi-part series chronicling my thoughts, dreams & changing ideals over the years (since 2018), including burnout, quitting the rat race, migration and trying to find my path in life

I know I’m very late to the party, do forgive me. But I recently read The Alchemist, and I can safely say that no other book has filled me with so many emotions nor resonated as deeply with me (especially in my current season of life) as this.

I was wandering around Kinokuniya during my recent Annual Leave, and walked past a book with a gilded and rather charming dust-cover. Being the visual creature that I am, I picked it up, read the blurb and began reading. After finishing a quarter of the book, I walked away and convinced myself I’d just get the e-book; after all, my bookshelf was already overflowing with books that I’ve only ever read once. I absolutely did not need to collect another book (famous last words).

But alas, the flesh is weak and I couldn’t stop thinking about the book, so I returned two days later to buy it. I spent an afternoon reading the book, annotating post-its with a near-religious fervour, and it spawned this behemoth (nearly a whole thesis) of a blogpost as well.

101 post-its because I refused to make any markings in the book itself

This is going to be a long but hopefully-not-too-rambling post about how The Alchemist resonated with my pursuit of my ‘Personal Legend’ (a recurring phrase in the book used to describe a person’s life purpose/goal), and the lessons that I’ve learnt along the way.

a tl;dr/summary of The Alchemist

This renowned novel hardly needs to be reviewed by yet another aspiring blogger, but I’ll give my two cents worth anyway. Btw, the last time I took a Literature class was when I was 14, so pardon my crude analysis.

The Alchemist is less a novel and more a self-help book, with the essence of a crossover between Aladdin and any John Green coming-of-age story. The themes I related to the most were self-sabotage, perseverance, self-discovery and sacrifice.

  1. Self-sabotage & the power of choice — Along the way, he meets various older individuals who could have achieved more in life but chose not to. Some feared change, some enjoyed the simplicity of their current lives, some were tied down by existing responsibilities, and some self-sabotaged (despite knowing they were well capable of more). Through those characters, I foresaw how the decisions I make in my current phase of life could affect and create regrets in future, but more on that later.
  2. Adaptability & perseverance — Santiago initially planned for a straightforward journey to the pyramids, but shit happened unexpected setbacks delayed his journey, forcing him to alter his course and delay the pursuit of his singular dream/’quest’. In the process, he found other sources of fulfilment and learnt life lessons along the way that helped him progress towards his goal. He was adaptable, tenacious and able to view his setbacks in an optimistic way.
  3. Self-discovery — The entire book chronicles Santiago’s (the protagonist) journey from his homeland in Spain, to Morocco, through the desert and its oasis, to the pyramids, and then back to his hometown in a beautiful full circle that spanned over 2 years. He lived through various hardships, exchanged ideas with people, broadened his horizons, and learned to be in tune with his heart/instincts.
  4. Sacrifice & love — Santiago’s father made a brief appearance in the beginning of the story, and it was mentioned that he was never able to fulfil his own dreams because he had to take on a stable job and provide for his family. Fatima’s sacrifice came in the form of love; she could easily have been selfish and told Santiago to stay in the oasis with her, but instead she encouraged him to chase his dream before returning to her (which he did, yay for love!).

It’s a quick read, and it’s more than worth an hour or two of your time to read from cover to cover. Even if you don’t read it, I’ll be quoting heavily from the book in this post like the basic Tumblr girl that I am, so you might end up reading half the book here anyway.


I googled around to see if anyone else had identified self-sabotage as a theme in The Alchemist, but alas, I seem to be the first. Perhaps I’m strange for interpreting the book this way, but I viewed some actions/decisions by side characters in the story as varying forms of self-sabotage.

I’d define self-sabotage as taking any action or making any choice that directly contradicts your personal goals & values, and it can be conscious (in the case of the Crystal Merchant) or unconscious. It is “insidious, profound, and universal and emanates from negative mindsets” (Berg, 2015). Self-sabotage is all too common, and if left unchecked, can spiral into a vicious cycle of us consistently doing things to harm our future and being filled with self-loathing.

There was the baker, who chose to run a bakery instead of following his dream of becoming a travelling shepherd, only because bakers were perceived by society to be more important. He traded an adventure-filled future for stability and respect.

Then there was the Crystal Merchant, also known as the King of Dumb Decisions & Self-Sabotage. He was well aware of his dream of making a pilgrimage to Mecca, and knew the concrete steps he needed to take to reach that goal. And yet, he spent decades actively doing the opposite, because he was terrified that he would have nothing left to live for once he fulfilled that dream. While I understand his warped logic behind this active self-sabotage, I would be loathe to end up like him.

Some of the more common reasons why we self-sabotage include:

  • Feeling threatened, stressed or scared. Our desire to reduce threats exceeds the drive to reach goals and we subconsciously try to avoid those threats instead of facing them head on.
  • We’ve learnt self-defeating behaviours from our parents/caregivers.
  • Previous trauma/rejection influencing us to push people away and avoid deep relationships.

how I nearly became my own biggest saboteur – the tale of how I nearly quit Housemanship

*This seems like an appropriate place for my usual disclaimer, so here it is: This is a personal blog. Any views or opinions represented in this blog are personal and belong solely to the blog owner and do not represent those of people, institutions or organizations that the owner may or may not be associated with in professional or personal capacity, unless explicitly stated. Any views or opinions are not intended to malign any organization, company, or individual.

Barely 3 months into Housemanship, I came very close to quitting, because I had been put in an environment which made my brain exist in a constant fight or flight mode. I was living counting down from hour to hour, feeling absolutely on edge, awaiting the next critique, and dreading the next day of work even once I left work. I knew that being consistently overworked and mentally burnt-out for the next 5-6 years of my bond would not be healthy or sustainable in the long run.

I had my exit strategy planned out perfectly in my mind, or so I thought. I was going to quit because of the toll that place was having on my wellbeing, then serve out my 5 year bond in the civil service, then…I realised I had too few transferable skills from my medical degree and no long-term career plans that weren’t related to practising as a doctor. Despite the lack of a concrete plan if I were to quit, I still vacillated between quitting and continuing with Housemanship.

I’m usually someone who plans things out in extreme detail, but the version of myself during that time felt that the situation was unbearable and distressing, so much so that I very nearly traded & abandoned my 5 years of medical education for a temporary respite and uncertain future. I nearly self-sabotaged because my mind was trapped in a place of fear, stress and feeling threatened. Somewhat akin to being trapped in a burning building, I was barely able to think clearly and rationally, and wanted to pick the fastest way out of that unpleasant situation.

Looking back, I completely understand and empathise with my past self. I would almost certainly have quit if I had been made to stay on in that situation, but thankfully since Housemanship postings are only 4 months in duration, I was rotated to my next workplace, and I’m so glad I didn’t quit, because the difference this second workplace had on my sanity wellbeing was like night and day.

I was scrolling through Paulo Coelho’s (the author) blog, and these paragraphs really hit home:

Oscar Wilde said: ‘each man kills the thing he loves’. And it’s true. The mere possibility of getting what we want fills the soul of the ordinary person with guilt. We look around at all those who have failed to get what they want and feel that we do not deserve to get what we want either. We forget about all the obstacles we overcame, all the suffering we endured, all the things we had to give up in order to get this far. I have known a lot of people who, when their personal calling was within their grasp, went on to commit a series of stupid mistakes and never reached their goal – when it was only a step away.

The quote reminded me of that dark period, which I find hard to believe was just 3-odd months ago, but it particularly resonated with me because I had come terrifyingly close to becoming that very person who nearly sabotaged her own dream, when she was startlingly close to it.

If I had quit, it would have been irreversible and I would have forever given up the chance to work as a doctor in Singapore, a dream which so many others would give and arm and leg to pursue. In my state of temporary suffering (although the pain was undoubtedly very real), I had nearly ruined the rest of my life, and I’m so thankful that I didn’t make that drastic decision.

And as it turns out, this is a phenomenon in psychology known as the approach-avoidance conflict: “The closer an individual comes to the goal, the greater the anxiety, but withdrawal from the goal then increases the desire.” Simply put, we want what we can’t have. When I was in the throes of dreaming up the 101 ways I would quit, I also imagined a future in which I was bitter about quitting during Housemanship, and would forever envy my friends who became full-fledged doctors and led more fruitful & exciting lives.

on what-ifs, regrets and unfulfilled dreams

All our choices have consequences, but it’s the what-ifs’ that really mess with your head. Imagine lying on your deathbed, regretting that one moment in your life where you made or didn’t make a decision, and you wonder how differently your life could have turned out if you had chosen the other option.

So, we, their hearts, speak more and more softly. We never stop speaking out, but we begin to hope that our words won’t be heard: we don’t want people to suffer because they don’t follow their hearts.

another quote from the book about the dangers of not listening to your heart

These are 3 of the what-ifs I’m most terrified of:

  • What if I had chased my dreams instead of leading a dull cookie cutter life?
  • What if I had told that person I liked them, would we have ended up together?
  • What if I had quit that soul-sucking job instead of staying on for 30 years?

Sometimes it’s absolutely terrifying to take that leap of faith and make a massive change in your life, especially when your current situation may feel pretty comfortable and acceptable.

For some, it may not be possible immediately due to circumstances, finances or responsibilities (or a government bond in my case), but for those who are able and willing to jump, please take that leap sooner rather than later, even if there may be an initial period of pain, discomfort and uncertainty.

Intense, unexpected suffering passes more quickly than suffering that is apparently bearable; the latter goes on for years and, without our noticing, eats away at our souls, until, one day, we are no longer able to free ourselves from the bitterness and it stays with us for the rest of our lives.

The Alchemist

Or if you like someone, yet fear rejection or fear that your confession might affect the friendship, go for it nevertheless; the alternative being you receiving an invitation to their wedding 5 years down the road. Life is too short to have regrets.


Let me preface the quote below with some context from the book. At this point, as the book draws to a close, our protagonist Santiago encounters the final and craziest obstacle standing between him and his dream of going to the Egyptian pyramids – a group of desert bandits demanded that he turn himself into the wind (it’s not as crazy as it sounds, but I won’t spoil the story).

“Before a dream is realized, the Soul of the World tests everything that was learned along the way. It does this not because it is evil, but so that we can, in addition to realizing our dreams, master the lessons we’ve learned as we’ve moved toward that dream. That’s the point at which most people give up. It’s the point at which, as we say in the language of the desert, one ‘dies of thirst just when the palm trees have appeared on the horizon.”

Therein lies the beauty of perseverance. Some days, especially very early on in Housemanship, I couldn’t see an end to the suffering, and it felt like I was always drowning. I forced myself through each hour, each day, each week, barely making it through some days & desperately trying to maintain my mental wellbeing with pathetic countdown apps on my phone, but I knew I would eventually make it as long as I kept showing up – showing up at work and showing up for myself, for the sake of my future. And eventually, because time is mercifully linear and not an endless loop of suffering, I made it past the 7-month mark.

Quoting the book, “The secret of life, though, is to fall seven times and to get up eight times.” It was not particularly enlightening (and I mean duh…if you fall you have to get back up), compared to all the other gems in the book, but you get the gist.

It also feels like I’ve been persevering and working towards some indeterminate goal for my whole life, but the only problem is that whenever I get closer to that goal, it moves out of reach again. First it was getting into the secondary school of my choice, then a university course, then this job, and I guess the next thing in the ‘Singaporean dream’ would be finding someone to BTO with and marry, and then the rat race continues ad infinitum and is repeated with the next generation…oh joy.

I’m still awaiting the day I wake up and figure out what I really want to do in life, versus just going through the motions of showing up to work day in and day out, not hating my job as a doctor, yet not being entirely convinced that it’s what I’m meant to do for the next 40-50 years of my life…


The book’s storyline revolves around self-discovery and finding one’s life purpose or ‘Personal Legend’:

Your Personal Legend is what you have always wanted to accomplish. Everyone when they are young knows what their personal legend is, at that point in their lives everything is clear and everything is possible. They are not afraid to dream and to yearn for everything they would like to see happen to them in their lives.

But as time passes a mysterious force begins to convince them that it will be impossible for them to realize their personal legend. To realize one’s personal legend is one’s only real obligation. When you really want something all the universe conspires in helping you achieve it. 

I’m 24 and a half years old, but I don’t have any clue what I’ll be doing in 10 years time. If I stay the path, I’ll be 34 and a half and still a doctor. If I wander off the path, who knows where life will take me?

I’m not aspiring towards any specific job; all I know is that I love writing, creating art, film (particularly cinematography & scriptwriting) and travelling. How I’ll integrate all these interests into my future or if I’ll be able to achieve any measure of success in any of these remains to be seen, but I’m excited nonetheless!

“Well, then, why should I listen to my heart?”

“Because you will never again be able to keep it quiet. Even if you pretend not to have heard what it tells you, it will always be there inside you, repeating to you what you’re thinking about life and about the world.”

Santiago questioning The Alchemist

There’s a multitude of unopened doors and endless possibilities, and I view them without fear, because I’m honestly more terrified of leading an uninspiring, comfortably complacent and dull life which I’ll regret when I’m old and dying.


Another overarching theme of this story is love. Love can manifest itself in the form of sacrifice; when you wish to unconditionally support someone and cheer them on as they pursue their dreams or thrive in life.

Like how Santiago’s father had given up on his shepherding dreams to provide stability for his family, my own parents have also had to abandon certain aspirations along the way or made decisions that would benefit our family over themselves (the individual), and it fills me with gratitude yet sadness.

And just as he gave Santiago his blessing and 3 precious coins to begin his unconventional journey, my parents are ready to support my dreams, even if the pursuit of those dreams eventually leads me away from doctoring entirely.

“The boy could see in his father’s gaze a desire to be able, himself, to travel the world—a desire that was still alive, despite his father’s having had to bury it, over dozens of years, under the burden of struggling for water to drink, food to eat, and the same place to sleep every night of his life.”

As for romantic love, I haven’t quite found the Fatima to my Santiago, partially because I haven’t met anyone whose long-term goals align sufficiently well with mine – after all, it’s rare to find people in Singapore who don’t subscribe to the BTO dream and seek adventure.

But I’m not in any hurry, because I much rather set out on my own path first, than put myself at risk of being influenced or subconsciously forced to alter my plans to suit another person’s life plans, especially if they just end up as a temporary detour in my life (and not ‘the one’).

“We are travelers on a cosmic journey, stardust, swirling and dancing in the eddies and whirlpools of infinity. Life is eternal. We have stopped for a moment to encounter each other, to meet, to love, to share. This is a precious moment. It is a little parenthesis in eternity.”

Maybe love (or finding love) will become a significant part of my Personal Legend somewhere down the line, but it doesn’t seem to be in the cards for me at this point in time.

final thoughts

I drew so many parallels between my own life and that of the various characters: I saw a bit of myself in Santiago’s initial bright-eyed idealism and single-mindedness in chasing his dreams, as well as the Crystal Merchant’s general jadedness and resignation towards his comfortably average lifestyle, and Fatima’s optimism & faith that her true love Santiago would return to her someday.

I suppose anyone reading this book would also relate to various aspects of each character (and their mistakes/choices), which is what makes this book such a gem. I’d highly recommend reading it; I know I’m going to be re-reading it before 2022, to reflect on how I can get closer to my dreams in the new year (lame, I know :P).

Apologies for an exceedingly long piece, but I reckon this will be my 2nd last post for 2021 (the last being my monthly ‘Life as a House Officer‘ post) so we might as well go out with a bang.

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