August 31

An author recommends the 7 books on how to choose a career


You’re stuck. You’ve spoken to countless people like your career counsellor, your friends, and yet you still aren’t sure about what career to choose.

People mention in passing the books they have read. And you, being that hardworking student, decide to research into the best books that will help.

You’re at the right place.

More than anything else, books saved me.

Not once, but twice.

Books on how to choose a career
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My story

In December 2015, I was depressed. I had just gotten the news that despite working so hard to craft a great portfolio for medical school in Singapore, they still needed the basic grades for me to get in.

My grades didn’t make the cut.

My world crashed around me.

I didn’t know what to do with my life. I had invested hundreds of dollars into books about medicine, only to find that now, it didn’t matter. I had even taken the BMAT, in preparation for entry.

Not knowing what else to do, I started asking seniors, and people around me about how to find a career they loved.

But all the advice didn’t seem to enter my head. I ended up depressed, and suicidal. In my mind, I thought,

What’s the point of living if you can’t get to your dreams?

It sounds foolish. But I acted on those instincts, taking a chair up to the highest floor of the apartment building every morning, in the leadup to Christmas.

Books on how to choose a career
You might feel like a limp vegetable, running out of passion.

I would stand on the parapet, and wonder if I should flip myself over. Fortunately I didn’t.

Else I would be ketchup, rather than here talking to you.

Yet that journey wasn’t the end.

3 years later, after graduating, I fell back into depression again. This time, I wondered if social work was the degree for me.

Isn’t it just a book?

Books played an important role in both journeys, helping me to elucidate what I wanted.

You might think,

Come on, it’s just a book. What can that really do?

But books help because of two reasons.

They offer a perspective of others who have struggled

Having read thousands of books about personal development, I’ve come to see that directly applying what the author tells you to do might not always work.

What works better is to learn perspectives of thinking from the author, that might instruct your own journey.

There are two types of books. Those that give ideas for thinking through, whilst others focus on implementation.

Finding what works better for you might bring you further along your journey.

They give clear exercises

When I was depressed and suicidal, I wondered why no one seemed to offer me the parachute book. As one of the most respected career books, it offered exercises that helped you to look back at your career history, so that you could actually understand where you had done well in the past.

The idea of finding a job to love is not a new struggle. Billions of people have faced the same struggle.

But we somehow find it difficult to use the advice others have thought long and hard about.

Here are some of the best books, split according to ideas, and implementation.

Vault! by John Lim

Having read through dozens of books, and interviewed 21 different individuals, I thought I would have a stab at writing a book that could help people make better career choices.

For those who did read it, they found it instructive at recognising just how work, wasn’t about the work, but also about the people.

They found it instrumental in understanding how people could destroy one’s hope in a job.

And my hope is that you will perhaps start to see that it’s not the career you hate, but the people.

Here’s why you should nurture your skills in your job
Here’s why you should nurture your skills in your job

Secondly, it also espouses the idea of nurturing one’s strengths, rather than switching constantly.

For example you might be at a point where you’re considering many different careers, and trying to chase your passion.

But you might not realise that passion is a fallacy. It will keep you feeling more and more unsatisfied because passion is an emotion.

It will fade. And eventually you would find yourself running out of passion. What do you do then? Find another career?


A better solution is to figure out your strength, and build a career on the back of it.

You can also get it here.

The Happy Student, by Daniel Wong

As a depressed 21-year-old, Daniel Wong quickly helped me by giving me his book. This was in March 2016, when I was lost, and didn’t know what to do.

I still had to pay $700 for one session too.

But reading his book brought me furthest along my journey than anyone else, because of how much I related to his story of being a high-achieving student, who still became unfulfilled.

Daniel’s framework is

  1. Define your own success
  2. Understand your own values
  3. Know what you want to be remembered for
  4. Craft your own purpose statement

This can help you in terms of thinking more broadly about your broader career, rather than just trying to focus on which university course to study.

Strengthsfinder, by Gallup

Reading this as a 23 year old in my second year of university, whilst on placement (yes, I was bored) excited me. For the first time, I could understand what my strengths were.

When you grow up, you always end up hearing that you have to focus on your weaknesses. But Gallup argues otherwise.

Stop looking at your weaknesses, and actually focus on the inherent strengths that are within you.

But you might ask,

What are my strengths?

They have a 45 minute survey that they put you through, where the themes are later clustered for you to make sense of.

Whilst it is true that strengths such as ‘strategic’ may seem less tied to a direct job, it helps you figure out just where to start looking.

What Color is Your Parachute, by Richard Bolles

If you still struggle, look no further than Richard Bolles. He created the ultimate guide for figuring out just how to find one’s strengths.

Credit to Richard Bolles for having tried so hard to categorise skills
Credit to Richard Bolles for having tried so hard to categorise skills

Range, by David Epstein

School corrals us into a steady, set path. It tells you that if you’re not focused and specialised, you will fail.

And you might feel lost today because you’ve many skills that don’t seem to be best suited for a specific career path.

But you won’t.

And Epstein proves that with numerous studies across sport, science and academics, to show that a range of skills can actually help, instead of hinder a person.

So Good They Can’t Ignore You, by Cal Newport

Cal Newport breaks open this book with the story of a monk. The monk had given up his career and studies, looking for his passion.

He (thought) he found it in eventually being a monk.

But even this did not bring lasting happiness.

Eventually he went back into computer programming, which brought him greater fulfilment, as he could see himself steadily growing in terms of his skill.

This book fundamentally shifts your thinking away from ‘what should I do’, to ‘what am I good at?’

It forces you to ask the question,

Why am I so enamoured with the idea of passion?

What if that wasn’t the most important thing?

The Almanack of Naval Ravikant, by Eric Jorgensen

Possibly the best all rounded book every person 27 and below should read.
Possibly the best all rounded book every person 27 and below should read.

This is by far, the best book I’ve read. And it is the one book I recommend to every young person.

Naval talks about high level concepts in money, fulfilment and happiness.

But one of the most important concepts is the idea of leverage in work.

He argues that in the past, financial capital was the leverage that got people wealthy.

The tweet storm by Naval
The tweet storm by Naval

But today, those with code and content capital rule the world. He encourages those who can to focus on these skills of creating and coding.

For those that are older though, he recommends that rather than chasing the hottest industry (like AI), you might want to ask yourself what you’re best at, and find some way to pull away from the pack.

Books work, if you work them

If you want books to work, you need to be willing to work them.

They don’t work if you just sit there and expect diffusion. If they ask you to do an exercise, do it.

And you may just find a career you’re great at, at the end of those books.



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