February 8

10 books about finding yourself in your 20s


I remember the time I went through my first quarter life crisis. It was the time when I was supposed to decide what I was going to study.

My dreams of becoming a doctor or a lawyer were dashed by my poor results.

I didn’t know what to choose, with the array of choices in front of me. I spent days trying to figure out my ‘strengths’ and my ‘passion’, drawing pros and cons charts of different degrees, and seeing which I liked best.

It became such an anxiety provoking time that I ended up stuffing myself with food to fill the anxiety within me.

Within a month, I grew by 8kg.

I hope that’s not happening to you today. What does a quarter life crisis look like?

The symptoms vary. But often, it looks like being at a fork in the road, and needing to decide how best to move forward. You are running out of time to decide. You feel confused and lost. You want a straightforward answer, but none is ready.

More importantly, you feel that you don’t have the capability to handle what’s in front of you. That’s when you feel inadequate to the task of solving the problem in front of you.

That’s the quarter life crisis.

When what you have learnt so far in life is unable to meet the challenges of what’s ahead of you.

What can help?

Naturally, you want a book. after all, that’s what school teaches, isn’t it? That you’ll find answers in another book, another exercise, another article. If you studied harder, then you would get the answer.

Don’t get me wrong. I’m not saying that books aren’t helpful. I know that during this difficult time of my life, books were particularly helpful in giving me practical handles on overcoming these issues.

A caveat about books

But the problem with books is that as much as you can read, you need to act.

You need to act. There’s no way around it.

You will learn best by doing. Books can give you great ideas, but unless you act on the ideas you’re given, you’re not going to find any breakthrough in life.

I’m a self-help junkie. Before you laugh, I spend most weekends reading books. I read to sleep and read to wake up.

I love reading books about self development. Whilst they have contributed greatly to my own development as an individual, I’ve come to see the limitations of books, especially during that phase of my life.

I remember browsing on Google about what the best books on finding one’s life purpose was. After seeing the list, I promptly went out to buy those books. But those books did little to assuage the anxiety within me. Why? Why didn’t they work?

It’s often the author’s personal, unique journey

You are not the author. The problem with self-help books, is that they are often opinions of the author about what has worked in their lives. Their lives have a unique context and position that isn’t the same as yours. That’s why even if you follow the exact instructions laid out, you still wouldn’t see the exact same results.

It’s the ‘robot’ fallacy, described by Shane Melaugh. We aren’t all robots. We can’t always be perfect. You can’t always take the advice perfectly too. That’s why you need to know how to approach your development so that you ask yourself how it applies to you.

What is helpful for me is to write notes in the columns about specific situations where I’ve encountered something where I can apply the idea. That way, it makes the books more personal, rather than another mass paperback.

It’s about acting consistently

Because I realised in hindsight that it wasn’t only about action. It wasn’t even about reflecting through the exercises in the book. It was about acting on the advice of the book, day after day, for at least a month, that I began to see the book’s effect take shape.

It’s like doing a workout. You can’t expect one single workout to change your body significantly. But if you do it day in day out, it will change you.

It’s not one book

If I look at the past 2 quarter life crises I’ve had, it hasn’t been a single book that has transformed my life. Rather it’s a series of books. More often than not, it’s a series of books, read again and again, that has prompted the most change for me.


Knowing this, do you still want books?

Here are the books that helped me.

How to stop worrying and start living (Dale Carnegie)

quarter life crisis books
Stop worrying, start living!

The biggest difficulty in overcoming the quarter life crisis is the worry that exists within you. I once heard a quote from a pastor who said,

Worry is like stepping on the accelerator with the gear in neutral. You get nowhere.

You’re worried about the future that lies ahead of you. You’re not sure what to do. You’re not sure where you will land up. That’s when worry starts popping up. You worry if you will ever make it as a person. You worry about what you will look like in front of your friends.

Dale Carnegie gives practical tips that help you worry less. One of the most useful exercises was listing out your worries and then the worst thing that could happen if it came to pass. Then, you asked yourself,

Can I deal with that?

If your answer is yes, then you would realise that you have what it takes to overcome the challenges in front of you.

The quarter life breakthrough (Smiley Powolsky)

quarter life crisis books
Smiley’s book offers practical exercises and more importantly, empathy that he understands where you’re coming from.

The quarter life breakthrough is a book that focuses a lot on the community aspect of overcoming your quarter life crisis. More importantly, you immediately feel a sense of empathy with the author, Smiley, as he describes his own quarter life crisis. You feel that you’re not alone on your journey.

If you want this book to be most effective though, you have to do the exercises and find someone you’re accountable to.

I didn’t. I flipped through the pages, thought I knew the book, and moved on. It didn’t work as well for me.

A Promised Land (Obama)

quarter life crisis books
Obama’s book offers a unique take on his thinking through the presidency, but also about how he persevered despite the long odds that were against him, something you may relate to as a young adult.

In your quarter life crisis, the most important thing you want to hold onto is hope. It is hope that will keep you going in the darkest times. Obama’s book offers that in large doses. You will read about the darkest days in his presidency, when he faced difficult opposition and didn’t know how to continue. You will see how he rallied the nation.

You will be inspired by how he persisted in the hope that no matter what happened, he held onto the belief of ‘yes we still can’.

Yes, you still can. If you still hope.

Becoming (Michelle Obama)

quarter life crisis books
This offers a reflective account of how Michelle Obama came to be THE Michelle Obama.

Becoming is a story of how Michelle Obama, came to age whilst growing into the stature of being the Presidential First Lady.

In your quarter life crisis, it’s also a stirring reminder that even (and especially) for those who seem like they have it all, they still faced a period where they were lost and unclear of where they were necessarily going.

It is a reminder that we don’t all have the answers.

So Good They Can’t Ignore You (Cal Newport)

This book was so good that I read it twice. It turned everything I knew about passion on its head. As Newport argues, today, we live under a passion hypothesis. That if we chased our passion, everything would be perfect. That may not always be the case.

Instead, what may be more important is chasing our strengths, or what you’re already good at.

Doing this will ensure that you’re in a better place to thrive, because whilst the process of improving your skills may be effortful, it does ensure that you’re constantly seeing progress.

As Haidt shows in his equation for happiness, the fit between yourself and your work allows you to feel the state of flow, daily.

Haidt's equation for happiness shows us that happiness can be found when we find flow in our work.
Haidt’s equation for happiness shows us that happiness can be found when we find flow in our work.

Passion is a process of working on your progress in your skill.

Harry Potter

Some days, you want a book that you can curl up with. You don’t want to think too much about the problem you have. That’s what fiction books like Harry Potter can teach you. And if Harry Potter teaches you anything, it’s that magic is possible. That miracles are possible, if you’re willing to believe.

Please don’t throw your mouse at me. I’m not saying you should run away from your problems. But I’m saying that often, it’s when you’re not thinking about it that you will get a breakthrough.

The Art of Execution

This is an investing book, but it was very important for me as a human being because it taught me how to quit. In your own quarter life crisis, as much as there are aspects you need to change in your life, there are also aspects that you need to close.

You may have a broken relationship you’ve yet to fix. Or you may be staying on in a job that you hate, because you’re scared. Learning to quit, is something that this book teaches you.

It tells you how to overcome the psychological biases, and how to move on with them.

What Color Is Your Parachute? (Richard Bolles)

quarter life crisis books
This offers a series of practical exercises that help you understand about your passions.

This is one of the most popular career advice books in the world. With Bolles’ trademarked Flower Diagram, and a systematic way to work through your interests, you get to find out what it is you’ve enjoyed doing.

If you don’t like using instinct to determine what it is you like, Bolles has an exercise where you write down 7 stories of accomplishments you’ve had and then asks you to tick a sheet of the skills you’ve demonstrated.

You would love this book if you love systematic principles.

One note about this book though. It focused a lot on the skills you enjoy using, and not necessarily those you’re excellent at.

They are not the same. One thing you realise about skills is that what you love doing may not be the same as what you’re great at. That’s why figuring out what those are, and finding the fit would be a much better option in the long run.

The Pathfinder

The Pathfinder is another hands-on book, filled with practical exercises. It helps you figure out where your strengths lie, and how you can use them to create a path for yourself. If you enjoy many (and I mean many) exercises, this is the one for you.

Strengthsfinder 2.0 (Gallup)

quarter life crisis books
Strengthsfinder is a great way to find your strengths in a methodical way.

The Strengthsfinder is a great way to find out what your strengths are. This is backed by rigorous scientific evidence, and the survey offers you a unique chance of confirming what you may already have suspected about yourself. The book offers you a way to look at how you can better use the skills that you have.

The Happy Student (Daniel Wong)

quarter life crisis books
Daniel Wong’s book is hands down the book that has transformed my life.

Hands down, this was the best book I ever got. It was given to me when I sought Daniel for advice about how to move forward with my life.

Why? Because there is a clear framework for finding your purpose in life.

It’s based on his four step model:

  1. What is your definition of success?
  2. What do you want to be remembered for when you die?
  3. What are your values?
  4. What is your purpose?

It works because the definition of success starts you thinking about what success means for you, rather than you compared to someone else. This is vital for you to achieving an inner scorecard, rather than an outer scorecard.

The legacy you want to live helps you to live with the end in mind.

I followed the framework month after month, reflecting on how these changed over critical incidents in my life.

This four step framework can help you to form a clearer frame to approach your problem with greater clarity of your ‘why’.


Are you facing a quarter life crisis today? It can look very scary. As much as books can help, you also need action, and someone to keep you accountable.

You’re not alone on this journey. You simply need to seek help, reach out, and be open.

Adulting is never easy, but it’s easier when you’ve people around you.


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