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5 brilliant books that are worth re-reading

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Selecting a really great book to read is always a bit of a gamble.

Is it going to be worth your while?

Or is it going to be yet another factory-made book filled with fluff to meet publishing standards of page count, instead of reading which you will have been better off reading a blog post on the subject?

And when it comes to selecting books worth rereading, the stakes get even higher.

At WinnerBrands, we love reading. And we have gone through our fair share of great and not-so-great books. Every once in a while, we come across books that stand the test of time, books that are worth rereading.

Books that tell stories important enough to be savoured over time like a fine vintage wine.

We have chosen these books carefully to represent 5 different but important fields – work culture, personal finance, habit building, entrepreneurship, and personal growth.

These are our collection of books worth reading again and again.

1. Rework- Jason Fried and David Heinemeier Hansson

Written by the co-founders of Basecamp, Rework is a light read, a book designed to be read in any order.

Rework forces you to relook at work and question some assumptions we may have made over the years.

First among these is the takedown of workaholism – which the authors decry, stating that workaholics miss the point entirely. They are trying to paper over intellectual laziness with inelegant solutions.

The book also makes a case for focusing on work that makes a “dent in the Universe,” by choosing to work on stuff that endorses soul over scale. A yardstick to measure this is customers referring to your product/service by saying, “this makes my life better.”

It is full of valuable nuggets of unconventional wisdom on how constraints and frugality can be a boon to businesses. The book celebrates small – the authors say that it is completely fine to be a small but profitable and sustainable business. In this age of blitzkrieg growth and incredible valuations, it is refreshing to see someone rooting for the small guys.

The book also offers some interesting observations on marketing and brand building. The authors state that great brands have a strong point of view in addition to a product/service. They are not afraid to take a stance and let the world know.

Rework also talked about something that we here at WinnerBrands are passionate about – teaching. The authors argued that brands could gain a competitive advantage by out-teaching their competitors – providing so much educational value to customers that they will keep coming back to you.

More than anything else, the book advocates constraints as a way to drive creativity in business, by focusing on only things that matter.

“Cool wears off,” the book says, “but useful never does. So build useful stuff. Always.”

2. Psychology of Money – Morgan Housel

Psychology of Money can really open your eyes to your relationship with money, and can also make you think “I never thought of it that way before!” – two signs of a great book.

The premise of this book is that doing well with money has little to do with how smart you are and a lot to do with how you behave.

And as such, the book takes a common-sensical view of wealth, greed, and happiness, explaining them through the lens of psychology and human behaviour.

Ultimately, the author, Morgan Housel, makes a compelling argument that financial success is not a hard science, but a soft skill, where how you behave is more important than what you know.

Though there are many critical takeaways from this book, our favourite one is captured in this sentence the author writes in his letter to his newborn, “I want you to be successful and I want you to earn it. But realize that not all success is due to hard work and not all poverty is due to laziness.”

Truly a book worth reading again and again.

3. Atomic Habits – James Clear

It’s almost a cliché to ask this now, but we’ll ask it nevertheless.

How many times have you made New Year resolutions only to break them in February, if not sooner?

Atomic Habits by James Clear is an operating manual of how to create and sustain habits for the long term.

The book urges its readers to forget about goals and focus on systems instead. Goals are only the results you want to achieve, systems are the processes that lead to these results. You don’t rise to the level of your goals, you fall to the level of your systems, the book argues.

If you want to master a habit, the key is repetition, not perfection. The key is to get started, and not endlessly plan for perfection. Start small, and master the habit of showing up to start the habit.

One of our favourite quotes from the book says – “Because of how we are wired, most people will spend all day chasing quick hits of satisfaction. The road less travelled is the road of delayed gratification. If you’re willing to wait for the rewards, you will face less competition and often get a bigger payoff.”

4. Zero to One – Peter Thiel

Peter Thiel, billionaire investor and an original member of the Paypal mafia, is a polarizing figure. You may agree with some of the ideas he states in his book, or vehemently disagree with few. But you won’t be able to disagree with the fact that he is provocative, and unafraid to state his mind, and this differentiates him from his peers.

It also makes his points land all the more strongly, and thus makes Zero to One a book worth rereading.

Aptly sub-titled “Notes on startups, or how to build the future”, Zero to One is a collection of online notes taken by Blake Masters for a Stanford University class on startups taught by Peter Thiel.

It covers a wide variety of topics ranging from the importance of a strong culture for startups, to the need for originality in the founding team to develop original visions for the startup. The book also talks about the importance of establishing a monopoly by cleverly weaving together a strong brand, proprietary technology and scalable products, supported by network effects.

5. The Almanack of Naval Ravikant – Eric Jorgenson

One of the reasons this book is interesting is because it distils Naval Ravikant’s (the investor philosopher of Silicon Valley and the co-founder of AngelList) wisdom and philosophy into accessible, bite-sized chunks. It covers a wide range of topics from how to build wealth to how to find happiness.

This book, much like Rework, is meant to be read in a modular fashion and contains self-sufficient nuggets of wisdom.

This is not really a tactical, how-to guide that walks you through step-by-step exercises. Instead, this book requires you to put in the work of thinking through how these truths apply to your life, but it’s an investment well worth making.

In summary

That’s it! That wraps up the key books we keep going back to again and again for their nuggets of wisdom. The beautiful thing about these really great books is that whenever we go back to re-read them, we come away with some fresh insight. Like fine wine, they age well.

What are your favourite go-to books worth reading again and again? Do you want us to add any books to this list?

Comment below and let us know!

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