10 Deeply Insightful Books I Re-Read Every Single Year

By AAwosika07 | Books

Jan 01

When I was lost, stuck, broke, and hopeless, I started diving into self-improvement and kept hearing the same piece of advice — read more books.

In the span of a year, I read roughly 75 books.

That year shifted my trajectory because those books opened my eyes to possibilities I didn’t know existed. This is why I’m okay with the endless barrage of articles telling you to read more books as well as the ones that make lists of recommended books. Out of all the self-improvement advice out there, ‘read more’ will never go out of style.

So, at first, you read many books. But after time, you find a few books that dramatically shift the way you view the world. You read them more than once and each time you read them it feels like a brand new experience because they’re packed with so many insights.

I re-read these books because their wisdom serves as the foundation for all the moves I’ll make this year and beyond. If you can afford it, buy all of these books and read them as soon as possible.

Rich Dad Poor Dad by Robert Kiyosaki

This book teaches simple fundamental lessons about money. The lessons themselves are nothing special and that’s what makes the book so profound. Society, academia, our parents, etc never taught us these basic fundamentals about building wealth.

And because of that people get stuck on the wrong side of the equation — one source of income through employment, debt, and a financial equation that simply doesn’t leave them with enough money in the long run.

The book is packed with lessons, but some of my favorites are:

  • Rich people buy assets first and liabilities second
  • Always focus on increasing cash flow. You want assets that continually put money in your pocket
  • You can’t build wealth by renting out your time for money.
  • Assets put money in your pocket and liabilities take money out of your pocket. The most controversial stance in the book is that traditional homeownership is a liability.
  • Work to learn, not for money. People who build wealth focus on building profitable skills first and making money second

The Incerto by Nassim Taleb

The Incerto is a series of books written by Nassim Taleb, a former options trader turned philosopher. The books in the series are The Bed of Procrustes, The Black Swan, Fooled By Randomness, Antifragile, and Skin in the Game.

All these books focus on risk. Risk is hard to understand. Because of this, people make tons of mistakes because they don’t understand how risk works. If you get on the right side of the equation you can use risk to your advantage.

You can become antifragile, which means you benefit from risk and chaos. I always use my profession as an example. Writing is an antifragile profession because randomness can help you, e.g., one of your articles goes viral or a book takes off.

It’s tough to cover all the concepts in the book, but some of my favorites are:

  • Convexity – Always aim for opportunities with a high upside and a known downside. When I write a book, I can’t sell negative books, but I have the potential to sell a million copies
  • The Turkey Problem – A turkey gets fed 364 days in a row. Each day it grows more confident in its future prospects until Thanksgiving. This is a metaphor for people in fragile positions who can succeed and thrive for a while until they don’t. Think levered up banks in 08
  • Fragility, Robustness, Antifragility – Fragility hates volatility — think someone living paycheck to paycheck. Robust is hedged against volatility and is stable — think an emergency fund for hard times. Antifragile benefits from volatility — think entrepreneurship with the potential for high payoff
  •  Skin in the game – Without people paying for the consequences of their actions, you can’t have a quality system. Lack of skin in the game is why policymakers, bankers, and other rent-seekers muddy the system
  • Survivorship bias – You only see the winners, never the losers who tried the same strategies and failed
  • Black Swan – Unforeseen events that you can’t predict, but are predictable in the sense that a fragile system will cause a negative black swan eventually. Also, positive black swans can happen due to the element of randomness.
  • Randomness – Much of what happens in this world is random, but collectively that randomness has an intelligence to it — think evolution.

These books taught me to constantly tinker, evolve, test, and make small bets that will never kill me if they fail but can pay off huge if they work.

On the Shortness of Life by Seneca

This book has a simple thesis: Life is long if you know how to live it. It talks about how life seems short because we waste so much of it. We spend most of our time on the insignificant and petty instead of meaningful activities. Our fear of death drives us to live passively.

We’re so preoccupied with the exact wrong aspects of life that it flies right by us. When you’re on your deathbed, you’ll have a different perspective on the way you lived than you did the whole time you were living. You might feel regret. You might wonder why you wasted so much time on petty BS. You’ll wish you had the time back, but it will be gone forever.

Full of insightful quotes, you should learn these lessons straight from the horse’s mouth:

  • “You act like mortals in all that you fear, and like immortals in all that you desire”
  • “It is not that we have so little time but that we lose so much. … The life we receive is not short but we make it so; we are not ill provided but use what we have wastefully.”
  • “It is not that we have a short time to live, but that we waste a lot of it. Life is long enough, and a sufficiently generous amount has been given to us for the highest achievements if it were all well invested. But when it is wasted in heedless luxury and spent on no good activity, we are forced at last by death’s final constraint to realize that it has passed away before we knew it was passing. So it is: we are not given a short life but we make it short, and we are not ill-supplied but wasteful of it… Life is long if you know how to use it.”
  • “People are frugal in guarding their personal property; but as soon as it comes to squandering time they are most wasteful of the one thing in which it is right to be stingy.”
  • “Life is very short and anxious for those who forget the past, neglect the present, and fear the future.”
  • “You live as if you were destined to live forever, no thought of your frailty ever enters your head, of how much time has already gone by you take no heed. You squander time as if you drew from a full and abundant supply, though all the while that day which you bestow on some person or thing is perhaps your last.”
  • “The part of life we really live is small. For all the rest of existence is not life, but merely time.”

I focus on mortality often. I write about it often. I’m still afraid of death, but lessons like these help me put it in the proper perspective. It’s hard to live like you’re not guaranteed more days. And rarely do people live this way. But the closer you can get to this attitude, the more life you’ll actually live.

Tiny Beautiful Little Things by Cheryl Strayed

This book contains a collection of advice columns from “Dear Sugar” the pen-name bestselling author Cheryl Strayed uses when giving advice to people with pressing questions.

She’s a fantastic writer and uses a unique style when giving advice. Instead of just giving advice, she will tell a story about her life related to that advice to identify with the reader. And she shares everything — traumatic experiences in her life like being molested, infidelity, going through a divorce, addiction, you name it.

I always take time to pop into the book periodically and read a handful of answers. I can’t read straight through the book for long stretches because the answers and passages take time to digest. The “advice as autobiography” style works so well because she removes any pedestals before giving advice. I try to emulate the foundations of this style and avoid giving advice on topics I don’t have any real familiarity with.

Let’s take a look at some of the profound quotes and insights from her answers:

  • “Most things will be okay eventually, but not everything will be. Sometimes you’ll put up a good fight and lose. Sometimes you’ll hold on really hard and realize there is no choice but to let go. Acceptance is a small, quiet room.”
  • “You cannot convince people to love you. This is an absolute rule. No one will ever give you love because you want him or her to give it.”
  • Don’t do what you know on a gut level to be the wrong thing to do. Don’t stay when you know you should go or go when you know you should stay. Don’t fight when you should hold steady or hold steady when you should fight. Don’t focus on the short-term fun instead of the long-term fallout. I know it’s hard to know what to do when you have a conflicting set of emotions and desires, but it’s not as hard as we pretend it is. Saying it’s hard is ultimately a justification to do whatever seems like the easiest thing to do—have the affair, stay at that horrible job, end a friendship over a slight, keep loving someone who treats you terribly. I don’t think there’s a single dumbass thing I’ve done in my adult life that I didn’t know was a dumbass thing to do while I was doing it.”
  • (For us writers!) – “Don’t lament so much about how your career is going to turn out. You don’t have a career. You have a life. Do the work. Keep the faith. Be true blue. You are a writer because you write. Keep writing and quit your bitching. Your book has a birthday. You don’t know what it is yet.”
  • “Trusting yourself means living out what you already know to be true.”

Zero to One by Peter Thiel

Something about this book just lights a fire under my ass when it comes to entrepreneurship and Peter Thiel is one of the most interesting thinkers I’ve ever come across.

He challenges you to be bold and always tries to look far into the future. Safe to say he’s been successful as far as future thinking goes. He co-founded PayPal with Elon Musk. He was an early private investor in Facebook. And he’s also helped start other billion-dollar companies like Palantir.

The book targets people who want to start unicorn venture-backed companies, but the lessons still apply to any sort of entrepreneur and the book has a ton of insights that are just fascinating.

Let’s take a look at some of my favorites:

  • Don’t compete, create a monopoly — Thiel argues that competition isn’t good for business at all. It eats profits and creates a race to the bottom. Instead, try to build a natural monopoly — a product with such a deep moat that others can’t compete — think Google.
  • Definite optimism – Definite optimists have a long-term plan for the future they execute and never waver from. Steve Jobs comes to mind, creating the iPod, iPad, and iPhone over the span of a decade. This goes against the thinking that you should build a minimum viable product and “iterate your way to success.”
  • Optionality is mediocrity – He makes the argument that trying to be well-rounded and keeping every option open kills long-term success. He argues that when it comes to your career and business, you should hyper-focus on one area for a long time.
  • Zero to one – Going from zero to one means you create ‘vertical technological progress’ meaning you create something unique that never existed before. He argues that, outside of information technology, we’ve made little to no tech progress in the past few decades.
  • Answer this question – What important truth do you disagree with most people on? His answer is that vertical technological progress is the answer to a better future, not globalism continuing to copy what already works.

Poor Charlie’s Almanack

Charlie Munger is like a professor of common sense. If you can execute his basic, grounded, and sensible approach to life, you can accomplish most of your goals.

One of my favorite quotes of all time that comes from the book spells out the approach perfectly:

“Spend each day trying to be a little wiser than you were when you woke up. Discharge your duties faithfully and well. Systematically you get ahead, but not necessarily in fast spurts. Nevertheless, you build discipline by preparing for fast spurts. Slug it out one inch at a time, day by day. At the end of the day – if you live long enough – most people get what they deserve.”

ming successful isn’t all that hard if you’re willing to play long-term games, avoid dumb mistakes, spend your life learning, and make a few solid decisions in your lifetime. That’s it.

An investor, Warren Buffets business partner, Munger has been successful mostly as a product of learning a lot and staying patient — saying no to almost all opportunities and betting heavily on a few.

The book has so many basic yet sharp insights:

  • Invert, invert, invert – Instead of trying to be smart, avoid being dumb. Instead of trying to make amazing decisions, avoid catastrophic ones.
  • The power of incentives – “Show me the incentives and I’ll show you the outcome.”
  • Build a latticework of mental models – Learn the foundations of many disciplines. With multidisciplinary knowledge, you can outperform people who have heavy expertise in one domain because they think too rigidly.
  • Play games you can win – Compete with idiots. Enter a field you have a solid shot at being one of the best.
  • Circle of competence – Don’t make bets on things you don’t understand well
  • Become a learning machine – Try to get a little smarter every day and it compounds just like interest.
  • Deserve what you want – To get what you want, you have to be the type of person who deserves it. Re-read that. Simple and profound.

Final Thoughts

I’ll leave you with a quote that shows you the right way to go about reading more books:

“Read what you love until you love to read.” – Naval.

When you go down your own rabbit hole and follow your curiosity you’ll find books that will change the way you view the world, too. You can create a custom education that leads to opportunities you wouldn’t have found otherwise. That compounding knowledge will make you a little bit smarter until you become much much smarter.

Start now.


About the Author

Ayodeji is the Author of Real Help: An Honest Guide to Self-Improvement and two other Amazon best-selling titles. When he's not writing, he enjoys reading, exercising, eating chicken wings, and occasionally drinking old-fashioned's.