The 10 Best Self-Help Books of All Time

Ayodeji Awosika
Jul 4 · 10 min read

It’s hard to figure out what the best self-help books are because…there are a lot of self-help books. Like, a lot a lot.

And 95 percent of them are mediocre or bad.

Self-improvement changed my life. At a point where I felt lost in life, reading a bunch of self-help books helped me immensely. See, self-improvement, when done right, is the key to getting everything you want.

But it’s very, very easy to quickly slip into “mental masturbation,” meaning you’re reading and consuming self-help and productivity content for the sake of consuming self-help and productivity content. When you treat it as the end itself, instead of the means to the end you want, you’ll spin your wheels.

Certain self-help books, the best-self help books, either light such an intensely hot fire under your ass or present the information in such a unique way that you feel compelled to act.

As follows is the list of books that did just that for me.

Relentless: From Good to Great to Unstoppable by Tim Grover

Tim Grover trained world-class athletes like Michael Jordan, Kobe Bryant, and Dwayne Wade. He had first-hand experience with some of the most competitive and driven people on planet earth. In relentless, he talks about the attitude it takes to become a “cleaner.”

Per Tim, there are three types of people:

  • Coolers — These are the followers. Foot soldiers if you will.
  • Closers — These people will step up to the plate, but only if they’re in the right position
  • Cleaners — DGAF. They relentlessly attack any scenario, regardless of the opponent

Get this book on audio. The narration will make you want to run through a brick wall. The key component to becoming a cleaner? Don’t ignore your dark side, harness it. People with real drive and tenacity — from top-tier athletes to corporate raiders — all have a bit of dark relentlessness that pushes them forward.

I love that this book has no qualms about its message. The book is about the entirely self-interested pursuit of success above all else. Some people do like living this way. I like living this way. If you’re a type A person and want to go from good to unstoppable, this is the book for you.

The 10X Rule By Grant Cardone

Grant Cardone is the type of person people love or hate. The quintessential brash, lavish, in your face, “get rich” advertiser, he’s also a genuinely pragmatic person with a sold philosophy if you take the time to listen.

Here’s the 10x rule in a nutshell: to get what you want, you have to work 10 times harder than you think you should have to, for 10 times the amount of time, to get 10 to even 100 times the result.

He contrasts this mindset of abundant effort and prosperity with the common person who:

  • Has nowhere near enough money saved to sustain them
  • Uses nowhere near the amount of effort they’re capable of
  • Finds themselves trapped in a life they don’t want because they live so low below their potential

The 10x rule isn’t just a lofty idea, it’s a hedge against the pitfalls of being average. See, being average is fine, so long as things so smoothly. In bad times, chaotic times, it’s the average who get screwed the most. See 2008–09.

Per Grant, getting rich and successful isn’t idealistic, it’s a pragmatic ethical duty.

Rich Dad Poor Dad by Robert Kiyosaki

I wish the government mandated every eighteen-year-old read this book. Of course, they’d never do that, because the teachings of the book would undermine all of their goals.

Rich Dad poor dad is about money. More importantly, how to think about money. His “poor dad” was his real dad — a teacher on salary, the prototypical average American. His “rich dad” was his best friend’s father who owned businesses.

The lessons from his rich dad are plentiful, but here are a few:

  • Gain assets — Assets are things that put money in your pocket repeatedly over time without you having to do much after initial creation, e.g, books, investments, income-generating rental property, etc.
  • Reduce liabilities — Robert counts anything that takes money out of your pocket and doesn’t produce cash flow a liability. He includes homeownership (without renting) as a liability.
  • Cashflow — You need cash, liquid investments, “mailbox money” as it were. You cannot get rich without multiple income-generating assets that produce cash flow. Impossible.

Contrast this with the normal American. Deeply in debt, their main investment vehicles (home & retirement) extremely illiquid, and one source of income that’s capped by time. No Bueno.

If you want to become rich, this book will tell you exactly how to do it. The first time I read it, I felt as if society had been lying to me for my entire life. And I was right, it was.

Tiny Beautiful Things: Advice on Life and Love From Dear Sugar by Cheryl Strayed

I had to read this book in pieces because some of the stories in it just floor you.

I consider this a self-help book because the author does what true help is meant to do — cut to the core of the problem to create room for change.

Cheryl Strayed, author of the runaway bestseller Wild and many other hits, once had an advice column under the pen name Dear Dugar. Tiny Beautiful Things is a collection of some of the best questions and answers from the column.

Strayed is a beast of a wordsmith and she’d answer the questions from readers by first giving these long-detailed accounts of her own life to meet the reader where they were at. Her answers would never say here’s exactly what to do. More like here’s a similar experience I went through, what I drew from it, and how it applies to your life.

Some of the stories she tells in the book are just brutal. Here’s how she opens one of her letters:

“Dear WTF,

My father’s father made me jack him off when I was three or four or five. I wasn’t any good at it. My hands were too small and I couldn’t get the rhythm right and I didn’t understand what I was doing…”

Yeah.

That’s what makes the book so special, though. She hides nothing about her own life, which makes the readers more comfortable sharing the raw truth. As a reader you get a window into human psychology you’re hard-pressed to find elsewhere because humans do a good job of burying and hiding these emotions.

Just reading the broad range of experiences from her readers and her own life helps you get perspective on what’s going on in your own life. It also teaches you compassion for others. You’ll see by reading some of these stories that people who seem okay on the surface are truly struggling with some dark demons. We all have them.

Reading the examples in the book will help you deal with them

The One Thing by Gary Keller

Momentum is the name of the game. You need momentum to become successful because success begets more success. To get said momentum, you need to line up your goals in the right order and focus on one thing at a time.

This creates a ‘domino effect.’ You begin with smaller goals to gain momentum, then, you’re able to complete larger goals more easily. You’ve heard this before, but the book lays out this concept in a way that might actually make it stick.

Aside from the core idea of focusing on one thing at a time, there are also some excellent nuggets from the book:

  • Balance is a myth — You need to live an unbalanced lifestyle to be successful. Go all-in on your one thing, all the time, until it’s done. Learn how to say no. Block out time for your work.
  • You don’t know your ceiling — You have absolutely no idea what you’re capable of and the estimates you make are well below what’s possible.
  • Big is better — The crabs in the bucket always tell us to shrink and stay small. Screw that, the bigger your dreams the better, so long as you work on one thing at a time to get there.

The entire ethos of the book is this question:

If you can truly get good at answering that question, the world will open up to you in a way you couldn’t imagine.

How to Win Friends and Influence People by Dale Carnegie

It’s actually astonishing how socially unaware some people are. How to Win Friends and Influence People basically teaches you the rules you learned in kindergarten, but these rules need reinforcement because adults still have a really hard time adhering to them.

It’s not that hard to get people to like you or do what you want.

Here are some of the classic rules from the book:

  • Smile — Simple concept, yet how many people do you see — male and female — walking around with resting bitch face all day?
  • Don’t be a know it all — If someone says something that isn’t accurate, let it slide. Correcting them just makes you look arrogant. People don’t want to be around a know-it-all.
  • Don’t argue with people — Ever. You gain nothing from it and only foster negative feelings.

There are many more rules, anecdotes, and stories, but this basic book covers 99.9 percent of everything you need to know if you want to be popular, or, just don’t want to be a pompous asshole with no friends.

The Meditations by Marcus Aurelius

Stoicism is a philosophy that can be summed up in two words. Chill out.

We’re constantly reacting to everything as if life is doing something to us when in reality we’re just perceiving what we believe to be reality. If you can change your mind, you can literally change your reality.

Just read these quotes from the book and you’ll want to buy it:

“How much time he saves who does not look to see what his neighbor says or does or thinks.”

“When another blames you or hates you, or people voice similar criticisms, go to their souls, penetrate inside and see what sort of people they are. You will realize that there is no need to be racked with anxiety that they should hold any particular opinion about you.”

“If you are pained by external things, it is not they that disturb you, but your own judgment of them. And it is in your power to wipe out that judgment now.”

“How much more grievous are the consequences of anger than the causes of it.”

The Obstacle is the Way by Ryan Holiday

You can credit Ryan Holiday for taking stoicism mainstream, particularly with TOITW.

Ryan comes from the Robert Greene school of writing. An insanely voracious, he uses carefully chosen anecdotes to bring the concepts to life. The entirety of the book is based on concepts you already know, which is exactly why it’s a great book.

All self-improvement is derived from the classics, philosophy, timeless wisdom, whatever moniker you want to give it.

Basics concepts like these are easy to understand but extremely difficult to practice. Why do you think there are so many self-help books? Why do you think it’s difficult to change your life even after reading the best self-help books over and over again? Because life is hard! We need reminders. The Obstacle is the Way is a great one.

The 48 Laws of Power by Robert Greene

I should’ve added this at the top because this is the best self-help book you’ll ever read. Actually, to call it a self-help book is a bit of an insult. The 48 Laws of Power is a guide to understanding how the world actually works.

The book has been called Machiavellian, amoral, cruel, ruthless, you name it. But at its core, the laws ring true. Accepting people for how they really are is a superpower.

People play power games, engage in politics, use coy maneuvers to get what they want, deceive, all the while pretending they aren’t doing any of it. Often, this happens on a subconscious level.

Here are some of my personal favorite rules:

  • Never outshine the master — Make your masters appear more brilliant than they are and you will attain the heights of power
  • Always say less than necessary — Power is in many ways a game of appearances, and when you say less than necessary, you inevitably appear greater and more powerful than you are.
  • Infection: Avoid the unhappy or the unlucky — When you suspect you are in the presence of an infector, don’t argue, don’t try to help, don’t pass the person on to your friends, or you will become enmeshed. Flee the infector’s presence or suffer the consequences.
  • Play a sucker to catch a sucker, seem dumber than your mark — Given how important the idea of intelligence is to most people’s vanity, it is critical never inadvertently to insult or impugn a person’s brain power.
  • Be royal in your own fashion. Act like a king to be treated like one — “The way you carry yourself will often determine how you are treated: In the long run, appearing vulgar or common will make people disrespect you. For a king respects himself and inspires the same sentiment in others. By acting regally and confident of your powers, you make yourself seem destined to wear a crown.”

Real Help by Ayodeji Awosika

Not to toot my own horn, but I genuinely believe this is one of the most comprehensive, useful, and straightforward self-help books you’ll ever read in your entire life.

Don’t just take my word for it, look at what other readers have said about the book:

This book will teach you how to:

  • Identify the key sticking points and blind spots that keep you stuck in loops of procrastination (even if you feel like they’re a mystery to you)
  • Stop being a ‘self-help junkie’ who never gets anything done and start executing your ideas
    Achieve massive success with little to no risk (even if you don’t have a ton of money or resources)
  • Develop the mental toughness you need to thrive in an unfair world
  • Start your first passion project or side business and make $1,000 per month (without needing to be an expert)

There’s 0.00 percent hyperbole. Just the straightforward facts and insights you need to change your life.


Grab your free checklist here The Ultimate Guide to Discovering Your Natural Talents and Strengths. Wanna keep in touch online? Follow me on Instagram here.

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