The best books on confidence building

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1. Brené Brown - Daring Greatly

Review: Brené Brown - Daring Greatly

The first book in this top 6 of the best books on confidence building is all about vulnerability. Many of us absolutely HATE feeling vulnerable, because we risk being burned. We feel exposed, so we reflexively try to shield ourselves from it. For instance, if you tell someone that you have a crush on her/him, you risk the chance of being rejected. Even the world around us tells us that being vulnerable is bad. They tell us it’s ‘weak’ to be vulnerable, and weakness is to be avoided at all cost.

According to the author of this book, research professor Brené Brown, you actually have to lean into vulnerability, even if that means you'll feel uncomfortable. That vulnerability is actually the key to living wholeheartedly. No, it doesn't mean you'll have to let it all hang out. You're not going to tell everyone and her neighbor your deepest darkest secrets. No, you also won't have to start living as a 'weak' person. It actually takes more courage to let yourself be vulnerable than to lug around a big shield to protect yourself with.

"I managed situations and micromanaged the people around me. I performed until there was no energy left to feel. I made what was uncertain certain, no matter what the cost. I stayed so busy that the truth of my hurting and my fear could never catch up. I looked brave on the outside and felt scared on the inside. Slowly I learned that this shield was too heavy to lug around, and that the only thing it really did was keep me from knowing myself and letting myself be known. The shield required that I stay small and quiet behind it so as not to draw attention to my imperfections and vulnerabilities."

Dr. Brown writes that in order be vulnerable, we first have to get past the obstacle of shame, which is in essence a self-image problem. It's that whisper in your ear which tells you that you ARE a bad person, instead of telling you that you DID a bad thing. This book will teach you how to become resilient to shame. Although it's a great help in learning how to develop more confidence and self-esteem, I can see how not everyone would like this book. Firstly, it's written in a descriptive style, which might strike a false chord with some people. Secondly, it's full of personal anecdotes. Thirdly, the structure of the book seems a little random, and at some points, it might even drag on a bit too much. 

All in all, however, the book is full of actionable and useful wisdom. Some might have to dig a bit deeper to find the nuggets of wisdom. Alternatively, you could also opt for one of her other books. Her older book is titled ‘The gifts of imperfection' (see below), which has a lot of overlap with 'Daring Greatly.' Since the latter (2010) is published after the former (2012), we recommend you to get 'Daring Greatly.' We have to admit that we haven't had the time to read Brené Brown's other books yet, called 'Rising Strong' (2015) and 'Braving the Wilderness' (2017).  For that reason we have chosen to include Daring Greatly into this top 6 of the best books on confidence building.

Update: After having read both Rising Strong and Braving the Wilderness, for the purpose of this list we'd still recommend you to start with Daring Greatly, as it will set you up for her more recent books. For those interested, Rising Strong explores the topic of getting back up after adversity, while Braving the Wilderness is about finding true belonging. Both are worth a read.

2. Kamal Ravikant -
Love Yourself Like Your Life Depends On It

Review: Kamal Ravikant - Love Yourself Like Your Life Depends On It

The second book in this top 6 of the best books on confidence building is called 'Love yourself - Like your life depends on it.' Don't worry, it's not touchy-feely book. I bet you can remember a point in life when you felt you've hit rock bottom. A period, whether it be a day or a year, where your self-esteem was at a low point and you felt you had nothing to live for. You might currently still even be in that phase. Maybe you've had a really bad breakup, a death in the family, or perhaps you might just feel worn out and numb from the emptiness of life. If you recognize yourself in this, then this definitely is the book for you!

"I was in a bad way. Miserable out of my mind. There were days when I'd lie in bed, the drapes closed, day outside sliding into night and back to day, and I just didn't want to deal. Deal with my thoughts. Deal with being sick. Deal with heartache. Deal with my company tanking. Deal....with....life."

I must confess that I was kind of hesitant in putting this book on the list, because there are some meditative practices in it. And since a lot of us associate meditation with 'woo-woo' or 'touchy-feely crap,' it’s very easy to dismiss this book. However, regardless of your stance on these practices, this book is full actionable wisdom. Timeless advice which will do wonders for your confidence and self-esteem. I’d especially recommend reading it when you feel you're at your lowest. You know how some people can read a certain book and feel empowered afterwards? We ALL need to have such a book. Just in case something happens. Well, this is THAT book.

3. Tim Ferriss - Tools of Titans
+ Tribe of Mentors

Review: Tim Ferriss - Tools of Titans

The third place in this top 6 of the best books on confidence building is not occupied by one, but two books, both authored by the amazing Tim Ferriss. Both of these books should be a mandatory read for everyone. They're both filled to the brim with confidence and self-esteem instilling wisdom, as well as actionable advice from many of the world’s high performers. The guests in these books range from from celebrities, athletes and special ops commanders, to investors, black-market biochemists and startup entrepreneurs. (Both Kamal Ravikant and Brené Brown, whom are both featured in this top 6 list, are featured in this book as well.)  It even has a foreword written by Arnold Schwarzenegger:

".... Never stop learning. Ever. That’s why you bought this book. You know that wherever you are in life, there will be moments when you need outside motivation and insight. There will be times when you don’t have the answer, or the drive, and you’re forced to look beyond yourself. You can admit that you can’t do it alone. I certainly can’t. No one can. Now, turn the page and learn something."

Review: Tim Ferriss - Tribe of Mentors

The lessons contained in Tools of Titans (the other book) are direct results from Tim's podcast guests, and given the wide range of professions these people are world-class in, their pearls of wisdom are equally wide ranging. This, however, also means that their life lessons are somewhat constricted when it comes to their age and geographical brackets.  That's not to say that their lessons aren't applicable for people outside of the United States or outside of their age-range. It simply means that there aren't many relatively young (or old) non-Americans represented in Tools of Titans. That's where Tribe of Mentors comes in. Around 90% of the guests in Tribe of Mentor's haven't appeared on Tim's podcast. Age wise, they also seem more varied compared to the guests in Tools of Titans (from world class performers in their 20's to world champion weightlifters in their 60's), as well as more geographically diverse. Tribe of Mentors is geared towards successfully navigating the moments in life where you reassess; which happen at multiple stages in life. These are the times where you step back and ask yourself if you're steering yourself in a direction which maximizes your well being, or as Tim says:

"Am I going in the right direction, or am I just going really fast with a lot of effort in the wrong direction? And have I missed a lot in life from being over-scheduled, or under-scheduled for that matter?"

Although Tribe of Mentors is an incredible book in its own right, it becomes even better when combined with Tools of Titans. They go together incredibly well, like peanut butter and jelly. Both Tools of Titans and Tribe of Mentors aren't structured as your run-of-the-mill guides in which you have to follow a predetermined step-by-step approach in order to reach your destination. These books have more of a ‘buffet,’ or as the author calls it, a pick-your-own-adventure kind of structure. You pick the topic or author you want to know more about and flip to the corresponding chapter.

How does this relate to confidence and self-esteem again? 
These books are chock-full of field-tested wisdom, ready to be applied in your own life. Although the information in these books isn't necessarily directly marketed towards improving your confidence and self-esteem, applying the actionable wisdom in your life will do wonders for them. That's because developing confidence and self-esteem not about getting a quick motivational 'fix'; it's about building a life which will act as a source of self-confidence and self-esteem. For that reason, we can also strongly recommend Tim Ferriss' other books. Although the titles might sound a bit 'scammy,' we can assure you that the content is life changing and will help your self-esteem and confidence skyrocket: 

4. Dale Carnegie –
How to win friends & influence people
+
How to develop self-confidence & influence
people by public speaking

The #4 of this top 6 of the best books on confidence building isn't a single book, but rather two different ones by the same author. One book will be providing the general foundation for your social skills, while the other book will focus on developing a specific skill. And let me tell you, skills are an essential source of self-confidence and self-esteem. The reason for picking two books to occupy the #4 spot is that they're recommended by none other than Warren Buffett, the seventh richest person in the world with a total net worth of $88.5 billion as of January 1, 2021. We know that wealth doesn't equal confidence, but having skills plays an important role in the road to confidence. After having read the book 'How to win friends & influence people,' which is the first Dale Carnegie book we're recommending, Warren Buffett signed up for a Dale Carnegie course on public speaking. Mr. Buffett felt that he needed to develop self-confidence in public speaking:

"You can't believe what I was like if I had to give a talk. I was so terrified that I just couldn't do it. I would throw up. In fact, I arranged my life so that I never had to get up in front of anybody."

According to Warren Buffett himself, this Dale Carnegie course changed his life. Since you cannot enroll in the same Dale Carnegie course anymore, we have chosen to substitute it with the second best thing: Dale Carnegie's book on public speaking.

Review: Dale Carnegie

The first book, ‘How to win friends and influence people,’ will lay a foundation. It will guide you in developing self-esteem and confidence through improving your social skills. Due to self-image problems, a lot of us have trouble with putting ourselves out there and connecting with other people. By improving your broad social skills and implementing them in your daily life, you will create a feedback loop, which in turn will raise self-esteem and confidence.

The second book, 'How to develop self-confidence & influence people by public speaking,' will let you develop a very specific social skill: public speaking. Take note that public speaking is not just about saying stuff while standing in front of big audiences. In essence, public speaking is about communicating clearly and confidently. It's about developing the ability and confidence to effectively getting your message across. The great thing about a skill like public speaking is that it will act as a force multiplier for other skills. Having self-confidence in public speaking will make other skills (which carry a social element) have a greater impact. And since public speaking is a widely applicable skill, it will have a positive influence in almost everything you will do. Everything from dating to befriending people will be positively impacted by it.

I know that some of us might be concerned about the book being dated, as the first edition of ‘How to win friends and influence people’ was published in 1937, and the first edition of 'How to develop self-confidence & influence people by public speaking' was first published in 1926 (under a different title). Well, no worries, because both books have definitely stood the test of time. Even if the language might be a touch archaic here and there, the content is as applicable today as it was back then. Proof of the timeless content: at the moment of writing this list (March 2021), ‘How to win friends and influence people’ ranks #19 in this week's Amazon Best Seller list, the world’s largest bookstore. That's 84 years after its initial publication year! That's why we've chosen to confidently include Dale Carnegie's books in this top 6 on the best books on confidence building.

5. Ryan Holiday - The Daily Stoic:
366 Meditations on Wisdom, Perseverance, 
and the Art of Living

Review: Ryan Holiday - The Daily Stoic

The fifth book in this top 6 of the best books on confidence building is 'The Daily Stoic - 366 Meditations on Wisdom, Perseverance, and the Art of Living.' Now, I know what you're thinking: What? Again with the meditation? Yes and no. Yes, it has the word 'meditations' in the title. No, the book is not about meditation in the sense of sitting down and saying "oooohmmm". What it is about?

“.... you picked up this book because you are learning how to live. Because you want to be freer, fear less, and achieve a state of peace.”

The Daily Stoic gives you small bites (one a day) of practical Stoic wisdom, which you can mull over throughout the day. These small bites of wisdom will help you rethink how to go through life and how to manage the emotions that come with it. And it's all done by using Stoicism as guidance. What is Stoicism you ask? Stoicism is an ancient Greek philosophy which teaches self-control and fortitude as a way to overcome destructive emotions rather than extinguish them.

The Daily Stoic is a book full of Stoic insights and exercises, which will let you redesign your emotional life in a way that will enable self-confidence and self-esteem to bloom. If you're constantly experiencing negative emotions, confidence and self-esteem won't even have a chance of growing. If you recognize yourself in this, fear not. The Daily Stoic will provide you with a set of twelve principles to overcome obstacles and achieving greater satisfaction in life.

6. Tucker Max – Mate: 
Become the Man Women Want
(Currently published under the title 'What women want'.)

Review: Tucker Max - Mate

The sixth book in this top 6 of the best books on confidence building is for the guys. Seeing as dating is a huge source of self-confidence and self-esteem, we couldn’t NOT include a book on dating. However, the dating book landscape is equally full of snake-oil salesmen as the self-help books one. This is actually the first book I've come across which gives honest and straightforward advice on dating.

"Most of the dating advice rampaging through our culture is outdated, irrelevant, or sex-negative. It got that way for one overwhelming reason: none of it is based on an empirical understanding of how humans and human mating actually work."

"Instead, the conventional wisdom about dating has been defined by political and religious ideologies, family traditions, and cultural norms whose self-serving notions of how the world should work shaped their ideas (and most likely yours). We are going to teach you a completely different approach, one based on science and evidence."

What makes this book qualified?
First of all, it’s written by a very interesting duo: Tucker Max and Geoffrey Miller. Tucker Max is known for having chronicled his tales of drinking and hooking up in his New York Times #1 bestseller I Hope They Serve Beer in Hell, as well as in his books Assholes Finish First, Hilarity Ensues and Sloppy Seconds: The Tucker Max Leftovers. Tucker is obviously providing the majority of the dating experience for this book (Mate). His counterpart in authoring this book is Geoffrey Miller, a leading evolutionary psychologist, best known for writing the book The Mating Mind: How Sexual Choice Shaped the Evolution of Human Nature. Together have done a great job in balancing theory and practice.

Secondly, the content is sober, realistic and actionable. It’s NOT a book which promises you that you’ll be able to date whomever you want in a year. It’s NOT a book in which the authors simply regurgitate common knowledge. It’s also NOT a book full of misogynistic ‘seduction’ advice, commonly found in the Pick-Up Artist scene. On the contrary, the book even teaches men how to understand and empathize with the position women are in when they’re being ‘chased’ by men. It’s none of that. Instead, you’ll be surprised to find an honest, necessary and straightforward guide to dating for men in the modern era, seen through the lens of evolutionary psychology.