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5 Books I Wish I Read in High School

16 min

I never read as much as I should have in high school, and I could have better navigated the earlier stages of my transition from teenager to young adult had I done so. Here are the top 5 books I wish I had read in high school.

I never read as much as I should have in high school. Heck, most of my assigned readings in class were seldom finished, and I couldn't be bothered with self-help books. After all, "I knew everything," just like any teenager.

I'm sure that those of you who do enjoy reading self-help books have your personal favorites, and I believe that as I continue to read more in my adult life, this list has the potential to change considerably. But for now, here are my recommendations for five books that I think every young man ought to read before he officially enters adulthood (and why I wish I had read them sooner).

1. How to Win Friends & Influence People by Dale Carnegie

A timeless classic. Take nearly any modern self-help book you know of, and there is a good chance that this beautiful offering from Dale Carnegie partially influenced it.

Initially published in 1936, this book receives periodic updates; however, the fundamental lessons remain unchanged. Carnegie has a simple but effective way of writing that gets right to the point. You get a sense that this book was written for everyone, and your intuition would serve you well because it was!

This book is about winning people to our way of thinking, not by arguing or belittling them, but by appealing to their interests. Furthermore, it attempts to help us to empathize more effectively with others. Almost a century after the book's publishing, people still fail to relate to others. This book enables us to handle people in virtually any type of situation.

It is in these ways that the book is, in my opinion, quintessential for any young person looking to blaze their trail in life, a path that will undoubtedly converge with the courses of others who also seek to achieve their hopes and dreams. If we want something, we need to learn how best to cater to people's interests to obtain what we want.

Much of our relational problems and disputes with others are predicated on our lack of understanding and a general disinterest in exercising empathy. Sometimes it's best to swap out our "hammers" for "velvet gloves" to get what we want and make things happen for ourselves and others.    

Carnegie's book is organized into four parts:

Each of the above sections can be summed up in two fundamental behaviors:

Fundamental Behavior #1: Take a Genuine Interest in Others

“You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.” - Dale Carnegie

Nobody cares as much about what YOU want as they care about what THEY want. If you are trying to gain influence over others and win them to your way of thinking, you have to start by taking a genuine interest in whatever they are passionate about.

In other words, what interests them ought to fascinate you. I have witnessed leaders who believe that this somehow merits respect from others under their rank or position of authority. Perhaps it does for some, but true leaders who are worth their salt will recognize that to succeed, they must have a vested interest in the achievements of those who follow them; because their followers' successes will culminate in the organization's success and, by extension, themselves.

There is a big difference between commanding respect and demanding it; can you guess which method someone in a position of authority is better able to garner more respect and admiration? On average, people will never truly go the extra mile for those in charge unless they feel their leadership is vested in their happiness and well-being. This is the bedrock for trust, and Carnegie knew that fact well.

"People do not care about how much you know until they know how much you care." - Theodore Roosevelt

Fundamental Behavior #2: Give Frequent Praise

When people pay us genuine and honest compliments for our work, our admiration for them increases. The keywords here are open and honest. If these hold and no ulterior motivations are present, you can bet that the person on the receiving end of the praise will feel more inclined to engage and entertain the one issuing that praise.

After all, it feels good to be recognized for our efforts, and words of affirmation have an uplifting quality.

"Begin with praise and honest appreciation. Call attention to people's mistakes indirectly. Talk about your own mistakes before criticizing the other person. Ask questions instead of giving direct orders. Make the fault easy to correct. Make the other person happy about doing what you suggest." - Dale Carnegie

I have witnessed it in the military and throughout other landscapes of life. There are people in positions of influence who choose to ignore the feelings and thoughts of others. In certain situations, it may be necessary; however, as a rule, it should be known that no soundly-minded individual wants to have their thoughts and feelings ignored. We are all human, after all.

So then why do people who are tasked with leading others choose, in some instances, to ignore praise for good work?

Because it is difficult to sustain interest in other people's thoughts and feelings, if it were easy, then everyone would do it...

If you are either someone in a position of influence or seeking to influence others in a meaningful capacity, you would do well to understand what Carnegie is teaching in his book.

"I can look back at my own life and see where a few words of praise have sharply changed my entire future. Can't you say the same thing about your life?" - Dale Carnegie


Many of our conflicts with others stem from our inability or disinterest in relating to them. Had I read this book as a teenager, I could have better learned to engage with others and navigate through some of the earlier conflicts that I faced as a teenager.

2. The 5 Love Languages by Gary Chapman

Here is a book I recommend to everyone I meet, quite literally. Another simple but effective offering, Gary Chapman's equally profound The 5 Love Languages, is a timeless, easy, and elegant guide to understanding how people give and receive love. Even if we are not in a place where we wish to pursue romantic relationships, I still cannot recommend this book enough.

This offering has helped me better understand friends, family, and even people I have worked within stressful environments because it has helped me know how best to communicate with them and meet their needs.

As humans, we all share the desire to feel loved, needed, and appreciated. By using this simple yet practical guide to understand both others and ourselves better; we can enhance virtually all of our relationships in life for the better.

For our romantic relationships, we need to recognize how best to give love to our spouse and understand how we receive it for ourselves. This all feeds into keeping our respective "love tanks," full, as Chapman puts it.  

“'Real love,' is a kind of love that is emotional in nature but not obsessional. It is a love that unites reason and emotion. It involves an act of the will and requires discipline, and it recognizes the need for personal growth.” - Gary Chapman

The 5 Love Languages described in Dr. Chapman's book are as follows:

I. Words of Affirmation - using our words to make people feel appreciated by paying compliments or acknowledging their efforts. For these types of people, simply verbalizing our appreciation can make or break their day.

II. Quality Time - using time spent together, in order to help your partner feel loved. This is referring to time engaged with one another, not by watching television or simply remaining present; but by genuine engagement.

III. Acts of Service - doing the things your partner wants you to do and showcasing love through your services.

IV. Receiving of Gifts - described as the physical "proof" of your love, this can help your partner to feel loved because it shows that at the moment that you procured an item, you were thinking of them.

V. Physical Touch - not limited to sexual acts, this language refers to the more nuanced deeds, such as rubbing your partner's back or placing your hand on her/his shoulder. Give them a kiss before you leave or a physical embrace when you are reunited. On some level, most people enjoy these physical acts, but for those who have this primary love language, it is all the more essential to them.

“People tend to criticize their spouse most loudly in the area where they themselves have the deepest emotional need.” -Gary Chapman

At first glance, to those who have not yet read the book, you may begin to instantly identify one or two love languages that you believe to be yours. However, if you read it from cover to cover (which isn't difficult to do given the book's relatively small size), I almost guarantee that you will be surprised at how much your opinions will change by the end of the reading.

Dr. Chapman gives examples via personal stories that help the reader see how these languages may be translated, and the genius resides in its simplicity. I never had more "aha!" moments than I did when reading this book (perhaps aside from Dale Carnegie's How to Win Friends & Influence People). This is a great starting point for anyone looking to get married one day or work professionally in an environment of people with varying backgrounds and beliefs.


Had I read this book while I was navigating through the tense world of high school, I could have better built my emotional intelligence by understanding what others were potentially feeling (and why) and being more capable of unpacking what I was feeling personally. I could have built and invested in better relationships with others, across the board, instead of deciding who I didn't need and burning some of those bridges to the ground.  

3. Rich Dad Poor Dad by Robert Kiyosaki

Much to my dismay, schools are failing to teach young people financial literacy... I know that this statement alone is enough to stir up quite a bit of controversy, but love it or hate it, building wealth in life is not nearly as much about following the "deferred-life path" as understanding how money works.

In his book, Rich Dad Poor Dad, Robert Kiyosaki makes one thing very clear from the onset, to which the entirety of this book is built; that there are effectively two types of people in this world:

  1. Employees (those who work for money)
  2. Entrepreneurs (those who make money work for them)
“Financial struggle is often the result of people working all their lives for someone else.” - Robert Kiyosaki

I am not here to convince you that employees are better or worse than entrepreneurs, nor is Kiyosaki; in fact, he talks about the importance of both. However, the "deferred-life path" suggests that the best way to navigate through life is to go to a good school, work hard, make good grades, compete to earn a job with solid pay and excellent benefits, and from there, work your way to retirement.

Kiyosaki unabashedly proclaims that these people are ultimately misguided IF they hope to build wealth in the short term. I certainly won't claim that I agree; however, I can tell you that abiding by life's "deferred path" does not always equate to building sustainable wealth, so keep an open mind and be willing to draw into question what you think you know.

“Often in the real world, it’s not the smart who get ahead, but the bold.” - Robert Kiyosaki

Kiyosaki decides to first zero in on the mindset of the wealthy and encourages the reader to become more financially savvy in areas of accounting, investing, the marketplace, and law. Kiyosaki argues that these are fundamental because by learning to speak these dialects better, anyone can learn the language of money.

What inspired me the most when I first read through this book was how Kiyosaki describes a life where we can all take some measured control of our destinies and obtain financial security. Some great key points that he makes are as follows:

“Success is a poor teacher. We learn the most about ourselves when we fail, so don’t be afraid of failing. Failing is part of the process of success. You cannot have success without failure.” - Robert Kiyosaki


Love it or hate it, Kiyosaki makes a lot of great points and remains a huge advocate of working smarter rather than harder. Had I read this book before entering college, I could have better understood the importance of building wealth much sooner and began making small, incremental (albeit effective) moves in helping to put more money in my pocket for the future.

4. The 5 Levels of Leadership by John C. Maxwell

Not everyone is born or meant to be a leader, and if we're being honest, not everyone should be or desires to be one... That is quite alright, but if you're not a leader, then you're a follower, and any faithful follower ought to have expectations of their leaders just as leaders ought to have standards and expectations for themselves.

Leadership guru, John C. Maxwell, has written countless books on leadership. Honestly, I could recommend any number of them as a part of this list, and it would ultimately achieve the same goal. As a starting point, I loved every bit of Maxwell's The 5 Levels of Leadership for the same reasons as all the aforementioned books; it's simple, clear, and complete.

Leadership is something that I have been passionate about since I was in high school and throughout college. I joined the Navy, attended a military college, and was commissioned as an officer because I wanted to lead others and inspire them to achieve more for themselves, and because of those same passions, I started Gentleman's Flair.

In my continual journey of leadership, I have stumbled, become humbled, flat out failed, and learned a tremendous amount about what it means to earn the title of a leader. Much of that journey began with this book. Maxwell's five levels are:

I. Position (where everyone must start, but the position does not make the leader).

II. Permission (people choose to follow you because they want to).

III. Production (understanding how to motivate and inspire people to produce results and get things done).

IV. People Development (learning how to produce other leaders).

V. Pinnacle (your reputation becomes known because you have demonstrated mastery of the levels mentioned above and are in the leadership game for the long haul).

I have worked for some great leaders and some awful ones. It has always remained my hope to continue growing as a leader and reach the pinnacle of leadership someday. Until then, I take it day by day.

I appreciate Maxwell's levels because they depict a process where every level feeds directly into the next. He clarifies that you can ascend the "ladder" of leadership to the next one after mastering a single level. I think this is important because we are so often swift to dispel the significance of people who are followed because their followers make a choice to do so (i.e., Level 2: Permission).

I have witnessed this during my time in the military. Too often do people take their professional positions too seriously. Yes, roles within bureaucratic and hierarchal systems are essential for order. Still, good leaders recognize that it is always more effective and rewarding to lead people who actively choose to be led by you, not because they have to, but because they want to. "Because I said so" is a poor demand and reasoning for anything.

"Positional leaders focus on control instead of contribution." - John C. Maxwell

Maxwell teaches that the point of climbing the ladder of leadership is to generate new leaders. He speaks very often of the necessity to add value to other people, and I agree wholeheartedly because this benefits our society as a whole. Getting to levels 4 and 5 in our leadership journey is seldom easy. Some people want to fast-track their leadership trajectory, but they fail to recognize that leadership success isn't something that they alone can dictate.

"It's not the position that makes the leader; it's the leader that makes the position." John C. Maxwell


Had I read this book much sooner in life, I could have better understood that any fool can hold a title or position of power, but what we do with that position and how we gain influence and build foundations for trust ultimately defines the kind of leader we are (and want to be).

I have witnessed too many people in positions of power because they "checked" a lot of life's boxes and stroked enough egos to advance themselves. But when it comes to being trusted and respected by people at the lowest levels of their organizations, they have missed the mark completely. I vow not to be one such person as I believe that it is the antithesis of authentic leadership.  

"Half of the harm that is done in this world is due to people who want to feel important... They don't mean to do harm... They are absorbed in the endless struggle to think well of themselves." - T. S. Eliot

5. You Are Good Enough by Robert J. Furey

Like all previous books, this one is simple to grasp and a relatively quick read. What makes this book special (to me) is that it vividly introduces the concept of shame.

This book is for people who deal with feelings of inadequacy. More specifically, for those whose sense of inadequacy has become such an opposing force in their lives that it prevents them from moving forward.

On some level, we have all felt that we were not good enough and for some of us, we become paralyzed at the thought of ridicule and failure. No one is exempt from these feelings, and even those who become wildly successful face these burdens (in some cases, more than the average person).

Referred to by the author as a "hidden epidemic," shame is ultimately defined as "a feeling of self-loathing brought about by thoughts of inadequacy." When we are ashamed, we feel a great distance between the person we perceive ourselves as and the person we wish we were. Much of this ultimately leads to a desire to conceal ourselves because we hate who we are.

"Guilt is the feeling that 'I've done something wrong.' Shame, on the other hand, laments the fact that 'I am something wrong.' Shame runs deeper than guilt; it gets rooted much further into our beings." - Robert J. Furey

This is a severe issue because attempting to conceal ourselves makes intimacy very difficult, if not impossible. Furey then describes how shame can afflict us in three distinct forms:

1. Mild Shame: Often exemplified in people who are competitive but notoriously tough on themselves, resulting in drawing comparisons between themselves and others. These comparisons cause augmentation for one's perception of their flaws when they feel that they are not measuring up, eventually causing a need to hide those flaws. For those suffering from mild shame, Furey discloses that the three main qualities are a sense of self-awareness, a sense of hope that combats despair, and the ability to garner support (more or less) for themselves.

2. Moderate Shame: Occurs when mild shame is extended and the pain which results is more significant than that of mild shame. Although those who suffer from moderate shame possess a feeling of general hope, it is more the thought that things could be worse amidst a flood of emotions that can cause those afflicted to feel stuck in their pain more than those who suffer from mild shame.

3. Severe Shame: The negative thoughts and feelings become unbearable, and a person's everyday life becomes almost impossible to navigate. Finding hope can feel very much outside the realm of possibility for those afflicted by severe shame.

"As you become more accepting of yourself, you will become more like the person you really are. Life will reach out to you and invite you to live and learn. The referees will fade from your world. At one time it seemed as if everyone was judging you; but no more. And all those who you thought were superior to you, well, their imperfections start to become more apparent. People will become more real to you. Gradually, the world will become friendlier and in time, fear will be replaced with gratitude." - Robert J. Furey


Had I read this book when I was going through high school, I could have better found a language to describe how I felt when I thought of myself as inadequate. In many respects, high school was the most stressful time of my life because it was the perfect storm of so many uncertainties. Nobody accomplishes anything serious at this stage of life, nor do they even know who they are, and that's okay.

I remember so many instances where I was compared to my peers, whether they be members of the faculty at my school or simply myself. Either way, what I was feeling was, in fact, mild shame. Thankfully, I had (and still have) incredible parents who were always my biggest fans in life and who wanted only the very best for me. Not everyone is so lucky...

I recommend this book to anyone in high school (or on the eve of adulthood) because many can be gleaned from its concepts. I not only learned about what I was feeling during my adolescence, but I also grew to understand that shame is a universal affliction that has a hold on everyone, some more than others. Realizing this has allowed me to relate better to the people I meet in life, and I believe it can do the same for anyone else.


What are you doing if you aren't finding ways to improve yourself each day? It took me too long to pick up and read these books (or books like them) and finish them cover to cover.

The most important asset that anyone can invest in is their mind. Knowledge is power and learning to navigate a world with assets to acquire, relationships to cultivate, and organizations to influence is paramount to living a successful and purposeful life. I encourage you to read any of these books if you haven't already.

I hope they help you as much as they have helped me.  

How To Win Friends & Influence People by Dale Carnegie

The 5 Love Languages by Gary Chapman

The 5 Levels of Leadership by John C. Maxwell

Rich Dad Poor Dad by Robert Kiyosaki

You Are Good Enough by Robert J. Furey


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