Personality and Trajectory (Part 1)

“The privilege of a lifetime is to become who you truly are.”

Carl Jung (1875 – 1961)

Personality has always been an interesting subject for me. I’ve always been interested in what makes people tick and what separates an individual from the rest of the crowd. Personality is one of the many factors which determine individuality. Personality can be thought of as a collection of qualities that make up our overall character. Over the years, there has been much debate over what those qualities are and how they present in human behavior. Today, multiple theories have been widely accepted by the public and are used in business practices.

Learning personality is a fantastic way to connect with and understand more people than we otherwise would, but I don’t just stop there, I like to use it to help determine a complimentary life trajectory. Learning about our own personality gives us an insight into what kind of life we would actually enjoy.

It’s too easy to get caught up building our life for other people or chasing romanticised ideals. This is how people get stuck with jobs and relationships that they hate. People think they want these things because someone else told them it was worth having or because they saw it in the media. I see this with my students all the time, they stress out over which career pays the most, is the most “secure,” or looks the most glamourous. I see students intentionally repress themselves in order to fit into a mold that they will never truly accept.

The trick to avoiding this pitfall is learning about what makes up our personalities and tailoring our trajectories to fulfill ourselves. If we know what we would like to do, then we can pick a role within society that can satisfy that. Sounds simple enough, but people don’t really act this way. We live in a complex society and there are roles that need to be filled by people of certain temperament. It’s better to fill these roles with people who naturally fit into them, rather than waste resources trying to fit a square peg in a round hole.

Our personality is something to take into account when we are designing the trajectory of our lives. It’s something we need to grapple with. It’s much easier to put ourselves in an environment which compliments our strengths, than to reject or ignore part of ourselves which cannot easily changed.

In this post, I’m going to talk about a popular theory of personality. It’s slightly outdated and not entirely scientifically inaccurate but it is widely accepted and used in many institutions, so it’s useful to “be in the know” with this information. Plus it’s fun party talk.

Myers-Briggs Personality Types

Myers-Briggs Personality Type Indicator or (MBTI) is a method of categorizing people through a questionnaire which outlines the differences in how they perceive the world and make decisions. It was created by American mother-daughter duo, Katharine Cook Briggs and Isabel Briggs Myers. MBTI is widely accepted throughout the business world as well as socially, especially in the United States.

Contrary to popular belief, MBTI does has significant scientific deficiencies, poor reliability, and is not entirely comprehensive of human personality. However, MBTI is useful to know because it gives us a common language with people who do accept it. MBTI is popular in the corporate world, because it does an excellent job in categorizing people without hurting anyone’s feelings. This theory of personality has a way of making everyone seem like they have no downfalls and can always contribute, which is powerful in business environments. Businesses tend to do better when the people who run it feel better. Empirical personality data isn’t as relevant to performance as we would expect. MBTI is also fantastic at providing a basic structure for understanding personality, but it’s crucial to know that it does not supply us with the whole picture.

MBTI is based on the assumption that people have specific preferences for interpreting experiences and pursuing our desires. It also draws from Carl Jung’s typology theories which suggest people have four modes of cognitive functions (Thinking, Feeling, Sensation, and Intuition) as well as one of two polar orientations (Extraversion or Introversion). Even though Jung’s theory of psychological types was not based on empirical scientific studies, they were based on clinical observation, introspection, and anecdotes. Since the conclusions did not originate from controlled scientific studies, they are not accepted by the scientific community. However, Carl Jung was an amazing thinker and I do believe he was one of the few operating with precision at the edge of our collective understanding. His conclusions, from his observations or otherwise, were always made with the intention of bringing man closer to truth that we all can accept.

MBTI sorts out personality in 4 major continuums. Each person leans more towards one pole of each pair similar to right-handedness or left-handedness. When a person determines which side of each continuum they express, they are assigned a type. There are a total of 16 different types, 1 for each combination of the letters.

Let me give an example using my own letters. I’m more introverted than extroverted. I’m more intuitive than sensory. I’m more of a thinker than a feeler. Usually I’m more perceiver than judger, but recently I have been more judger than perceiver. This gives me the letters INTJ. (Some days I’m an INTP) The letters come from the capitalized letter in each word: Introverted, iNtuitive, Thinking, Judger.

Extroversion vs. Introversion

MBTI and Jung use introversion and extroversion in similar ways. Introversion meaning inward-turning and extroversion meaning outward-turning. These both are often referred to as attitudes that one uses to function in the external world.

Simply put, extroverts are recharged by people while introverts are recharged by alone time. Each type is usually drained by the opposite activity, extroverts are drained by alone time and introverts are drained by social interaction. However, there are other notable differences between them.

Extroverts direct their energy towards people and objects while introverts direct theirs towards concepts and ideas. We can always find out which attitude people take by paying attention to the topics of their conversation or asking them what their ideal weekend would look like. If someone is frequently talking about people and things they’re most likely extroverted. If someone is frequently talking about concepts and ideas they’re most likely introverted. An extrovert’s ideal weekend is probably spent going out and seeing a bunch of people, celebrating at the club, or another type of high energy ordeal. An introvert’s ideal weekend would probably be spent inside with a good book or TV show along with ample time for reflection.

This is not to say that extroverts can never be alone, or that introverts hate being with people. Everyone needs some amount of social interaction and alone time. Our attitudes merely reflect our preferences and how we choose to interact with the world around us. Neither attitude is more advantageous or otherwise, they are simply two sides of the same coin.

The following statements will apply to you if you are more extroverted:

  • I am seen as “outgoing” or as a “people person.”
  • I feel comfortable in groups and like working in them.
  • I have a wide range of friends and know lots of people.
  • I sometimes jump too quickly into an activity and don’t allow enough time to think it over.
  • Before I start a project, I sometimes forget to stop and get clear on what I want to do and why.

The following statements will apply to you if you are more introverted:

  • I am seen as “reflective” or “reserved.”
  • I feel comfortable being alone and like things I can do on my own.
  • I prefer to know just a few people well.
  • I sometimes spend too much time reflecting and don’t move into action quickly enough.
  • I sometimes forget to check with the outside world to see if my ideas really fit the experience.

Sensing vs. Intuition

This dichotomy is based on how we psychologically perceive the external world. These are both functions of gathering information. Sensing individuals tend to trust information that is tangible, concrete, and understood by the five senses. They’re less likely to trust “gut feelings” or other “hunches” that come out of nowhere. For them, meaning lies in the data, what is in front of them.

Individuals driven by intuition tend to trust information that is remembered or discovered through analyzing patterns. Since they trust information that doesn’t have to fit within the five senses, they tend to be more excited by what the future has in store. For them, meaning is not in the data but the principles and theories which underlie the data.

The following statements will apply to you if you perceive through sensing:

  • I remember events as snapshots of what actually happened.
  • I solve problems by working through facts until I understand the problem.
  • I am pragmatic and look to the “bottom line.”
  • I start with facts and then form a big picture.
  • I trust experience first and trust words and symbols less.
  • Sometimes I pay so much attention to facts, either present or past, that I miss new possibilities.

The following statements will apply to you if you perceive through intuition:

  • I remember events by what I read “between the lines” about their meaning.
  • I solve problems by leaping between different ideas and possibilities.
  • I am interested in doing things that are new and different.
  • I like to see the big picture, then to find out the facts.
  • I trust impressions, symbols, and metaphors more than what I actually experienced.
  • Sometimes I think so much about new possibilities that I never look at how to make them a reality.

Thinking vs. Feeling

Thinking and feeling are based on how we prefer to make choices in the external world. Both thinkers and feelers make rational choices based on certain kinds of information which were gathered from their senses or intuition. Thinkers tend to make their decisions based on objective measures while aiming to be reasonable, logical, or causal. They are usually personally detached from their decisions and try to match their choices to a given set of rules. Thinkers also tend to have low tolerance for those who are inconsistent or illogical. Thinkers give direct (and sometimes harsh) feedback and view the truth as more important than feelings.

This is not to say that thinkers never make emotional decisions, MBTI simply lets us know one’s preference in decisions making and is not a predictor of behavior. They also don’t “think better” than their feeling counterparts. MBTI doesn’t measure cognitive ability, just preferences.

Feelings types tend to make their choices based on empathy, balance, harmony, and with consideration for others’ needs. Feeling types try to see what works best for everyone involved and are willing to sacrifice logic and truth for the good of the majority. 

Thinking types will have a hard time leading a healthy and productive life if they make their choices based on their feelings, while feeling types will have a harder time leading a healthy and productive life if they make their choices based on their logical reasoning. Both types tend to lack the opposite senses necessary to make good choices. Similar to our attitudes toward the external world (extraversion vs. introversion), one isn’t better than the other, they are both different sides to the same coin.

The following statements will apply to you if you decide through thinking:

  • I enjoy technical and scientific fields where logic is important.
  • I notice inconsistencies.
  • I look for logical explanations or solutions to most everything.
  • I make decisions with my head and want to be fair.
  • I believe telling the truth is more important than being tactful.
  • Sometimes I miss or don’t value the “people” part of a situation.
  • I can be seen as too task-oriented, uncaring, or indifferent.

The following statements will apply to you if you decide through feeling:

  • I have a people or communications orientation.
  • I am concerned with harmony and nervous when it is missing.
  • I look for what is important to others and express concern for others.
  • I make decisions with my heart and want to be compassionate.
  • I believe being tactful is more important than telling the “cold” truth.
  • Sometimes I miss seeing or communicating the “hard truth” of situations.
  • I am sometimes experienced by others as too idealistic, mushy, or indirect.

Judging vs. Perceiving

This dichotomy is based on how we relate to our perceptions of the external world. This continuum is heavily influenced by our sensing and/or intuitive natures, because we are either judging or perceiving the information obtained through those perceptions.

Judging types take in information with the intention of using it later and, in the words of Myers, like to “have matters settled.” They usually have a plan in mind and are only interested in information if it’s related to their goal in some way. They tend to be more comfortable once decisions have been made and the environment around them is under control.

Perceiving types take in information for the sake of learning. They love knowing things just to know them. Perceiving types learn about and adapt to the world around them rather than structure it themselves.

The following statements will apply to you if you perceive your information by through judging:

  • I like to have things decided.
  • I appear to be task oriented.
  • I like to make lists of things to do.
  • I like to get my work done before playing.
  • I plan work to avoid rushing just before a deadline.
  • Sometimes I focus so much on the goal that I miss new information.

The following statements will apply to you if you perceive your information by through perceiving:

  • I like to stay open to respond to whatever happens.
  • I appear to be loose and casual. I like to keep plans to a minimum.
  • I like to approach work as play or mix work and play.
  • I work in bursts of energy.
  • I am stimulated by an approaching deadline.
  • Sometimes I stay open to new information so long I miss making decisions when they are needed.

For more information on each of the MBTI traits, I suggest going to myersbriggs.org. It’s the place to go for more thorough explanations of everything MBTI and where I got most of this information, like the relevant statements for each type.


Like I said earlier, personality changes throughout our lives and these letters are just letting us know our proclivities, not defining who we are as people. However, knowing my MBTI can give me an insight into what kind of life trajectory I would be the most satisfied with with the least friction.

According to my MBTI, I would most enjoy a trajectory which: provides me with ample alone time (I). opportunities to discover new information (N). puts me in environments where the culture values reason, logic, and causality (T). gives me the opportunity to make decisions on my own time at my own pace (J).

Through understanding our personality, we can create paths for ourselves which compliment our proclivities. For example, if I were extroverted, I would probably best enjoy myself in an environment surrounded by others.

While MBTI can give us delightful insight into what life trajectories would best compliment our nature, there are some criticisms that are important to consider:

  • These types are generalizations which do not accurately describe an individual.
  • There are people who do not fit nicely into these 16 groups.
  • MBTI suggests that there are no negative personality traits.
  • MBTI is widely accepted in the workplace, even though there is no evidence that supports MBTI is predictive of performance.

There are others, but these are the ones I’ve encountered to be the most substantial. All these criticisms bring up the question:

Why still use MBTI?

It can give us a rough idea of what kind of life trajectory we would fit well with and as I’ve talked about in my other posts, we do things badly before we can do them well. If we want to design a beautiful life trajectory, we need a rough starting point. MBTI is great for that. Plus it’s fun party conversation if you ever run into an MBTI nerd. Additionally, since MBTI is commonly accepted in the workplace, it’s useful to be in the know when people try to use it’s coded language.

Find your letters and start discovering which paths most align with you.

In the modern world we have choices, why not choose what fits us?

Categories
Education Productivity

The Valley of Disappointment

“We often expect progress to be linear. At the very least, we hope it will come quickly. In reality, the results of our efforts are often delayed. It is not until months or years later that we realize the true value of the previous work we have done. This can result in a “valley of disappointment” where people feel discouraged after putting in weeks or months of hard work without experiencing any results. However, this work was not wasted. It was simply being stored. It is not until much later that the full value of previous efforts is revealed.”

James Clear

The Expectancy Curve

In James Clear’s fantastic book Atomic Habits, he explains the idea of the expectancy curve. I think it’s a great tool to overcome imposter syndrome or any other form of the attack. The expectancy curve helps us keep going by giving us a frame to understand our insufficiencies.

Whenever we learn something new, we expect our progress to follow a straight line but in reality our progress is more parabolic. This results in a period of time when we are performing at a lower level than we’re expecting. This time period is called The Valley of Disappointment and it’s duration depends on the skill and how much deliberate practice we choose to put in.

When we feel like we’re underperforming, it’s easy to feel like we aren’t “meant” to do that new thing but all we need to do is stick with our newfound skill until we reach the critical point. The critical point is where the level of our skill matches our expectations. When we reach the critical point we stop suffering from imposter syndrome, feel more confident in our abilities, and (most importantly) keep developing our skills.

Most people stop cultivating their skills when they’re in the valley of disappointment but the ones who make it to the critical point can start to reap the benefits of their faith, consistency, and hard work.

I’ve seen this play out in a number of skills but I found this especially true in music production, hurdling, and cooking.

It can take weeks, months, or even years to get to the critical point. When I first took up music production, I was told that I would have to practice producing for 5 years before I would be able to compose, mix, and master a song from start to finish.

This was me kind of understanding The Expectancy Curve and The Valley of Disappointment years before I could articulate it. The idea of The Valley of Disappointment and taking 5 years before I could complete a song gave me a longer time frame for proficiency. This longer time frame is what made it easier for me to cut myself some slack. That freedom to make mistakes helped me grow. I always thought that made me a little insane but [Kobe Bryant] talks about having the freedom to make mistakes and how that leads to accelerated growth too.

This isn’t to say that The Valley of Disappointment isn’t a tough place to be. It’s easy to think all the work we’re putting in is futile and insane but it isn’t. The work we put in while we’re in the valley is exactly what gives us the ability to move out of it and enjoy the fruits of our labor later on. Deliberate practice is never wasted effort. Our efforts compound over time and this is especially true with skill development.

It’s difficult to move past The Valley of Disappointment but I do think as we learn more we find peace in our insufficiencies. The more I learned about music production, the more I realized that the experienced producers who said music production had a 5 year valley of disappointment were right. The more I learned, the more I realized how much I didn’t know. (Which totally applies to everything btw)

“Be not afraid of going slowly; be afraid only of standing still.” 

Chinese proverb

The whole idea is to stick with things for a while. Ask people in the field how long it took them to feel comfortable and confident in their position. I remember an ER doc saying it took him 10 years before he felt like he reach his critical point. Proficiency take time.

I find that knowing The Valley of Disappointment exists helps me get through it. The upset is temporary and I know I’m right around the corner from being a badass.

Categories
Lifestyle Productivity

The Mamba Mentality

“To sum up what Mamba Mentality is, it means to be able to constantly try to be the best version of yourself. That is what the Mentality is -it’s a constant quest to try to better today than you were yesterday.”

Kobe Bryant (1978 – 2020)

The Mamba Mentality is a highly effective way of developing your skills. Kobe Bryant, aka Black Mamba, developed this method after his first season playing basketball. The Mamba Mentality is a tested and proven way to bring you from the bottom of the dog pile to the Greatest of All Time.

A trip through time…

When Kobe Bryant was about 10 or 11 he was in a summer basketball league. During this season, he scored a grand total of 0 points for the ENTIRE season. Naturally, he was crushed and his father told him it doesn’t matter if you score 0 or 60 points I’m going to love you either way. This gave Kobe the confidence the needed to confront failure powerfully but he didn’t want to score 0 points. After that season, he spent his days focused on the fundamentals while his teammates relied on their athleticism. Eventually, practicing of the fundamentals caught him up to his teammates and his athleticism followed shortly after. By the age of 14, Kobe was the best basketball player in the state regardless of age.

This sounds like an incredible accomplishment but Kobe says it’s simple math: If you are playing for 2-3 hours every day and everyone around you is playing 1-2 hours twice a week, who’s going to be better? Skill development is not only a function of time, but time is a necessary ingredient.

There are two main pillars of the mamba mentality:

  • Show up and work every day, no matter what.
  • Rest at the end not in the middle

Incremental Consistent Progress

Putting work in every single day, even just for a few hours, is the edge you need over your competition. The sad fact of the matter is, not everyone will be giving their 100%. So, if you are giving your 100%, then you can’t lose. And part of that effort is showing up every. single. day. no. matter. what. By the time a years rolls around, or even 6 months, the results are noticeably different. I’ve seen this idea represented in Jeff Olson’s The Slight Edge and I’ve tried it for myself.

I apply this pillar of the mamba mentality to my learning. I learn something new every single day no matter what. It brings a child-like bliss into my life and I become a better person every day. After a few years, people have no considered me an expert in things that I would never dare claim expertise in. Apply this everywhere and watch the unimaginable unfold.

Restful rest vs. Stressful Rest

The difference between restful rest and stressful rest lies in the second pillar of the Mamba Mentality. Kobe suggests to rest at the end and not in the middle. This can apply to workouts, homework assignments, projects, whatever goal you have with a definite end. When we forstall resting and push all the way to the end, we train ourselves in endurance and tenacity but we also get to rest much more peacefully. When we rest at the end, we know the work is over and we can enjoy the much deserved breakrestful rest. When we rest in the middle, we have to get over the activation energy required to start again (which sucks) but we also can’t rest as peacefully because we are anticipating the stress to begin again – stressful rest.

I’ve applied this to my workouts and I’ve gotten better results than when I was resting whenever I felt tired. Make no mistake, it’s painful to rest at the end but it’s worth it. I’ve also applied this to cleaning my room, writing, making music, working, and tons of other places.

In this interview Kobe beautifully lays out the foundation of the world renowned, Mamba Mentality.

Starts at 2:11

Show up every damn day and just do it. Don’t stop until you accomplish what you set out to do. Apply these two principles and skill development is a piece of cake.

Categories
Education Lifestyle

My Must Read Book List

“A reader lives a thousand lives before he dies . . . The man who never reads lives only one.”

George R.R. Martin (1948 – )

Here’s a list of all the books that had a massive impact on my life and would bring tremendous value to everyone else too – in no particular order:

Laws of Human Nature (2018) – Robert Greene

This is hands down one of the best books ever written. When I read the title, I thought it was too ambitious to try to capture human nature in a book but Robert Greene was the perfect man for the job and he did it fantastically. Greene beautifully outlines the underlying forces that control our behavior and gives us the tools to recognize them within ourselves and others. After reading this book, I was given new insights on what really drives human beings and the pitfalls that we should be aware of as we navigate life. I was especially impressed and surprised with the chapters on narcissism and envy. Greene opened my eyes to how deep those two forces run in our society today and how dangerous it can be. I went to a book signing when it was first released and Robert said it’s important to read this book as as insight into ourselves rather than as insight into other people. I cannot say enough positive things about this book. Right now, it’s my #1 most recommended book for everyone to read. Buy a copy for yourself. Buy a copy for someone you really care about. Then buy another copy for someone they care about. This book is too important to skip over.


Outwitting the Devil (1938) – Napoleon Hill

Napoleon Hill is the O.G. when it comes to writing about success. OTD isn’t as popular as Hill’s best seller, Think and Grow Rich, but it shares many similar themes. The concepts that Hill uncovers in this book laid the foundation for a majority of my own personal development. Styled as an interview between an intelligent human and the devil himself, Hill captures how the devil is very much alive and well in our world — just not in the way that we think. Idle hands truly do the devil’s work. He cautions us of the dangers of being a drifter, the power of definitive purpose, independent thought, and hypnotic rhythm. A fantastic read for anyone who wants to get into reading and doesn’t know where to start. This book really helped me out when I first got out of college. It really gave me the tools to outwit the devil that I didn’t even know I was battling.


Tao Te Ching (~4th Century BC) – Laozi

This ancient Chinese religious text details the common principles of Eastern thought. A must read if you want to live well. The wisdom written in this book is timeless. The book itself is a practice of minimal necessary effort. So it’s a short, easy, but deep read.


Show Your Work! (2014) – Austin Kleon

This book is so great for creative types who have trouble putting their work out. It’s also great for those wondering how to get their creative endeavour started. It’s given me new and fantastic perspectives about creativity and what it means to make art. We should all strive to be amateurs – Sharing my art inspires others and contributes to the culture around me – No one artist or genius was created in a vacuum. This book has shown me countless ways to be inspired by and inspire others. It’s also filled with creative methods from so many unique creative types. If you want to unleash the creative side of yourself – read this book.


Lord of the Flies (1954) – William Golding

Lord of the Flies is a masterpiece. It’s about a group of boys stranded on an island and their attempt to govern themselves. Golding perfectly nails the complexities of the human spirit. He captures the everlasting struggle between our desire for order and tendency for chaos. This book is gripping and perfect for anyone looking for a good story. Even putting the themes aside, the plot is interesting and the characters are lovable. This was one of the first books that opened my eyes to the power of reading. For the first time, I saw that characters in a book can be as complex as people in real life. I used to think characters in books were just representations of the author, but Golding showed me that people can put enough thought and care into a book and create a literary mural that represents humanity.


The 48 Laws of Power (1998) – Robert Greene

I think about this book at least four times a week. This is the book that Andy from The Office should have read to truly win over Michael Scott. This was Robert Greene’s first book and it took the world by storm. He explains each of the 48 laws of power with examples from history of how each law can be used to one’s advantage and disadvantage. In his early days, similar to Benjamin Franklin, Robert Greene found himself getting the short end of the stick on many situations. He took his intense frustration and anger and articulated each and every trick that his superiors would use on him. This book helped me understand the power plays used on me in the past but the best part, is being able to spot the power moves others try to pull on me now. The world belongs to those who read.


Poor Richard’s Almanack (1732) – Benjamin Franklin

Benjamin Franklin is one of my favorite people in history. He’s accomplished enough for 10 men and in Poor Richard’s Almanack he lays out his basic principles which set the foundation for his success. I love this book because the principles are so simple and, for the most part, common sense. It’s essentially a list of 670 nuggets of wisdom. Most people link the famous idioms “Early to bed and early to rise makes and man healthy, wealthy and wise,” or “An apple a day keeps the doctor away” with this book. One of my favorite quotes was “Keep thy shop, and thy shop will keep the.” It’s one of those books that you can go back to and always find something new. The best part is it’s free and you can probably read the whole thing over your lunch break.


I Will Teach You To Be Rich, Second Edition (2019) – Ramit Sethi

Yeah, the title is sounds scammy but it’s legit. Ramit Sethi goes over all the financial knowledge necessary to build an automated money machine that can help you live a rich life. This book gave me a solid understanding of financial fundamentals to take control of my own finances. Since I didn’t study anything financial in my formal education, it was really helpful to learn about credit card optimization, 401(k)s, Roth IRAs, Health Savings Accounts, Target Date Funds, stocks, and bonds. He even includes scripts to negotiate down interests rates, remove banking fees, and asking for raises. Admittedly, I read the book in two weeks and applied the principles over a four week period but by the end of it, I established my own automated money machine equipped with an emergency fund, multiple savings accounts and a retirement investment portfolio. However, the most important thing I learned from this book is that we can learn how to do anything if we decide to go out and look for the information. Investing my money and learning all the financial jargon seemed out of my depth, but this book showed me that everything can be learned.


On The Shortness of Life (49 AD) – Seneca

I first heard of this book from Maria Popova. She is a fantastic writer and runs a blog (there really should be a different word for what she does) called Brain Pickings. It’s a huge archive of the deepest ideas from an extremely well articulated writer. Maria recommends people to start with her post about this book. I read her post and loved it. Then I read this book and it changed my life. Seneca talks about how there is more time than life. So much more that we actually waste it. How much of our lives are spent trying to answer the question at a dinner party, “so what do you do?” We give most of our time to others and much of the time dedicated to ourselves is in the service of impressing others. It’s no surprised life is exhausting. The key is to take the time back for ourselves. Seneca suggests that if we were to give all the time we were allotted on Earth to ourselves then we would greet death with open arms. This book has given me a damn good reason to let go of the idea that life is short.


The 4-Hour Workweek (2007) – Timothy Ferriss

Oh boy. To be honest, I’m not sure where to start with this book. Read it. It’s literally a manual to escape the 9-5 and live like the new rich. This is the first book I’ve read from Tim Ferriss and I fell in love with it. Tim breaks down what it means to start and automate a business that gives you the money and freedom to live your dream life. Tim started a mega successful online business in his 20s which gave him a pretty solid fortune. However, he was spending literally all of his time working (specifically replying to emails). Tim, being the unique thinker he is, found a way to restructure his business to maximize his efforts and run his company with only a few hours of work a month. This book isn’t literally about cutting your workweek down to 4 hours, its about maximizing the output of the work so you can free yourself up to do the things that really matter. He has ways to increase productivity with lower levels of stress and effort for all types of jobs. Whether you own your own business, work for an idiot boss, or are looking for a way to escape the rat race, this book is a must read. He’s included little “life hacks,” mindset switches, and resources that you may need to start an automated business. Pair this with Ramit Sethi’s just as scammy sounding book I Will Teach You To Be Rich and you have the tools necessary to design and live out your rich life.


Mastery (2012) – Robert Greene

Robert Greene is a powerhouse and heavy hitter when it comes to writing damn good books. This book is a guide to mastering anything. Robert researched masters from all walks of life throughout time and found the common threads between each of them. He covers everyone from Mozart to Charles Darwin to Temple Gradin to Freddie Roach. My favorite person he writes about in this book is Benjamin Franklin. I love how Greene outlines Franklin’s journey to mastery in writing and social interactions. Robert goes above and beyond for this book (as usual) and takes things much further than the typical skill acquisition advice like the 10,000 hour rule or practicing every day. I saw Robert Greene at a book signing and he said that he writes books out of anger. When he wrote this book, he said he was angry that people couldn’t make things well anymore. So I like to think of this book as a guide to learning how to do things well.


The Art of War (~5th Century BC) – Sun Tzu

Perfect reading for learning war strategies on a battlefield. Also perfect reading for MBA types about to enter the business world. Also perfect reading for anyone who finds themselves in adversarial situations. This book is pure wisdom when it comes to war, or anything that can resemble a war. Sun Tzu’s philosophy on war is to win without fighting. Running in head first into a battle is a sure way to get yourself killed, lose resources, and cause long term damage to the state. It’s better to cultivate your defenses, fortify your plans, and only fight when you know you are going to win. This is a quick and short read. The Art of War was originally written for military strategy but that doesn’t mean it can only be applied in the literally battlefield. Much of our encounters and challenges we experience today are war-like and the principles discussed in the book are worth applying to other areas of life. I have a thing for books written mad long ago but are still relevant now. This was written around 5th century BC but the lessons have been true throughout time. Timeless books are the best books.


The 4-Hour Body (2010) – Timothy Ferriss

One of Tim’s main goals in life is to learn something once and never have to learn it again. To make this happen, he takes meticulous notes on his diet, work out, habits, etc. so when he sees a picture of himself years prior he knows exactly what he was doing to get the body he had. He also keeps journals too, so he can do a similar type of assessment with his mental health as well. The combination of his meticulous note taking, years of experimentation, and hours of consulting physicians has given us this unconventional guide to healthier and easier living. Similar to The 4-Hour Workweek, this book is about getting the maximum results for the smallest effort. This book is filled with Minimum Effective Dosages (MEDs) for fat-loss, muscle gain, better sex, better sleep, reversing injuries, and much much more. I highly recommend this book for anyone that wants a guide to the human body.


Letters From A Stoic (65 AD) – Seneca

This book came up in the afterglow of reading On The Shortness Of Life. It’s a collection of letters Seneca wrote to his friend Lucilius. There are 224 letters and each one is on a profound topic. Reading these letters made me feel like I was getting to know Seneca personally. I love his humor and his unapologetic fanboy attitude towards Epicurus. What I loved the most about this book is that it explains Stoic philosophy within the context of something relatable which made it easy to see the usefulness of stoic practices. Wisdom is an art and this book is filled with it. Each letter is short but the ideas introduced will have you thinking about them for years to come. Every time I pick up this book it’s an absolute mindfuck. Seneca was able to articulate some of the most complicated thoughts I have ever had but never been able to say. This book was simultaneously a justification and condemnation of my perspectives and value structures and I love it. This book has wisdom beyond my years and I’m excited to see what else I’ll learn as I read the book with older eyes. This book has an extremely high reread value. Similar to Robert Greene’s The Laws of Human Nature, this is a book that you study – not read.


12 Rules for Life: An Antidote to Chaos (2018) – Dr. Jordan B. Peterson

Let me start by saying if you haven’t checked out Dr. Jordan B. Peterson’s work – check all of it out. This is his 2nd book and it’s more than worth the read but diving into his hours of lectures on YouTube will really take you for a ride. Peterson is a clinical psychologist from Canada who taught at the University of Toronto and Harvard. He’s spent decades studying the world’s best thinkers and reading some of the most complicated and influential texts. And through those studies, he’s articulated the true importance of meaning and responsibility. This book is a small part of that perspective. It originally was a list of 40 rules Peterson wrote in response to a post on Quora: “What are the most valuable things everyone should know?” Peterson cut down the list to 12 and wrote this book. Peterson said that these 12 are not necessarily the most important rules, but they do make a cohesive narrative together.


Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers (2016) – Tim Ferriss

Another Tim Ferriss masterpiece. Tim Ferriss is to me what Epicurus is to Seneca. Tools of Titans was written after Tim’s 4-Hour trilogy. The book was created from a plethora of interviews from The Tim Ferriss Show. Tim interviews the world’s highest performers about their habits, mindsets, and personal quirks that make them successful and put that in this book. He interviews everyone from Jocko Willink to B.J. Novak to Rick Rubin to Sam Harris to Maria Popova. Since there are so many people in this book, it’s easy to look up people that you already admire as well as discover new people to learn from. He breaks up the book in 3 sections (I love that it’s inspired by Ben Franklin): Healthy, Wealthy, and Wise. My favorite chapters were in the Wise section, but that’s just me. There is enough information in this book to build empires and has an extremely high reread value.


Updated October 20th, 2020
The Essays of Arthur Schopenhauer: The Wisdom of Life (1851) – Arthur Schopenhauer

Probably my favorite piece of work from the Great pessimist. I thought the title was too grandiose at first, but Artie delivered. This book truly contains the wisdom of life. There are some things he was pretty off on, but for the most part he was on point. He captures the beauty, rarity, and absurdity of life in a way that doesn’t play them up or down.

I also think this book is great because it’s like a collection of blog posts Schopenhauer would have written if blogs were a think in the 19th century. I’ve already written things in my blog that I don’t completely agree with and I could imagine that if Schopenhauer wasn’t bounded by his time that he would redact some of what he said. When we write down what we know, we are sure to be wrong but I believe it’s worth it to capture the things we got right.

Schopenhauer is a thinker for the ages and I highly suggest this book is someone who wanted to check out his work. He wrote it later in his life so his words carry the wisdom of his past works and it shows.


Games People Play (1969) – Dr. Eric Berne

This fantastic book goes over something called transactional analysis which is the study of how humans interact with each other. Berne suggests that everyone had 3 primary ego states — Child, Adult, and Parent and those ego states communicate with each other. The “games people play” are dependent on which ego state is communicating with what and how they do so. For example, there’s a game refers to as NIGYSOB (Now I’ve Got You Son Of a Bitch) is a game played between one’s parent ego state and the other’s child ego state. I might do a post on the different games mentioned in this book (at least the one’s I’ve found most prevalent) sometime because it’s almost unbelievable how much of human interaction are simply games.

On top of the incredibly deep analysis of human interaction, he sprinkles in humor throughout the book with smart ass comments and witty names for the games. This is book spelled out many ideas that I knew existed, but couldn’t articulate for myself and having access to these ideas gives me a greater understanding of human interaction and a special peace of mind.


The Seagull (1896) – Dr. Anton Chekhov

This is the first play I’ve put on this list and admittedly, the first play I’ve read since my appreciation for literature blossomed. I read this when I was at a point in my life when I felt like I had to choose between pursuing medicine and being creative and I was shocked to discover Anton Chekhov, famed playwright/physician. I first heard of Chekhov in Robert Greene’s Laws of Human Nature and I was so blown away from his story that I had to check out his work.

This play is super short and can easily be read in a few hours. The characters are brilliant and the story is beautiful. It’s a fantastic dramatization of the violence that occurs when a beauty is misplaced. One of the ideas I took from this play was “beautiful creatures in beautiful places will lead to destruction if things are not in their right place.” Chekhov created an excellent depiction of the realities of true rage, the struggles of the creative spirit, and the dangers of not being seen in the hearts and minds of others.

This play also gave me insights into what I was feeling as a creative person. If a Russian playwright could perfectly write about a similar struggle and capture my feelings perfectly, then what I was feeling must have been universal and archetypal. This realization lifted a huge burden on me because I realized that what I was dealing with could be surmounted by man and didn’t have to crush me.

If we’re not careful, we can all be like Treplieff.


The Checklist Manifesto: How to Get Things Right (2009) – Dr. Atul Gawande

I wouldn’t suggest this book to beginner readers, as most things written by doctors are long-form and operate at a certain level of complexity, but if you’re comfortable reading lengthy texts, then this is a great book.

I originally didn’t want to put this book on the list, but as I continued to write my blog and work with my students I’ve noticed how much this book changed my thoughts and actions. Any book that changes how I act and think on a daily basis for the better is worth putting on this list.

I guess that’s precisely what Dr. Gawande was referring to in the book as well — the idea that checklists are so easily overlooked, but also so effective.

Checklists are my primary go-to method for organizing the chaos and getting things done right. They are too simple and too effective to ignore.


Collected Works of C.G. Jung, Volume 9 (Part 1): Archetypes and the Collective Unconscious (1959) – Dr. Carl Gustav Jung

This is the deepest book I’ve ever read. On top of that, Jung is the smartest person I’ve ever had the privilege of reading. He accurately sums up the most abstract and complicated ideas in a concise way that’s easy to understand. Jung believes that humans encounter the experience of the unknown in similar ways, through archetypes. These archetypes are patterns of behavior coded in us from millions of years of human evolution and are the same no matter what society we’re from. The archetypes give us access to the collective unconscious which allows us a greater understanding of the human psyche.

Jung puts this way better than I could and has been a MASSIVE contributor to everything I do. The way I teach and conduct myself in the world is informed through my knowledge and understanding of the collective unconscious.

He doesn’t go into as much detail as I’d like in this volume, but he touched upon his famed archetypal ideas in a way that provides a rudimentary understanding to those who aren’t familiar. He talks in depth (by not deep enough) about the Shadow, the Anima (Great Mother), the Animus (Judgemental Father), and so many more.

This is the only book (so far) that I haven’t finished yet, but I’ve gotten through a good chunk of it. It’s so dense and rich with knowledge and wisdom. I knew that I had to put this book on my list when I was just a few pages in.

This guy sees the edge of human knowledge and goes there. Jung is probably my favorite author of all time. Read this book and get your mind blown.


Man’s Search for Meaning (1946) – Dr. Viktor Frankl

This book changed me life and I cannot understate it’s value. Everyone needs to read this book. It details the horrors of the Holocaust from the perspective of Jewish psychiatrist, Dr. Viktor Frankl. He is an incredible writer and captures such powerful images despite being traumatized himself. The images he describes were vivid and dark, but the lessons he learned about human beings are both beautiful and tragic. This book also outlines a method of created for his medical practice – logotherapy, which is based on the premise that meaning is our fundamental driving force as human beings.

This book is one of the most beautiful pieces of work ever created. Frankl showed us how people can really find meaning, even in the most hopeless situations. Meaning will carry us through any and all suffering.


Self-Reliance (1841) – Ralph Waldo Emmerson

This book is so dope. It’s written in a slightly outdated language, but the message is evergreen and powerful. He talks about the importance of self-reliance, giving to yourself, and the morality of only involving ourselves with the things which concern us.

In a weird way, this book was able to give me the reasoning I lacked to only concern myself with matters that concern me. I used to feel like I couldn’t act purely in my own interests, but this book has shown me that it isn’t only okay to act in my own interests but a moral duty, especially if my interests can make things better for me, my family, and my community.

One of the most amazing parts about it is that this was written while Emmerson was away from society locked up in a cabin in the middle of the woods. Then fast-forward almost 200 years, I’m reading it on an iPad in the comfort of my own bed. This realization had nothing to do with what he wrote, but it speaks to the power of writing. After I read this book, I was able to find the strength within me to write more vigorously and focus on myself and that led to incredibly important groundwork.


The Practicing Mind: Bringing Discipline and Focus Into Your Life (2006) – Thomas M. Sterner

Everything worth achieving requires practice and Thomas M. Sterner gives us techniques to develop the focus and discipline necessary to practice successfully. I’ve written an entire blog post based on the principles from this book that highlights some of the ideas that I thought were the most worth knowing.

Reading this book gave me a much-needed perspective on what it means to practice effectively. It’s so easy to see practicing as work, but after applying the methods Sterner talks about in the book, practice becomes a time full of meaning and purpose. Focusing on the process and intentionally staying present are highly underrated ideas that will bring out the best in anything.


The Personal MBA: Master the Art of Business (2010) – Josh Kaufman

This is a fantastic book on business. Honestly, it could be THE book on business if there was one. It’s cool to see all the fancy business jargon wrapped up all nice and neat and it’s doubly cool to see a book that’s kind of like the book I’ve been writing but in a completely different field.

It’s been a huge influence on me and how I run my business and is a must-read for anyone who’s interested in entrepreneurship. It goes over everything from value creation from marketing to sales to finance to the mind to creating systems and so much more.

I’m constantly finding myself going back to this book. It’s full of amazing information that is extremely useful when starting a business, especially since I never had any formal training. I read it shortly before starting my 1st official company and while I was reading it, I knew that I was going to be going back to it for years to come.

Whether you’re an expert or a beginner in business, this book is a must-read if you want to be intentional about your business.


The Slight Edge (2005) – Jeff Olson

When I first read this book I didn’t think the slight edge could be true because of the sheer simplicity of it, but then I started trying it in my own life.

I think everyone should still read this book (obviously because it’s on this list), but the slight edge as a concept is pretty simple — small disciplines over time is what determines our life outcomes. The good things we do make our life better, the bad things we do make our life worse. These outcomes work on an exponential basis so over time, the successful win more often and the losers lose more often.

The slight edge really is what separates the successful from the failures. Olson says the slight edge is what’s the difference between a beach bum and a multimillionaire because he’s been both.

I’ve also seen Kobe Bryant talk about this being the reason why he was so much better than everyone else in the NBA. He kept pushing when everyone else didn’t. It’s probably a cognitive bias thing, but after I read this book I’ve noticed it in so many places.

Like everyone – this list is forever in a state of becoming.