Jeff's Recommended Self-Improvement Reading

Below is an annotated list of some of my favorite books related to self-improvement and the general pursuit of excellence. It’s a pretty long list, so feel free to skip around to the areas that most grab your interest and come back to revisit when you’re looking for something new. It’s by no means comprehensive, and I’ve always got a whole stack of books waiting to be read, so expect updates and additions down the road. The books below are listed alphabetically by author’s last name within each category.

No time for even skipping around to your favorite categories? Check out my top three.

 

The TL;DR Top Three

As mentioned above, the following list is pretty extensive, and I know you’ve got plenty to do, so here are the three that I would recommend everyone here read regardless of your interests.

Tools of Titans by Tim Ferriss

Developed from hundreds of interviews available as The Tim Ferriss Show podcast, this book deconstructs the habits, ways of thinking, and tools of top performers in multiple fields, from Arnold Schwarzennegger to Tony Robbins, there’s something in here for everybody. If you’re unfamiliar with Tim Ferriss and don’t have a more specific need (like working out or learning to cook), I recommend this book as the best starting place, as it captures much of what is in his other three, but with added insight and development.

Deep Work by Cal Newport

One of the most recent additions to this list, this book has changed my life. I know you hear that all the time, but I literally mean every day of my life I consciously plan, act, and reflect differently since reading this book than I did before. Recommended to me by a close friend who is as obsessed with personal betterment as I am, it makes the case that in a world of increasing education and automation, the key differentiating skill you can build is the ability to focus deeply on things that matter. I especially recommend this book if you struggle with distraction, feel hassled or hurried all the time, or ever wonder what happened to the days where you could sit and concentrate on one thing for hours at a time. You can sample a lot of Cal’s work at his excellent blog Study Hacks.

The War of Art by Steven Pressfield

Seth Godin called this “The most important book you’ve never read” in his forward to Do the Work. I keep a copy where I can see it at all times, and it has deeply influenced how I think about work and productivity and life. It’s core argument is that we are all struggling against Resistance, an active, malignant force that grows out of our evolutionarily-derived monkey brains and the pressures of society to hold us back from achieving what we might and to share our individual spark with the world. Extremely motivating and extremely brief - I read it on a flight from Houston to Dallas and was finished before we got to the gate.

 

Excellence

Ever since studying Classics and Ancient History in college, I have been obsessed with the concept of arete - a Greek word that captures the related concepts of excellence and virtue and striving to be the best. It has shaped my love of self-improvement, and it is constantly in my mind. These two books embody that concept, giving specific directions on how to strive for arete, even if they don’t call it that. If you only read one book on this list, I recommend one of these.

Tools of Titans by Tim Ferriss

Developed from hundreds of interviews available as The Tim Ferriss Show podcast, this book deconstructs the habits, ways of thinking, and tools of top performers in multiple fields, from Arnold Schwarzennegger to Tony Robbins, there’s something in here for everybody. If you’re unfamiliar with Tim Ferriss and don’t have a more specific need (like working out or learning to cook), I recommend this book as the best starting place, as it captures much of what is in his other three, but with added insight and development.

Deep Work by Cal Newport

One of the most recent additions to this list, this book has changed my life. I know you hear that all the time, but I literally mean every day of my life I consciously plan, act, and reflect differently since reading this book than I did before. Recommended to me by a close friend who is as obsessed with personal betterment as I am, it makes the case that in a world of increasing education and automation, the key differentiating skill you can build is the ability to focus deeply on things that matter. I especially recommend this book if you struggle with distraction, feel hassled or hurried all the time, or ever wonder what happened to the days where you could sit and concentrate on one thing for hours at a time. You can sample a lot of Cal’s work at his excellent blog Study Hacks.

 

Productivity

This is a personal favorite topic of mine, and the one where I find myself most often helping coaching clients. While it is only a piece of improving your life, it is one that has ripple effects in all other areas. Getting better at using your time, at working in an effective way, and at keeping track of what you need to do frees up mental bandwidth for the more interesting stuff and opens up your calendar to give you time to decide what you want to do - whether that’s start a business or put ships in bottles.

Getting Things Done by David Allen

This is the 800 pound gorilla of personal productivity books, and with good reason. David Allen clearly analyzes what stops us from being productive and breaks down work into separate tasks that can be optimized, and then delivers a totalized system for doing so. I use several of the concepts from this book in my own life and productivity coaching, but let me give you a word of caution: if you try to jump into this whole hog from day one, you are setting yourself up for trouble. It’s just too much stuff at once to do on your own for effective behavioral change. I have found the blog Restart GTD a tremendously useful supplementary resource, and it led me to one of the books I recommend below.

The Seven Habits of Highly Effective People by Stephen Covey

The granddaddy of self-improvement books here, it really focuses on a wider area than just productivity and time management, but that is what it is best known for. It synthesizes the information from hundreds of previously written self help books and lays out seven big picture habits for an effective life. My personal favorite is Habit #7, which is Sharpen the Saw - the reminder that from time to time you have to step back from the work you’re doing and improve your tools.

The Four Hour Workweek by Tim Ferriss

This is the book that kicked off my own personal journey into productivity and self-improvement more generally - as well as turning me into a lifelong Tim Ferriss fanboy. I credit it with my ability to simultaneously do a great job at work, crush an MBA, and land a management consulting job. While a lot of the specific tools and strategies recommended are extremely useful, this book is most valuable for forcing you to re-examine your assumptions about careers, entrepreneurship, and what you’re uncomfortable doing. Check out Tim’s blog for a taste of his approach and the kinds of material you might find in the book.

Do the Work by Steven Pressfield

This is a sequel of sorts to The War of Art below, and it is extremely encouraging in a gruff sort of way. I recommend reading both together, and then revisiting whichever one you think you need every year or so for the rest of your life. They’re both short, you can read them both in an afternoon. Here, Pressfield argues that the best way to overcome Resistance (more on that below) is a dogged workmanlike professionalism, and then proceeds to detail specific actions to take to develop that attitude. While the book is geared towards creative types, using the writing of a book as its case study, I find it is equally applicable to knowledge work of all sorts.

 

Exercise & Behavioral Change

I’ve lumped these two together because there’s a lot of overlap between habit building and exercise, especially any kind of reading about exercise. At the end of the day, we all know that to exercise, we need to do things that are hard physically, and do them regularly. Everything beyond that is details, which is why it’s so important to figure out the doing it regularly piece.

The House that Cleans Itself by Mindy Starns Clark

Okay, this one is a bit of an odd ball on this list, but here me out. I stumbled onto this book through the blog Restart GTD, and while it has a lot of great advice on how to make it easier to keep your home neat, it also taught me one of the most valuable behavioral change insights I’ve ever come across: if you have tried to do the right thing multiple times and failed, the answer is to make doing the right thing easier. It sounds ludicrously simple, but we have all fallen into the trap of “well, this time I’ll do the same thing I’ve tried before, but I’ll try harder.” Trying harder isn’t the right answer, you were trying hard last time. This book shows you a better way.

The Four Hour Body  by Tim Ferriss

I don’t have a ton of material on exercise in this list, which makes it look under-emphasized or unimportant, but nothing could be farther from the truth. Exercise is the practice that will have the biggest multiplicative effect on your life. Besides being stronger and faster (which is cool), you’ll also be smarter, happier, and healthier. Simply put, exercising makes you better at life. This book is my favorite guide to ways to optimize your approach to diet and exercise in a way that gets you the most positive outcome for the least effort necessary. Tools of Titans covers a lot of new ground in these areas, but The Four Hour Body helps to encourage the approach and mindset you need to realize you really can make massive changes to your body, health, and strength.

Learning

I have a passion for learning and want to do so as effectively as possible. These books focus on the skill of “meta-learning” - in other words, how you get better at the act of learning itself. These will act as accelerators for your interest in any of the other categories you see in this list.

The Four Hour Chef by Tim Ferriss

Man, this Tim Ferriss guy keeps showing up on here, doesn’t he? This is another book “in disguise” like The House that Cleans Itself. While it bills itself as a cookbook that will take you from “how do I boil water?” to complex and impressive meals, all of that is really a vehicle for teaching you meta-learning. Worth the price of admission for the first chapter alone, which breaks down Tim’s approach to learning new skills and tells you how to do the same. Oh yeah, and the recipes are pretty delicious as well.

The Art of Learning by Josh Waitzkin

Josh Waitzkin was the basis for the book and movie Searching for Bobby Fisher, and he has displayed a remarkable ability to learn and compete across a wide variety of fields from chess to Brazilian Ju Jitsu. This book discusses his approach to learning and distills it down to principles. It is a bit less immediately practical than some  of the other books on this list, but it is deeply wise and rewards re-reads and ongoing study. 

Philosophy & Motivation

It is all too easy to look past philosophy as some ivory tower pursuit divorced from day to day life - and indeed, a lot of more recent philosophy has become that. But when you turn back to the practical wisdom of the Stoics or Lao Tzu or the Buddha, you find specific recommendations on how to live the best life possible. These books will be especially useful in helping you figure out why exactly you care about being able to get more stuff done or build new habits.

Meditations by Marcus Aurelius

One of my best friends handed me a copy of this book my freshman year of college and said “read this, it’s good for you.” And man, was he right. Since then, the stoics have made up one of the biggest chunks of my personal philosophical thinking and reading. Meditations is great because Marcus Aurelius wrote it to himself, often in the form of short admonitions that make good instructions for us trying to follow the same example. 

The Art of Mindfulness by Thich Nhat Hanh

This delightful and brief book explains how to incorporate habits of mindfulness into your life. I’ve used it to find ways to meditate while walking into work from the parking garage, making coffee, or even just watching the wind in the trees. I have found meditation an extremely valuable habit to pick up, and this book is a nice straightforward primer. I’ve also recently been enjoying the blog Live and Dare, which has a nice, comprehensive explanation of the different types of meditation. A useful explanation of a term that often gets thrown around without being made very clear.

Ego is the Enemy by Ryan Holiday

An excellent examination of how Ego cripples our ability to succeed, destroys us when we’re on top, and pours gasoline on the fire when we fail. It uses numerous historical examples, good and bad, such as General Sherman and Howard Hughes, Jr. It is one of his works on applying stoic philosophy to the modern world, and I have found it a thoroughly useful corrective when I start getting too big for my britches.

Psycho-Cybernetics by Maxwell Maltz, M.D.

This is an oldie-but-goodie. Don’t be thrown off by the slightly goofy title, which might make you think of Terminator. It was a pioneering work in the importance of making use of your psychology to achieve your goals, and the role that internal self talk and visualization play in that. The tone can feel a little dated, but if you imagine of those 1950’s advertisement poster cartoons narrating it to you, it becomes charming rather than distracting.

Zen and the Art of Motorcycle Maintenance by Robert Pirsig

I have revisited this book time and again. The first time I read it, I found much to disagree with, but it was still deeply thought provoking. Over time, I’ve come to find it more and more useful and convincing. Probably my favorite aspect of it is how it finds the common threads in Eastern and Western philosophy. Not a lot of specific “how to” advice here, but it is remarkably valuable for making you think.

The War of Art by Steven Pressfield

Seth Godin called this “The most important book you’ve never read” in his forward to Do the Work. I keep a copy where I can see it at all times, and it has deeply influenced how I think about work and productivity and life. It’s core argument is that we are all struggling against Resistance, an active, malignant force that grows out of our evolutionarily-derived monkey brains and the pressures of society to hold us back from achieving what we might and to share our individual spark with the world. Extremely motivating and extremely brief - I read it on a flight from Houston to Dallas and was finished before we got to the gate.

Awaken the Giant Within by Tony Robbins

Tony Robbins is energetic and motivating to the point of intimidation. I as myself “how can that guy be so pumped all the time?” Well, this book is your starting place. I consider it a manual for overhauling your mental operating system. Whether you want to quit smoking or start a business, this book has the specific techniques you need to make it happen. It’s a bit long, but that’s because there’s a ton of valuable stuff in there.

Letters from a Stoic by Lucius Annaeus Seneca

A fun note - Ryan Holiday pointed out, and I’ve since observed the same thing, that people who like Stoic philosophy come in two flavors: Seneca and Marcus Aurelius. One or the other just seems to “click” with people, where the other doesn’t to the same degree. I enjoy both and find them both useful, but I’ve gotta count myself a Seneca man. He wrote these letters to a friend and protege of his in a very straightforward, friendly, and approachable manner. He uses practical examples and sympathizes with the difficulties of following stoic advice. The letters are also available as an audio book called The Tao of Seneca, which I was looking forward to recommending based on the samples I’ve heard via the Tim Ferriss Show (he published it and recorded the forward), but the Amazon reviews indicate that the audio quality is poor - so check it out at your own risk!

Antifragile by Nassim Nicholas Taleb

I’m a huge fan of all of Taleb’s works, but this was the one that hooked me and the one I come back to most often. It contains useful advice on personal finance and organizational design and diet, but really it is a work of philosophy, and it’s central premise is to highlight the existence of things that are neither fragile nor durable, but actually antifragile - they are improved by exposure to time, chance, and chaos. Things like your immune system or life on this planet as a whole all get better by exposure to “bad” things. I think of this book’s discussion of risk and what it really means daily.

The Tao Te Ching by Lao Tzu

Cryptic and mysterious, the seemingly paradoxical nature of much of this work is precisely its value. As a rational, straightforward kind of guy, I often have trouble thinking in more oblique or ambiguous ways, and this book is excellent training in that. I’d also point out that with all works originally composed in a foreign language, the selection of a translation can make all the difference in how useful, intelligible, or engaging it is. I’ve linked here to a well-regarded translation, but any time you’re considering buying a translated work, do some googling to find people’s thoughts on the different versions and compare the pros/cons.

 

Creativity

A Technique for Producing Ideas by James Young

Another wonderfully brief but extremely valuable book, this one steps through the process for coming up with creative ideas individually. While we’re all familiar by now with the idea that the subconscious works on things under the radar and suddenly ideas will seemingly appear, this book lays out the crucial steps before and after “just put it out of mind for awhile.” 

The Power of Innovation by Min Basadur

This one is a bit harder to find and lesser known, but details several tools that have transformed my professional life and greatly enhanced my ability to be creative consistently and effectively. Recommended to me by one of my mentors in consulting who studied with Dr. Basadur, this work emphasizes the importance of separating active divergence and active convergence, and details an 8 step creative problem solving cycle that can be usefully applied to all manner of business and personal situations. An extremely powerful set of tools for working creatively in any field, whether alone or as part of a group.

A Whack on the Side of the Head by Roger von Oech

A fairly well-known classic, this book is great for the practical tools it provides for being more creative. My personal favorite tool is the use of “oracles” - some kind of randomized input that you then have to make sense of. This technique can produce amazingly creative results.

Lateral Thinking by Edward de Bono

Here, de Bono spells out the difference between traditionally logical linear thinking, such as you use in mathematics, and the more freewheeling lateral thinking. He is careful throughout not to denigrate linear thinking, as it is necessary and useful in a lot of super important contexts, like science, but he does emphasize that lateral thinking has gotten the short end of the stick in our logic-worshipping western culture. The most exciting insight from this book for me was the notion that sometimes you have to have a bad or silly idea in order to get to a good idea. 

 

Personal Finance

While I don’t especially focus on personal finance, it is an essential element to get right in an extraordinary life, and I’ve found the following books very useful in thinking about and taking action on my own financial situation.

I Will Teach You to Be Rich by Ramit Sethi

I’m a big fan of Ramit’s, and I’ve purchased several of his courses online after reading and getting use out of this book. The actual financial advice here is reasonably straightforward and not too dissimilar from what you’d find elsewhere, but Ramit’s focus is on psychology and actually changing behavior, which is what I think makes this book stand out from the rest. It gives step by step instructions to build systems for consistently doing smart things with money automatically rather than wagging its finger at you to put together a detailed budget. If you want to set up some interesting compare and contrast, pair with my newest favorite money blog Mr. Money Mustache.

Money: Master the Game by Tony Robbins

This book is a bit of a doozy, but it is jam packed with specific advice and insights from some of the world’s most successful people in finance and investment. As with his other works, Tony makes it a point to step you through why something is important, what actions you need to take, and committing to yourself that you will take them. If you are already reasonably well versed in investments and personal finance, a fair chunk of this book will be remedial, but the advanced stuff is pretty great. My favorite technique from this book was pre-committing to a fixed percentage of all raises that will go straight into savings/investments so that you can increase your savings year over year and not even notice.

 

Leadership & Management

With a background in management consulting and the military, I get pretty excited about organizations and the people who direct them. These are a few of my favorites on how to run effective teams and get results.

Extreme Ownership by Leif Babin & Jocko Willink

Written by that stereotypical designator of badassitude “ex Navy SEALs”, this book has the highest bang for buck of any on leadership I’ve ever read. It presents simple (but not easy) leadership principles and illustrates them with engaging illustrations from the authors’ time in Ar-Ramadi, Iraq. Where I turn to Tony Robbins when I need to be more enthusiastic, I turn to Jocko when I need to be more of a hardass - this book will challenge you to be better and make you believe you can. One of the authors, Jocko Willink, also has his own podcast that I find extremely enjoyable and educational - and it will reveal the incredibly thoughtful and reflective mind that doesn’t necessarily come to mind when you hear “ex Navy SEAL”.

The Managerial Moment of Truth by Bruce Bodaken & Robert Fritz

Also recommended to me by a mentor in consulting, this book attacks the endemic problem of ineffective feedback and mediocre organizations due to a lack of honesty. Not that most folks are actually lying, this book makes it crystal clear that in unpleasant situations like falling short at work, it is all too easy to accept flattering or comforting views of reality instead of figuring out what to improve. It provides a step by step procedure for managers to instead give accurate, useful feedback that people can really act on. The most valuable habit from it is the seemingly simple technique to state and get agreement on the objective truth of what has happened that will be discussed.

Team of Teams by Stanley McChrystal

This book describes the challenges faced by the Joint Special Operations Command under General McChrystal in Iraq as they were facing off against Al Qaeda in Iraq in the aftermath of the coalition invasion, and the steps they took to address them. It describes their lessons learned in building organizational agility within the enormous bureaucratic monstrosity of the United States military and the remarkable results they achieved. I have used this book to inform my thinking on how to scale Agile work practices in large enterprises. This book pairs perfectly with the next one down on Scrum.

Scrum: The Art of Doing Twice the Work in Half the Time by Jeff Sutherland

Sutherland describes a project management methodology that was developed in the world of software development and is one way of embodying the Agile Manifesto’s ethos. What I have found using this method in several strategy consulting engagements is that it is extremely effective in other fields as well. While I don’t recommend you try to use the full-on Scrum methodology to run your own personal life, I have found the concepts of quantifying tasks by how much “effort” they’ll take along with retrospectives to facilitate continuous improvement absolutely invaluable. 

 

Conclusion

Whew, thanks for making it with me all the way down here! These books have had the biggest impact on my own self-improvement journey. Do you have any favorites that you don’t see? Let me know what they are! I’m always looking for new tools, new ways of thinking, and insights.


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