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My Operating Manuals for Life

If you accept that you have your own User Interface, you’re going to need some instructions on how to set it up and maintain it. As you know, my go to source for just about everything is books, and I have found those on the list below especially useful for hacking together my own mental operating system. They currently sit right on my desk where I can see them every day and think about what they mean to me.

Tools of Titans

This is the most practical book on this list, and I’m most confident it will be immediately useful to you.  I consider it the 80/20 solution of self-help books, the one to read if you can only read one.  Chock full of amazing tips, tricks, and strategies for improving your life in every dimension, I have adopted more ideas from here than I can keep track of. While all three of Tim Ferriss’s previous books have had a tremendous positive impact on my life, this is the capstone.

Awaken the Giant Within

Tony Robbins’s main work on personal transformation and behavior change. I have used this book not only to shape my approach to coaching but also to upgrade my own mental Operating System across the board. I have used it to ditch bad habits, take positive action in my life, and otherwise convince myself that my life is what I make of it. If you aren’t sure what you think of Tony Robbins, check out the Netflix documentary I Am Not Your Guru to get a good taste of what he’s about.

The Choose Yourself Guide to Wealth

The most recent edition to my collection, a month or two back my friend was like “you need to read this right now,” and he was right. James Altucher argues three main points in the book: secure corporate employment for your entire life is dead and gone, it’s up to you to bring value to the world, and the best way to do that is to follow a daily practice that nourishes and improves yourself mentally, emotionally, spiritually, and physically. He supplements all of this with a number of specific techniques on freelancing, selling, networking, and so forth. Some of the books on this list had already laid the groundwork for believing that financial success comes from no other source than me, but this book gave me the tactical kick in the butt I needed to start acting.

Deep Work

Equal parts manifesto and field guide, Cal Newport argues that focusing on one thing at a time and choosing important, hard work is a super power in a world of constant distraction. My own experience bears this out - when I most seriously follow the approach explained in this book, not only do I get more work done, I feel more fulfilled and happier about it to boot. This book is essential reading if you want to achieve mastery in anything or even just stand out from your peers at work.

**The Art of Learning **

One of the more challenging books on this list. I have revisited it multiple times, and every time I find a new insight I didn’t pick up before. Waitzkin has thought deeply and internalized several principles on learning and performance at the highest levels through his experience as a child chess master, world champion Tai Chi Push Hands competitor, top tier Brazilian Jiu Jitsu trainer, and a coach for the most successful hedge fund managers in the world. At times bordering on the mystical and opaque, you have to do your own share of the work with this book. Rather than concrete, actionable strategies, this book deals in fundamental principles that are relevant no matter the strategy you choose: which can be frustrating at times, but is more rewarding and useful in the long run.


Another book that doesn’t present easy, pre-digested material. We’ve talked about it somewhat extensively before. While there are a few specific how to’s scattered throughout, such as approaches to diet and exercise, it is far more useful as a foundational text on how to think about uncertainty. It’s another book where I find something new and get smarter every time I revisit it.

Zen and the Art of Motorcycle Maintenance

The only novel on this list, but don’t let that fool you - it’s still loaded to the gills with insight and useful introspective tools. This book was one of the first to seriously shake my arrogant belief that I understood myself deeply or even what “self” means. I agree with more of it every time I come back to it, and it has also been my personal bridge between stoicism and eastern philosophy - a more compatible pairing than you might think. If you’ve always thought Buddhism sounded like crazy woo-woo bullshit, start here.

The War of Art

The shortest book here, it punches way over its weight. I first read it cover to cover on an hour long flight and it lit my mind on fire. If you have anything remotely creative inside you trying to get out, you owe it to yourself to read this book. It is uncomfortable and galvanizing at the same time - like a cold shower, you will flinch from it at first, but emerge ready to take on the world. It is medicine I take whenever I find myself getting lazy and complacent.

Letters from a Stoic

A quick note on translations: these last two books were obviously not written in English, and the translation you select will have a big impact on what you think of it - generally stay away from the free Kindle editions, as these tend to be old, public domain translations of mediocre quality. If you want to get into the nitty gritty of why I chose these translations, shoot me an email and we can geek out.

My personal favorite work of stoic philosophy, it barely edged out Marcus Aurelius for my token Stoic book. Stoicism is such a central part of my personal philosophy that I could have easily chosen nothing but stoic books. Here’s a good overview of stoicism generally, but at the core of it are three men, each impressive in his own way: Marcus Aurelius, Seneca, and Epictetus.  While I appreciate all of them, turns out I’m a Seneca guy. It is shocking how modern and relevant his 2,000 year old letters feel. Writing to a young friend and protege, Seneca’s advice has the wisdom and clarity of an older mentor who has been there, wishes he had done better, and now advises his young friend to learn from his experience. Friendly, worldly, but with an unceasing dedication to living a good life, these letters are good for you.

The Poetic Edda

Based on the rest of the list, this may come as something of a surprise entry, but I find the myths in it both beautiful and meaningful. The Germanic myths lack the neat and tidy systemization imposed on Greek myth, leaving them with a raw vitality and tantalizingly missing pieces. With all my focus on rational stoicism and conscious improvement, I find it useful to remember the murkier subconscious parts of my mind that can only be accessed through stories of gods, monsters, and magic. Plus they’re viking myths so they’re super metal. If you’re still not convinced and insist on directly useful, you’ll find fewer collections of wisdom poetry more straightforward than the Havamal.

I know that there’s quite a lot to read here, but these are special and well worth the time. I encourage you to pick just one new book and give it a go today. It just might change your life.

Last modified on 2017-07-14