I was specifically asked to write on the topic of this post a while ago. It’s about time I got around to it.

A friend requested that I talk about the resources that helped me transition from a law firm office in Washington, D.C. to where am now. I don’t mean the packed bus in the-middle-of-nowhere Myanmar where most of this post was written, but rather traveling while working to make a location independent lifestyle a permanent reality.

Anya, this is for you. I hope it’s helpful.

I actually get the question fairly often. What did I do to prepare for quitting my job to begin traveling? My answer is always the same: Nothing. I just quit and let the chips fall where they may.

Eh, not quite. In truth, I spent over two years planning my exit and put significant effort into giving myself the highest chances of success when I finally did leave. My goal was to learn as much as I could about the world I was about to enter. I read dozens of books in the business, lifestyle independence, and personal development genres. I also scoured the web and listened to dozens of podcast episodes.

Because I did, you won’t have to. Here is my short-list of favorite resources for someone seeking to ditch the grind and pursue a more independent lifestyle.

Business and Entrepreneurship

The Four Hour Work Week by Tim Ferriss

Start here. In this groundbreaking title, Ferriss provides a fantastic summary of important concepts, location independent lifestyle business models, and essential resources. I let this one sit of the bookshelf for four years before I finally got around to reading it. Don’t make the same mistake.

The Personal MBA: Master the Art of Business by Josh Kaufman

Kaufman delivers a comprehensive review of the most important concepts in business and entrepreneurship. For me, this is an indispensable foundational read, along with 4HWW, for transitioning to an independent, entrepreneurial lifestyle.

The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future by Chris Guillebeau

Travel can be cheaper than a normal life, but it still costs money. One of the biggest obstacles to leaving the 9-5 to pursue location independence is just knowing the universe of income-producing alternatives. There are many titles that help fill that gap and this is the best I found. It’s an easy to navigate summary that includes practical examples of how-to’s and what-not-to-do’s from individuals who have made a similar transition.

Work the System: The Simple Mechanics of Making More and Working Less by Sam Carpenter

Carpenter used his own experience as an overworked business owner to develop a comprehensive process for leveraging systems to work smarter, not harder. Via the book and his online WTS resources, he provides concrete steps and an array of helpful templates for systematizing your approach to business. The principles and concepts are applicable well beyond just business.

The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It By Michael E. Gerber

This is an oldie but a goodie. The revised 2004 edition walks through the business lifecycle from startup to mature operation. It’s not specifically focused on lifestyle independence, but the framework complements the core concepts of the digital nomad lifestyle.

Productivity and Personal Development

Uncertainty: Turning Doubt and Fear Into Fuel for Brilliance by Jonathan Fields

A major challenge for anyone leaving a traditional career to adopt a non-traditional lifestyle is dealing with the fear and doubt that are inherent to such a drastic change. Fields provides a helpful summary of tools for achieving creative action in the face of extreme uncertainty. Uncertainty is especially valuable for personalities prone to risk-aversion (I’m looking at you, attorneys).

The Black Swan: The Impact of the Highly Improbable by Nassim Nicholas Taleb

Less tactical and more strategic than the other books on this list, The Black Swan brilliantly discusses the concept of risk and risk assessment. It is absolutely certain to impact the way you look at and interact with the world around you.

Getting Things Done: The Art of Stress Free Productivity by David Allen

GTD sets the standard for improving your personal productivity and is an essential tool for preserving mental energy for the things that truly matter. Allen describes a simple and practical system for effectively managing your personal and professional lives. Combining the GTD system with the Evernote app has had a profound impact on my personal productivity.

The First 20 Hours: How to Learn Anything Fast by John Kaufman

Kaufman describes a practical system for incorporating just-in-time learning into your daily life. For better and worse, the internet age has allowed human knowledge to be effectively outsourced. The First 20 Hours gives you a system for leveraging modern tools to learn what you need to know when you need to know it, and not a minute before.

Language Intelligence: Lessons on Persuasion from Shakespeare, Lincoln and Lady Gaga by Joe Rohm

From one of my favorite writers, this is an interesting and informative manual for anyone aspiring to rhetorical excellence. Language Intelligence contains invaluable techniques for improving and refining your communication skills.


That’s a pretty long list. Wading through that whole list, which I absolutely recommend, would take a lot time and effort. Because I don’t want you to suffer, here’s a secret that will dramatically reduce that time that it takes to become familiar with concepts in these books. Start your dive into the world of lifestyle independence here: http://sivers.org/book. Derek Sivers’ trove of book reviews is an amazing resource. Take advantage of it.

"Why would you do that? That's crazy!"