Some books you finish reading and you say, “Hmmm, that was interesting” and move on with your life.
Other books you highlight the crap out of, write down copious amounts of notes in the margins, and recommend to all your friends.
This post is full of the latter.
These books will teach you about running your own business, how to grow as an individual, and there are even a few jam-packed with inspiration. (A few of which you may have seen on the resources page.) You could easily read all of these in one year, and most of them are old enough for you to pick up for free at the library. I’ve read each of these books and I recommend that you do the following:
- Read them cover to cover.
- Use them as a reference throughout your life.
- Reach out to the authors to thank them for making your life better.
Below are the top 20 books that I consider “must-read” if you are looking to escape your cubicle, start working for yourself, or earn money online.
Amazon Listmania: The Essential Cubicle Renegade’s Library![]()
The Personal MBA by Josh Kaufman
I dropped five figures on a night-school MBA program while working full-time immediately after my undergraduate studies because my company fronted about 75% of the bill. If I were to do it all over again I may just have picked up The Personal MBA and used the time and money spent on an MBA to start a business instead. There are so many useful lessons and actionable pieces of advice you’ll be taking tons of notes when you read this book.
If you pick up just one book on this list, it should be this one. I even had the privilege to speak with Josh over Skype last week after he reached out to me through Expert Enough. He is already hard at work on another epic book (topic yet to be announced) and I’m excited to read that when it comes out too.
The Education of Millionaires by Michael Ellsberg
The Education of Millionaires is the most highlighted book on my Kindle. Michael set out to discover whether or not education has anything to do with success. He interviewed a lot of millionaires that either dropped out of college or never went, but have gone on to become the best in their field.
This book isn’t just filled with amazing behind the scenes stories from people that have become wildly successful in business though, Michael breaks down all the takeaways into excellent easy-to-understand lessons.
The Art of Non-Conformity by Chris Guillebeau
Chris is the one blogger that has been the most inspirational in my life. Heck, I bought the domain name PocketChanged.com and installed WordPress the night before I met him on his book tour just so I had a “blog” to tell him about.
This book doesn’t disappoint. The AONC lays out a framework to help you start living the life that you want. It also features a bunch of stories from people that are going against the grain and living unconventional lives. Pick this one up if you haven’t read it yet.
Book Yourself Solid by Michael Port
Whether you are a freelancer, business owner, or a service provider (meaning people pay you to do something for them) pick up and read Book Yourself Solid. The book lays out a simple system to follow for running all aspects of a one or multi person business successfully. The book covers everything from how to sell without being sleazy to a perfect system for increasing the amount of referrals you get.
I’m currently on my second time through this book and I’m picking up a ton of great actionable advice again. If you are struggling to really pin point what you want to do as an entrepreneur this book can help you narrow that down too.
The Thank You Economy by Gary Vaynerchuk
In this book Gary lays out a theory that money is not the most important currency online. Your riches can be measured in Thank You’s. The more people you directly help one-on-one online (whether that be through a simple reply on Twitter or an email) the more successful you will become. People want help and when you help them they will be your fan forever.
“It’s not the number of followers you have or “likes” you get, it’s the strength of the bond with your followers.” - Gary Vaynerchuk
Crush It! by Gary Vaynerchuk
If you need a swift motivational kick in the pants, pick up Crush It. Gary tells a bunch of stories of how getting to where you want to be in life is not about getting a lucky break or being born rich, it is about working hard.
Now is the time to start working towards where you want to be in life. Not tomorrow. Not next year. Now.
“The best marketing strategy ever: CARE.” - Gary Vaynerchuk
Career Renegade by Jonathan Fields
Once I started considering ditching the 9-5 grind I picked up both this book and the book by Pam Slim below. Jonathan lays out a plan for you to follow if you are looking to break out of the monotony of doing the same thing day-in and day-out.
This book is about the professional revolution that is taking place around the world. People are realizing that: You don’t need to do work you hate to make a living. You can do things you are passionate about and people will pay you to do it. Once you start to realize that this theory isn’t just a pipe dream people are trying to sell to you, your mind will open to all the opportunities available to you.
Uncertainty: Turning Fear into Fuel for Brilliance by Jonathan Fields
Jonathan’s follow-up to Career Renegade targets two specific issues that people have in life: Fear and Doubt. People resist doing what they want in life because these two words creep into their head whenever they are trying to do something new, risky, or scary.
Through a series of stories and themes, Jonathan shows you how to use what used to hold you back to propel you to higher levels of success than you ever imagined.
“One of the single greatest determinants of high-level success as an innovator or creator in any realm is the ability to manage and at times even seek out sustained high levels of uncertainty, bundled lovingly with risk of loss and exposure to criticism.” - Jonathan Fields
How to Win Friends and Influence People by Dale Carnegie
In one word: classic. Don’t let the phrase “win friends” make you think that this book is at all disingenuous. The tactics and strategies laid out by Dale in this book will make you more personable and just an all-around friendlier person.
“Everybody in the world is seeking happiness - and there is one sure way to find it. That is by controlling your thoughts. Happiness doesn’t depend on outward conditions. It depends on inner conditions.” - Dale Carnegie
Escape from Cubicle Nation by Pamela Slim
If you know you want to make the jump from desk jockey to entrepreneur read Escape from Cubicle Nation by Pam Slim. This book will help lead you through all of the essential exercises you’ll need to do mentally to prepare yourself for “the leap”. It also gives you incredible advice on how to actually make the transition. (Including things like self-paid insurance and benefits.)
I’ve had the privilege of seeing Pam’s coaching first hand at the World Domination Summit and she knows how to help people figure out exactly what their heart wants them to do. If you can afford it, hire her for one-on-one help.
Your Money or Your Life by Joe Dominguez & Vicki Robin
I’ve written before about how I think this is the single best personal finance book available. It is less about the technical “dollars and cents” pieces of personal finance and more about the philosophy you should have towards earning and spending money.
Anyone at any financial point in their life could benefit from YMOYL
. While there are other books that relate better to specific areas of personal finance (debt, investing, etc.), reading one book on finance is not how you become financially independent. For an all encompassing book for someone that really wants to tackle their finances, this would be my first recommendation.
Rework by 37 Signals
If you are in any position of power (i.e. you are in charge of anyone or anything), this book is the best book of business advice you can pick up. Written from the experiences of the small, agile software development company 37 Signals, this book is an absolute must-read for anyone looking to be or already is an entrepreneur.
There are so many great parts of this book that it is hard for me to pick just one quote, but this one has always stood out to me most.
“Don’t sit around and wait for someone else to make the change you want to see.” - 37 Signals
The Power of Less by Leo Babauta
You can’t expect to be able to break the confines and comforts of a 9 to 5 career if your life is a mess. You know what I mean: your schedule is jam-packed, your home is cluttered, and you just have too much of everything in your life.
The first and best step you can take towards creating a more meaningful life for yourself is to understand that your life needs less. Less stuff, less commitments, less everything. Leo lays out the best ways to limit yourself to the essential in both business and life in this book. I’ve read through it three times in the past couple years when I start to feel overwhelmed.
The Millionaire Fastlane by MJ Demarco
Ignore the potentially cheesy name or cover on this book. The Millionaire Fastlane has some really great advice. After talking briefly about how the sidewalk (living paycheck to paycheck) and slow lane (working a regular job till you retire) are not the best paths to take, MJ dives into how to create a business to earn wealth faster.
The second half of the book is where it really picks up. He lays out ways for you to determine whether or not the business idea you have is really worth a dime. It is a pretty quick read too.
The Lean Startup by Eric Ries
The concept of starting a company in Silicon Valley, getting angel investors to throw a ton of money your way, and selling your share of the company once it hits the jackpot is still a dream for many people. The trend now though is to create a company that is small, agile, and still ridiculously profitable.
In The Lean Startup, Eric dives into what makes these companies so successful without the size and capital of larger firms.
The key? Continuos innovation.
Trust Agents by Julien Smith & Chris Brogan
If you are looking to grow your presence online, pick up Trust Agents. In order for people to be interested in what you are saying enough to pay for what you are offering (or even give you their email address) they need to be able to trust you.
Without trust, no one is going to care about you. You need to build up that trust with other people, not tear it down in the heat of competition.
“We don’t need to make another team lose to win ourselves. There’s plenty of room.” - Trust Agents
The 4-Hour Workweek by Tim Ferriss
While this book may have lead to false beliefs about quitting your job to be a location independent entrepreneur, it also started a significant movement of people saying goodbye to the status quo.
If you haven’t read this yet, read it now. Just realize that not everything in the book is right for you in every situation. Use it more as a field guide and reference it often.
(Note: This is one of the few books that I recommend people get in paperback form instead of digital. It reads more like a series of blog posts than it does a book, so you’ll want to be able to access certain parts quickly.)
Never Eat Alone by Keith Ferrazzi
Another book that I consider to be classic, Never Eat Alone turned the word networking into a word I don’t cringe for anymore. This book lays out a ton of great tactics for connecting with people and building real relationships with them. This is a must-read book if you are an introvert or don’t have a network of people you can turn to if you need help.
“You can be more successful in two months by becoming really interested in other people’s success than you can in two years trying to get other people interested in your own success.” - Keith Ferrazzi
Linchpin: Are You Indispensable? by Seth Godin
This book will not only help you when you go out on your own, it will help you become the “go-to employee” in your organization when it comes time for leadership roles, promotions, and raises. The foundation of this book is based on the fact that you need to stand out if you want to be successful. Be the unique linchpin of your organization and you won’t be the one shuffled out the door come layoff time.
“Being tall helps you become a star in basketball, but how many of us have a shot at playing in the NBA? It’s not about what you’re born with; it’s about what you do.” - Seth Godin
Tribes: We Need You To Lead Us by Seth Godin
Tribes is listed last, but it is possibly the best book in the list if you are looking to grow a following around yourself or your cause. Seth discusses the principle that you need to be interesting and different enough for people to want to follow you.
If you want to be successful in business you are going to need to build a tribe. This tribe must then consist of people that are ridiculously enthusiast about what you do.
(Think die-hard Apple fanboy enthusiasm.)
BONUS: Firms of Endearment by Rajendra Sisodia & David Wolfe
This one I haven’t read, but is next up on my list. This book was recommended to me by Jacob Sokol from Sensophy a few weeks ago. He sent me the notes he took while reading the book and about halfway through them I realized, “Damn, this is good stuff. I really need to read this book.”
It discusses how world-class companies (such as Southwest Airlines) profit year after year due to focusing mainly on both passion and purpose (and NOT on just merely being a business that makes money).
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Even if you just read one or two of these books your mind could be opened to a new idea you hadn’t thought of before or possibly even a new direction to take your life or business in.
If you’ve read any of the above books I’d love to hear from you in the comments below what your biggest takeaways were.
Please share this post using the buttons below this post if you picked up a few new books to read. I really appreciate the help.
(Inspiration for this post came from The Art of Manliness’s Essential Man’s Library // img)







{ 41 comments… read them below or add one }
Thanks for this list Caleb. I’m always looking for books to read. I’ve read some of them on the list, reading Millionaire Fastlane now, and someone sent me The Lean Startup. That’s a good start.
I loved Millionaire Fastlane Benny. Interested to hear your takeaways when you’re finished.
How’s the reading of The Millionaire Fastlane and The Lean Startup going?
I’ve read most of the books on this list, and I think they’re all worth it.
I think Millionaire Fastlane is an underrated book by some. I found there to be some concepts that were new to me in terms of why you should get into the entrepreneurial mindset since it’s incredibly hard using “get rich slow” modes like saving and investing.
Tribes is my favorite Seth Godin book as well.
I think that The Millionaire Fastlane was really hurt by the title and cover of the book. It has some great advice in the second half.
I love reading other people’s recommended reading lists. Good to see I’ve read a lot of these too.
The Personal MBA I’ve heard about a couple times but never actually sat down to buy and read. Ill definitely do that now.
People seriously underestimate the power of writing a blog post about a book.. about 5 books I bought after reading posts on Tim Ferriss’ blog, and that’s also how I found out about Ramit Sethi.
Same is true here!
Thanks for more good stuff to read..
Hope you’ve gotten a chance to read some of the books from the list by now. I’d love to hear which ones you are reading right now.
Greaaaat Selection Caleb! “The Personal MBA” and “The Power Of Less” are part of my favorites. I plan to read “The Thank You Economy” from Gary Vee. Thanks and keep on reading and inspiring us!
Will do! If I find new books I’ll let you know about them.
This is an awesome list Caleb. I added Education of Millionaires and Neve Eat Alone to my wish-list. Thanks!
One book I’d add to this list is “The Travelers Gift.” It might seem unconventional to have a fiction book on this list, but it’s all about success and filled with well illustrated philosophies we all need to make it.
I barely kept off a few fiction books from this list, namely The Alchemist. I’ll add your book to my wish list.
Such a great list Caleb. There were only a few I’d not heard of but more importantly there are way too many that I’ve had on my list, like yours, and have still not read. Luckily I’ve fired up my Kindle and iPad and have them ready and waiting to read while I’m biking through Africa.
Next time we meet I’ll be way smarter
Hopefully you don’t do too much reading while you’re on your bike. Wouldn’t want this to happen to you: http://www.youtube.com/watch?v=n_A1WoUMcqg
I just searched my library’s online catalog, and they don’t have most of these books! I’m so bummed. I’ll be borrowing the 2 or 3 they do have this weekend though.
Bummer! That’s not a very good library then, is it?
Most of these can be found for roughly $10 on Amazon and even cheaper used on Half.com. This kind of education is cheap compared to college or graduate school.
I’ve been meaning to read a lot of this list, and have found quite a few very helpful. Namely, The 4-Hour Workweek and Escape From Cubicle Nation have been the most encouraging and inspiring to me thus far.
Looks like I need to start reading more!
One that I would add to the list, though it’s not necessarily about breaking out of the 9-5, is Eckhart Tolle’s A New Earth: Awakening To Your Life’s Purpose. It helped me to enjoy what I currently have, while working toward a much bigger goal. There’s no reason why one should wait to enjoy life. It aided in my perspective reframe!
Totally agree Amy! Even when you are working towards a bigger goal and you know you want to make big changes in your life it doesn’t mean that you need to sacrifice happiness in the now.
Great point.
Just what I needed! I set a goal for myself to read at least 27 books this year, so I think I may pick up a few books you listed on here. Thanks Caleb.
That’s a great goal Aaron and definitely achievable. Are you on track so far? Have you started reading any of the books on this list?
Caleb, good info here. I’ve read some of the books on your list and I’m currently reading Tribes. I’ve never heard of the Personal MBA. I’m writing a series on my blog called the 45-Minute MBA so I’m interested read Josh Kaufman’s viewpoint on the subject. Thanks for sharing your recommendations.
I would totally pick it up. Excellent read.
I liked lots of these too, but far and away the book that made the hugest difference in my life was Hugh MacLeod’s Gaping Void. Whether it’s that one - which teaches a creative professional how to manage through the madness of a day job - or his follow-up Evil Plans which helps to get you off your butt, his stuff is amazing.
There’s a third coming out this spring.
Enjoy.
Hey Stefan, I hadn’t heard of Hugh MacLeod until now. I’ll check him out.
You might also want to look at some of Anthony Robbins’ success books. They’re excellent!
Hey Kimberley,
I haven’t read anything by Tony Robbins, but I’ll check them out.
Thanks!
This is an absolutely great list! I’ve found some new books that I’m going to definitely check out ASAP. I’m a big fan of Gary Vaynerchuk, and I absolutely loved Crush It. The Dip by Seth Godin should be high up on your honorable mention list too. Great list!
I liked The Dip as well for suggested reading if someone is struggling with whether to quit at something. Thanks for bringing it up Hank.
This is a great list, Caleb! (And not just because it have my own book, though I do appreciate that
Really this is a curriculum for a significant business education you’ve put together here-it has a lot of my favorite books on it. Thank you for the props!
My pleasure Michael. I’ve throughly enjoyed the book and have recommended to many people so far.
I’m reading one business book a month and reading The 4-Hour Workweek by Tim Ferriss. Definitely, I will pick up some book ideas on this list. What should I do in April?
Hey Kent,
If you haven’t read either The Personal MBA or The Education of Millionaires I would start with one of those. Both offer a ton of hands-on business advice as well as include inspiring stories of successful people and businesses.
I’d love to hear what you think of them when you’re done.
Thanks Caleb,
I’ve read a few of those but based on where I am at, Never Eat Alone and Tribes are the one’s I should read. I haven’t heard of Never Eat Alone so that’s a a good thing!
Another book that everyone raves about is Made to Stick which I am surprised to see you haven’t listed. Have you read it?
However I do feel I am reading for too many books and need to start acting on what I have learnt for my own career.
I haven’t read Made to Stick, but it is on my extended list of what to read next.
Lately I have been acting way more than reading though and it is amazing what kind of results you can get just by doing things!
Thanks for this list, Caleb. I have only read one of them, and I read about 100 books a year! I’ve already got a few of these, so will start reading them. These seem especially applicable right now.
No problem Dolly. There are books I’ve read that I purposely kept off this list because I wanted to only recommend the best of the best! If you read a 100 books a year I’m sure you could get through most of these in no time.
Caleb,
Thanks for the list. I’ve read a few of these but am missing on quite a few as well. Can I recommend two?
“The war of art” by Steve Pressfield and “Switch” by the Heath brothers.
Both touched on addressing fear, resistance, and uncertainty in life. Switch in particular with dealing with change or helping others with it. Both have been very instrumental in helping me along the way.
Thanks again for bring up these reads. Going to be keeping me an my kindle happy for a while.
I like “The War of Art”, but I hadn’t heard of “Switch” before Justin. Thanks for the heads-up.
Awesome! Keep dominating with the podcast! Let me know if you end up taking in “Switch”
Great collections. Have read quite a few on the list currently iam reading Lean Startup….loving it so far
I agree about the millionaire fast lane book, it’s good but only gets going in the second part. If you have read any financial self help books, you’ll be agreeing with what he says but you’ll have heard all the advice before. Dare I say, he verges onto cliche in some parts at the beginning. The second part is much more useful and should be read a few times to let it sink in and make it your own.
Great list! I just bought The Personal MBA by Josh Kaufman and I can’t wait to read it.
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