Business Life

5 Books That Gave Me The Courage To Quit My Job

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Full disclosure: I’ve quit the 9-to-5 life 3 times. The first time I quit, I did the most and decided to run my business full-time, move to another state and jump into a serious relationship. At the same damn time. Probably not the best idea to make several major life decisions at once. So yeah, don’t do that. I went back to cubicle life twice after that after getting sick without health insurance. Debt ensued and I went back to what I knew.

Though a traditional job offers stability and health insurance, some of us are just wired in a way that ensures that will never be enough. Just being clear, there’s no shame in doing what you have to do to pay your bills and provide for your family. However, if that entrepreneur life keeps calling your name you owe it to yourself to go for it. Here are 5 books that helped me along my journey.

1. Escape From Cubicle Nation by Pamela Slim

I didn’t expect much from Escape when I bought it. I was browsing the $5 bin at Borders Bookstore (RIP) and I found this gem. This was the first time I got the quitting itch and I was desperate to make some kind of move. The title of this book really spoke to me, so i figured I’d give it a shot. This book gave me the push I needed to start my online t-shirt shop.

2. The Fire Starter Sessions by Danielle LaPorte

This book was a gift from a friend. I love books that are interactive and workbook-y that make me really think and ask myself questions. This one fits the bill. LaPorte’s writing style doesn’t mesh with everyone. It’s a very stream of consciousness/hey girlfriend kind of vibe, but I liked the informality of it. I still pull it out and complete the companion Workbook O’ Fire whenever I feel like I’m losing direction.

3. The 4-Hour Workweek by Timothy Ferriss

Parts of this book may be dated at this point (I believe it was last updated in 2009), but this was the first book I read that really sold the idea of working smarter, not harder. I’m not saying a 4-hour workweek is something that is achievable starting out, but it’s definitely a worthy goal to strive for. The idea of removing yourself as a bottleneck so your company can run without your constant input was extremely eye-opening. If you take anything away from Workweek, it should be delegate, outsource and delegate and outsource some more. They key to doing less work is to have someone else do it.

4. Is Your Genius At Work? by Dick Richards

Sometimes you know that you don’t want to do what you’re currently doing, but you’re not exactly sure what you’re meant to be doing. If you find yourself having constant existential crises about what your purpose in life is, you should explore what really makes you feel fulfilled. Genius has a lot of exercises and questions that can help you zero in on what your unique genius is.

5. Small Time Operator by Bernard B. Kamoroff C.P.A.


Numbers make me itch. I’ve never been good at math or accounting. If this sounds like you, then you need this book. It explains taxes and things in a way that even the numerically illiterate can understand. Yes, it’s awesome to have an accountant handle all of that stuff for you but you may be in for a rude awakening if you don’t understand what’s going on with your finances at all.

6. Extra Credit

The Strangest Secret by Earl Nightingale

If you want an instant kick in your ass, listen to this. It’s stuff you probably already know, but Nightingale delivers it in such a way that makes you really question why you’re not where you want to be…and then take action.

The Upside Of Quitting by Freakonomics Radio

I was always taught that quitting was a bad thing, but often giving up really is the right thing to do. Learn about the benefits of quitting from the economist’s perspective. Freakonomics Radio is hosted by Stephen Dubner and featuring Steven Levitt, the same guys who wrote the popular book series.

What books would you recommend to entrepreneurs who are reluctant to leave their job? Please comment and share!

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