3 Books To Read Before Leaving Your Job

I quit my last corporate job in 2008 where I was a programmer for a bank. It was In retrospect I didn’t do the best job of preparing myself, my family or our finances for the process we went through the next three years after quitting. The only books I had read about going solo described the joys of working for yourself and being your own master. They talked of a place where independence, business wisdom and revenue coincided to create a euphoric mountain top experience.

The problem was these books didn’t describe the valley that lays between the starting point and the mountain top. This valley is full of sink holes of debt, thorny forests of failed marketing, deserts of unpaid invoices, and bogs of scope creep.

A friend recently asked me what books I would suggest he read before going solo. Similar to my journey he is a programmer for a large corporation. I think it’s important when starting out to have your eye on the mountain top because nobody survives a journey without a vision of the destination. But it’s more important to focus on your next steps so that you can successfully navigate the valley. With that in mind here are three books that I would suggest reading before leaving your job so that you survive the valley and come out on top.

3 Books to Read Before Leaving Your Job

1. “Quitter: Closing the gap between your day job & your dream job” by Jon Acuff

The first book I suggest is called Quitter, but it’s all about the valley. The book describes the hustle time where you are working one job while you make your dream job a reality that will support you.

When I first read this book it was like looking in the rear view mirror. Acuff described with wit and humor being in a place where you were one thing, but desperately wished to be something else. He talks about the mountain top place as a ‘dream job’, but he doesn’t romanticize it. His first chapter is titled “Don’t Quit Your Day Job” and talks about having an understanding that checks don’t appear in the mailbox just because you turned in your resignation. If you’re going to jump off a ship you need a lifeboat, and if you jump to soon and underprepared you’ll have a life boat with dozens of tiny holes that look like your household bills.

To prepare for your eventual departure Acuff encourages you to fall in “like” with your job. Your current job keeps your way of life afloat while you hustle in the margin time of nights and weekends to build your dream job. If your current job is absolutely insufferable he says, don’t quit and go for the dream that hasn’t materialized, but find another job you can fall in like with while you work on the dream job.

One of the most important points in the book is about integrity. It is imperative to your current job, and do your character that you do only the work of your job while you are at work. No checking your phone for emails, no taking long coffee breaks to write code. It is essential to honor the commitment you made to your day job and keep your dream-job-hustle to nights, early mornings and weekends.

2. “E-Myth Revisited: Why most small businesses don’t work and what to do about it” by Michael Gerber

The second book I suggest is a book all about failure and dispelling myths. The first chapter is “The Entrepreneurial Myth” and talks about the difference between what people think it is like working for yourself and the reality.

The first five chapters are worth the price of admission because it opens the readers eyes to the fact that working for yourself is not simply doing the tasks they did when working for someone else without the nuisance of a boss. Gerber explains that when people quit their one job to start a business they are actually taking on three jobs at once – the Entrepreneur, the Manager, and the Technician. These chapters accurately set expectations so that when the business owner encounters the rope bridge of “if I don’t do it, it won’t get done” they don’t fall into the chasm.

3. “The $100 Startup: Reinvent the way you make a living, do what you love, and create a new future” by Chris Guillebeau

The first two books set the stage for hustle to create a dream job and described the roles it would take to keep the dream job alive. This book is different because it is an exploration of what is possible with a little bit of money and a lot of creativity. The book shows that the best way to the mountain top isn’t a straight line, but perhaps involves some different turns.

Guillebeau gets right down to the point in showing how to take your expertise and package it into something that people will pay you for. It’s not about following your ‘passion’ it’s not about tricking someone to pay you to do your hobby, but it’s about being useful, helpful and providing value in the marketplace.

The best part of the book is that it is chock full of examples and case studies of people who have done this very thing. Nothing motivates me more than reading about the success of real people!

Bonus: “Don’t be an Idiot: Learn to run a viable business” by Curtis McHale

I talked about starting to again take on freelance work and I’ve already described how my first three years of working for myself were more a valley of sorrows than a walk in the park. This book is useful for anyone who is specifically setting out to do freelance work in design and/or development.

I’ve had the honor to be able to chat with Curtis McHale who is a much more successful freelancer than I ever was. His book talks about the details of having savings, having the support of your spouse, structuring your work, setting goals, and marketing yourself. He digs into specifics of billable hours, work schedule and pricing.

In addition to the print book you can get access to 13 video interviews with other successful freelancers and business owners. Just like the case studies in $100 startup these interviews are useful to motivate and inspire.

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