Recently, I decided to quit my very stable, yet stressful as hell, teaching job. Yes, in this economy. After 6 years in the classroom, it just wasn’t what I wanted to do anymore. I wanted to write. But these days–with newspapers and print magazines collapsing left and right–I couldn’t figure out a way to follow my passion without starving to death.

Then, I picked up Barbara J. Winter’s book, How to Make A Living Without A Job, and my mind opened completely up. Halfway through the book I realized that I was holding myself back, not the economy or the fact that glossies are folding. Me.

Because I love you Clutchettes, I’m going to share 5 tips that helped me quit my job, follow my dreams, and still be able to live normally (no starving artist b.s. for me!).

Step 1: Pick…

Many of us have dreams of grandeur. We want to write the next great novel. We want to travel around the world. We want to learn underwater basket-weaving. Whatever. One of the first steps to breaking out of a job you hate is to pick something you LOVE doing. Think about something you’d do even if you didn’t get paid for it. For me, that was writing. For you, it might be totally different.

Step 2: Work with what you got…

Once you’ve picked your niche, assess your skills. What are you good at? What talents do you have? List them all out, now search for ways you can turn those into money makers. For writers, we can churn out press releases, write website copy, work for news organizations, and basically do anything relating to the written word. Perhaps you are very tech savvy. The market for graphic designers, coders, and tech consultants is booming. Figure out your talents and exploit them for YOUR benefit, not someone else’s.

Step 3: Think outside of the box…

In her book, Barbara Winter says we need to ditch the idea of a “good” job versus a “bad” job. Many will see teaching as a good job, but might view tutoring, or working at Starbucks, or being a plumber as a “bad” job. Winter reminds us there are no such things as good and bad jobs. If you love what you do–despite the money you make–it is a good job and you’ll feel more fulfilled doing it.

Step 4: Run the numbers…

Before you quit your job, you need to figure out JUST how much money you need to get by. In my case, I taught full time and freelanced on the side, so I was generating a healthy amount of extra income. However, at the end of the month I was still scrounging around in my purse looking for change. Why? The more money I made, the more I spent on random things. I thought I couldn’t quit my job because I’d be broke. I felt trapped and hopeless.  After reading Winter’s book I decided to actually run the numbers and list out all of my obligations (rent, bills, son’s tuition, car payment, savings, etc.). What I found was that I didn’t need NEARLY as much money as I thought I did. This gave me hope and helped me to realize that I could easily make it on my freelance income if I just cut back on frivolous spending. By knowing exactly what I needed I no longer felt trapped, I felt empowered.

Step 5: Generate multiple streams of income…

This step is  key. Many time we think we want to do one thing and one thing only, but don’t know how we’ll make ends meet. As I mentioned before freelancing writing is notoriously unpredictable. So, if I was going to quit my job, I knew I needed to supplement my income with other things. Because I’m I was a teacher, tutoring is an easy way for me to make extra money while I write. If you have a college degree, or better yet, a teaching credential, you can make upward of $30-$45 an hour tutoring. So, even though I’ll have to get out of my PJs and leave my desk, it won’t be for the entire day. While I build my rep as a writer (doing what I LOVE), I can still make a substantial income on the side doing what I’m good at. It’s the best of both worlds.

Clutchettes and Gents…have you successfully quit your job? Do you have any other tips to share? 



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  • Sparkle

    Thank you for this! I have been thinking of changing jobs so I was reading a book called How To Find the Job You Love Even When No One is Hiring”. One of the activities was to visualize my ideal workday, office environment etc.

    I have always been attracted to to the opportunities of being an entrepreneur but it was then that I realized my ideal workday and environment was one where I don’t have to “report” to an office at all. I will be definitely checking out the book you reccommended. :-)

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  • http://naeicanrepeatit.wordpress.com Nae

    I am in the middle of developing a strategy to quit my job to pursue writing as well. Thanks for the great tips, and I am definitely going to buy that book. You go girl!!

  • Lady P

    First of the year (2013), Im going to go for it.

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