This post is from staff writer Sierra Black. Sierra writes about frugality, sustainable living, and getting her kids to eat kale at Childwild.com. (It’s also her birthday today.)

Who doesn’t dream of quitting their day job? Every day, countless hours are spent in corporate cubicles daydreaming about lives of adventure, creativity, and play — lives spent doing what you love.

Last month, I took the leap. I quit my day job to write full time. Now I’m sitting in Buenos Aires writing while my kids play with their grandparents nearby. And I’m getting paid for it.

To say this is the achievement of a dream would be a vast understatement; I’ve wanted to be “a writer” since kindergarten. But I didn’t just want to be a writer — I worked hard and planned for it.

Should You Quit Your Day Job?
Chasing a dream isn’t for everyone. There are plenty of people who prefer the stability and security of a job. Many creative, interesting, passionate people like the advantages of a steady paycheck, good benefits, and the ability to leave work behind at the end of the day.

Before you consider quitting your day job to follow your passions, ask yourself:

  • How comfortable am I taking a risk with my livelihood?
  • Am I willing to maintain a business?
  • How will I handle the business management aspects of my new career?
  • Do I want to do this all day, every workday, or will that strip the joy from it?
  • Will my family and friends support this move?

If you still think you might want to go after your dream, some preparation can make the risks easier and the rewards greater.

Take Your Dream For A Test Drive
It’s a big leap from karaoke night at the local bar to American Idol. See if you can find a way to test-drive your dream life before you leap into it all the way. This will give you a chance to be sure it’s what you want. You’ll also get to fine-tune the details of how you want to go for it.

You may discover that you don’t want to do turn your passion into your career. That’s fine. One of the most talented singers I’ve ever known makes her living in psychiatry. As the daughter of two musicians, she knew firsthand singing wasn’t the right career for her.

Many people test-drive their dream jobs by freelancing on weekends or evenings. This works for creative fields like writing, photography and music. It’s harder if your dream is to open a restaurant or become a civil rights lawyer; some things, you can’t just dabble at. But you can still try some jobs on for size by taking a class or finding a mentor. Take a law class at a local university. Cook meals for family and friends. Pick up some night shifts as a chef’s assistant.

J.D.’s note: When I was a boy, I not only loved writing, I loved computers. I thought I wanted to be a computer programmer. In the late 1990s, I took classes and read books to learn C++ and various scripting languages. I got my dream job as a computer programmer. I hated it. Sierra’s right: It’s an excellent idea to test-drive your dream job before you buy into it all the way.

Do What You Love
Yes, it’s useful to network and gain experience. But don’t sacrifice your time and energy to do things you’re not interested in.

When I started freelancing, I had friends and relatives offer me gigs writing ad copy for their businesses or editing their thesis papers. Those are jobs that use the skills I’ve built up as a writer, but they’re not my driving passion.

Since I wasn’t depending on my freelance business to support me, I turned those jobs down. I focused on what I wanted to do: creative essay writing and blogging. Staying focused helped me joy out of the work and brought me more opportunities to do exactly what I most love.

Fake It ‘Til You Make It
Play make-believe with yourself right from the beginning. Don’t say, “I want to be a singer someday.” Say, “I am a singer.” You may feel a little dopey at first, but you’ll slowly condition yourself to believe it.

J.D.’s note: Sorry to intrude on Sierra’s article again. I remember the first time I responded to the question, “What do you do?” by saying, “I’m a writer” instead of “I’m a box salesman.” It was liberating. I felt like I’d escaped from a straight-jacket. And after saying it out loud, I began to find ways to make this a reality.

The most important aspect of “faking it ’til you make it” is to be professional. That means setting aside time to work at your vocation, even if it means turning down other fun stuff. It means following up on leads, keeping commitments, and presenting yourself like a pro.

Growing up, my mother told me over and over again, “Writers write.” That’s true. But any “dream life” has more working parts than the dreamy bits. Writers write, but they also network, edit, invoice clients, build relationships with editors, brainstorm ideas, and read other writers.

Find out what professionals in your chosen field actually do — maybe through an informational interview — and start doing those things. Right now.

Does your dream require a portfolio? A credential you don’t have? A new website? Make sure you have the professional tools to do your work, and then do it. Don’t spend a lot of money or time getting set up, though; you’ll learn more about what you need as you go.

Make a Road Map
Simply saying “I want to be a writer” was like trying to catch the moon in my hands. Clear goals helped me work. I knew what I was working towards, and I could break down the steps to get there each day.

Don’t be afraid to aim high. If you want more than anything in the world to be a contestant on American Idol, write that down and then draw up a plan to get there. Even if you don’t wind up singing on TV, the work you do pursuing while pursuing this goal will take you somewhere good.

And you may surprise yourself. When I made my list of dreams and goals, being published in The New York Times seemed like a pipe dream. When it happened, it was just one more step forward with a writing career that was beginning to pick up its own momentum after a year of hard work.

Bank Your Success
By the time I started making money writing, I was sure I wanted to do it full time. So I banked my paychecks in a savings account. My intention was to save up enough money to cushion the ups and downs of freelance income.

Even more important, I wanted to avoid “lifestyle inflation“. I realized that if I simply added my freelance income to my household budget, I’d risk gradually increasing my spending until I depended on my day job and my freelancing just to stay afloat.

So I hid that money from the household budget in its own savings account. I’ve appreciated having those savings this month while I’m traveling and unable to collect or cash my writing paychecks.

Do the Work
A dream job is still a job. Let me repeat that: A dream job is still a job. When your passion becomes your day-to-day grind, you have to be willing to show up for it just like you’d show up for a factory shift. Be on time, be ready to work, be respectful of the needs of the job. You need to do the boring bits as well as the fun parts, and you need to do it even when you’re uninspired or tired or distracted. Just like a real job.

Know When to Quit
How do you know when it’s time to quit your day job and go full force into your dream job? Sometimes the date is chosen for you. You’ve gotten into law school, or been hired as an English teacher abroad, and your new contract spells out the dates.

But if you’ve been running a side business, you’ll need to choose a date and leap. You’re probably ready to take that step if:

  • You have substantial savings built up to cover the financial risk of quitting your regular job.
  • Your “side business” is demanding more time from you than you can give it without harming your current career and family obligations.
  • You have ongoing relationships with other professionals and with clients, so you know where your next paycheck is coming from.
  • You can reliably expect to make enough money to cover your living expenses.
  • You’ve been doing this on the side for awhile, and you still love it.

If you’ve built up a professional life doing what you’re passionate about and you’re ready to take the leap, go for it with love and joy. Be happy. I’m incredibly grateful to all the readers, editors, and publishers who’ve made it possible for me to have this career.

It’s hard work, but worth every second of it.

This article is about Career, Choices, Entrepreneurship  Thursday, 22nd July 2010 (by Sierra Black)  

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