Five Things to Do Before You Quit Your Job and Chase Your Dreams

It's one thing to pursue a goal -- be it to become an artist or a rancher -- and another to pursue it wisely.
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I'm forever urging people to look beyond money, to take some big risks in life and dare to reach for their dreams. We recently got a letter here at MSN Money from someone who suggests I reconsider this advice before more people end up like she did.

This woman left a large Eastern city in 1990 with her husband and four teenagers to live the simple life on 40 acres of virgin land in the American West. They lived in tents and hauled water for three years while clearing the land and digging trenches for telephone, water and power lines.

The simple life cost a lot. "It is very expensive if you are trying to recreate the infrastructure most of us now take for granted," she wrote. The couple spent their life savings -- $245,000 over 11 years -- and watched wildfires twice destroy much of their work.

One by one, the kids grew up and left home, although one girl reported her parents to a child protection agency and went to live with a cousin. The wife left, too, and now lives in a small urban apartment trying to earn enough to replace the investments that were lost to the land, where the husband lives still in a Quonset hut. She asked me to warn others to take off their rose-colored glasses and face reality.

Rude Awakening

When I discussed the story with my editor at MSN Money, he told me his own story about a friend whose dream is to become a cartoonist, a dream he's been pursuing for 10 years while living off a small inheritance in a beautiful apartment overlooking the Pacific Ocean. The cartoonist has run out of money and, at age 45, faces the prospect of entering the workforce with no assets, few marketable skills and no recent work experience.

The cartoonist and the pioneers have a good deal in common. Both put all their eggs in a high-risk basket without adequately considering the downside. Both pursued a romantic ideal with no contingency plans.

What are the lessons here? I'm afraid I've been giving advice from my own perspective, based on my own experience and my own liabilities. In my case, I always dreamed of becoming a writer. But I grew up poor, and writing fiction or poetry would have been seen as incredible self-indulgence. So I set myself to establishing a career as a journalist and made decisions that would be good for that career.

When I decided two years ago to give fiction writing a try, the main obstacle I had to overcome was the nagging voice that said I would compromise my family's financial future, make a fool of myself and so forth. And so I've given

you

advice about how to overcome

my

obstacles.

I still think each of us deserves to become the most we can possibly be, but it's important to recognize that it probably won't happen overnight. Investing in yourself is a long-term proposition. Because it can also be high-risk, you need some conservative investments to be properly diversified.

Before You Chase Dreams

So here are five things I think you need to do before you quit your job to build single-engine airplanes or paint watercolors in Taos.

Consider your obligations

. No one should spend his life doing something he hates just to provide an affluent lifestyle for his family. On the other hand, marriage and children are a responsibility. It doesn't seem right to derail your family's future because you've decided you want to be a florist rather than a corporate lawyer. In my case, when I decided two years ago to work on a master of fine arts degree in fiction writing, I discussed it with my family. The program would be expensive. Not only that, but I'd have to cut back on work to make time to do it, reducing my income by about a third. We couldn't take as many trips or be as extravagant at holidays or birthdays. The family has to buy into that.

Think about what you really want

. Perhaps you think you want to operate a bed & breakfast. Do you enjoy working with people? How about listening to them complain about the breakfast quiche? Think through what it is that really appeals to you. Maybe it's landscaping the gardens or shopping for antiques for the bedrooms. If you go slowly and keep your options open, you can learn wonderful things about your strengths and your talents. Too many people dive into an enterprise they're ill-suited for because they haven't worked through what it is they really like and don't like about it.

Set realistic goals

. Suppose, like my editor's friend, that you are 45 years old and want to be a cartoonist. The chance that you'll produce the next "Calvin & Hobbes" or become a regular in

The New Yorker

next year is extremely remote. The chance that you will make a good living as a cartoonist next year is only slightly less remote. Your ultimate goal may well seem impossibly far off today, but maybe you can get there by taking some smaller steps that give you some satisfaction along the way.

And hang on to your day job to pay the bills while you nurse your dreams. That takes a good deal of energy. If you don't have it, I'm afraid you'll have to stick with the day job.

Take it one step at a time

. What would it take to make you feel like you've captured your dream? Suppose you love books and want to own and operate a bookstore. The book business is crazy, and independent booksellers are in danger of extinction. But buying and selling used books might be a viable way to get started. You might start out selling at swap meets, and then rent a storefront that's open only in the evenings and on weekends in the beginning. Gradually, you can add employees and build it into a full-time business over five or 10 years. Think, too, about taking steps to acquire skills you might need to earn more money. Do you know what rare books are worth? Could you set up a Web page to buy and sell them online?

Don't bet it all unless you're sure you'll win

. I'm a risk taker, and I think you should be, too. But we have to keep our perspective. I'm not cashing in my retirement portfolio or my kids' college fund to support myself while I write a novel. Everyone deserves to go after his dreams, but each of us is responsible for our future security, too. I think you can have both with some careful planning.