Thinking about quitting your job? Want to pursue your dreams of becoming an entrepreneur, freelancer, or just a couch-surfing nomad? It takes more than guts and a good eye for business opportunities. It’s a road full of waiting and wrong turns, and I hope you give it a try at least once.

When my husband James quit his engineering job last year, he had been doing iPhone app development for almost a year and had already started Digital Media Interactive with two other guys. He would still be up working when I woke up for our daughter’s middle-of-the-night feedings. He was doing well at his day job, and was somehow not collapsing from all the pressure. He did drink an awful lot of Rockstars, though.

It takes time to plan a big change like this. I like to think he did the best he could, and here’s what we learned from the process.

Don’t quit on a whim. We’ve heard the stories about the people who quit on impulse, after a particularly bad day. If you just can’t take another TPS report, it’s best to bide your time, give your required two weeks and wait it out. James gave about 2 months notice, because he felt it important for the project he was working on. Depending on how long you’ve been at the job, or the level of skill involved, give your company time to find a replacement. Also, you don’t want your health insurance to lapse because you couldn’t hold on a little longer.

Don’t expect things to fall into place the minute you quit. You may think that when you start spending 8 hours a day on your side job, it will magically pay the bills… even if it hasn’t been lucractive yet at all. Have safeguards in place long before you think about quitting. In our case, we dramatically lowered our expenses, started the process to sell our house and took a serious look at our savings.

Don’t venture out alone. Even if you do one thing really well, there are so many other aspects to running a business you may not be good at. James was lucky to have connected with two people who complimented his technical skills with their ability to find clients and handle creative and administrative tasks. Yes, with a sole proprietorship you are in complete control, but I’m assuming you don’t want to quit your job want to divide your time between a million things and still work all day and night.

Don’t believe in the myth of the The 4-Hour Workweek. The name itself is a gimmick, and Tim Ferriss’ empire certainly wasn’t built on working 4 hours a day. Maybe it is now (or his 4 hours includes only things he doesn’t consider work, like the things he hates to do) but I doubt it. Two things that were important to James were the development of passive income from things like ad revenue and finding qualified people to outsource projects to. While he’s still working on this aspect of his business, it took a long time for me to understand that he wouldn’t be able to cut back his hours overnight.

Don’t burn bridges at your job. What I do love about the 4-Hour Workweek is he says you can almost always go back to the industry you left, without much penalty. Keep up with your co-workers on Facebook. Tell your boss you’ll be available for consulting or help with any of the stuff you’ve worked on in the past. It was difficult for James to leave a job he had worked at for almost 6 years and had spent 5 years getting a degree for (along with the student loan we are still paying). If he decides to go back, we hope he’ll have glowing reviews.

Don’t give the real reason for quitting. Want to get to the Full Moon Party in Thailand before you’re 35, or sleep in every state in America? It’s best not to say that you feel trapped in the corporate world and need some breathing room. If necessary, blame your quitting on someone else, like a demanding baby or sick relative. Keep the reasons appropriate for business and you’ll keep your positive image.

Don’t be afraid to ask for a layoff. Enjoy the benefits of a bad economy and ask to be laid off, to work less hours for less pay or to take a sabbatical if you’re not ready to quit. LifeHacker has some great advice about how to enjoy your job if you can’t quit right now. However, some industries are still laying off employees right and left, and might jump at the chance to drop your salary. Unfortunately, James couldn’t take advantage of this one.

Don’t waste your spare time at your 9-5. Many a small business has been started at a day job. It’s not talked about, but it is a smart use of your time (while the company may not agree.) If you have your own office, or at least a few cubicle walls, you can do some work for your side job on paper. Avoid the computer because most companies nowadays have a way to monitor this.

Don’t try to change everything at once. Need to lose weight, find love, and get your new career started? Stick to one thing at a time or else you’ll probably fail miserably at the others. Prioritize what is most important to you, and complete that before you move onto another life change. It’s hard to adhere to a diet when you’re stressed about paying your bills and it’s impossible to find love if you’re working all day and all night. That said…

Don’t use life as an excuse. You may think that once you have a family, it’s too late to follow your dreams. James was willing to risk us living on the street, but when Baby J came along, it seemed a lot scarier to go without a guaranteed paycheck. If you have that entrepreneurial spirit and ambition, you will find a way to make ends meet. In the end, it was the fact that he wanted to spend more time at home with his daughter that got the ball rolling.

Whether you’re quitting your job to travel or to look for work you love, I wish you the best!

Photo by Phil and Pam (Not of James, because he wouldn’t be caught dead using a PC.)