Living without a job while still maintaining a sense of comfort is a goal that very few will reach. It's not impossible, but it requires a sense of determination, sacrifice, and dedication that most will find to be too strenuous. However if you have the determination and you aren't afraid to go against the grain, this is how you can live well without a job.
Decide why you want to be job-free. Living without a job can be a long and hard process so if you don't have any motivation you probably won't succeed.
Pay off all of your debt. This includes your mortgage. This will most likely be the most time-intensive step; however it is the most important. Expenses need to be at a minimum so eliminating debt is key. Consider trying Dave Ramsey's snowball method in order to pay off debt without getting discouraged.
Live frugally. While paying off debt it's important to not accumulate more debt. Clipping coupons isn't enough. Get rid of unnecessary expenses like cell phones and cable plans. Consider downgrading to one car. Don't buy a new car, buy used. Scrap your vacation plans and cook homemade foods. Think about what is more important; unnecessary luxuries, or living job free.
Discover what you love to do. While you don't have to have a job to make a living, you do need to have a source of income. Write down your hobbies and then begin to plan how you can make money from it.
Write an action plan. Write down how long it will take you to pay off your debt, save up some living expenses, and get your income source or sources off of the ground. This plan should be divided into steps so you won't get discouraged by the lack of immediate progress.
Have patience. Living without a job takes time and dedication. There are a lot of sacrifices that have to be made to make this a realistic option in a reasonable time period.
Your monthly living expenses are likely the most draining resource on your finances. Focus on paying off your house so that you will always have a place to live. If you don't own a house, concentrate on saving so that you can buy one with very little mortgage required, if any mortgage is required at all. Some prefer the 100% down plan. Do not count on anyone for support beside yourself for support. Most people are not cut out to live frugally while following their dreams. Start looking at the world with a new pair of eyes. You have to erase everything you've been taught and adopt a new view in order to succeed in living a job free by choice lifestyle that's not due to poverty.