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Mistake #6: Quitting a job to stay at home or pursue a dream. The problem with quitting your job to stay at home (with children, for example) or to pursue a dream (such as starting your own business) is twofold. One, there’s no way of knowing what the future may bring. You may have enough money to live on for several years, or your significant other may be able to support you while you do so, but what happens if circumstances change and you need or want to go back to work? Two, you can find yourself having to start completely over at a much lower salary (especially if you were originally in a fast-changing field) if you do choose to go back to the salaried world. I personally ended up starting over at a 38% salary reduction after four years of being strictly self-employed.

Solution: The solution isn’t “don’t quit your day job”. It’s “don’t quit your day job without a well thought out plan”. I feel that people who have a strong desire to do something other than the usual 9 to 5 should make every effort to make it happen. The best chance of living your dream is to have a plan that includes worst-case scenarios such as the death of a sole provider or the need to return to work for other reasons. Be sure that you’re able to cut your expenses to the bare bones if necessary. Be sure you have a VERY large fund set aside to live off if necessary. (I’d recommend at least two years’ worth of expenses, and that fund should not be your retirement fund or your home equity.)

Most importantly, stay ACTIVE in your old field even if you never intend to do it again. I figured I’d probably never do web design again, and so I didn’t spend the time I should have learning new ways of coding. Big mistake, and I’m literally paying for it now. Maintain your old contacts. Talk to them on a regular basis — at least once every month or two. Create new contacts as well, ideally by volunteering at something that could eventually become a paying job or that gives you skills that are easily transferable to a paying job. Your best bet at finding work if necessary is to be well-acquainted with people in your field of interest who can point you to potential openings.

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