Q: I am a divorced, self-employed 56-year-old. I own a home with at least $350,000 in equity even in this slow market, and I have $100,000 in savings and zero debt. But I'm the definition of house poor: All my disposable income goes into maintaining my property. The cost of living is so high in my area that a decent income still leaves me with little left over. I should have sold during the last craze, but I was afraid that if I moved, I would lose my clients. I dream about taking a big risk—living in the country and writing plays—but my friends think I'm crazy. There's got to be a smart way to leverage my assets. How do I summon the courage to make a bold move?

A: You already have the makings of a great play about navigating a major life change. In fact, I want you to apply your creativity to figuring out the viability of this move. Act I is all about exploring the possibilities. I'm thrilled that you have no debt, and your home equity is a great asset. But be aware that only the first $250,000 in capital gains from a home sale is tax-free ($500,000 for couples). Earnings beyond $250,000 will be subject to a federal capital gains tax of up to 15 percent. Additionally, the home must be your primary residence, and you can claim the full exclusion only if you lived in it for at least two of the past five years. So you need to calculate what your net after-tax profit would be from selling, then figure out the price of living in the country. Remember, even dream houses come with utilities and property taxes, so be sure your move would sharply reduce your monthly living costs.

Act II involves making a practical transition. So often we approach decisions as all or nothing. How about a little of both? Can you move and continue to work with clients? That's important because your $100,000 isn't enough for a comfortable retirement. I want you to make it a goal to put away at least $10,000 a year until you're 65. With those savings plus what you've already got, you could have a $350,000 nest egg by the time you're 65. That's a decent sum, and Social Security should provide more income.

You say you're afraid of losing clients. Have you even asked them? Make them an offer they can't refuse by presenting a detailed plan of exactly how you'll be able to deliver the same high-quality work from a distance. Or consider other income sources if you ditch your city life. Perhaps there's a teaching opportunity in the area you're thinking of moving to.

The final act, if you decide it makes sense, is to move. Even if you can afford to buy a home, I recommend renting for a year. Living in the country isn't the same as vacationing there. After that trial period, if it's everything you hoped for, go ahead and buy. If it's not what you expected, you can walk away—confident that you can come up with a whole new plan.

Please note: This is general information and is not intended to be legal advice. You should consult with your own financial advisor before making any major financial decisions, including investments or changes to your portfolio, and a qualified legal professional before executing any legal documents or taking any legal action. Harpo Productions, Inc., OWN: Oprah Winfrey Network, Discovery Communications LLC and their affiliated companies and entities are not responsible for any losses, damages or claims that may result from your financial or legal decisions.


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