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A financial planner in his late 50s had long yearned to leave chilly suburban Connecticut for San Diego, where he could golf and boat year-round, so without closing his business, he bought a house in the new area and took his clients with him, by Skype.

As this true story illustrates, technology has made it all the more possible for people to relocate without changing jobs. Those making such a major housing move aren’t just the self-employed. An increasing number of people working for a large organization can now telecommute from a distant location.

“Working remotely is more and more common,” said Jim Weinstein, a life coach in Washington, D.C.

But life coaches emphasize the importance of factoring in financial considerations, including housing costs, before making a major move.

“Many millennials — now in their 20s and 30s — are saddled with student debt. That limits their chances of moving to a more expensive part of the country,” said Ashley Stahl, a coach based in both Los Angeles and New York.

Sheree Bykofsky, a literary agent and co-author of a life-planning book called “Me: Five Years from Now,” urges those planning a major geographical move to take a methodical approach.

“The key is to decide just exactly what’s right for you. You really want to make sure you come home to a place you love,” she said.

Here are a few other pointers for those seeking a happier living situation they can afford:

Shape your housing choices in the context of a larger life plan.

Inevitably, making a lifestyle change involves personal trade-offs. As Bykofsky notes, such choices are highly personal and best made after a period of planning and reflection.

“You have to ask yourself questions, focusing on your needs and desires and figuring out which ones are strongest,” she said.

Beyond the pencil-and-paper exercises found in life planning books, Bykofsky recommends you use visualization techniques to picture how your ideal future would look. In doing so, she says you should take into account not only your housing preferences and finances, but also whether your social life would thrive in the next location.

“It’s not just about the money,” said Eric Tyson, a personal finance expert who also advocates taking a holistic approach.

Though financial planners can help, Tyson says many tend to overlook non-financial variables when advising clients on housing choices.

“Suppose you’re torn between spending your discretionary funds on a lot of foreign travel versus having a big house payment in the new setting. Deciding between these two is not really a financial decision,” said Tyson, author of “Mind Over Money: Your Path to Wealth and Happiness.”

Factor retirement savings into your planning.

Before you upgrade your housing, Tyson urges you to review your preparations for retirement, especially if you’re a Baby Boomer and don’t want to live solely on Social Security after you retire.

To gauge how well prepared you are for retirement, he suggests you use the free online planning calculators provided by such mutual funds as Vanguard and T. Rowe Price.

Take into account the expenses associated with owning a bigger property.

Suppose your housing dream involves a much larger place, complete with elaborate landscaping. If a financial analysis shows you can afford it, should you go ahead on that basis alone?

Not without considering the effect that owning a much larger property might have on your time, Tyson says.

“Time is precious. Maintaining a really big home can be draining, both emotionally and physically,” he said.

Tyson, co-author of “Home Buying For Dummies,” suggests people carefully review their personal priorities before taking on ownership of a property that will suck up their time.

“You may want to rethink your dream if it involves a high-maintenance home that means you’ll have much less time to spend with friends and family. People can be house-poor in time as well as in money,” he said.

Consider moving to a lower-cost area if your goal is to live large.

As Tyson says, many who are already retired are in a strong position to upgrade by taking advantage of the wide disparity in housing costs within the United States and around the world.

“Contrary to popular belief, not all boomers want to downsize and simplify when they retire. Some are still holding out hope for that castle. Now that your kids are through college and your career is behind you, it could be possible to fulfill your big-house fantasy without breaking the bank — assuming you make a long-distance move,” he said.

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