If you're thinking of retirement, you need to prepare -- emotionally and financially. And don't mistake a vacation for a way of life Dear Bob …I’m taking a vacation on a beautiful island. No pressure, no deadlines, no politics. And I’m starting to wonder if I want to go back to the grind.[ Get sage advice on IT careers and management from Bob Lewis in InfoWorld’s Advice Line newsletter. ] Based on this vacation, I’m starting to think I could enjoy life as an expatriate someplace where the cost of living is a lot lower.What do you think? Should I just retire and enjoy life? Or is all the hassle worth it?– Bob Dear Bob … Now there’s a question with no answer. You’ll have to ask yourself if you’re ready, starting with what “ready” means. It ought to include the following:Have you accomplished what you want to accomplish in your career? If you’ve set goals for yourself and leave them undone, be sure you won’t be afflicted with what Harry Truman once called “the most crippling of emotions:” regret.How are your finances? The key to wealth is, of course, to want what you have. Nonetheless, anyone who wants to retire needs to look at their combination of investments and Social Security to see what sort of cash flow they’ll have. Translate that to the lifestyle you’ll be able to live in the location you’re thinking of and make sure it will be sustainable. (And don’t worry about the “Social Security will go away” nonsense. It might — starting sometime in the 2040s, a point that’s important for public policy but not for your retirement planning).Speaking of finances, think long and hard about your health care alternatives. Many of the places that are economical to live don’t have terrific health care. And you’ll still need health insurance until Medicare kicks in.As an expatriate you’ll be living in a different culture and, even lonelier, a different language. Ask yourself how well you’ll do when you aren’t able to comfortably converse with your neighbors. It’s more challenging and fatiguing than you might think.And finally, there’s the boredom problem. A lot of people retire and love it; others retire and find themselves bored stiff. There’s a difference between a vacation and a lifestyle. Just be sure you’re prepared for the lifestyle.Not that I’m trying to talk you out of anything. Among my other limitations on this subject is this: I’ve never retired, so all of my knowledge is second- and thirdhand. This is a big decision, and while it isn’t purely a one-way door, it’s close enough that you’ll want to be confident you’re ready for it.– Bob, on vacation on Santorini Technology Industry