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Does Owning a Vacation Home Make Sense?

It was a crisp, cloudless autumn day in 2004. My son and I set off on mountain bikes from a trailhead in rugged north Georgia. We climbed gradually on an abandoned logging road. It led up through beautiful old hardwood forest to near the summit of a stately mountain. We leveled out, then began the …

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The 6 Crucial Questions to Answer Before You Retire

Readers and friends often ask me about the retirement decision-making “process.” How do you prepare, a year out, 6 months out, 3 months out? Do you need a written plan in advance? What about contingencies? Do you just pull the plug, or is there a more systematic way? When is it really safe to leave? …

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Financial Simplicity: What is Your Time Worth?

“Is the oil spilled? Is a little wine stolen? Say on the occasion, at such price is sold freedom from perturbation; at such price is sold tranquility…” –Epictetus Money is a stepping stone to more important things. If you’re on track to your financial goals, you may not need to manage your wealth so tightly. …

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Shopping Obamacare: Comparing Plans / Awaiting a Verdict

Much of my journey to early retirement was carefully planned. I saved a lot, invested carefully, read extensively. But in one area — health care — I was just plain lucky. Health insurance is one of the most critical issues in retirement: To live without it before Medicare starts at age 65 is to court …

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Financial Freedom on a Shoestring

I’ll admit it. I’ve led a life of some privilege. Maybe I didn’t have it easy. But I didn’t have it hard either. Simply by virtue of birth, I inherited most of the essential assets for my journey to financial independence…. No, my parents weren’t wealthy or powerful. I wasn’t given money or land or …

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Roth IRAs and Roth Conversions: Who Needs Them?

Roth IRAs are the darling of the financial media. Maybe it’s because they’re relatively newer. Or because the rules have changed, allowing more people to access them now. Or because, in some situations, they can save you more on taxes. Whatever the reason, there is a pervasive belief that Roths are somehow a better place …

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My Investment Portfolio: 2015

What makes a successful investor? Is it getting double-digit returns? Beating a certain stock index? Outperforming the market for years, and making millions? Or is it just growing and protecting your wealth well enough to achieve your lifetime goals? If you came here looking for sophisticated investing strategies from a self-assured financial wizard, you’ll probably …

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My Favorite Personal Finance Blogs: 2014

I believe in blogs. In a world where hidden agendas and conflicts of interest abound, personal finance blogs provide some of the most unbiased information available for managing your money wisely. The bulk of my weekly reading comes from blogs, not the mainstream media. The best blogs are written by smart people with actual experience …

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10 Tips for More Accurate Retirement Calculations

Retirement calculators are not all created equal. And the differences between them are more than just an academic issue. Why? Because you’ll be using these tools to make one of the most important decisions of your life. If you’re approaching retirement, or want to someday, either you or an advisor will likely use a retirement …

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The Best Retirement Calculators

What’s so important about retirement calculators? Why are these tools of more than just technical interest? Well, they’re important because either you, or a financial planner, will use the results from a retirement calculator to make one of the most crucial decisions of your life: Are you financially independent yet, or not? If you get …

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Should You Be a Dividend Stock Investor?

Dividend stock picking is the most compelling investment strategy that I’ve never tried. I’ve been tempted several times over the years, including recently when we had some new money to invest. The arguments for holding more dividend-paying stocks are attractive. Dividends provide reliable income, and the total returns can be impressive. People I respect have …

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Should You Work One More Year?

I’m “retired,” but I took this past summer off anyway. I wrote less on the blog. I postponed some personal projects. And, I worked on my bucket list — doing the things I couldn’t do while working full time, while raising a son, while living back east. This was the first summer since my 20’s …

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Annuity Shopping: Time to Buy a Deferred Income Annuity?

I want to buy an annuity. As I’ve written before, they make sense to me, in theory. In practice, I’m having a hard time pulling the trigger…. We received a modest inheritance. It doesn’t change our financial picture substantially, but it does mean we have some free cash to put to work — money we …

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The Good News About Retirement

There is no shortage of bad news about retirement: The population is aging. Workers haven’t saved enough. Market returns will be lower going forward. Inflation is bound to return. Health care is expensive…. Many of you, even those who are relatively well prepared, are concerned about the prospects for your golden years, afraid to make …

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Money News, Calculator Reviews and What You Might Have Missed…

It’s been a good year at CanIRetireYet.com. There are tens of thousands of visitors here every month. This blog is mentioned often in major media, and I frequently turn down opportunities for more publicity. My primary purpose is still to deliver practical, do-it-yourself commentary on the real issues in a prudent, retired lifestyle. I hope …

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Our Retirement Expenses: Where Does the Money Go?

What will it cost you to live in retirement? You may be asking this question as you plan your future. You could try to answer it by looking at national statistics on living expenses. The Consumer Expenditure Survey from the Bureau of Labor Statistics, is widely cited. But truly, you are the only one with …

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Y2K and Black Swans: Investing for the Next Crisis

It was late 1998 and I had traveled across the country to present at a software conference. In the lobby of the hotel was a group handing out literature on the impending “crisis” that would become known as “Y2K” (Year 2000). I hadn’t heard of it, so I began reading. I could see there was …

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What Will You Do When You’re Retired?

“If all the year were playing holidays, To sport would be as tedious as to work.” –Shakespeare Mention “retirement” at the office. Most people will be conjuring visions of sun-drenched beaches, lush golf courses, soaring mountains, or shimmering pool sides. Everybody knows that retirement has to be awesome, because vacations are awesome, and retirement will …

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Review: The Pralana Retirement Calculator

The reviews of free retirement calculators here have been some of the most popular posts on the site. There are certainly some useful free calculators available. And since no one calculator has a corner on predicting the future, it’s nice to have the option to run several and compare the results, without having to pay …

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Do-It-Yourself Estate Planning

Benjamin Franklin famously noted that “in this world nothing can be said to be certain, except death and taxes.” Death and taxes. Two of our least favorite topics — also two of the most inevitable. In keeping with the generally upbeat mood at this blog, I rarely focus on either of these morbid subjects. But, …

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My Income Taxes: 2014

Are taxes going to be your single biggest financial concern in retirement? A ravenous velociraptor stalking your financial security? Many pundits say so. Or, are taxes just another expense, and by no means your largest one? Despite their scary reputation, I don’t worry about taxes much. I laid out the reasons why — my political …

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