How To Plan For A Happier, More Enjoyable Retirement


By Walter Updegrave, RealDealRetirement, @RealDealRetire

Ask Real Deal Retirement

I’m in my mid-60s, retired and financially secure—but bored. Any suggestions for what I can do to have a more enjoyable retirement? More»

How To Navigate Your Way To A Satisfying And Secure Retirement

By Walter Updegrave, RealDealRetirement @RealDealRetire


It was a tough gig, but someone had to do it. Last week, I joined a team of financial experts who spent eight days aboard the Crystal Symphony luxury liner as part of MONEY Magazine’s “Building the New Retirement” Cruise. Despite the harsh conditions—we were forced to feast nonstop on exquisite cuisine and enjoy excursions at interesting ports of call like Quebec City and Halifax, Nova Scotia—the plucky MONEY team still managed to dispense investing guidance and retirement planning advice to our fellow MONEY cruisers. Here are three tips I’ve distilled from our sessions at sea that can help you chart a course to a more satisfying and secure retirement. More»

The Simple Secret To Being A Sophisticated Investor

By Walter Updegrave, RealDealRetirement @RealDealRetire


“Simplicity is the ultimate sophistication,” Steve Jobs, the late Apple co-founder, once said. That applies not just to designing Macs and iPhones that perform complex tasks yet are easy to use, but to investing as well. So whether you’re a newbie just starting to build a portfolio or a veteran investor looking to improve results in a challenging market like today’s, ignore the complicated-is-better model that passes for wisdom on Wall Street and instead follow these three tips for creating a simple-but-sophisticated investing strategy. More»

How Much Must I Invest To Retire With A $1 Million IRA?

By Walter Updegrave, RealDealRetirement @RealDealRetire


Ask Real Deal Retirement

I want to start a Roth IRA account and build the balance to $1 million. How much do I have to invest to do that? More»

Looking For An Easy Way To A More Secure Retirement? Cut Investing Fees

By Walter Updegrave, RealDealRetirement @RealDealRetire


When it comes to investing, most people focus on returns (or lack of them given today’s wobbly market). But if you really want to enhance your long-term financial security—especially in light of projections for subpar investment gains in the years ahead—you’d do better looking for ways to pay less in fees. More»

Should Investors Root For A Rout?

By Walter Updegrave, RealDealRetirement @RealDealRetire


Most investors cringe at the thought that recent market volatility could be a prelude to a crash. But if you’re investing money you don’t plan to draw on for many years, a good old-fashioned market meltdown that scares the bejeezus out of investors could be a blessing in disguise. More»

Should I Put Some Savings Into An Immediate Annuity?

By Walter Updegrave, RealDealRetirement @RealDealRetire


Ask Real Deal Retirement

I’m retired and have about $800,000 invested in a conservative mix of stocks and bonds. Social Security and pension payments cover my basic expenses, but I’m skittish about the market volatility and would like to have a guaranteed source of income that’s not subject to the market’s ups and downs. Should I put some of my savings into an immediate annuity? More»