Riding The Social Security Merry-Go-Round

By the time you read this article, I will be recovering from shoulder surgery. I’d like to tell you that I hurt myself doing something exciting or interesting like doing an Iron Man competition, or maybe hurting it while making the final push up to the summit of Mt. Everest. Nope, not me. Unfortunately, my […]







Watching The Tax Proposal Duel Unfold

When Susan Roman and I sit down with folks to help them design their retirement system, we usually discuss whether it makes sense to use investment vehicles that result in growth or income on which taxes are paid currently, or whether we kick the can down the street and pay taxes later. A question we […]







The Journey Of Your Tax Refund

Once again, we find ourselves approaching tax time. That time when we are either excited to get back some of our hard-earned money, or disappointed to see that we owe even more than we’ve already paid. As we do our taxes, most of us have our eye on that one number, either the amount we […]







Find Your Own Taxable ‘Sweet Spot’

In anticipation of my 50th birthday, I have challenged my three kids to race against me in the Falmouth Road Race next August. I have bet them each that I will beat them. So, about two months ago I began my quest to do just that. Each morning I have been exercising, trying to become […]







Required Minimum Distributions, Do I Need To Worry?

Last week was a long week. In Jeff’s endless pursuit of physical fitness (not really), he hurt himself. All of us in the office tell him he will be fine, but the poor guy had to take it easy for quite a few days. Both of our schedules were a bit thrown off as a […]







Are You Planning On Social Security?

The future of Social Security is a concern for many, young and old. In the retirement planning course that Susan Roman and I teach, we always get questions about Social Security.   Actually, in these classes we often get many questions, most of which concern either investing or Social Security. Our one request is that […]







The “Blood, Sweat & Tears” Era For Investors

I’ve often heard the stock market being compared to a roller coaster. It goes up; it goes down. It twists and it turns. It even can make you sick to your stomach sometimes. All of this is true. But my issue with that comparison is that a roller coaster always returns to where it started. […]







Capital Gains Taxes On A Loss? How?

As most of you know, we teach a retirement course at Cape Cod Community College. In the class, we teach folks how to build a retirement system. Part of the class is designed to help folks understand the impact of capital gains taxes on that system.   At our last class, I was explaining the […]







Retirement Calculators—Tools Or Fools?

If you’re like most people worrying about your financial future, you have likely found yourself in this scenario: It’s 2 AM and you are lying awake in your bed, worrying about the cost of your kid’s college, market volatility, the future of Social Security, and numerous other concerns. If so, then you have probably also […]







Paying Taxes For Safety

About a week-and-a-half ago I had an appointment with a very nice couple. They are married, in their middle to late 60s, are very successful, have brought up a very nice family and are recently retired. Let’s call them Dan and Ann. Dan and Ann have about $2 million or so in assets and are […]