Roger Whitney, age 51, calls himself The Retirement Answer Man. As a financial planner, investment analyst and podcast host, he focuses on helping Baby Boomers craft a traditional (past-age-60) retirement.
Today, he joins me to answer two questions that come in from our community.
Our first question is from Emily, who says:
“I’m trying to help my mom decide if she should retire.”
“My dad was a CPA and then a CFO, making great money, until 16 years ago when he was diagnosed with early-onset Alzheimers. My mom never took care of their finances before, or knew anything them … she took a few years to get everything in order, but during that time, they burnt through their retirement savings.”
Their house sold in fall 2009, for just enough money to cover their mortgage balance and keep another $75,000 to invest.
Today, Emily’s mom is 64 and wants to retire. She’d like to use her small investment balance to buy a home outright, in cash, so she won’t have to worry about rent or mortgage in retirement.
Emily’s recommendation is that her mom waits until she’s 65 so she gets Medicare. But what if market correction happens? Will they regret not cashing out the investment at the peak?
Our second question is from Yvonne, who asks:
I’m 52, and I’m going to retire at age 53-and-a-half. (Hooray!!)
I’ve been getting notices from Social Security, telling me that “if I keep working” until age 62, or 65, my payment will be such-and-such amount. The key words, of course, are “if I keep working.”
How will an early retirement affect my Social Security benefits?
After taking these two calls, Roger and I chat about his new book, Rock Retirement.
Resources Mentioned:
- Social Security lifetime earnings: sign into your account first, and then click on the link that says “view earnings record.” (This link won’t display unless you’re signed in.)
- Social Security calculator
- #71: This Ain’t Your Grandpa’s Retirement, with Roger Whitney
- Track Your Net Worth
- How to Start a Blog in 5 Minutes


Thanks to our sponsors!
Tired of buying clothes that don’t fit? Hate crowds? Sick of clutter? Avoid shopping for clothes, yet still wear stuff you like, with our sponsor Le Tote.
They’ll mail you a box of clothes and accessories, which you can wear for as long as you like, and then send back whenever you want something new. No more clutter. No need to leave home.
Boxes start at $59 a month. Try them for 50% off by entering coupon code “Paula”.
Save time by using Freshbooks, an easy-to-use, cloud-based accounting system that takes the stress and hassle out of bookkeeping and, especially, invoicing. You can create an invoice in a few seconds, and Freshbooks’ automated system will handle the rest. They’ll help you get paid faster, with less hassle.
Wanna try them for free?
Visit Freshbooks.com/paula for a free 30-day trial. Please mention this show when they ask how you heard about them.
John W.
There are so many factors involved as to when to take SS benefits. Wife and I retired early 2016 at ages 61 and 62 respectively. We had 5 different scenarios associated with our retirement plan. Based on the end of plan value and lifestyle changes we are planning, it was best for us to start our benefits at 65 in conjunction with Medicare. That scenario was better than starting at 62 and just a bit reduced should we had waited until 70. This may not be the answer for everybody but it was the answer for us. During our early retirement years we’ve not paid any taxes and our health insurance is good and due to our managed income very affordable. In the meantime we are more active and living better than we had when working.