Should I File for Social Security If I’m Still Working?

Are you curious about the changes that are coming next year on the Retirement Answer Man show? Today, you’ll have a sneak peek at one of our new segments: the Rock Life segment. Bobby Dubois joins me to discuss how to ensure that you have enough energy so that you can rock retirement. 

On this episode, you’ll also hear my holiday gift-buying suggestions as well as the listener questions segment. Don’t miss out on hearing what to do with a settlement, whether to file for Social Security if you are still working, and whether you should simplify your investments in retirement. 

Don’t miss this episode to hear the answers to these listener questions, get a preview of what’s to come next year, and to get some fantastic gift ideas. My holiday gift guide 

Buying and receiving gifts later in life can be challenging since many of us already have so much. I prefer to give experiences over anything else, but when an experience isn’t appropriate a game is my go-to gift. These are some of the games that I enjoy playing or might make great gifts for someone you love

Sequence - easy enough for the whole family to enjoy

 Quix - a fast-paced dice game

Euchre - a midwesterner’s favorite

 Left Center Right - this can actually be played with dice or cards

 Ticket to Ride - a longer board game that’s worth learning

 Pictionary - great for parties

 Scattergories - another classic party game

 Kids Against Maturity - a twist on Cards Against Humanity that might be more appropriate for the family

 Play Nine - when golf meets cards

 Tri-Ominos - a triangular domino game

Listen in to hear what our listeners recommend. One listener has a fantastic tip for learning new games. Should James apply for Social Security while still working full-time? 

James is still working and approaching full retirement age. He would like to apply for Social Security but continue to work yet he is confused by the whole process. There isn’t much information about collecting Social Security while working full time. 

An added complication is that signing up for Social Security will automatically enroll him in Medicare. However, he still has healthcare coverage through his employer and would like to continue his employer’s coverage. 

James is right. There isn’t much information about collecting Social Security and enrolling in Medicare while still employed full-time. And what is out there is really confusing. 

You can collect Social Security at full retirement age while still working. The financial ramifications may push you into a higher tax bracket. Boomer Benefits can help you navigate Medicare’s complexities 

One aspect of choosing to collect Social Security at full retirement age is that it will automatically enroll you in Medicare part A. Parts B and D can be delayed, but they must be turned on within eight months of leaving your employer-sponsored health plan. The good news is that Medicare part A will coordinate with your health insurance if you end up hospitalized. 

Since there are so many difficulties in navigating this question, I recommend that anyone in this situation contact a Medicare navigator like Boomer Benefits.

Boomer Benefits is a company that deeply understands Medicare and the entire enrollment process. They don’t charge the consumer and aren’t trying to sell you anything–they are simply trusted advisors. They have numerous educational resources both on their website and on YouTube. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN GIFT BUYING GUIDE 

• [1:34] Roger’s holiday gift buying guide

LISTENER QUESTIONS 

• [10:30] Should James file for Social Security if he is still working?
• [14:10] What to do with a settlement
• [23:10] Whether to simplify investments
• [29:20] If I just retired can I still make a Roth contribution?

ROCK LIFE SEGMENT WITH DR. BOBBY DUBOIS 

• [30:37] The 3 pillars to building energy in our lives
• [34:32] Intentionally observe what works for you

TODAY’S SMART SPRINT SEGMENT 

• [45:00] Go buy a game or experiment on yourself

Resources Mentioned In This Episode
Cozy Earth - enter RAM at checkout to receive a 35% discount!
Boomer Benefits
Boomer Benefits on YouTube
Whoop
Oura Ring
Stacking Benjamins
Rock Retirement Club
Roger’s YouTube Channel - Roger That
BOOK - Rock Retirement by Roger Whitney
Roger’s Retirement Learning Center