Retirement Answer Man

This is the fourth and final episode of the Healthcare Before Medicare series. On this episode, we discuss two more options to consider when thinking about healthcare before Medicare: taking on a part-time job for the insurance benefits and COBRA. We also answer some listener questions and comments in the practical planning segment of the show. Learn more about which companies are the best for part-timers to receive healthcare benefits as well as whether COBRA may be a good option for your healthcare coverage needs listen in to gain more knowledge about how to maneuver our complex medical insurance system.

Have you thought about pretirement?

Will you take a pretirement phase of retirement? Would you enjoy finding low-key meaningful work to ease yourself into full-blown retirement? I often refer to this option as pretirement. A part-time job can be a fun way to work your way into retirement and it could also provide you with insurance benefits. You could find something fun that you enjoy doing as a part-timer. One example of this is if you enjoy handy work you might enjoy a part-time position at Home Depot. You’ll definitely want to factor in your physical limitations and you certainly don’t want to go back to the grind of full-time employment. Listen to this episode to find out which companies offer benefits to part-time employees.

Would COBRA work for you?

You can maintain COBRA coverage for up to 18 months after leaving your work so if you are close to Medicare age you may want to consider COBRA. COBRA is also a good option if you don’t qualify for ACA subsidies. The good news is that you have 60 days to notify the insurance company that you would like to elect COBRA coverage. COBRA is probably the closest you will come to your current healthcare coverage, so if you have many healthcare needs you may want to consider this option. There are a lot of great benefits when choosing COBRA, listen to this episode to hear them all.

How do you decide what the right choice is for you?

Are you curious to find out which healthcare option I will choose? This entire series has come at a great time for me since my wife recently left her job and we are seeking alternative healthcare options. The ACA is a nonstarter for my family due to the exorbitant costs for us without a subsidy. We have narrowed our choices down to Medishare and COBRA. Planning for every eventuality is challenging, especially since no one wants to think about a catastrophic medical event happening to them, but that is the point of having medical insurance. Listen to this episode as I walk through my thought process in making this decision for myself and my family. Who knows, maybe my process may help you with a difficult decision of your own.

Who do you turn to help you figure out health insurance?

As usual, my listeners have some fantastic questions and comments. One listener asks, who can help you figure insurance out? An insurance broker, a financial planner, a tax consultant? That’s a tricky question! Listen to the answer to this question and a few others during the practical planning segment. There are so many different factors to consider when choosing the right healthcare option for you before Medicare kicks in, be sure to listen to the whole 4-part series to help you make your healthcare before Medicare decision.


  • [1:22] April’s theme will be all about bonds


  • [3:55] Will you take a pretirement phase of retirement?
  • [5:12} What kind of work might you enjoy?
  • [9:12] Would COBRA work for you?
  • [12:24] What are my options?
  • [22:21] How do you decide?


  • [24:46] A listener comment from a health insurance broker
  • [28:55] Who is the best person to talk with about healthcare?
  • [31:48] A customer comments about their Medishare experience
  • [34:41] What are some other options and ethical questions?


  • [38:30] Check out the think up affirmation app


  • [40:14] Identify one area where you need to be healthier

Resources Mentioned In This Episode

Forbes Article on benefits for part-time workers

Think Up App

BOOK - Rock Retirement  by Roger Whitney

Ask Roger a question

Work with Roger

3-video Series: 5 Minute Retirement Makeover

Roger’s Retirement Learning Center

The Retirement Answer Man Facebook Page

Intro music by

Direct download: RAM214.mp3
Category:general -- posted at: 6:00am CST