We’re living longer. That’s good news—but it also means we need to rethink what retirement really looks like over a longer period of time.
This 70-year-old proactive ProAger happens to like being semi-retired. And I want to thrive, stay engaged and enjoy life for many more years to come.
I’ve always loved the spirit behind Hunter S. Thompson’s famous quote about life being a journey—not one where we arrive at the end perfectly preserved, but one where we can look back and proclaim, “Wow! What a ride!”
Decades later, and this part still resonates with me.
The “totally worn out” part? Maybe not so much.
We’re becoming much more conscious of how the choices we make today can affect how we live tomorrow. I don’t want to simply add years to my life. I want those years to be years I can enjoy—living my best life, one day after the next!
And that changes the retirement conversation.
That’s why I reached out to Jay Thompson, creator of Retired.Living.
What started as one conversation quickly grew into something much bigger: a six-part Boomer Bytes Podcast series, Retirement Planning for ProAgers.
Why six sessions?
Because there isn’t one retirement play.
The First Play: Medicare Open Enrollment
We decided to begin our six-part series with Medicare Open Enrollment because it’s one of those important dates that rolls around at the same time, year after year—and it’s not something you want to glaze over.
I encourage you to watch the video of our first session, Episode 13 of the Boomer Bytes Podcast.
Jay provides valuable insight into Medicare Open Enrollment, what you should be reviewing and why taking the time to look at your coverage each year matters.
And our conversation is just the beginning.
Jay also wrote an in-depth article that dives even deeper, with more details to help you understand Medicare Open Enrollment and the decisions you may need to consider.
Read -> Jay Thompson’s Medicare Open Enrollment article
Jay brings the retirement-planning knowledge. I bring the questions many of us are asking—or perhaps haven’t thought to ask yet, or feel ackward to ask.
For many of us, retirement could last another decade, two decades—or even longer. That’s a substantial chapter of life.
It makes sense to have a playbook for it.
Not a playbook for getting older. A playbook for continuing to live your best life.
What’s in Your Retirement Playbook?
When I say playbook, I mean it much like the playbooks used in sports. You don’t go into the game with one play and expect to win.
You need different strategies for different situations. You make a plan, adjust when circumstances change and determine the next play.
I think the same is true for the game of life.
Our playbook must have numerous strategies to consider if we want to plan effectively for a more secure future—while continuing to enjoy the life we’re planning so carefully for.
Throughout the six sessions, Jay and I will explore:
- Retirement income and creating a paycheck after the paycheck stops
- Medicare
- Social Security
- Taxes and retirement planning
- Healthcare and long-term care
- The lifestyle side of retirement—including purpose, relationships, health, structure and what comes next
If we want to thrive throughout a longer retirement, we need our own play-by-play strategies.
How will we create income? When should we take Social Security? How do we navigate Medicare? What about taxes, healthcare and long-term care? And how do we plan for the lifestyle we actually want to live?
Think of it as another resource for your retirement playbook. 
Medicare isn’t something to choose once and then forget about. Plans, costs, medications and our own needs can change.
Being a proactive ProAger means paying attention, asking questions and making informed decisions—not simply letting another Open Enrollment period pass by.
Stay Tuned — There’s More to Come
Medicare is only one part of the retirement playbook.
Session 2 of Retirement Planning for ProAgers will air the third week of November, when Jay and I will continue adding more strategies to the retirement playbook.
In the meantime, start thinking about your own.
Who needs to be on your team? What questions do you need to ask? What areas of your retirement plan deserve another look?
You don’t need to figure everything out at once. Start building your team, create your playbook and add the strategies you need along the way.
There’s no time like now to get started!
After all, we’re not planning simply to grow older. We’re planning to thrive, enjoy the years ahead and keep living our best life—one day after the next.
Choose ProAge, not Old Age. 🌻
P.S. Have questions about retirement planning? Drop them in the comments. Jay and I will do our best to answer your questions in an upcoming session.