Estimated reading time: 5 minutes
Key Takeaways
- A Chicago Bears comeback reminds us that big wins are still possible—especially in retirement.
- Retirement isn’t about slowing down; it’s about choosing what matters most.
- The best retirements include a strong support system, a clear strategy, flexibility, and a personal definition of success.
- Like sports, life doesn’t always go according to plan—and that’s okay.
- “Winning” in retirement looks different for everyone.
On Sunday (1/11/26), the Chicago Bears beat the Green Bay Packers in the final minutes of the game. It was thrilling—an emotional rollercoaster, especially for a Bears fan like me.
For most of the game, the Bears were behind. Momentum wasn’t on their side. It didn’t look good.
| Team | Packers | Bears |
|---|---|---|
| First Quarter | 7 | 3 |
| Second Quarter | 21 | 3 |
| Third Quarter | 21 | 6 |
| Fourth Quarter | 27 | 31 |
And yet, something shifted.
The team came together. They believed they could do it. They wanted to win.
And they did.
That kind of comeback isn’t just exciting—it’s a powerful reminder of what’s possible in life.
Life Lessons from Sports
Watching the celebration in the Bears’ locker room after the win got me thinking about life in general—especially this stage of life.
As we enter or move closer to retirement, it’s easy to assume the big wins are behind us. But I believe the opposite is true. Retirement is not about slowing down—it’s about prioritizing what matters most.
Whether it’s planning a bucket-list trip, staying fit enough to keep up with grandchildren, or finally having time to pursue something meaningful, having something to look forward to adds energy, purpose, and joy to your days.
Sports remind us of that.
Here are four lessons that translate especially well to retirement.
1. Have a Team Behind You
No team wins alone—and neither do we.
In retirement, your “team” might include:
- A financial advisor and/or accountant
- Doctors and healthcare providers
- A fitness trainer or physical therapist
- Trusted friends or family members
Surrounding yourself with the right people provides confidence, support, and better decision-making—especially when challenges arise. Many of us struggle with retirement budgets, finding purpose, or staying healthy. You don’t have to figure it all out on your own. Having people to lean on becomes even more important as we age.
2. Have a Strategy
Winning doesn’t happen without a plan. Your retirement strategy doesn’t need to be complicated, but it should be intentional.
Ask yourself:
- How do I want to spend my time?
- Do I want to travel?
- How will I stay active?
- Will I volunteer or mentor?
- Do I want to learn something new?
- Where do I want to live?
When you know what you’re working toward, your days feel more purposeful—and a lot more fun.
Here’s why this matters:
- Nearly 47% of Americans don’t have a written financial plan, meaning many head into retirement without clear goals or strategies (Investopedia).
- Several studies show early retirement may be associated with a 6–7% higher mortality rate, often tied to a lack of purpose or structure.
- At age 65, Americans can expect about 19.5 more years of life—longer for women than men (CDC).
- Physical activity plays a huge role. People in the top activity quartile may live 5+ years longer than average.
When you realize you may have 20 more years ahead of you, the question becomes: How do you want to use them? Having a strategy helps ensure you enjoy those years—especially before health issues enter the picture.
3. Have an Alternate Plan
Even the best teams adjust mid-game.
Life doesn’t always go according to plan, and retirement is no different. Flexibility is key:
- Budgeting for unexpected expenses
- Adjusting travel or lifestyle plans
- Preparing for health changes
Having a backup plan doesn’t mean expecting the worst—it means being prepared so you can move forward with confidence.
I’m learning this lesson right now through golf. I’ve been practicing hard, taking lessons, and playing nearly every day. About a month ago, I shot my personal best for nine holes—a 39. Lately, I can’t seem to break 45.
What’s going on?
It’s about reassessing the plan, enjoying the process, and not taking things too seriously. Retirement is the same way—progress isn’t always linear, and learning to adjust without losing joy is part of the journey.
4. Define What “Winning” Looks Like for You
Winning in retirement doesn’t look the same for everyone.
For some, it’s financial peace of mind.
For others, it’s good health, strong relationships, or waking up excited about the day ahead.
Some mornings feel quiet after a busy career. There’s time for lemon water and coffee, a workout, laundry—and sometimes boredom. That’s where projects and volunteering can make a difference.
Recently, I’ve been learning to use Canva and helping design the program book for the Breakthrough T1D Gala. Learning a new skill and putting it to use in something meaningful—and beautiful—was incredibly fulfilling.
The key is deciding what your win looks like—and making choices that move you closer to it.
Just like that Bears comeback, retirement can surprise you—in the best possible way. With the right mindset, support, and plan, the final score can still be very much in your favor. 🏈
If retirement were your fourth quarter, what would “winning” look like for you?