February 6, 2026
What I Know Now...Retirement doesn't always happen as planned
Friends,
Retirement doesn’t arrive the same way for everyone.
My brother-in-law didn’t plan some long, graceful exit. He turned 61 in July, looked at an overbearing boss and a company that hadn’t contributed to his pension in nearly a decade, and decided he was done. With my sister still working—and able to carry the health insurance—he walked away from the 7-to-3 grind and never looked back. (much to the surprise of my sister!)
Some people plan it carefully. Others have the decision made for them—by a boss, a layoff, or a moment where they simply say, I’m done.
What I’ve heard, over and over, is that the difference between a stressful transition and a confident one often comes down to asking the right financial questions before the paycheck stops.
This week, I published Part 1 of a new three-part series on those questions—starting with income.
In this post, I walk through:
- How to think about retirement income realistically (not optimistically)
- Building a dependable income “floor” you can count on in any market
- Social Security claiming decisions—and why they matter for spouses
- Pension choices, guardrails, and whether part-time work is about need or choice
👉 Read Part 1: The Financial Questions You Should Be Asking Before You Retire (But Probably Aren’t) – Income
Link HERE
Next up: expenditures—what retirement really costs, what’s flexible, and why spending clarity often matters more than portfolio size.
As always, my goal is to help you approach this next chapter with fewer surprises and more confidence.
Thank you for being here. As always feel free to email me with ideas or comments. I love to hear from you! Email Me at: OverSixtyInsights@Outlook.com
Warmly,
Wendy
Founder OverSixtyInsights
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