Retirement planning insights from the WhenIm64 team.
Open enrollment runs October 15 to December 7. The first decision, Medicare Advantage or Medigap, is the one that's hard to undo. What changed for 2027 and which states let you switch back.
October 4, 2026
If you do nothing by December 7, your Part D plan renews at its 2027 price. Deductibles on every national plan, what expensive plans really buy, and the hidden cost of switching.
October 4, 2026
Most people who claim Social Security early know they're getting a smaller check. What they don't know is what early claiming does to their IRA, their future RMDs, and their lifetime tax bill.
March 30, 2026
I tried to build a straightforward Medicare Part D plan chooser for WhenIm64. What I discovered instead was a maze of hidden pricing, fine print deductible rules, and a government plan finder that leaves out the one number that matters most.
March 28, 2026
The required minimum distribution on a post-2020 inherited IRA is not the recommended distribution. If you follow tax rules you will be hit by huge tax bill after 10 years.
March 21, 2026
Most people treat their HSA like a medical debit card — spend it, reset it, repeat. But used correctly, the HSA is the only account in the tax code that gives you three tax breaks at once: no tax going in, no tax on growth, and no tax coming out. Here's what I wish I had known before I retired, including the one move almost nobody knows you can make once you leave your employer.
March 17, 2026
I maxed my 401(k) for decades and thought retirement taxes would be simple. I was wrong. Here's what I learned about RMDs, Roth conversions, and the narrow window to get ahead of both.
March 15, 2026
The workaround sounds simple. The pro-rata rule is not
March 12, 2026
I did my homework before retiring. It still wasn't enough.
March 8, 2026
I spent my career in software and still thought AI was overhyped. Retirement changed my mind.
March 8, 2026