Retirement planning insights from the WhenIm64 team.
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
My employer knew about the HSA and Medicare enrollment trap. I had to find out the hard way.
March 8, 2026