Is Rolling Your 401(k) to an IRA Always a Good Idea?
Rolling your old 401(k) into an IRA gives you control, but it can cost you the backdoor Roth and the Rule of 55. How the answer changes over a career.
October 26, 2026
Articles
Retirement planning insights from the WhenIm64 team.
Year-End Tax Planning for Retirees: Three Decisions Before December 31
Gains and losses, your last Roth conversion, and the January 15 payment: the three year-end tax decisions for retirees, in the order that matters, with a worked example you can open yourself.
October 13, 2026
Before December 31: Take Your Gains and Losses on Purpose
A capital gain uses the same room under an IRMAA threshold as a Roth conversion. How gains, loss harvesting and year-end fund distributions play out for a sample retirement plan, and why you decide what to sell first.
October 13, 2026
Your Last Roth Conversion of 2026: Size It in December
Your 2026 conversions set your 2028 Medicare premiums, measured against 2028 thresholds. Why the last tranche waits for December, two hidden costs, and what it means if you're 63 or 64.
October 13, 2026
Pay for Your Roth Conversion by January 15, Without a Penalty
A December Roth conversion comes with a January 15 tax bill, and paying late can still cost a penalty. The safe harbors, the withholding rule that counts as paid all year, and the annualized method.
October 13, 2026
The 2030 Inherited IRA Tax Bomb — And How I Found It By Accident
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
Crossing the Tax Valley
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 IRMAA Nightmare Nobody Warned Me About
I did my homework before retiring. It still wasn't enough.
March 8, 2026