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.
Your Social Security Statement: The One Number Your Plan Needs
Your Social Security statement shows nine estimates. Your plan needs one. What the age-70 number assumes, why it can drop after you retire, and how COLAs fit in.
October 26, 2026
Brand-Name Drugs and Part D: Why the Cheapest Plan Is Still the Safe Bet
Taking a brand-name drug? In 728 drug lists, the lowest-premium Part D plan was usually the best and never cost more than about $400. How to read the labels.
October 24, 2026
For 3 in 4 People, the Lowest Part D Premium Wins
For about 3 in 4 people, the lowest-premium Part D plan is the right one. The one check for your situation, how exceptions work, and the cost of picking wrong.
October 24, 2026
An Even Better Reason to Wait Before Claiming Social Security
The bigger check is the usual reason to wait until 70. The better one: the years to empty your IRA, so your children never pay tax on it.
October 22, 2026
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
How to Choose a Roth Conversion Strategy
Every Roth conversion rule compares your tax rate with your heirs'. Almost nobody asks who your heirs are. How heirs, charity and a surviving spouse decide which conversion strategy wins.
October 11, 2026