Why I Built WhenIm64™

The Problem: Feast or Famine

As you approach 65, retirement information arrives in two very different forms. First, the flood: hundreds of pieces of mail from insurance companies and brokers selling Medicare Advantage, Medigap supplements, and Part D prescription drug plans. Every mailer claims to be the best option, but none of them explain how any of it actually works — or which plan is right for your specific situation.

Then there's the other side. When you have a real question — about enrollment windows, penalties, the interaction between your income and Medicare costs — you find yourself holding for over an hour just to reach someone at the Medicare office or the Social Security Administration. And when you do reach someone, the answers aren't always consistent.

I had no idea terms like IRMAA, Tax Valley, RMD, or QCD were even relevant to me until I stumbled into situations where they mattered — a lot.

The IRMAA Nightmare

IRMAA — the Income-Related Monthly Adjustment Amount — is a Medicare surcharge that higher earners pay on top of their standard Part B and Part D premiums. It's based on your tax return from two years prior, which means the year you retire and your income drops significantly, you're still being charged at your pre-retirement income level.

There's a form you can file — SSA-44 — that asks Medicare to use your lower current-year income instead. After multiple calls with hold times exceeding an hour each, I eventually learned about it, filed it, and thought I was in the clear.

What I didn't anticipate was a mutual fund capital gains distribution at the end of December — the kind that shows up with no warning and quietly pushes your Modified Adjusted Gross Income over an IRMAA threshold. Mine did. I received a letter from the SSA informing me of an IRMAA surcharge, followed by an invoice for back payment.

The invoice didn't match the letter. Not a single line item added up the same way. I called Medicare — over an hour on hold. They told me to call Social Security. Another hour on hold. The Social Security representative told me, with full confidence, that he had never heard of IRMAA and could not help me. My case was escalated. Someone would call me back “within a few weeks.”

With the payment deadline approaching, I called again. A different representative told me just as confidently that I didn't owe IRMAA at all. Eventually, a second-level specialist called back and was finally able to explain the charges — which, by the way, were never broken out comprehensibly on the invoice itself.

The whole experience cost me weeks, several hours on hold, conflicting information from multiple government representatives, and more stress than it should have. I had done my homework — and it was still this hard.

Why I Built This

I didn't want others to go through that alone.

I spent my career building software — tools that take complex, technical things and make them understandable and actionable for real people. When I retired and ran into the wall of complexity that is Medicare enrollment, IRMAA, Roth conversions, Required Minimum Distributions, and retirement tax planning, I did what came naturally: I built a tool.

WhenIm64 is a single place to get clear, personalized guidance on the financial decisions that actually define retirement — without the junk mail, without the hour-long hold times, and without the experience of being passed from department to department by people who give you different answers.

The name comes from the Beatles song. My wife and I used to joke about it when retirement seemed far away. Now it's here — and we want to help you make the most of it.

What WhenIm64 Covers

Everything I wish I'd had in one place before I retired:

• →Medicare enrollment windows, Parts A–D, Medigap vs. Medicare Advantage, and how to avoid late-enrollment penalties
• →IRMAA thresholds and how Roth conversions, QCDs, and income timing affect your Medicare premiums two years out
• →Social Security claiming strategy — Full Retirement Age, delay credits (8%/yr), spousal and survivor benefits, and break-even analysis
• →Roth conversion optimizer — model bracket fill, IRMAA management, and the Tax Valley between retirement and RMD age
• →Required Minimum Distributions — project future RMDs, see how conversions reduce them, and understand inherited IRA rules for your heirs
• →Quarterly estimated tax reminders — in retirement there's no paycheck withholding, so you need to pay four times a year
• →Qualified Charitable Distributions — a powerful tax-free giving strategy for IRA owners 70½ and older