He Retired Early and Beat the Tax Clock

John hated taxes.

Not in a casual, grumbling-at-April kind of way. In a this keeps me up at night kind of way. So when he retired at 61, his first question wasn't about travel or hobbies. It was: how do I keep as much of my money away from the IRS as possible?

He had a plan. Roth conversions. And he wanted to move fast.

What he didn't realize was that the clock had already started — and the first two years were the most valuable ones he had.

The Man Who Retired With a Target on His Back

John was 61, in great health, and sitting on a solid nest egg. No pension. No Social Security yet. Just a portfolio full of pre-tax money that the IRS would eventually want its share of.

He knew future tax rates were likely heading higher. He wanted Roth money — tax-free money — and he wanted as much of it as possible before the rules made it harder.

The fear wasn't dramatic. It was quiet and persistent: every year I wait, this gets more expensive.

Why Most Retirees Sleepwalk Through This Window

The common approach is to start Roth conversions gradually, whenever it feels convenient. A little here, a little there, no real urgency.

That's a bit like arriving at a restaurant right when it opens, seeing no line, and deciding to wander around the block first. By the time you're back, there's a wait. The empty window was always the opportunity — you just didn't treat it like one.

For John, that empty window was ages 61 and 62. He wasn't on Medicare yet. And because Medicare has a two-year lookback period, conversions done now wouldn't affect his premiums.

That's a narrow gap. Most people miss it entirely.

The Strategy That Made the Most of Every Year

We leaned into those first two years. Deliberately. Purposefully. Slightly more aggressive with conversions before 63, then carefully calibrated from there. We didn't worry about this IRMAA cliffs yet, untl we later were hyper-focused on them.

Why the shift? Because Medicare premium surcharges — what John called "basically a tax" — can stack up fast. At the higher income tiers, an extra $300–$500 per month in Medicare costs is real money. Avoidable money.

So we built a conversion plan that ran all the way to age 75, when required distributions will start. Front-loaded early. More measured later. Every year mapped to a bracket, a threshold, a tier.

Not reckless. Not timid. Strategic.

What Life Looks Like When the Plan Actually Works

John sleeps better now.

He's not paying unnecessary Medicare surcharges. He's moving money into Roth accounts year by year, building a reservoir of tax-free income for the decades ahead. And he's doing it in a way that respects the timeline — not fighting it.

The win isn't just financial. It's the feeling of being in control of something that once felt inevitable. Taxes, surcharges, future rate hikes — John isn't powerless against any of it.

He just needed a plan that took his first two retirement years seriously.

The One Thing Worth Remembering

If you're in your early 60s and not yet in the Medicare look-back window, you may be sitting in the most valuable tax window of your retirement. Most people don't treat it that way.

The gap between when you retire and when Medicare IRMAA matters isn't just a waiting period. For the right person, it's an opportunity.

Thank you for reading!

Last thing – I read every single reply to these emails.

I use these responses to guide my content, so your question might become next week’s deep dive.

Happy retiring,

Josh Rendler, CFP® Founder, Motion Retirement​ Partner, Award-Winning Retirement Firm​