Gap Years
The two Roth five-year rules, and why a December conversion counts for the whole year Robert turned his laptop around so I could see the conversion form from his custodian. "Before I sign this, I want to know one thing," he said. "Once the money is
What this tax season taught me about the new $6,000 deduction, and why it was worth less than most retirees expected By mid-March, at least a dozen clients told me the same thing: "I thought the senior deduction would cover it." They meant the Roth conversion
IRMAA & RMDs
Richard slid a printout of my Roth window piece across the table before Joan had even sat down. "We read this," he said. "We're 75 and 73. The window closed years ago, didn't it?" It's a fair question, and I&
IRMAA & RMDs
I haven’t published in a few weeks, and if you’ve been reading for a while, you probably noticed. The reason is simple: this month was packed with extended tax returns, and when you run a CPA practice, those take priority over the newsletter. That’s the truth—September
The tax bill hiding inside every joint retirement plan, and how to defuse it while you still can Diane came to see me last winter, about fourteen months after Walter passed. She was not there about grief. She had a stack of paperwork and a specific question: why had her
Gap Years
The math the IRS won't let you skip Joe sat across from me, proud of his spreadsheet. He had mapped out a five-year Roth conversion plan, aiming to fill his lower tax brackets between retirement and age 73, just like we discussed before. The numbers were straightforward
Income-Growth Framework
Sequence of returns risk, explained: why the order of your returns matters more than the average. Eleanor asked me the question in March of 2023. She was 66 and had retired at the end of 2021, almost exactly at the market’s peak, though no one knew that at the
People talk about fixed index annuities as if they're a single product. They aren't. The label covers a wide range of contracts, and the differences between them are not cosmetic. They reflect fundamentally different jobs that the money is being asked to do. In my last
The mechanics of converting during the gap years, step by step A few months ago, I wrote about the most dangerous years of retirement, the quiet stretch between your last paycheck and your first Required Minimum Distribution. That piece made the case for why those years matter. This one is
Income-Growth Framework
Why the goals conversation should always come before the product Rene came in with a folder. That's usually a good sign. It means someone is organized, prepared, and taking this seriously. But as I started going through the documents she'd brought, something became clear within the
The Behavioral Side
For many retirees, the problem is not a lack of funds. It is feeling unsafe using what they have. This is the retirement failure no one discusses. The financial industry obsesses over solvency, projections, simulations, withdrawal rates, and not running out of money. These matter, but only measure one kind
Here is a number worth sitting with. If you are 60 years old with $800,000 in a traditional IRA, and you earn a modest 6% annually between now and age 73, you will arrive at your first Required Minimum Distribution with roughly $1.7 million in that account. You
