We see the same issue again and again with high-net-worth families entering retirement.
It isn’t market returns. It isn’t whether they saved enough. By the time they walk through our door, most of them have done that part beautifully — decades of disciplined saving, smart accumulation, real wealth built.
The issue is taxes.
And more specifically: the absence of a real plan for when the IRS comes knocking in the years that matter most.
The Critical Years
There’s a window — roughly from age 60 through the first decade of retirement — where small decisions compound into very large tax bills. Or very large tax savings. Most families don’t realize they’re standing in that window until it’s behind them.
A few of the dominoes:
Medicare at 65. Your premiums are tied to your income. Cross the wrong threshold by a single dollar and you’ll pay surcharges (called IRMAA) for the entire year. We’ve seen families pay thousands more than they had to because nobody coordinated the income side of the equation with the Medicare side.
Required Minimum Distributions. The IRS eventually forces money out of your retirement accounts whether you need it or not. Many families don’t need that income to live on — but the withdrawal is mandatory, it’s taxable, and it can push them into a higher bracket they spent thirty years trying to stay out of.
Social Security. It can become partially taxable in retirement, and the rules around how much depend on the rest of your income picture. Get the picture wrong, and you’re paying tax on a benefit you already paid into.
Large IRA balances. Left unattended, they don’t sit quietly. They grow. They compound. And every dollar that grows inside them is a dollar that will eventually come out fully taxable — to you, or worse, to your children at their highest earning years.
That’s the ticking tax bomb. It’s quiet. It’s polite. It doesn’t go off until the choices you could’ve made about it are already gone.
What a Real Plan Actually Does
Our planning team has to get three things right for a family to be genuinely tax-efficient in retirement:
Sequencing — which accounts you draw from, and in what order.
Timing — when you take income, when you convert, when you wait.
Coordination — making sure every decision in one account knows what every other account is doing, and that the people advising you (advisor, CPA, estate attorney) are actually working from the same page.
That last one is where most families fall apart. Not because they have bad people in their corner — because they have separate people in their corner. An investment guy over here. A CPA over there. An estate attorney they haven’t spoken to in six years. Each one giving good advice in isolation, none of it adding up to a plan.
There’s a real difference between an investment relationship and a planning relationship. The first one watches your portfolio. The second one watches your life.
The Window Closes Quietly
The hardest conversations we have aren’t with families who walk in early. They’re with the ones who walk in after the dominoes have already started falling.
By then, we’re not building the plan. We’re picking up the pieces.
A tax-healthy retirement isn’t something you assemble at 70. It takes years. It takes coordination across accounts, across advisors, and across the calendar. The families who keep the most aren’t the ones who earned the most — they’re the ones who started planning for this part of the story long before they needed to.
That’s the work. That’s what we do.
If you’ve built something worth protecting and you’re inside that window — or approaching it — we should talk. Not a pitch. A conversation.
