True Wealth Design

A Roth conversion may not look compelling when today’s tax rate matches the expected future rate. But if one spouse dies early and the survivor lands in a much higher bracket, the math can change fast.

When one spouse dies, the surviving spouse may face higher tax brackets even though many retirement distributions stay the same. That can turn an already difficult transition into a much more expensive tax situation.

Paying almost nothing in taxes can feel like a win, but it may also mean you’re missing a valuable planning opportunity.

Tyler explains how large retirement accounts and future required minimum distributions can push retirees into higher tax brackets, and why strategically taking income earlier could potentially reduce the tax hit down the road.

It’s easy to put health insurance on autopilot and simply choose the plan with the best coverage every year.

But as retirement approaches, it’s worth comparing premiums, deductibles, HSA options, and your actual healthcare needs before open enrollment, because the most expensive plan isn’t always the smartest choice.

High-income retirees may face IRMAA surcharges that increase their Medicare Part B premiums. Retirement can create an opportunity to appeal those charges but the year you retire matters.

Tyler explains how retirement timing, future income and deferred compensation payouts can affect when you can appeal and what you ultimately pay.

Your retirement date could cost you an entire year of employer matching contributions.

Some companies require you to remain employed through December 31 to qualify for a lump-sum match paid the following year.

Before choosing your final day at work, check the fine print—you may discover that retiring just a few days early comes with a surprisingly large price tag.