Taxes & Tax Planning

You’ve spent decades saving, only to find out that Medicare has a "success penalty." It’s called IRMAA (Income-Related Monthly Adjustment Amount), and it is a cliff. Go one dollar over, and you pay the full surcharge. But there is a defensive move most retirees miss. Tax loss harvesting to...

You worked for 40 years, paid your FICA taxes, and finally retired. You assumed your Social Security check was yours. Then you get your tax bill. Not only is the IRS taking a cut of your benefits, but Medicare just sent a letter saying your premiums are doubling next year. Welcome...

You’ve been generous your whole life. In retirement, you continue to support the charities you care about, writing a check for a few thousand dollars each year. You feel good about it, and you assume your generosity is at least giving you a bit of a break on your...

You did it. You won the game. By saving aggressively & living intentionally, you've achieved the dream of early retirement. But as you stare at that massive 401(k) or IRA balance, you're realizing the game isn't over. You've just reached the final boss: a multi-million-dollar tax time bomb. As a...

Look, everyone on every forum like Reddit will tell you the best time to do a Roth conversion is during your "low-income years." For pre-retirees approaching Medicare, that is some of the most dangerous, incomplete, and costly advice you can get. It completely ignores the ticking time bomb in...

After nearly 30 years in financial planning, the most painful conversations I’ve had were with clients blindsided by a massive tax bill after selling their home. They thought their profit was simply the sale price minus what they originally paid. A costly mistake. That's why I created this home...

The couple sat across from me, retirement 18 months out, staring at a $380,000 tax bomb they didn't see coming. Their advisor had told them to "let it ride" in their pre-tax 401(k). Now, they were trapped. A Roth IRA conversion eliminates federal income tax on all future qualified withdrawals....

On January 1, 2021, Tennessee officially eliminated the TN Hall Income Tax, which previously taxed certain investment income. This move positioned Tennessee among the few states without any form of personal income tax, including taxes on capital gains.  Honestly, that's a pretty big deal – a state where you get to keep...

That phone call usually starts with a heavy heart, but then reality kicks in: "Michael, Dad left me the house in Plano and his $380,000 Fidelity account. I'm grateful, sure, but now what? The property's worth $625,000 now. Am I going to get hammered with a six-figure tax bill...

That phone call… it often starts with a mix of grief and a touch of bewilderment. "Michael," they'd say, voice still shaky, "I've just inherited Mom's house in Dallas, TX and honestly beyond the emotions, I'm clueless about what this means financially, especially with taxes. Where do I even...