They Finally Got the Tax Flexibility They Always Wanted

First and foremost—Thank You.

It’s been an incredible past 4 months building this community with you all. There is plenty more to come, but I want to take a moment to thank each and every one of you, and wish you all a very Happy New Year! 🎆

Now, let’s take a look at a recent client success story …

Jim and Maggie came to us thinking they had their taxes under control.

Every December, their previous advisor would harvest capital losses from their brokerage account. It felt proactive. Strategic. Like they were outsmarting the IRS.

But when we looked under the hood, we realized those losses weren't helping them at all. In fact, they were quietly creating a tax trap that would follow them into retirement.

Jim, 75, had retired years earlier after a long military career. Maggie, 69, was wrapping up her final year of work. Together, they'd built a solid financial foundation with about $1 million in their brokerage account and traditional retirement savings.

What they really wanted was tax flexibility in retirement. Different buckets to pull from. Options. Control over their tax bill instead of feeling stuck every year.

Their previous advisor had been harvesting capital losses for years, thinking it was a win.

But here's the problem. Those losses could only offset $3,000 per year of Maggie's W-2 income. The rest just piled up, unused. Think of it like collecting coupons you can never redeem. You feel like you're saving, but you're not actually getting anywhere.

Worse, all that loss harvesting had reset their cost basis to almost nothing. Their $1 million brokerage account was now a ticking tax bomb. Every dollar they withdrew in retirement would trigger big capital gains, spiking their taxable income and affecting their Medicare premiums.

They thought they were taking control. In reality, they'd lost it.

We had one shot to fix this: Maggie's last working year.

While she was still employed and covered by her employer's health plan, Medicare premium surcharges weren't a concern yet. So we wiped the slate clean. We realized all those accumulated capital losses and matched them with an equal amount of capital gains from her concentrated employer stock. No extra tax. Just a clean reset.

When Maggie retired the following year, their brokerage account had a high cost basis again. That changed everything. Now we could pull money from that account with little to no tax consequence, which meant we could fund their living expenses and pay the taxes on Roth conversions without stacking up their taxable income.

Today, Jim and Maggie finally have what they always wanted: tax diversity.

We're doing meaningful Roth conversions every year, filling up the 24% tax bracket without triggering Medicare surcharges. Their living expenses come from the brokerage account with minimal tax impact. And when Maggie's required minimum distributions start, they'll be much smaller than they would've been, keeping her Medicare premiums low and preserving more wealth in tax-free Roth accounts.

They're not just managing their taxes anymore. They're controlling them.

If you're harvesting losses every year without a clear reason why, ask yourself: is this actually helping my long-term plan, or just making me feel productive?

Tax strategy isn't about activity. It's about positioning yourself for flexibility when you need it most.

Know someone who wants their own retirement breakthrough?

We work with a limited number of families each year who value clarity, confidence, and living well in retirement.

_{For privacy, names and minor details were changed. Education only, not advice. Consult your professional(s).}