The Situation

Linh spent nearly nine years at Meta, the last three as a product design manager. After her team shipped a launch she’d poured herself into, she did something she’d been quietly planning for years: she gave notice and took a gap year. Part of it was travel, part of it was helping her mother through a knee surgery back home in the Pacific Northwest, and part of it was simply figuring out what she wanted the next decade to look like. At 36, single, and debt-free, she had the savings to do it.

She’d done a lot right along the way. She’d maxed her 401(k) every year, built a healthy emergency fund, and sold enough RSUs at vest to avoid being dangerously concentrated in META. By the time she left, she had roughly $850,000 in pre-tax retirement accounts and a comfortable taxable brokerage balance. What she didn’t have was a plan for the one thing that made this year unusual: for the first time in her adult life, her income was about to fall through the floor.

The Gap We Found

Linh’s CPA filed her returns accurately every spring, and her old 401(k) sat untouched at her former provider. Neither of those facts was a mistake. But nobody was looking at the calendar. With no W-2 income for roughly fourteen months, Linh was about to spend a year — possibly two tax years — in the 10% and 12% federal brackets after a career spent in the 32% and 35% brackets. That low-income window is the single best time to move pre-tax retirement money into a Roth, and it was going to pass unused unless someone planned for it deliberately.

What We Did

We mapped out a multi-year Roth conversion strategy designed to “fill up” the lower brackets without spilling into the higher ones. A Roth conversion means moving money from a traditional, pre-tax account into a Roth account — you pay ordinary income tax on the amount converted today, and in exchange it grows tax-free for the rest of your life and comes out tax-free in retirement. Because Linh’s taxable income was near zero, we could convert a large slice of her $850,000 at a 12% to 22% effective rate instead of the 32%-plus rate she’d have paid while working — and the rate she’ll likely face again once she’s back at a senior tech salary.

We spread the conversions across two calendar years to keep each year’s conversion from pushing her into a higher bracket, and we coordinated the exact dollar amounts with her CPA so there were no surprises at filing. We funded the resulting tax bill from her taxable brokerage account rather than from the converted funds, which let the full converted balance keep compounding inside the Roth. Because conversions create income with no withholding attached, Alphanso’s AI agents tracked the tax owed in real time, calculated each quarterly estimated payment, and flagged the deadlines before they hit — so she never tripped an underpayment penalty while she was off the grid in another time zone.

[CHART: before/after — blended tax rate on converted funds, ~18% now vs. 32%+ as a working manager]

The Result

• Roughly $210,000 converted to Roth over two low-income years, taxed at a blended rate near 18% instead of the 32%+ she’d have paid as a working manager — an estimated $95,000 in lifetime tax savings on those dollars alone.
• Decades of tax-free growth ahead, with no future required minimum distributions on the converted balance.
• Zero estimated-tax penalties, with every quarterly payment handled proactively.
• A clear, written plan she could follow even while traveling — and the confidence that her gap year was building wealth, not draining it.

[CHART: savings breakdown — where the lifetime savings come from across the two conversion years]

Why This Worked

A CPA files what already happened; an investment advisor manages the portfolio in front of them. Neither is built to spot that a single low-income year is a rare, closing tax window — that insight only comes from looking at the whole picture at once. Because Alphanso is a flat-fee fiduciary, we had no reason to discourage Linh from a strategy that moved money out of accounts we manage; we were paid the same either way, so the only question was what was right for her. If your income is about to drop — a sabbatical, a founder year, an early retirement, or a gap year like Linh’s — that window is worth planning around before it closes. Request a callback and we’ll take a look.

Disclosure

This case study is a composite illustration based on real Alphanso client scenarios. Names and identifying details have been changed for privacy. Results are not guaranteed and will vary based on individual circumstances. All investing involves risk, including the possible loss of principal. Alphanso LLC is a registered investment adviser.