Tax Strategies
Planning the decisions that drive the return, not just filing it
Taxes are usually the largest expense of a working career and the largest expense in retirement. Most of it is unavoidable. Some of it isn’t, and over a lifetime the difference can be enormous. Tax strategy is the part of planning that finds that difference and acts on it, year after year.
We don’t prepare returns. We work alongside your CPA so that the decisions that drive the return, which accounts you use, when you sell, when you convert and when you give, are made on purpose rather than discovered in April.
Where the biggest wins usually are
The right asset in the right account
Which investments sit in taxable, tax-deferred and Roth accounts matters as much as which investments you own. Bonds and high-turnover funds in deferred accounts, broad index funds in taxable, the highest-growth assets in Roth. Done well, this is often worth more than picking better funds.
RSUs, ESPPs and options on a calendar
Stock compensation creates tax bills on its own schedule, and the default withholding is usually short. Planning vest dates, sales and estimated payments ahead of time avoids the April surprise and the concentration risk. See our year-end RSU checklist.
Filling low brackets with Roth
In lower-income years, the gap between retiring and starting Social Security is the classic one, converting traditional IRA dollars to Roth at a low bracket permanently reduces lifetime tax. Timing and amount are everything. See Should you do a Roth conversion before year-end?
Every dollar of room the IRS allows
For 2026 the 401(k) employee deferral limit is $24,500, with an $8,000 catch-up at 50 and $11,250 at ages 60 to 63; IRA contributions are $7,500. If your plan allows after-tax contributions and in-plan Roth conversions, the mega backdoor Roth can move far more into Roth than the standard limits. Above the Roth IRA phase-out, the backdoor Roth IRA remains available, subject to the pro-rata rule.
Which account to draw from first
In retirement, the order you draw from taxable, tax-deferred and Roth accounts, and how you time Social Security, determines your bracket, your Medicare premiums and how long the money lasts. Required minimum distributions now start at 73 (75 for those born in 1960 or later), and the penalty for missing one is 25% of the shortfall, reduced to 10% if corrected promptly.
Simple moves that add up
Realizing losses to offset gains, donating appreciated stock instead of cash, bunching deductions and using a donor-advised fund in high-income years. None of it is exotic; all of it is repeatable, and together it compounds.
Roth Conversion Bracket Filler
Enter your expected income and filing status. See how much you can convert this year without jumping a bracket or crossing a Medicare premium tier.
How tax planning fits into your plan
A tax review before year-end deadlines: conversions, harvesting, charitable gifts, estimated payments and any last contributions, with a short action list you and your CPA can work from.
A check-in once your return is done to catch anything that changed, adjust withholding for the year ahead and confirm the plan still matches the numbers.
Equity events, a job change, a sale, an inheritance or retirement itself each reset the tax picture. We model the year before it happens rather than explaining it afterward.
We share the plan, the projections and the lot-level detail so the return reflects the strategy. If you don’t have a CPA, we’ll introduce you to one we trust.
Run your own numbers first
Three of our free calculators are built for the tax questions we hear most: the Roth Conversion Bracket Filler, the Backdoor Roth IRA Eligibility Checker and the RSU Tax Withholding Gap Calculator. Full current-year brackets, limits and thresholds are in our 2026 tax table.
Suspect you’re paying more than you need to?
Bring last year’s return and a recent statement. The first conversation is free, and you’ll leave knowing which of these levers actually apply to you and roughly what they’re worth.
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