Wealth management
The return reports the year. The plan decides it.
Tax planning is the work of deciding, years in advance, which income lands in which year, so a household pays tax at the lowest rates the law allows over a lifetime rather than the lowest amount in any single April. In 2026 a married couple can fill the 12% bracket up to $100,800 of taxable income and realize long-term gains at 0% up to $98,900, and those lines only help a household that planned around them before December. We do not prepare returns or give tax advice; your CPA does that. We build the multi-year plan, coordinate it with your CPA, and carry it out inside your portfolio.
The situation
Most of the tax you will pay in retirement is decided before you file.
A working household’s tax return is mostly set by the paycheck. Once the paycheck stops, almost every line becomes a choice: which account funds the year’s spending, whether to convert part of an IRA while the bracket is low, when to claim Social Security, how much gain to take, whether a gift comes from a checking account or straight from the IRA. Each choice moves income into one year and out of another, and the return only records what was decided.
Those decisions interact in ways a single-year view cannot see. A conversion that fits neatly under the 22% bracket can raise a couple’s Medicare premiums two years later. Drawing from the IRA first can pull more of a Social Security check into taxable income; drawing from the taxable account first can leave a required distribution at 73 that lands in a higher bracket than it needed to. Our guide on whether taxes get simpler in retirement shows how often the answer is no.
High earners face the same problem in a different form: restricted stock vesting on the company’s calendar, bonuses, option exercises, and a concentrated position whose gain is waiting for a lower-income year that will not arrive without a plan. This page describes what our tax planning service includes and how it is delivered. The investment-side techniques, asset location, loss harvesting and fund structure, have their own page on tax-efficient investing.
Why it’s complex
Five decisions we plan across years, not one
Which bracket to fill each year
Between the last paycheck and the first required distribution, taxable income can fall well below what the household spends. That gap is room to recognize income on purpose: an IRA withdrawal or a conversion taxed at 12% now instead of 22% or 24% later. The 2026 joint 12% bracket ends at $100,800 of taxable income, and the room beneath it is the first number in every plan.
Where the 12% bracket ends in 2026Roth conversions: how much, and when
A conversion pays tax today to remove an account, and its future required distributions, from the tax system for good. It pays off when today’s rate is lower than the rate the money would face later, for you or for your heirs. Sizing one means projecting both rates, keeping the Medicare thresholds in view, and setting aside cash outside the IRA to pay the tax.
When conversions pay off, and how to size themThe order the accounts are drawn
Spending the same dollar from a taxable account, a traditional IRA or a Roth produces three different tax results, and the sequence over a decade shapes the size of required distributions and how much of Social Security is taxed. Above $44,000 of provisional income, one dollar of IRA income can make $1.85 taxable for a couple. The withdrawal order is written down and revisited every year.
Which account to draw firstMedicare premiums with a two-year lag
Part B and Part D premiums in 2026 rise once a couple’s modified adjusted gross income on the 2024 return passes $218,000, and one dollar over the line costs the full first-tier surcharge for both spouses. Conversions, gain sales and rollovers all count. We keep a running IRMAA calendar so that crossing a line is a decision made with the cost in hand.
The IRMAA cliffGiving from the right pocket
From age 70½, a qualified charitable distribution sends up to $111,000 a year per person from an IRA directly to charity and can satisfy a required distribution without adding to income. Younger donors and larger gifts often do better with appreciated shares into a donor-advised fund, deductible at market value. The pocket a gift comes from changes what it costs.
Qualified charitable distributions in 2026Sources: IRS Rev. Proc. 2025-32 §§4.01, 4.03; CMS, 2026 Medicare Parts A & B Premiums and Deductibles; IRS Notice 2025-67; IRC §401(a)(9)(C) as amended by the SECURE 2.0 Act; IRC §86.
Our approach
How the service is delivered
Tax planning at the firm is part of the ongoing planning that comes with investment management, not a separate product. Your CPA prepares and signs the return and gives the tax advice; we build the multi-year plan, carry it out inside the portfolio, and make sure the two of us are working from the same numbers. This is the sequence.
Build the multi-year projection
We start with the last two returns, every account by tax type, Social Security and pension estimates, and any equity award schedules. From those we project taxable income year by year through the start of required distributions, marking where each bracket, the $32,200 standard deduction, the 3.8% surtax line and the Medicare thresholds fall. The projection is the tax section of your initial plan, delivered within 60 days of receiving complete information.
Set the year’s moves with your CPA
In September or October we reconcile the projection against the year’s actual income and agree on the moves: a conversion amount, the gain budget, the withdrawal order for the coming year, charitable gifts, and any withholding or estimated-payment adjustment. Your CPA sees the plan before the last trade of the year, and a written memo records what was decided and why.
Handle the decisions as they arrive
A vesting, a bonus, a home sale, an inheritance or an unusually low-income year each changes the projection. We rerun the numbers, talk with your CPA when the return is affected, and carry out what the portfolio side requires. For equity compensation that includes the withholding gap: the 22% federal default on a vest is often below the rate the income is actually taxed at. Our guide on RSU withholding shows the arithmetic.
Keep it in sequence through Quarterly Rounds
Tax is the fourth of our four quarterly reviews, after cash flow, risk and estate, because it depends on the other three. Each Quarterly Round checks realized gains against the budget, the IRMAA calendar, conversion progress and withholding, so that April confirms decisions already made rather than revealing them.
Reconcile and reset
When the return is filed we compare it to the projection line by line, note what moved, and reset the coming year’s plan. Over time the projection becomes a record of what each decision cost and what it saved, which is the evidence for the next one.
The work
What you’ll work through with us
- A multi-year taxable income projection through the start of required distributions, with bracket, surtax and IRMAA lines marked
- An annual Roth conversion recommendation: the amount, the timing, and where the tax is paid from
- A written withdrawal order across taxable, tax-deferred and Roth accounts, updated each year
- An IRMAA calendar showing which year’s income sets which year’s premiums, and the cost of each crossing
- A capital gains budget for the year, coordinated with rebalancing and any concentrated position
- A charitable giving plan: qualified charitable distributions, appreciated shares, and donor-advised fund timing
- An equity compensation tax calendar for vesting, exercises and sales, with the withholding gap estimated in advance
- A fall tax memo to your CPA, and a post-filing reconciliation of the return against the projection
Tax planning at the firm is led by Theo Halbardier, CFP®, CIMA®, CAIA®, the firm’s founder. The CFP® curriculum covers income tax planning in depth, which is what lets the projection, the portfolio and the CPA’s return work from one set of numbers. We are fee-only: no commissions, no product sales. About Theo
Questions
Common questions about tax planning
Do you prepare tax returns or give tax advice?
No. We do not prepare returns or provide tax or legal advice; your CPA or enrolled agent does that and signs the return. What we do is plan the multi-year picture, decide with you which income lands in which year, carry out the portfolio side, and share the plan with your CPA in writing before year end, so the return reflects decisions made on purpose. If you do not have a CPA, we can suggest a few to talk with.
What is the difference between tax planning and tax preparation?
Preparation reports what happened last year and files it accurately. Planning decides what will happen next year and the years after: how much to convert, which account to draw, when to realize a gain, how to give. Preparation is one season and one return; planning is a projection that runs through retirement and is revisited each fall. Both are needed, and they are done by different people who should be looking at the same numbers.
Is tax planning included, or is it a separate fee?
It is part of the ongoing financial planning that comes with an investment management relationship, at no additional charge. Households that want a one-time analysis, for example ahead of a business sale or a large conversion decision, can engage us for a standalone plan or a scoped consulting project. We do not offer ongoing tax planning on its own, because most of the value comes from carrying it out inside the portfolio each year.
When should tax planning for retirement start?
Ideally five to ten years before the paycheck stops, and no later than the year it does. The most valuable window is often the years between the last paycheck and the first required distribution at 73, when taxable income can be low enough to convert or realize gains at 12% or 0%. Social Security timing, Medicare enrollment and the conversion plan all interact, so the earlier the projection exists, the more of those years it can use.
Should I convert my IRA to a Roth?
It depends on the rate you would pay today against the rate the money would face later, for you or for whoever inherits it. Conversions tend to fit households with a low-income window before required distributions, cash outside the IRA to pay the tax, and heirs in higher brackets. They fit less well when the conversion would cross a Medicare threshold or when the account is likely to go to charity. We size them year by year rather than all at once.
How does IRMAA affect the plan?
Medicare premiums in a given year are set by the modified adjusted gross income on the return from two years earlier, and the 2026 first tier begins above $218,000 for a couple, or $109,000 for a single filer. One dollar over the line triggers the full surcharge for that year. We track which year’s income sets which year’s premiums, and when a conversion or gain sale is worth crossing a line, we do it knowing the cost rather than discovering it in a letter.
How are you paid?
We are a fee-only firm: our only compensation is a simple advisory fee based on the assets we manage for you. No commissions, no product sales, no hidden or layered fees. This structure keeps our interests aligned with yours. In other words, we do better when you do better.
Reviewed by Theo Halbardier, CFP® · Updated September 2026 · Figures current for 2026
Bring the last two returns. We will bring the projection.
The first conversation is 30 minutes. Your most recent return and a statement from each account are enough to start; no preparation needed.
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