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Retirement Tax Planning Services

You Saved the Money. Now Plan the Taxes On It.

A large pre-tax balance is a deferred tax bill with a due date you can still influence. We build the conversion, contribution, and withdrawal plan — with dollar amounts and deadlines — then file the returns that execute it. CPA-led, roughly 1,500 clients, all 50 states.

A guide by Taxstra Tax & Accounting — CPA-led tax strategy for business owners

Last updated: June 2026 · Bryan Martin, CPA, MBA

What This Service Is (and Is Not)

Tax strategy for your retirement money — not portfolio management

Retirement tax planning is the service of deciding, with actual numbers, how your retirement money gets taxed: which accounts you fund while working, when pre-tax dollars convert to Roth, and which account you draw from first when income stops. We deliver a written plan, then prepare the returns and coordinate the moving parts so it gets executed.

What it is not: investment management. We do not pick funds, hold your assets, or charge a percentage of them. That separation matters — when the firm recommending a Roth conversion also earns fees on your account balance, the advice has a thumb on the scale. Ours is flat-fee tax work, coordinated with whoever manages the portfolio.

If you want the educational background first — how retirement income is taxed, what RMDs and IRMAA are, how the three tax buckets work — read our free retirement tax planning guide. This page describes the service for people ready to have it done.

Key Insight
The core problem we solve: a large traditional 401(k) or IRA is taxed as ordinary income on the way out, and required minimum distributions eventually force that income whether you need it or not — stacking on top of Social Security and pushing Medicare premiums up with it. The window to change that outcome is the ten to fifteen years before the forced income starts. That window is the engagement.

Who Retirement Tax Planning Is For

Three situations where the math gets large

High earners with big pre-tax balances. If you have maxed a traditional 401(k) for fifteen or twenty years, you have done the saving right and the tax location wrong-by-default. Seven-figure pre-tax balances produce large forced distributions later. The earlier the rebalancing between tax buckets starts, the cheaper it is.

Business owners and 1099 professionals. Owners are not limited to employee contribution caps — plan design is the lever. A consistent six-figure-profit business can often deduct multiples of what a standard 401(k) allows through a solo 401(k), layered profit sharing, or a cash balance plan. This is regular work for us across physicians, consultants, and agency owners.

People within about ten years of retirement. The years between the last paycheck and the start of required distributions and Social Security are usually the lowest-bracket years of your adult life. They are also temporary. A deliberate plan uses them; the default wastes them.

Taxstra CPA Tip
The earlier of two milestones should trigger this work: your pre-tax balances crossing roughly the seven-figure line, or your planned retirement date moving inside ten years. At either point, the difference between a planned and unplanned tax sequence stops being rounding error.

What the Engagement Includes

Deliverables, not generalities

Every engagement follows the same arc — diagnose, design, implement — and produces specific deliverables:

DeliverableWhat it containsWhy it matters
Account inventory & projectionEvery account, balance, and income source projected through retirementThe baseline: what happens if you change nothing
Contribution planDollar-specific funding order across 401(k), HSA, backdoor Roth, taxableStops bracket-blind saving into the wrong bucket
Roth conversion scheduleYear-by-year conversion targets sized to brackets and Medicare thresholdsMoves pre-tax money out at low rates, on purpose
Business owner plan designSolo 401(k), SEP, 401(k), or cash balance plan comparison and setup coordinationOften the largest single deduction available to an owner
Withdrawal sequencing frameworkWhich account to draw from, in what order, once income stopsControls lifetime tax, not just this year's
Implementation & filingsDeadlines, payroll coordination, plan-provider follow-through, and the returns themselvesA plan that actually gets executed

Two things distinguish the implementation step. First, deadlines: many business retirement plans must be established by year-end, employer plan features take months to confirm, and Roth conversions cannot be undone after December 31. We run the calendar so the plan does not die of timing. Second, the filings: because we also prepare your returns, the plan and the tax return are produced by the same firm, and the conversion that was modeled is the conversion that gets reported.

Watch Out
The December scramble is where retirement tax planning goes to die. Conversions executed in a rush get oversized and trip Medicare income thresholds; plans opened at the deadline miss design options. Almost every strategy on this page works better with a six-month runway. If you are reading this in the fall, start now; if you are reading it in spring, you have the luxury of doing it right.

The Strategies We Implement

The toolbox, matched to the right situations

The strategies themselves are not secrets — the value is in sizing them to your numbers, sequencing them across years, and executing the paperwork correctly. The ones that carry most of the weight:

  • Roth conversion schedules — multi-year, bracket-targeted conversions, modeled against Medicare thresholds and state tax. Full mechanics in our Roth conversions guide.
  • Backdoor and mega backdoor Roth — Roth funding above the income limits, with the pro-rata trap checked before any money moves, since other pre-tax IRA balances can make a backdoor conversion partly taxable.
  • Solo 401(k) design for owner-only businesses — often the highest-leverage account a 1099 professional has. See the solo 401(k) guide.
  • Defined benefit and cash balance plans for consistently high-profit owners — large deductions in exchange for funding commitments and actuarial design. We compare the trade-offs in defined benefit vs. defined contribution plans.
  • HSA maximization and NUA review — the HSA's deduction-growth-withdrawal treatment makes it a stealth retirement account, and employer stock inside a 401(k) deserves a net unrealized appreciation analysis before any rollover, because a routine rollover permanently forfeits the option.

Which of these apply — and in what order — is the design problem. A W-2 tech employee, a locums physician, and a practice owner with staff get three different plans from the same toolbox.

A Worked Example: Bracket-Fill Conversions

What 'planned' looks like in dollars

A composite, anonymized example of the most common pattern we see:

Key Insight
The setup. A couple retires at 62 with $2 million in traditional 401(k)s and modest taxable savings. They delay Social Security to 70. From 62 to 70 their taxable income is low — they are sitting near the bottom of the brackets for the first time in decades. Left alone, the $2 million keeps compounding until required minimum distributions begin in their mid-70s, forcing six-figure ordinary income on top of two Social Security checks, at higher brackets and with Medicare premium surcharges attached.

The plan. Instead, they convert roughly $90,000 from traditional to Roth each year from 62 to 70, sized each December to fill the lower brackets without spilling into the next one or crossing a Medicare income threshold. Over eight years, roughly $700,000 moves to Roth at rates they chose, future required distributions shrink because the pre-tax balance is smaller, and the Roth side grows with no tax on the way out.

The exact numbers depend on brackets, state tax, health coverage subsidies, and market behavior — which is precisely why this is modeled annually rather than set once. The point of the example is the shape: the same lifetime income, re-sequenced on purpose, taxed on your schedule instead of the default one. No outcome is guaranteed; the discipline of running the math every year is the product.

Why Taxstra for Retirement Tax Planning

Planning-first, flat-fee, and built to execute

  • A proactive planning firm, not a once-a-year preparer. Retirement tax outcomes are set by decisions made years before the return is filed. Our engagements are quantified, multi-year, and revisited annually.
  • No assets under management, no product to sell. Flat-fee tax work means the conversion and contribution advice is driven by your tax math alone. We coordinate with your financial advisor rather than competing with them.
  • Deep business-owner bench. CPA + MBA-led, with daily work in S-corps, reasonable compensation, and owner retirement plan design — the place where the biggest retirement deductions live.
  • Nationwide remote, roughly 1,500 clients, all 50 states. Including genuine multi-state expertise for clients who plan to retire in a different state than they worked in — a tax decision in its own right.
  • Trusted in the physician community. White Coat Investor platinum sponsor; Bryan appeared on WCI Podcast #459. High-income professionals are who this firm was built around.

Retirement planning rarely travels alone — it usually pairs with the bracket, entity, and equity work described on our high-income tax planning page. One firm, one coordinated plan.

Retirement Tax Planning FAQs

What prospective clients ask before engaging

It is a CPA-led engagement focused on the tax side of retirement: which accounts to fund and in what order, when to convert pre-tax dollars to Roth, how to sequence withdrawals, and how to keep required minimum distributions, Medicare surcharges, and Social Security taxation from compounding later. We deliver a written plan with dollar amounts and deadlines, then handle the filings that execute it.

Get a Retirement Tax Plan With Numbers In It

Book a free 30-minute call. We'll look at your balances, your timeline, and your brackets — and tell you honestly whether planning would move the needle for you.

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