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Retirement Tax Planning Services

Retirement Tax Planning: 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, 1,000+ clients, all 50 states.

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

Quick Answer
Retirement tax planning decides which accounts to fund, when to convert pre-tax dollars to Roth, and which account to draw from first in retirement, distinct from investment management. It matters most for high earners with large pre-tax balances, business owners who can deduct more through plan design than a standard 401(k) allows, and people within about ten years of retirement.

Worked example

Bracket-fill Roth 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.

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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. Once you bring on employees, the plan menu changes; see our SEP IRA vs SIMPLE IRA comparison for the small-business options.

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.

What the Engagement Includes

Deliverables, not generalities

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

DeliverableAccount inventory & projection
What it containsEvery account, balance, and income source projected through retirement
Why it mattersThe baseline: what happens if you change nothing
DeliverableContribution plan
What it containsDollar-specific funding order across 401(k), HSA, backdoor Roth, taxable
Why it mattersStops bracket-blind saving into the wrong bucket
DeliverableRoth conversion schedule
What it containsYear-by-year conversion targets sized to brackets and Medicare thresholds
Why it mattersMoves pre-tax money out at low rates, on purpose
DeliverableBusiness owner plan design
What it containsSolo 401(k), SEP, 401(k), or cash balance plan comparison and setup coordination
Why it mattersOften the largest single deduction available to an owner
DeliverableWithdrawal sequencing framework
What it containsWhich account to draw from, in what order, once income stops
Why it mattersControls lifetime tax, not just this year's
DeliverableImplementation & filings
What it containsDeadlines, payroll coordination, plan-provider follow-through, and the returns themselves
Why it mattersA 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, and our Roth 401(k) vs 401(k) comparison for how to set the deferral election. Hospital and nonprofit employees with a 403(b) face a similar sequencing question; see 403(b) vs Roth IRA: which to fund first.
  • 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.

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, 1,000+ 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. As featured in White Coat Investor (Podcast Episode #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

What is a retirement tax planning service, exactly?

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.

How is this different from working with a financial advisor?

Advisors manage portfolios; we manage the tax consequences. We do not sell investments or take a percentage of your assets, so the recommendation to convert, contribute, or withdraw is driven purely by the tax math. The best results come from both working together, we coordinate directly with your advisor so the tax plan and investment plan agree.

Do you manage investments?

No. Taxstra does tax strategy, planning, and the returns that implement them. We will tell you which account type to fund, how much, and when a conversion makes sense, and we leave fund selection and portfolio construction to your financial advisor. If you do not have one, we can suggest what to look for.

Who gets the most value from this service?

Three groups, in our experience: high earners with large pre-tax balances who are heading toward big required distributions; business owners and 1099 professionals who can deduct far more than a standard 401(k) allows through plan design; and people within roughly ten years of retirement who want a deliberate conversion and withdrawal sequence instead of defaults.

When do Roth conversions make sense?

Usually in years when your tax bracket is temporarily low relative to where it is headed: early retirement before required distributions and Social Security begin, a sabbatical, a low-income business year, or a market dip. Conversions are calendar-year decisions that interact with Medicare premium surcharges and state tax, so we model the amount each year rather than guessing in December.

What retirement plans can a business owner use beyond a 401(k)?

Depending on income, staffing, and consistency of profit: a solo 401(k) for owner-only businesses, SEP or safe-harbor 401(k) designs with employees, and defined benefit or cash balance plans for owners with consistently high profit who want six-figure annual deductions. Plan choice is a design problem, entity type, payroll, and cash flow all matter, and we model the options side by side.

How does the engagement start, and what does it cost?

It starts with a free 30-minute call to understand your accounts, income, and timeline. If we are a fit, we quote a flat-fee planning engagement up front, no percentage of assets, no hourly surprises. Most clients then stay on for annual planning and tax preparation so the plan gets executed and updated every year, not filed away.

“I recently had the pleasure of working with Taxstra, and I must say, the experience exceeded my expectations. From start to finish, their professionalism, expertise, and customer care were outstanding.”
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Get a Retirement Tax Plan With Numbers In It

Book a free 30-minute consultation with our team to discuss your needs, our services, and whether Taxstra is a fit. Tax advice, document reviews, and analysis require a paid engagement.Your tax plan and specific advice come after you engage. The call is about fit and next steps.

Tax planning slots are limited before year-end.