Tax Planning

Your tax return is a roadmap, not a receipt. We read it, project it forward, and tell you what to change before filing.

Our Methodology

How We Create Tax Plans

Tax planning is not tax filing. Where filing tells the story of what already happened last year, planning is the work of deciding how to write that story, while the year is still open.

At Gatewood, we read returns like an x-ray. Your return tells us which bracket you landed in and how much room was left in it. From there we project every year forward to retirement — because the years between your last paycheck and your first required withdrawal are usually the cheapest years you will ever pay tax in, and they do not last. That is the difference between planning and filing: filing reports the year, planning decides it.

Watch our Partner, Brian McGeehon, explain why it matters.

The Deliverables

What Our Service Includes

Every service in our planning model produces tangible, measurable deliverables that you can expect to receive.

Tax Bracket Projection

A year-by-year projection of which bracket your income lands in, from now through retirement, so the years with room left in them get used before they close.

Tax Return Review

We read last year's return line by line and report what it shows about this year — deductions missed, income worth shifting, and anything to change before December.

Roth Conversion Analysis

A breakdown of how much can move from pre-tax to Roth this year without tipping you into the next bracket, what the tax on it would be, and what it changes about your future RMDs.

Capital Gain and Loss Summary

What has been realized in your taxable accounts so far this year, short-term and long-term, and what is still available to offset against it before the year closes.

IRMAA and Medicare Premium Analysis

Medicare premiums are set by your income from two years earlier. You see which bracket you are on track for, and how close you are to the next one, while it can still move.

Charitable Tax Strategy

Giving directly from an IRA, bunching two years of gifts into one, or funding a donor-advised fund with appreciated stock — each one priced against what it saves you.
No More Tax Time Surprises

Plan Ahead. Maximize Returns.

Your advisor recommends a Roth conversion in October. Your CPA sees it for the first time in February, on a 1099 nobody warned them about. Neither one is at fault — they work at different firms and have never spoken.

Our team works to close the loop. We project your year in advance and connect with our tax team, or with your own CPA. We follow this routine every year, because it's a part of our process with all clients.

That is why we can tell you in October what April will look like, and why tax time won't come as a surprise.

A ring divided into four arrow-shaped stages that run clockwise and feed into one another, turning once every year. Read your return, to see what last year actually shows. Plan the year, deciding conversions, gains and charitable gifts while they can still be changed. Project your return, so the figure is known before the year closes. File, handled by the same firm that made the plan. The filed return is where the next year starts. Read your return Plan the year Project your return File
  1. Read your return. What last year actually shows.
  2. Plan the year. Conversions, gains and gifts, decided before December 31.
  3. Project your return. The figure known before the year closes.
  4. File. Handled by the same firm that made the plan.
How it All Works Together

What Your Fee Covers

We charge one advisory fee for household wealth management, calculated on the assets under our management. The fee schedule works like tax brackets, so the blended fee percentage declines as the portfolio grows. Trading and rebalancing sit inside that fee rather than being charged separately.

  • Personal Tax Preparation is billed as a separate engagement through Gatewood Tax and Accounting.

  • Any insurance products sold are subject to commissions, per industry standards.

You can read more in-depth about what we charge, how you're billed, and what your fees might be at the link below.

A ring of six segments around a centre labelled "your plan". Clockwise from the top: financial planning, cash management, investment management, insurance management, tax planning and estate planning. Each segment links to that service. Financial Planning Cash Management Investment Management Insurance Management Tax Planning Estate Planning Your Plan
Our Team-Based Approach

An Integrated Family Plan

A truly comprehensive financial plan involves tax, investments, cash, insurance and your estate — which all require their own expertise.

Your Client Care Team sets the bracket target for the year, our investment committee knows which lots can be sold and what gain comes with them, and our tax team confirms what the return will actually look like before anything is done. Your plan gets advice guided by experience and all aspects of your plan fit together to support your goals.

That is what we call Firm-to-Family®, and it is how we create plans that endure for generations. Your advisor will one day retire, but your plan will outlast any one relationship.
Multigenerational family walking together on the beach.
Before You Begin

Frequently Asked Questions

Tax planning is a proactive approach to understanding what your taxable income will be before the year ends and maximizing your tax return potential. That planning process incorporates which accounts you draw from, how much you convert from pre-tax to Roth, when you realize a gain or a loss, and what vehicle you'll use when you give to charity, if you so choose.

It is not the same as tax preparation or filing, which is the process of reporting your income after the year is over. Tax planning looks ahead, while tax preparation looks back.

A preparer works with a year that is already finished. By the time a return is being filed, the conversions, the sales and the gifts have all happened, and the only remaining question is what is owed.

Planning happens before, while there is still time to adjust and think ahead. In practice that means we are running projections in the fall, not in March — our clients do not arrive on April 15th surprised by the bill, because the bill was modeled months earlier.

A Roth conversion moves money from a pre-tax retirement account into a Roth account. You pay income tax on the amount converted in the year you do it, and qualified withdrawals from the Roth after that are tax-free.

The amount comes from the projection: we look at how much space is left between your income and the top of your current bracket, subtract anything that would push you over an IRMAA threshold, and convert into what is left. Converting more than that is possible, and sometimes it is the right call — it just has to be a decision rather than an accident.

IRMAA stands for Income-Related Monthly Adjustment Amount, and it is the surcharge added to Medicare Part B and Part D premiums when income is above a threshold.

It uses your income from two years earlier, which is what makes it a planning item rather than a billing one: the return you file this year sets your premiums for the year after next.

A large conversion or a single big capital gain can move you up a tier without anyone noticing until the premium arrives.

No. Plenty of our clients keep the preparer they have, and we work from the return that preparer files. What we add is the part that happens before the return exists — the projection, the conversion sizing, the gain and loss planning, the giving strategy.

We'll coordinate with any professional you work with outside of Gatewood, just like we would with our own Gatewood Tax and Accounting Team when tax season comes.

If you would like to see what that looks like against your own numbers, send us last year's return and we will read it and tell you what we see.

Yes, we are held to a fiduciary standard on all of our advisory accounts as well as by our teammate's designations such as CFP® and CFA®.

Gatewood is compensated by an advisory fee calculated as a percentage of the assets we manage and billed quarterly.

You can read more about our fee schedule here.

Built on Relationships

Hear What Our Clients Say

“My wife and I moved to St. Louis four years ago and became Gatewood clients in 2024, on a referral from our daughter-in-law. Her father was an established attorney who had said good things about the team, and that recommendation was passed down to us. That introduction set an expectation, and the people there have matched it. We've met a lot of the team by now, and the impression has been consistent with every one of them. Each person we're introduced to is professional, smart, and they work together well as a group — which says something about the people Gatewood hires…” Read more.
Dale D., Retired Corporate Professional | 08.17.26

Important Disclosure: The statements provided are testimonials by clients of the financial professional. The clients listed have not been paid or received any other compensation for making these statements. As a result, the client does not receive any material incentives or benefits for providing the testimonial. These views may not be representative of the views of other clients and are not indicative of future performance or success.

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