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Bruce@cramercapitalmanagement.com
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Tax Planning, Not Just Tax Season

What you keep matters as much as what you earn. We look at the decisions that drive your tax bill while there is still time to change them.

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The Work Happens Before the Return Is Filed

Tax preparation records what already happened. By the time a return is being prepared, the year is closed and most of the choices are gone.

Tax planning looks forward instead. Which account a withdrawal comes from, when a gain gets realized, whether a conversion makes sense in a low-income year, how a large sale lands across two tax years. Those are decisions, and they have deadlines. We work on them through the year and coordinate with your CPA so the tax advice and the investment strategy are not quietly working against each other.

What Most People Find Out Too Late

Three facts about the tax code, from government sources rather than from us. None of them are about rates going up. All of them are about what happens when no one is watching.

More than half

of Social Security recipients will owe federal income tax on their benefits this year.

Whether you owe comes down to your total income, which comes down to decisions about withdrawals, conversions, and when you realize gains. Those are choices, not accidents.

Congressional Budget Office, The Taxation of Social Security Benefits, August 2026.

1994

the last year the income limits for taxing Social Security benefits were changed.

Those limits are not adjusted for inflation. Incomes rise, the line stays where it is, and more retirees cross it every year without changing a thing.

Congressional Budget Office, The Taxation of Social Security Benefits, August 2026.

1.9 billion

hours Americans spend each year just filing individual income tax returns.

That is the cost of reporting what already happened. It buys no influence over the number itself, because by filing season the year is closed.

Tax Foundation analysis of IRS and Office of Information and Regulatory Affairs paperwork burden data, 2026.

None of this is exotic. It is the ordinary arithmetic of a tax code that keeps moving while most people look at it once a year. The work that changes your outcome happens in the months before the return gets filed, not during it.

What We Do

Six pieces of work that run through the year. Most of them matter most before a decision is made, not after.

Tax Loss Harvesting

When an investment falls below what you paid for it, selling turns a paper loss into one that can offset gains you have realized elsewhere. You stay invested by moving into something similar rather than sitting in cash.

What this includes
  • ◆Watching for opportunities through the year, not only in December
  • ◆Offsetting realized gains and, within limits, some ordinary income
  • ◆Staying in the market so your allocation does not drift while you wait
  • ◆Taxable accounts only, since gains inside a retirement account are not reported year to year

Asset Location

Asset allocation is what you own. Asset location is which account you own it in. The same investment can be taxed very differently depending on where it sits, and moving it costs nothing.

What this includes
  • ◆Matching investments to taxable, tax-deferred, and Roth accounts
  • ◆Keeping the most heavily taxed holdings in sheltered accounts where that fits the plan
  • ◆Revisiting location when new money arrives or the allocation changes
  • ◆Coordinating across every account you hold, not one at a time

Capital Gains Management

Selling is a tax decision as much as an investment decision. We look at what a sale will cost before it happens rather than explaining it afterward.

What this includes
  • ◆Timing realized gains across tax years
  • ◆Holding period, and how it changes the rate that applies
  • ◆Rebalancing with the tax consequences counted, not ignored
  • ◆Spreading a large sale across more than one year where that helps

Roth Conversion Analysis

A conversion pays tax now to avoid it later. Whether that is a good trade depends almost entirely on which year you do it in, which makes it a timing question.

What this includes
  • ◆Finding the low-income years that are worth using
  • ◆Sizing a conversion so it does not push you into the next bracket
  • ◆Checking the knock-on effects on Medicare premiums and the taxation of Social Security
  • ◆Reviewed every year instead of decided once

Withdrawal & Distribution Planning

Which account a withdrawal comes from changes what it costs you, and so does the order you take them in. This is where tax planning and retirement income planning meet.

What this includes
  • ◆Withdrawal order across taxable, tax-deferred, and tax-free accounts
  • ◆Required minimum distributions, and planning the years before they begin
  • ◆Managing income to limit surcharges on Medicare premiums
  • ◆Fitting withdrawals around when you claim Social Security

Coordination With Your CPA

We do not prepare returns. What we do is bring the decisions that will land on your return to the table while there is still time to do something about them.

What this includes
  • ◆Working from your actual return rather than assumptions about it
  • ◆Raising items mid-year, when they can still be acted on
  • ◆One set of numbers for your tax advisor and your investment plan
  • ◆No attempt to replace a relationship that is already working

Tax Questions We Are Asked Most

What is the difference between tax preparation and tax planning?
Tax preparation records what already happened. Tax planning tries to change what happens next. By the time a return is being prepared, the year is closed and most of the choices are gone. Planning happens while the choices are still open, which usually means the middle of the year rather than the end of it.
Do you prepare my tax return?
No. Your CPA or tax preparer does that, and we are not trying to replace them. What we do is bring the decisions that will show up on that return to the table while there is still time to do something about them, and make sure the investment side and the tax side are not working against each other.
What is tax loss harvesting?
It means selling an investment that has dropped in value so the loss can offset gains you have realized elsewhere, and within limits, some ordinary income. You stay invested by moving into something similar rather than sitting in cash. Done through the year rather than in December, it can improve what you keep without changing your long-term strategy.
Does tax loss harvesting apply to my IRA or 401(k)?
No. It only works in taxable accounts, because gains and losses inside a retirement account are not reported year to year. This catches people out, and it is one of the reasons which account holds which investment matters as much as which investments you own.
What is asset location, and how is it different from asset allocation?
Asset allocation is what you own. Asset location is which account you own it in. The same investment can be taxed very differently depending on whether it sits in a taxable account, a tax-deferred account, or a Roth account. Getting the location right costs nothing and changes what you keep.
Should I do a Roth conversion?
Sometimes, and the answer depends on the year you do it in. A conversion means paying tax now to avoid it later, so it tends to make sense in years when your income is unusually low, and much less sense in years when it is high. We look at it every year rather than treating it as a one-time decision, and we run it past your tax advisor before anything happens.
Why does my Medicare premium depend on my tax return?
Medicare Part B and Part D premiums are tied to your income from a prior tax year. Cross a threshold and your premiums go up, which means a large capital gain or a big withdrawal can raise your healthcare costs a couple of years later. It is a cost people do not see coming, and it is one of the reasons we look at the whole picture before realizing income.
When should we be having this conversation?
Throughout the year, and especially before anything large happens. A business sale, a big gain, a retirement date, an inheritance, or a year when your income drops are all moments when the timing matters more than the amount. The least useful time to start is after the year has closed.

This information is not intended as tax or legal advice. Please consult a qualified tax professional or attorney about your own situation.

The Year Is Still Open

Most of what can be done about a tax bill has to happen before the year closes. If you have had a large gain, sold a business, set a retirement date, or landed in an unusually low-income year, that is the moment worth a conversation.

Schedule a Conversation

Already working with a CPA? Good. We would rather coordinate with them than replace them.