Most of what gets called tax planning happens in the spring, which is roughly the point at which very little can still be changed. The return documents decisions made months earlier. Whatever was going to work already worked, and whatever was going to be expensive already was.
Real tax work happens during the year, and often several years ahead of the event it concerns. It shows up in which account an asset sits in, which year a gain is realized, which year income is deliberately taken rather than deferred, and how a gift is structured before it is made. None of those decisions is visible on a tax return. All of them determine what the return says.
The Via Luce point of view
Tax is not a separate service line. It is the seam where planning and investing meet, and it is where a good decision on one side can be undone by inattention on the other. An investment change that looks obviously correct in isolation can be a poor decision once the realized gain, the account it sits in, and the household’s income for the year are accounted for.
So we treat tax as a constraint that is present in every planning and portfolio conversation, not as a topic that gets its own meeting in April. That means knowing where the household’s income is likely to land before the year is over, understanding which thresholds are in play, and coordinating with the CPA who will actually prepare the return — before there is a return to prepare.
It also means being clear about the boundary. We do not prepare returns and we do not give tax advice. What we do is make sure the tax consequences of a decision are on the table while the decision is still open, and that the professional who does advise you has the information to do so.
Core concepts
Asset location: the same portfolio, a different result
Two households can hold identical investments and keep different amounts of what those investments earn, purely because of which account each holding sits in. Interest income, short-term gains, and ordinary-income distributions are taxed at higher rates and generally do more work inside tax-sheltered accounts. Long-held equity exposure with favorable capital-gains treatment often belongs in taxable accounts, where it also becomes available for charitable giving and receives different treatment at death.
What makes location worth attention is that it is largely a free decision. It does not require a view on markets, it does not change the risk of the overall portfolio, and it compounds quietly for as long as the assets are held. What it does require is coordination — the household has to be viewed as one portfolio across all its accounts rather than as several portfolios that happen to belong to the same family.
Harvesting is a discipline, not a December event
Tax-loss harvesting is widely described and frequently done badly. Done well, it means capturing losses when markets provide them, using them against gains you actually intend to realize, and replacing the sold position with exposure that keeps the portfolio positioned the way the plan intends. Done poorly, it means selling something at a loss in late December because the calendar said to, lowering the basis, and relocating a gain into a future year at a rate nobody has estimated.
The same logic applies to gains. There are years when realizing a gain deliberately is the right decision — a low-income year, a year with losses available to absorb it, a year before a threshold moves. Harvesting and rebalancing belong in the same conversation, because a portfolio change that ignores the tax consequence and a tax move that ignores the portfolio consequence are both incomplete.
The conversion window
Roth conversions are a bracket-management tool. They move money from tax-deferred to tax-free by paying tax voluntarily, in a year you choose, at a rate you can estimate. Whether that trade is worthwhile depends on the rate you would pay now against the rate you or your heirs would likely pay later — which makes it a forecast about your own income, not about markets.
The years when a household’s taxable income is unusually low are where conversion work concentrates: after employment income ends and before required distributions begin, in a year between business ventures, or in a year with substantial deductions available. These windows tend to be quiet and easy to miss, because nothing forces the decision while they are open. Planning through them, rather than noticing them afterward, is most of the value.
Charitable giving is a structure decision
For households that give, the question is rarely whether to give — it is what to give, from which account, and in which year. Appreciated securities held long-term are often a more efficient gift than cash, because the embedded gain is handled differently. Concentrating several years of intended giving into one tax year can matter more now that a portion of charitable deductions falls below an income-based floor. Donor-advised funds and, for older households, distributions made directly from an IRA to charity each solve different problems.
None of this changes how much a family gives or who receives it. It changes what the same generosity costs the household, which usually means there is more available to give.
Concentrated positions carry a tax problem
A large, low-basis position — from a company’s stock plan, a founding stake, or a long-held holding — presents a planning problem that is really two problems wearing one coat. The first is concentration risk. The second is that the obvious fix triggers a tax bill large enough to stop most people from acting.
The workable answers tend to be gradual and coordinated rather than decisive: staged realization timed against income, using charitable structures for the most appreciated shares, coordinating sales with loss availability, and taking into account how the position would be treated if held rather than sold. What rarely works is waiting for a year when selling feels cheap. That year does not arrive on its own.
Residency and state-level exposure
State tax is where the largest surprises live, particularly for households with equity compensation, business income, or property in more than one state. States generally source income to where it was earned, and equity awards can remain connected to a former state long after a move. Residency itself is determined on facts a state can examine, not on a change of address.
The planning work here is mostly documentation and sequencing — knowing which income is sourced where, what evidence supports a residency position, and whether a realization event belongs before or after a move. It is unglamorous work that tends to matter a great deal at exactly one moment.
For business owners, the entity is part of the plan
An owner’s tax picture is not really a personal one. How the business is structured, how the owner is compensated, what the retirement plan looks like, and how much profit stays inside the company all interact — and they interact with the personal return rather than sitting beside it.
Retirement plan design is the clearest example. The plan an owner chooses determines how much can be set aside pre-tax each year, and the range between a basic arrangement and a well-designed one is wide. For an owner with consistent profitability, an older ownership group, or a small number of highly compensated employees, plan design can potentially move a meaningful amount of income out of the current year — while also serving as a retention tool for the people the business depends on.
Entity structure raises related questions: how income is characterized, what is subject to employment taxes, how state sourcing works if the business operates across lines, and what happens to the structure at a sale. Those decisions are made with the CPA and the attorney, not by us. But they belong in the planning conversation, because an owner’s personal plan is largely a function of decisions made on the business side, and the two are usually reviewed by different people who have never spoken to each other.
The coordination point is the whole idea. When the business decisions, the personal plan, and the portfolio are reviewed together, the tax consequences of each are visible to the others. When they are not, the owner absorbs the difference.
How this gets done
Tax work sits inside the planning cadence rather than beside it. Income for the year gets estimated while the year is still open. Realization decisions are made against that estimate. Conversion capacity is identified when it exists rather than described after it closes. And your CPA is part of the conversation, because a plan the accountant has never seen is a plan that gets discovered at filing.
Nothing here removes tax from the picture, and no process assures a particular result. What a deliberate process aims to do is make sure the decisions that determine your tax outcome are made on purpose, in the year they can still be made.