Last-minute tax savings for high-net-worth individuals now

The short answer is that real last-minute tax savings for high earners come from a handful of levers: pulling income into different years, shoving expenses into this year, fixing your entity structure, using retirement and health accounts hard, and cleaning up your investment and charitable strategy. If you want a single resource on Last-minute tax savings for high-net-worth individuals, that is probably where I would start, but let me walk through what actually moves the tax bill right now, not in theory. Some ideas are obvious, some are less pretty, and a few might feel slightly uncomfortable because they show you where you have been overpaying for years.

You might already know parts of this. The point is not to memorize tax code. The point is to know which knobs to turn when the year is almost done and the numbers are mostly locked in.

The closer you are to year‑end, the more your tax planning shifts from “what structure should I build” to “what can I legally accelerate, delay, or reclassify before the clock hits midnight.”

I am going to assume your income is high, you either own a business or have sizable investments, and you are tired of feeling like the IRS is your biggest expense. If that sounds harsh, it is, but it is also usually true on a numbers basis.

Let us go piece by piece.

How to think about last‑minute tax moves when the year is almost over

Most high earners react to tax season. They send documents to a CPA in March and hope something magical happens. That is not planning. That is reporting.

In the last weeks of the year, you mostly have three levers left:

• Timing: What can you pull into this year or push into next year.
• Character: What income or gains can you change from one tax type to another.
• Wrapper: What can you move into a different vehicle, like a retirement plan, HSA, or entity.

If your CPA is only talking about deductions, they are missing at least half the game. At your income level, entity structure, retirement plan design, and investment tax management matter more than another 500 dollar deduction.

If you are paying high six or seven figures in tax and your strategy fits on a single page, it is probably not a strategy. It is a receipt.

Let us start with the things that can often be changed in a few days if you already have accounts and entities in place.

Business owners: where the fastest savings usually hide

If you own an S‑corp, partnership, or even a single‑member LLC that reports on Schedule C, your business is probably the biggest lever you have. The tax code gives owners more room to move things around than it gives to employees with only W‑2 income.

1. Accelerate expenses and defer income (carefully)

This sounds plain, but I still see high‑income business owners not doing it.

You look at your year‑to‑date profit. If it is a lot higher than the prior year and you do not need that income to show up this year for financing or some other reason, you can pull some levers:

• Prepay certain expenses for the next year if you are on cash basis and allowed to do so.
• Order equipment and put it in service before year‑end so you can depreciate or expense it.
• Delay sending some December invoices by a few days so the cash comes in next year.

The last one is where people overstep. You still need to follow your normal business patterns and avoid tricks that do not match reality. The goal is to move within the rules, not pretend revenue did not happen.

One quick but often missed step: look at any large vendor checks you know you will write in January. If mailing them in late December does not hurt your cash flow or relationships, send them early so they hit this year.

2. Clean up S‑corp salary and distributions

If you run an S‑corp, officer compensation can make or break your tax bill.

Too low, and you risk an IRS challenge. Too high, and you pay far more payroll tax than needed. The sweet spot is “reasonable compensation,” which is annoyingly vague but still powerful.

Before year‑end:

• Look at total S‑corp profit vs the W‑2 salary you paid yourself.
• Compare your salary to industry norms for your role and hours.
• Adjust the last payroll or run an extra payroll if you are clearly far off.

If you took big distributions but paid yourself a very low salary, talk to your CPA now, not in April. Fixing it late in the year with an adjusted payroll is often cleaner than explaining it during audit.

There is a flip side. If you ramped income this year and overpaid yourself, you might reduce or skip a final payroll cycle and leave more as distributions, which saves payroll taxes. That has bounds, but it is often missed.

3. Stack retirement plans on top of your income

A lot of high earners think of retirement plans as 22,500 dollar or 23,000 dollar problems. That limit is just the employee deferral cap on a 401(k). For a high‑net‑worth business owner, the ceiling is way higher.

With the right design, you might be able to push multiple six figures into tax‑deferred or pre‑tax accounts, even late in the year.

Common options:

• Solo 401(k) for owner‑only businesses or owner plus spouse.
• Traditional 401(k) with profit sharing for businesses with staff.
• Cash balance or defined benefit plan layered on top for even larger contributions.
• SEP IRA if you need something fast and simple, although it can block backdoor Roths.

The catch is paperwork and deadlines. Plan documents often need to be in place by year‑end, even if you fund the contribution the next year. If you sit on this until January, you might miss the window for certain plans.

The most common regret I hear from high earners is not about missing deductions. It is about waiting one more year to set up a real retirement plan for their business and losing a six‑figure tax shelter they can never get back.

If you already have a 401(k), you can still:

• Push your year‑end paycheck deferrals to the max allowed.
• Decide on employer profit sharing based on final profit numbers.
• Look at whether a cash balance plan still fits, even if tight on timing.

Investment moves that still work in the final weeks

Your portfolio is another large tax lever, especially in taxable accounts. The good news is that many investment‑related moves are still possible very late in the year, as long as trades settle by the deadline.

4. Tax loss harvesting without wrecking your strategy

This is often presented as a trick. Sell losers, book a loss, buy back something similar, avoid the wash sale, lower your tax bill. The logic is fine, but the way it is done can be lazy.

The basic idea:

• Sell positions with unrealized losses in taxable accounts.
• Use those losses to offset capital gains this year.
• Use extra losses to offset up to a small amount of ordinary income.
• Carry forward any remaining losses to future years.

The part that matters is what you buy back. If you sell an S&P 500 fund at a loss and sit in cash for 31 days, you are taking market risk for no reason. If you sell one large‑cap index fund and buy another that tracks a similar but not identical index, you stay invested and still book the loss.

You also need to watch wash sale rules. If you or your spouse or your IRA buys the same security within the 30‑day window before or after, you can lose the loss.

I like to think of loss harvesting as a balance. You want to capture value, but you do not want your portfolio to drift just because you chased tax games.

5. Realize gains on purpose, not by accident

Sometimes the counterintuitive move is to take gains now, not later. This can make sense when:

• You are in a rare lower‑income year and your capital gains rate is better now than in the near future.
• You want to reset your cost basis in a holding you plan to keep long term.
• You want to diversify out of a concentrated stock position.

For high‑net‑worth individuals, a “low” year might still look very high from the outside, but relative to other years it is the valley. If you sold a business last year and this year is quieter, or you had a one‑time bonus that does not repeat, the timing of gains and losses matters.

Sometimes people cling to unrealized gains so long that risk builds up quietly. Taxes matter, but so does not having 60 percent of your net worth in one stock that can drop 40 percent in a quarter.

6. Asset location tune‑up before year‑end

You might not be able to reengineer your whole investment strategy in December. Still, you can clean up where things live.

Usually:

• Put tax‑inefficient assets like high‑yield bonds and actively traded funds in retirement accounts when you can.
• Hold low‑turnover index funds and long‑term positions in taxable accounts.
• Keep an eye on foreign funds that kick out large dividend distributions.

This is not always a last‑minute move. Still, if you are already trading for loss harvesting or rebalancing, you can fix some asset location issues while you are in there.

Charitable giving: give what you planned to give, just smarter

If you already give to charity, you have one of the cleanest levers available. If you do not give, then using charity only as a tax move usually feels hollow and you might skip it, which is fine.

For those who do give, the question is how, not whether.

7. Bunch donations into high‑income years

With higher standard deductions, many high earners who do not have a mortgage or large state taxes find that their normal yearly charitable gifts do not create any extra tax value. They would have taken the standard deduction anyway.

A simple fix is bunching. Instead of spreading gifts evenly over many years, you group several years of giving into one big year, push yourself above the standard deduction by a wide margin, and then go back to standard deduction in other years.

A common tool here is a donor‑advised fund (DAF):

• You give a large amount to the DAF in a high‑income year.
• You get the full deduction right away.
• You grant the money out to charities over time, on your own schedule.

That allows you to pair your giving with high tax years without rushing checks to every charity before December 31.

8. Give appreciated stock, not cash

If you have a taxable portfolio with positions that have grown a lot, you can usually get a double benefit by giving shares instead of cash:

• You avoid paying capital gains on the built‑in gain.
• You still get a deduction for the fair market value, subject to limits.

You can give directly to some charities or into a donor‑advised fund. Either way, you are swapping a tax‑heavy asset for a deduction.

It sounds simple, and it mostly is, but the process can take a bit of time. If it is already late in December, your brokerage’s transfer deadlines might be tight. This is where “last minute” can become “too late”, so if you think you will do this, do not wait for the last business day of the year.

Retirement, HSAs, and other account‑based moves

Retirement plans and health accounts can offer some of the highest value per dollar contributed, yet high earners often leave them half‑used.

9. Max out 401(k), 403(b), and similar plans

If you are an employee or you own a business with a plan, check:

• Have you hit your elective deferral limit for the year.
• Are you making catch‑up contributions if you are over 50.
• Are employer match and profit sharing calculated correctly.

For many people, payroll systems allow you to change contributions pretty late in the year, at least for the final pay periods.

Sometimes, if cash flow allows, it is worth temporarily raising contributions to hit the cap by year‑end, then lowering them in the new year.

10. Health Savings Accounts: small line, strong impact

If you have a high deductible health plan and you are eligible for an HSA, that account acts like a “triple benefit”:

• Contributions are pre‑tax.
• Growth is tax‑deferred.
• Qualified medical withdrawals are tax‑free.

High‑net‑worth families sometimes treat HSAs as an investment account, pay current medical costs out of pocket, and let the HSA grow. The limit is smaller than a 401(k), but the tax characteristics are hard to match.

Before year‑end, check if you have room left and adjust contributions if your payroll permits it. If your employer plan is rigid, you might still be able to write a check to the HSA provider directly, as long as you follow the rules and stay under the limit.

11. IRA contributions and Roth strategies

Some IRA moves, like prior year contributions, extend into the next year, so they are not strictly “last minute” in December. Still, you should know where you stand before the year closes, especially if you use:

• Backdoor Roth contributions.
• Roth conversions from traditional accounts.

For high earners, backdoor Roths often make sense, but only if you watch the pro‑rata rule. If you have pre‑tax IRA money, the conversion can trigger more tax than you planned.

Roth conversions are a different animal. They can make sense in some lower income years, or when you expect future tax rates to be higher for you or your heirs. They also increase your current year income, which can push you into higher brackets or phaseouts.

So yes, they are a tax move, but not always a tax saving move in the short term. More a long‑term tax planning lever. If someone pitches a conversion as a guaranteed win this year, they are skipping the nuance.

Income timing and managing “spiky” years

High‑net‑worth individuals often have lumpy income: business sales, bonuses, stock vesting, K‑1 allocations. The last weeks of the year are where you can sometimes smooth those spikes a bit.

12. Shifting bonuses and contract income

If you control when you bill or when a bonus is paid, you might move income by a few weeks in either direction.

This is not about hiding income. It is simply about choosing which year owns it when you have real control. Examples:

• As a business owner, you might pay a year‑end bonus early in January instead of late December, or vice versa, based on your current and expected tax brackets.
• As a consultant, you might schedule a milestone payment for early next year if it does not harm the business relationship.

The logic depends on your bracket now versus expected bracket next year, and on other events like a future business sale.

An odd detail: For some high earners, pulling income into a year where they already hit certain caps can actually reduce marginal taxes compared with spreading it. This is where math matters more than instinct.

13. Watching net investment income tax and surtaxes

You probably know that above certain thresholds, you pay extra taxes on investment income and sometimes Medicare surtaxes on wages. When your income is right around those lines, small timing decisions can push you above or below.

This is more about awareness than drama:

• If a year is already high income and it will be high either way, adding a little more might not change your marginal rate as much as you think.
• If you are just at the edge, taking a gain or a Roth conversion might trigger extra layers of tax.

This is why it often helps to model both years side by side instead of looking only at this year in a vacuum.

Real estate and depreciation moves at year‑end

Real estate can be both a tax shelter and a cash drain. The last weeks of the year are not the best time to buy property just for tax reasons, but they do matter for those who already own rentals, buildings, or an office.

14. Cost segregation and bonus depreciation

If you bought or built property this year, it might still be possible to complete a cost segregation study. The detail depends on the size and type of property, and you need specialists who know what they are doing.

The idea is to split your property into components with shorter depreciation lives so you can expense more up front.

For high‑net‑worth owners of:

• Medical or dental offices.
• Warehouse or industrial buildings.
• Short‑term rental properties.

Accelerated depreciation can create large paper losses, which then interact with your active or passive status, income levels, and other rules. It is not something to rush without guidance, but the deadline is still the tax year in which the property was placed in service.

15. Classifying repairs vs improvements

If you did work on a building, the question of what counts as a repair vs an improvement affects timing of deductions.

The tax rules for this are more complex than they look on the surface. Some smaller projects might qualify for safe harbors that let you expense more this year. Larger ones are more likely to be capitalized and depreciated.

At year‑end, you want at least:

• Invoices and descriptions that clearly explain what the work covered.
• A discussion with your tax advisor on how to treat major projects.

This sounds minor, but for large projects, the difference between expensing and capitalizing can be very large in year one.

Estate and gifting moves with a year‑end flavor

This is where tax planning crosses into family planning, and it is not always just about the math. Still, if you are already thinking about wealth transfer, year‑end does offer some defined lines in the sand.

16. Annual exclusion gifts

Each year, you can give a certain amount per recipient without touching your lifetime estate and gift exemption.

High‑net‑worth families often:

• Gift to children directly.
• Fund 529 plans for education.
• Use irrevocable trusts that receive annual exclusion gifts.

These gifts often need to be complete by year‑end to count for that calendar year. If you have an estate attorney, they might have reminded you already. If not, and you are planning large lifetime transfers, this might nudge you to schedule a talk.

17. Big picture: estate tax versus income tax

Here is where opinions differ. Some families want to drive estate tax to zero, even if it costs more income tax now. Others are more concerned with near‑term cash and lifestyle and accept some future estate tax exposure.

That choice changes how aggressive you are with:

• Roth conversions.
• Charitable bequests vs lifetime giving.
• Moving assets into certain trusts.

There is no single correct answer. That is also why you should be slightly suspicious of anyone who claims one structure fits all high‑net‑worth families. It does not.

Common mistakes in last‑minute tax planning for high‑net‑worth individuals

At this point, it might all sound like a big list of options. It is, but not all options are equal, and some have more downside than benefit if rushed.

Here are problems I see over and over.

18. Waiting for a miracle deduction

People often ask for a single move that will erase a large tax bill. Something like “Can I buy a car through my business and wipe out 100k of income.”

Usually, no. Or the tradeoffs are severe.

Real savings tend to come from:

• Structures: entities, plans, long‑term portfolio design.
• Patterns: how you earn, spend, and give over many years.
• Timing: which year owns which income and deduction.

If someone offers you a scheme that sounds like magic, be cautious. The IRS tends to shut those down eventually, and you are the one on the hook.

19. Overfunding things you do not understand

Some high earners are sold products as tax tools: complex insurance arrangements, opaque partnerships, odd shelters that rely on hard‑to‑defend assumptions.

If you cannot explain in plain words how something saves you tax and what the tradeoff is, you probably should not put a large part of your net worth in it.

Hesitation here is healthy.

20. Ignoring state and local tax rules

If you live in a high tax state, or you have income in multiple states, your last‑minute moves may have state‑level effects that differ from federal rules.

Examples:

• Some states treat retirement contributions or certain entities differently.
• State and local tax deduction caps change how much benefit you get from extra property or income taxes.

This is another reason it helps to work with someone who goes beyond filling in federal forms.

A quick comparison of popular last‑minute moves

How to prioritize if you feel behind

If you are reading this late in the year and feeling slightly overwhelmed, that is normal. You do not need to do everything. You probably cannot.

A simple way to rank moves:

1. Check what is already in place: entities, retirement plans, charitable habits, investment accounts.
2. Identify anything with a hard deadline before year‑end: payroll changes, plan setups, stock gifts, trades.
3. Focus on items that match your situation: business owner vs employee, investor vs concentrated in salary, etc.
4. Run basic numbers: how much income, what bracket, any unusual events this year or next year.

Then, pick two or three moves that give most of the benefit with the least complexity. You can always layer in more structure next year on a calmer timeline.

A brief question and answer to ground this

Q: If I only have time and mental energy for three moves before year‑end, what should I look at first as a high‑net‑worth individual?

A: The exact answer depends on your facts, but in practice, the three highest‑impact areas for many high‑income people are:

• Retirement and entity clean‑up: Make sure your 401(k) or similar plan is maxed in a sensible way, check if a profit sharing or cash balance layer is still possible, and if you have an S‑corp, review your salary vs distributions before the last payroll.
• Investment tax tuning: Harvest losses if you have real ones, clean up any large embedded gains you actually want to realize this year, and use appreciated stock for part of your charitable giving instead of cash.
• Charitable and timing decisions: If you already give, look at bunching several years of gifts into a donor‑advised fund or similar structure during a high‑income year, and see if any income or bonuses that are within your control can be timed more intelligently across this year and next.

If you work through those three areas with numbers in front of you and with someone who pushes back when something does not make sense, you will usually find that your “last minute” tax result is far better than what you have had in previous years. Not perfect, but significantly more deliberate.