Solutions

Start with the decision in front of you.

Borrowing, selling, diversifying, converting, giving, retiring, inheriting, passing wealth on. Every one of these decisions has a tax consequence, and most have more than one reasonable answer. Find the one closest to your situation below. Each links to the strategies that may apply and the trade-offs that come with them.

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This page describes common planning situations in general terms. It is not a recommendation and not tax or legal advice. Tax descriptions reflect federal law as of October 7, 2026. Whether any approach is appropriate depends on facts specific to you, and anything involving tax or legal judgment requires your CPA and attorney.

01

Access cash

Getting money out of a portfolio is a tax decision before it is an investment decision.

Borrow against your portfolio instead of selling

A securities-based line of credit can cover a home purchase, a tax payment, or a bridge to a transaction without selling appreciated assets and realizing gains. The planning is in sizing the line conservatively, choosing what collateral to pledge, and having an exit plan before you draw.

Trade-off to knowIf the collateral falls, the lender can require more collateral or sell holdings, potentially at a bad time and with a tax bill. Borrowed funds generally cannot be used to buy securities.

Sell investments with the tax bill in mind

When you need cash from a taxable account, which lots you sell matters as much as how much. Selecting high-basis or loss lots, pairing gains with harvested losses, spreading sales across tax years, and drawing from the right account type can change the tax on the same dollar of spending.

Trade-off to knowSelling to manage tax can leave you with the positions you would otherwise have sold, and delaying a sale exposes you to price declines in the meantime.

Material limitations

Borrowing creates the risk of collateral calls and variable interest costs. Selling realizes gains that are taxed in the year of sale. Either choice can leave the remaining portfolio further from its intended risk level. Which is appropriate depends on your tax situation, time horizon, and the size and duration of the need.

02

Reduce risk

Lowering risk usually means selling something, and selling something usually means a tax bill. The work is deciding how much risk is worth carrying to defer how much tax.

De-risk a concentrated stock position

Whether the position came from an employer, a founder, or decades of holding, the choices are the same: sell over time against a gain budget, hedge, exchange into a diversified pool, or give. Most plans combine several, sequenced over years.

Trade-off to knowEvery approach leaves some risk in place, costs something, or gives up something: upside, liquidity, or control.

Diversify an older portfolio without a large tax hit

Portfolios built over decades often hold dozens of low-basis positions and outdated funds. A transition plan can move toward a target allocation over several years, using losses harvested along the way, gifting of the lowest-basis shares, and in some cases a fund-structure exchange.

Trade-off to knowA gradual transition leaves the portfolio away from its target for longer. Section 351 exchanges are under active IRS review as of September 2026.

Reduce risk ahead of retirement or a major purchase

Shifting from growth to stability as a goal approaches is usually done with sales, and sales in a taxable account create gains. Using new contributions, dividends, required distributions, and tax-deferred accounts to rebalance first can reduce how much has to be sold.

Trade-off to knowRebalancing slowly to avoid tax leaves more market risk in place for longer. Lower-risk assets generally carry lower expected returns.

Material limitations

Every approach to reducing risk involves trade-offs. Gradual approaches leave risk in place while they run. Hedging limits upside and carries its own costs and tax rules. Diversification does not ensure a profit or protect against loss in a declining market, and deferring tax is not the same as eliminating it.

03

Taxes now and later

The same income, spent the same way, can produce very different lifetime tax bills depending on timing and which accounts it comes from.

Manage a big tax bill

A large bonus, a sale, or a year of heavy gains does not have to be met with the portfolio sitting still. Realizing losses, choosing which lots to sell, locating income-heavy assets in tax-deferred accounts, timing charitable gifts, and coordinating estimated payments with your CPA are all on the table.

Trade-off to knowHarvesting lowers cost basis and can raise tax on a later sale. Wash-sale rules apply across all of your accounts.

Decide whether a Roth conversion makes sense

A conversion trades tax now for tax-free qualified withdrawals later. The decision turns on your bracket today versus later, Medicare premium thresholds, state tax, how the tax will be paid, and who inherits the account.

Trade-off to knowConversions cannot be undone, and the benefit depends on future tax rates no one knows.

Turn savings into tax-efficient retirement income

The order you draw from taxable, tax-deferred, and Roth accounts, when you claim Social Security, and how required distributions and charitable distributions are handled all change what you keep from the same spending.

Trade-off to knowEvery income plan rests on assumptions about longevity, returns, inflation, and law, and needs regular revision.

Material limitations

Tax planning depends on current law, which can change, including retroactively, and on assumptions about your future income and tax rates that will not match reality exactly. Loss harvesting generally defers rather than eliminates tax. Roth conversions cannot be undone. Tax determinations belong to your CPA.

04

Life events

Most planning windows open before the event and close soon after it. The earlier the conversation, the more options remain.

Prepare to sell a business

The years before a sale are when entity structure, qualified small business stock, gifting to family or trusts, charitable transfers, and the plan for proceeds can still be shaped. After a letter of intent, most of those options narrow quickly.

Trade-off to knowMany steps must happen well before a deal is agreed to be respected for tax purposes, and many structures are irrevocable.

Make decisions about equity compensation

Restricted stock units, incentive and non-qualified options, and employee stock purchase plans are each taxed differently. The questions are when to exercise, how much alternative minimum tax exposure to accept, and how to keep new grants from adding to single-company risk.

Trade-off to knowExercising can create tax before any shares are sold, and the stock can fall afterward.

Manage an inheritance

Inherited taxable assets generally receive a new cost basis at the date of death, which can make diversifying them far less expensive than it would have been for the original owner. Inherited retirement accounts are different: most non-spouse beneficiaries must empty them within ten years, so the timing of withdrawals matters.

Trade-off to knowBasis and distribution rules depend on how the asset was held and who the beneficiary is. Confirm treatment with your CPA before acting.

Roll over a 401(k) when you change jobs or retire

Rolling a plan to an IRA is not automatically the right move. Plans holding appreciated employer stock may qualify for net unrealized appreciation treatment, and plan features, fees, creditor protection, and future Roth conversions all factor in.

Trade-off to knowA rollover recommendation involves a conflict of interest when the adviser is paid on the rolled-over assets, which is disclosed in Form ADV.

Material limitations

Planning opportunities depend on facts, timing, and law that may change, and some require lead time a given event will not allow. Decisions involving entities, trusts, or tax elections require your attorney and CPA. No strategy assures a particular result.

05

Legacy

Estate and charitable decisions are mostly irreversible, which is why they deserve the most modeling before anything is signed.

Coordinate your estate plan and wealth transfer

With a federal exemption of $15 million per person in 2026, the questions shift from avoiding estate tax to what to give, when, and in what structure, and to whether trusts are actually funded and accounts titled the way the documents intend. Long-term families may also consider dynasty trusts and generation-skipping planning.

Trade-off to knowNew Jersey still imposes an inheritance tax on transfers to certain beneficiaries. Drafting belongs to your attorney.

Give to charity with appreciated assets

Giving shares rather than cash, bunching gifts through a donor-advised fund, giving from an IRA after age 70½, and using charitable remainder trusts can each change the after-tax cost of the same gift. New rules for 2026 make timing more important for itemizers.

Trade-off to knowGifts are irrevocable, and deductions are subject to income limits and a new 0.5 percent of AGI floor for itemizers.

Material limitations

Trusts and charitable gifts are generally irrevocable and reduce your access to and control of the assets. Gifted assets generally do not receive a step-up in basis. Legal documents are drafted by your estate attorney; this practice does not draft documents or provide legal advice. Law can change.

06

Real estate

Real estate often carries the largest embedded gains on a family's balance sheet and the least coordination with the rest of the plan.

Plan liquidity and taxes as a real estate investor

Rental and investment property raises its own questions: when a sale makes sense, whether a like-kind exchange fits, how depreciation recapture affects the decision, and how real estate concentration fits with the rest of the balance sheet.

Trade-off to knowExchange deadlines are strict and transaction structure belongs to your CPA, attorney, and intermediary.

Material limitations

Real estate is illiquid and concentrated, and exchange and depreciation rules are technical and strictly timed. Deferred gain is generally recognized eventually, and depreciation recapture is taxed at higher rates. Real estate tax positions and transaction structure belong to your CPA, attorney, and qualified intermediary.

Not sure which of these applies?

Most situations involve several at once. A first conversation is about thirty minutes and is used to sort out which decisions matter most and in what order.

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