December 17, 2025

As the year comes to a close, many investors focus on performance alone. Account balances, gains, and year-to-date returns often take center stage. Yet portfolio outcomes are shaped by more than market movement. Taxes play a meaningful role in what investors ultimately keep.
That is why year-end portfolio reviews matter. They create an opportunity to evaluate not only how investments performed, but how those results interact with tax rules. One of the most practical tools reviewed during this process is tax loss harvesting.
Tax loss harvesting is not about reacting to headlines or predicting markets. It is a structured review process that looks for ways to improve tax efficiency without changing long-term strategy.
Tax loss harvesting is the process of selling investments in taxable accounts that are trading below their purchase price in order to realize a capital loss.
These realized losses can be used to offset capital gains, which may reduce overall tax liability. When applied correctly, tax loss harvesting focuses on improving after-tax results rather than chasing short-term performance.
It applies only to taxable investment accounts. Retirement accounts such as IRAs and 401(k)s follow different tax rules and are not part of this strategy.
To understand tax loss harvesting, it helps to start with how gains and losses are treated under tax law.
A capital gain occurs when an investment is sold for more than its original purchase price. A capital loss occurs when an investment is sold for less than what was paid for it. These gains and losses are recognized only when an asset is sold.
When gains and losses occur in the same tax year, losses can be used to offset gains. This reduces the amount of taxable income tied to investment activity.
If losses exceed gains in a given year, a portion may be used to offset ordinary income, subject to IRS limits. Any remaining losses can be carried forward to future years. Those carried-forward losses may offset gains later, creating ongoing tax value.
This interaction between gains and losses is the foundation of tax loss harvesting. The goal is not to create losses, but to use existing ones thoughtfully when they appear.
Many investors associate tax loss harvesting with market stress. That assumption overlooks how portfolios actually behave in real conditions. Even when headline indexes rise and account balances move higher, dispersion inside a portfolio is common. Some holdings advance while others lag, stall, or decline.
That difference is where tax loss harvesting remains relevant.
Portfolio growth does not mean uniform performance
A portfolio is not a single position. It is a collection of assets purchased at different times, under different market conditions, and for different roles. During strong markets, several forces can create losses at the position level even when the portfolio value increases.
Common drivers include:
These movements are normal. They do not indicate a broken strategy. They do create opportunities to review capital losses with intent rather than emotion.
Why year end reviews focus on positions, not just totals
A year end portfolio review examines each holding on its own merits. The goal is to understand how every position contributes to risk, diversification, and tax exposure.
This position level review supports tax efficient investing in several ways:
By separating position analysis from total account performance, tax loss harvesting becomes a planning decision rather than a reaction to market noise.
Gains elsewhere can increase the value of harvesting losses
In years with realized gains, tax loss harvesting often carries more weight. Capital gains trigger tax exposure. Capital losses can reduce it.
When gains exist:
This relationship is why tax loss harvesting is reviewed even when portfolios perform well. The presence of gains does not eliminate the value of losses. It often amplifies it.
A practical example without changing strategy
Consider a diversified taxable portfolio that appreciated over the year due to equity exposure. Within that same portfolio:
A year end review may identify capital losses in these positions. Realizing those losses does not require abandoning diversification or altering long term objectives. It allows the portfolio to remain aligned while improving tax efficiency.
In some cases, capital can be reallocated to maintain similar exposure. In others, the review supports broader portfolio management decisions tied to rebalancing and tax planning.
Read: 12 Strategies to Help Lower Long-Term Capital Gains Taxes
Why this matters for disciplined portfolio management
Tax loss harvesting is not about seeking losses. It is about responding to them with structure. Markets do not move evenly. Portfolios reflect that reality.
Reviewing tax loss harvesting during strong markets reinforces several principles:
This approach supports consistency across market cycles. It also reinforces that year end portfolio reviews are about refinement, not reaction.
Tax efficiency is rarely achieved through a single decision. It is built through repeated, deliberate reviews that account for how portfolios actually behave in real markets.
Tax loss harvesting only works when it respects IRS rules. One of the most important of those rules is the wash sale rule. It exists to prevent investors from claiming a tax benefit while effectively keeping the same investment exposure.
Understanding how this rule works is critical for tax efficient investing, especially during a year end portfolio review when capital losses and capital gains are evaluated together.
What the wash sale rule actually restricts
The wash sale rule applies when a security is sold at a loss and the same or a substantially identical security is purchased within a defined time period.
The rule creates a 61 day window:
If a purchase occurs anywhere in that window, the IRS treats the transaction as a wash sale. The capital loss cannot be claimed in the current tax year.
This applies across all taxable accounts owned by the same taxpayer, including individual accounts and joint accounts. It also applies even if the repurchase happens in a different account than the sale.
What happens when a wash sale occurs
A wash sale does not eliminate the loss. It defers it.
When a wash sale is triggered:
This means the loss may still be recognized later. It simply cannot be used at the time the original loss was realized.
From a planning standpoint, this distinction matters. The objective of tax loss harvesting is timing. A deferred loss does not serve that purpose in the year it was intended.
Why timing matters during tax loss harvesting
Timing is the difference between a usable capital loss and a deferred one.
During tax loss harvesting reviews, trades are evaluated carefully to avoid:
This is especially important when portfolios include multiple funds or similar strategies that track related market segments.
A disciplined review process accounts for both the sale and the surrounding activity to help ensure losses are usable under IRS rules.
Substantially identical does not mean exactly the same
One of the more nuanced aspects of the wash sale rule is the phrase substantially identical. The IRS does not define this term precisely in all cases.
In practice, this means:
Because of this ambiguity, tax loss harvesting decisions tend to be conservative in interpretation. The goal is to reduce the chance of a disallowed loss rather than testing gray areas.
Maintaining diversification during the waiting period
Avoiding a wash sale does not mean stepping out of the market entirely.
In some situations, temporary substitutes may be used during the 31 day waiting period to maintain diversification and manage risk exposure. These substitutes are selected with care and reviewed within the context of overall portfolio management.
Key considerations during this period include:
Any temporary adjustment is evaluated as part of the broader portfolio rather than as an isolated trade.
How the wash sale rule fits into year end portfolio reviews
During a year end portfolio review, the wash sale rule becomes part of a larger planning discussion.
That discussion typically includes:
This coordination helps ensure that tax loss harvesting improves tax efficiency without disrupting portfolio structure.
Why this rule reinforces process driven investing
The wash sale rule highlights why tax loss harvesting is not a mechanical exercise. It requires awareness of timing, coordination across accounts, and alignment with long term strategy.
Handled correctly, it supports tax efficient investing. Handled casually, it can delay the very benefit it is meant to create.
That is why the wash sale rule is reviewed in detail as part of portfolio management rather than treated as a footnote. It sits at the intersection of tax planning, investment structure, and disciplined execution.
Tax loss harvesting works when it is integrated into portfolio management rather than treated as a one time tax tactic. The decision to realize a loss affects cash flow, allocation, risk exposure, and future tax planning. For that reason, it is evaluated alongside portfolio structure, not after the fact.
A tax loss on its own has limited value. Its impact depends on how the portfolio is positioned before and after the trade.
Loss realization as a capital reallocation decision
When a loss is realized, capital becomes available for redeployment. That redeployment is intentional, not automatic.
Common portfolio level uses of that capital include:
This is where tax loss harvesting connects directly to portfolio management. The sale is not the decision. The reallocation is.
Rebalancing and tax efficient investing
Rebalancing often creates tax consequences in taxable accounts. Tax loss harvesting can help manage those consequences.
When losses are available:
This relationship is one reason tax loss harvesting is reviewed during year end portfolio reviews. It supports both structural discipline and tax efficiency.
Holding replacements and long term fit
Not every sale represents a permanent exit.
In some cases:
In other cases:
Both outcomes are valid. The distinction depends on how each position contributes to the overall plan.
Tax decisions evaluated within portfolio structure
Tax loss harvesting does not operate independently from asset allocation. Every decision is reviewed in context.
Key questions addressed during the process include:
This framework helps prevent isolated tax decisions that unintentionally distort portfolio balance.
Managing short term movement without reacting to it
Market prices move daily. Portfolio management focuses on long term alignment.
Tax loss harvesting respects that distinction by:
This is why tax loss harvesting fits within disciplined portfolio management. It responds to what has already occurred rather than attempting to predict what comes next.
Integration with ongoing tax planning
Tax loss harvesting influences more than the current tax year.
Realized losses may:
For that reason, portfolio management and tax planning are reviewed together. The goal is not a single outcome, but continuity across years.
Why integration matters
When tax loss harvesting is disconnected from portfolio management, it risks becoming mechanical. When integrated properly, it becomes part of tax efficient investing.
That integration helps ensure:
Tax loss harvesting works best when it is treated as one component of a broader process that balances investment management and tax awareness over time.
One of the more practical outcomes of tax loss harvesting is the ability to carry losses forward and apply them in future years. This aspect often receives less attention than year end tax results, yet it plays an important role in long term tax planning and portfolio management.
Loss carryforwards do not create immediate tax relief in isolation. Their value shows up over time as portfolios evolve and capital gains are realized.
How loss carryforwards work in practice
When capital losses exceed capital gains in a given tax year, the unused portion does not disappear. Under current tax rules, those losses can be carried forward indefinitely.
That carryforward can be applied in future years to:
This creates a form of tax flexibility that can be used as circumstances change.
Why loss carryforwards matter beyond the current year
Portfolios are not static. Over time, investors may rebalance, change allocation, or sell appreciated assets as part of normal portfolio management.
Loss carryforwards can become relevant during:
Having losses available in those moments can help manage the tax impact of otherwise necessary decisions.
Loss carryforwards and year end portfolio reviews
Year end portfolio reviews are a natural time to assess existing loss carryforwards.
That review typically includes:
This context helps tax loss harvesting serve long term planning rather than only addressing the current tax year.
A planning tool rather than a tax shelter
Loss carryforwards do not eliminate taxes. They influence timing.
Their role in tax planning is to:
This distinction matters. Treating loss carryforwards as part of a broader strategy helps prevent short term thinking and supports consistent portfolio oversight.
Coordinating loss carryforwards with portfolio management
Loss carryforwards are most effective when considered alongside portfolio structure.
During planning discussions, factors often reviewed include:
This coordination helps ensure losses are applied thoughtfully rather than reactively.
Why consistency matters
Tax planning works best when it is revisited regularly. Loss carryforwards reinforce that principle.
They encourage:
Loss carryforwards are not about avoiding taxes altogether. They are about managing how and when taxes are recognized as portfolios change over time.
This is why tax loss harvesting is viewed as a continuing process rather than a one time action taken at year end.
Tax loss harvesting also plays a role in maintaining discipline.
Investors can become emotionally attached to individual positions, even when those positions no longer serve a clear purpose in the portfolio. Realizing a loss requires acknowledging that an investment did not perform as expected, which can be difficult.
A structured review process reframes losses as accounting tools rather than personal failures. By treating positions as components of a system rather than symbols of success or failure, decision-making becomes more objective.
This mindset supports consistency and reduces the likelihood of holding underperforming investments solely due to emotional bias.
Year-end portfolio reviews act as a natural checkpoint, but they are not the finish line. They are one point in a continuous oversight process that accounts for market movement, tax considerations, and changes in investor circumstances throughout the year.
Markets do not wait for December. Portfolio oversight cannot either.
Why year-end reviews still matter
The end of the calendar year creates a clear boundary for tax reporting. Realized capital gains and losses are measured on a yearly basis, which makes year-end an efficient time to evaluate how investment activity interacts with tax rules.
A year-end review typically focuses on:
This review is less about making sweeping changes and more about confirming that the portfolio remains intentional.
Why oversight continues beyond December
Investment portfolios are influenced by ongoing forces such as interest rate changes, market rotation, and shifts in risk sentiment. These forces do not follow a calendar.
Throughout the year, oversight allows portfolios to be monitored for:
This ongoing review creates flexibility. It allows tax aware decisions to be evaluated when conditions change rather than waiting for a fixed date.
Market volatility and opportunity awareness
Periods of volatility often surface opportunities that are not visible during calm markets. Price swings can create temporary declines in individual holdings even when long-term outlooks remain intact.
Ongoing monitoring helps identify:
This approach supports tax efficient investing without tying decisions to market forecasts.
Post year-end reviews and portfolio continuity
After the new year begins, portfolios are often reviewed again with a different focus. Attention may shift toward rebalancing, cash flow planning, and adjustments needed to maintain alignment.
Post year-end reviews often address:
Each review builds on the last. Nothing is reset. Information carries forward.
Why continuity improves decision making
When portfolio oversight is consistent, decisions tend to be calmer and more deliberate. Tax awareness becomes part of the process rather than a reaction to deadlines.
This continuity supports:
The result is a portfolio that evolves with intention rather than one that is adjusted only when prompted by the calendar.
Year-end reviews matter because taxes are measured annually. Ongoing oversight matters because portfolios live every day. When both are combined, investment management becomes more structured, more aware, and better aligned with long-term planning goals.
Tax loss harvesting can improve tax efficiency, but its value depends on individual circumstances. Factors such as taxable income, realized gains, and time horizon all influence its impact.
When implemented within a structured portfolio framework, tax loss harvesting is designed to maintain overall allocation and risk exposure. It focuses on tax outcomes rather than speculative changes.
Losses can be used in the year they are realized and carried forward if unused. The benefit depends on the presence of gains and applicable tax limits.
The intent is to support long-term strategy, not replace it. Any changes are evaluated in the context of portfolio goals and constraints.
No. Tax loss harvesting does not attempt to predict market direction. It focuses on tax treatment of existing positions.
Tax loss harvesting is one part of a broader investment management process. It does not rely on forecasts or short-term views. Instead, it focuses on using existing tax rules to improve efficiency over time.
Year-end portfolio reviews provide a structured opportunity to evaluate gains, losses, and alignment with long-term plans. When combined with ongoing oversight, this process supports consistency and clarity in decision-making.
Taxes are one of the few variables investors can plan for with some degree of control. Paying attention to them is part of responsible portfolio management.
Tax rules are complex and personal circumstances vary. Portfolio decisions that involve taxes are often coordinated with tax professionals to help ensure alignment with individual situations.
A disciplined review process helps ensure that investment decisions consider both market behavior and tax implications, without relying on assumptions or shortcuts.
For investors, the value lies not in any single tactic, but in a consistent approach that balances structure, awareness, and long-term perspective.
Landsberg Bennett is a group comprised of investment professionals registered with Hightower Advisors, LLC, an SEC registered investment adviser. Some investment professionals may also be registered with Hightower Securities, LLC (member FINRA and SIPC). Advisory services are offered through Hightower Advisors, LLC. Securities are offered through Hightower Securities, LLC.
This is not an offer to buy or sell securities, nor should anything contained herein be construed as a recommendation or advice of any kind. Consult with an appropriately credentialed professional before making any financial, investment, tax or legal decision. No investment process is free of risk, and there is no guarantee that any investment process or investment opportunities will be profitable or suitable for all investors. Past performance is neither indicative nor a guarantee of future results. You cannot invest directly in an index.
These materials were created for informational purposes only; the opinions and positions stated are those of the author(s) and are not necessarily the official opinion or position of Hightower Advisors, LLC or its affiliates (“Hightower”). Any examples used are for illustrative purposes only and based on generic assumptions. All data or other information referenced is from sources believed to be reliable but not independently verified. Information provided is as of the date referenced and is subject to change without notice. Hightower assumes no liability for any action made or taken in reliance on or relating in any way to this information. Hightower makes no representations or warranties, express or implied, as to the accuracy or completeness of the information, for statements or errors or omissions, or results obtained from the use of this information. References to any person, organization, or the inclusion of external hyperlinks does not constitute endorsement (or guarantee of accuracy or safety) by Hightower of any such person, organization or linked website or the information, products or services contained therein.
Click here for definitions of and disclosures specific to commonly used terms.