Practicing Good Estate Plan Hygiene

Category: Estate planning

Posted on

Published May 26, 2026

At a Glance

  • An estate plan drifts. Beneficiary designations, fiduciary appointments, and trust funding fall out of sync with real life faster than most families realize.
  • Annual reviews are short. Think of it as a physical for your plan — a scheduled check that catches small issues before they become expensive ones.
  • Five areas to check each year: beneficiaries, fiduciaries, trust funding, life-change triggers, and where your originals are stored.

It’s tempting to think of an estate plan as a one-time project — sign the documents, file them away, and check the box. But an estate plan is only as good as the life it reflects, and your life keeps moving. Beneficiaries change. Fiduciaries age out. Assets get retitled, sold, or acquired. Laws shift. A plan that was airtight three years ago can quietly drift out of alignment with what you actually want today. We covered the foundation of this work in Protecting What’s Yours (After You Pass).

That’s why we encourage clients to think of estate planning the way they think of an annual physical: a short, scheduled review that catches small issues before they become expensive ones. Even in a year without major life changes, a yearly checkup is worth the hour.

Here are five areas worth reviewing each year.

1. Confirm your beneficiary designations

Most of your assets pass under your will or trust. But a meaningful share — retirement accounts, life insurance, certain annuities — passes by beneficiary designation, which overrides whatever your will says. That makes these designations one of the most common sources of unintended outcomes.

Check that named beneficiaries still reflect your wishes. Common red flags: an ex-spouse still listed on a 401(k), a deceased relative as a sole beneficiary (which can force the asset through probate), or a custodian arrangement for a child who is now an adult. Most custodians let you update beneficiaries online in a few minutes. It’s one of the highest-leverage estate planning tasks you can do.

2. Revisit your fiduciary appointments

Your fiduciaries — trustees, executors, agents under power of attorney, health care proxies — are the people who carry out your wishes when you can’t. The right choice ten years ago may not be the right choice today. (We walk through each of these documents in The Core Four.)

Health changes, deaths, and shifting relationships are obvious reasons to update. Less obvious: a sibling you named when your children were small may now reasonably be replaced by an adult child. Check in with named fiduciaries each year — and after any plan update — to confirm they’re still willing and able to serve. Don’t forget the backups.

3. Make sure your trust is actually funded

A revocable trust only works for the assets that are titled in its name. We see this often: a client signs a trust, then buys a new home, opens a new brokerage account, or inherits property — and never retitles it. Those assets bypass the trust and often head straight to probate, defeating one of the main reasons the trust exists. Kiplinger has a useful primer on which assets belong in a revocable trust if you want a refresher on the categories.

Each year, walk through your asset list and confirm everything intended for the trust is properly titled. Real estate, business interests, and non-retirement financial accounts are the usual suspects. (Retirement accounts generally stay in your name with beneficiary designations rather than being retitled into the trust.)

4. Reflect recent life changes

Marriages, divorces, births, adoptions, and deaths in the family are all triggers for a plan review. So are larger financial shifts — the sale of a business, a meaningful inheritance, or a significant change in your overall net worth.

Two reminders that often get overlooked. First, moving to another state matters. Estate and probate rules vary, and community property states have particular rules around spousal rights to retirement assets. Second, federal tax law changes can meaningfully alter the calculus on lifetime gifting, the estate tax exemption, and trust structures. When Washington moves, it’s worth checking whether your plan still does what you think it does.

5. Store documents securely — and accessibly

A plan no one can find is a plan that doesn’t work. Originals of your will, trust, powers of attorney, and health care directives need to be stored somewhere safe and somewhere your fiduciaries can actually get to them when the time comes.

A fireproof home safe or your attorney’s secure storage are usually better choices than a bank safe deposit box, which can require a court order to access after death. Digital copies are useful for reference, but courts and financial institutions generally require originals with wet signatures.

Your fiduciaries don’t need a complete list of account numbers. They generally need to know which institutions hold your assets — with that, a death certificate and your Social Security number are usually enough to identify everything.

Estate planning is a process, not an event

Most annual reviews are short. But a regular cadence is what makes the bigger updates — after a major life change, a relocation, or a tax law shift — feel routine rather than overwhelming. For the procedural side of what your family will face after you’re gone, our estate planning framework walks through it step by step. Protection during your lifetime gets its own treatment in Protecting What’s Yours (While You’re Alive).

If it’s been more than a year since you looked at your estate plan, that’s a reasonable starting point for a conversation. We’re happy to coordinate with your estate planning attorney to make sure what’s on paper still matches what you want for your family today.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

Data sources for returns and standard statistical data are provided by the sources referenced and are based on data obtained from recognized statistical services or other sources we believe to be reliable. However, some or all information has not been verified prior to the analysis, and we do not make any representations as to its accuracy or completeness. Any analysis nonfactual in nature constitutes only current opinions, which are subject to change. Benchmarks or indices are included for information purposes  only  to  reflect  the  current  market  environment;  no  index  is  a directly  tradable investment.  There  may  be  instances  when  consultant  opinions  regarding any fundamental or quantitative analysis do not agree.

The  commentary  contained  herein  has  been  compiled  by  W.  Reid Culp,  III  from  sources  provided  by  TAGStone  Capital,  as well  as  commentary  provided  by  Mr.  Culp,  personally,  and  information independently  obtained  by  Mr.  Culp.  The  pronoun  “we,”  as  used  herein,  references collectively the sources noted above.

TAGStone Capital, Inc. provides this update to convey general information about market conditions and not for the purpose of providing investment advice. Investment in any of the companies or sectors mentioned herein may not be appropriate for you. You should consult your advisor from TAGStone or others for investment advice regarding your own situation.

Posted on

At a Glance

  • Geopolitical conflicts can trigger short-term market volatility
  • Diversified portfolios are designed to withstand these periods
  • Midterm election years often bring volatility, but historically lead into strong market periods

Periods of geopolitical tension can cause sharp market reactions and unsettling headlines.

Recently, events in the Middle East have escalated rapidly. On Feb. 28, the U.S. and Israel launched an attack on Iran, setting off a rapidly escalating conflict across the Middle East. Fighting has spread to other countries, bringing with it destruction and loss of life.

In addition to the humanitarian toll, the conflict is making economic waves globally. As of 2025, 20 million barrels of oil per day—about 20% of global consumption—traveled through the Persian Gulf. That traffic came to a standstill after the attack, and oil prices climbed swiftly.

These events have investors worried and markets reacting. In early March, the CBOE Volatility Index jumped to its highest level since the near bear market last April.

What Exactly Has Markets Concerned?

Investors worry that rising oil prices could slow the economy. Energy is a key input for transportation, manufacturing, and other activities. When oil prices spike, many industries face higher costs.

Investors are also concerned about inflation. Higher energy prices can lead to broader price increases. What’s more, many investors were hoping the Federal Reserve would lower interest rates to boost the economy. If inflation rises, the Fed may be less likely to do so.

Your Portfolio Is Built for Moments Like This

While the headlines are alarming, periods like this are not unusual in long-term investing. At TAGStone, portfolios are designed with the expectation that geopolitical events, economic shocks, and market volatility will occur from time to time.

It’s important to remember that your diversified investment portfolio is built to withstand moments like this.

For instance, your portfolio already includes allocations to U.S. and international stocks, bonds, and cash. The fixed income portion of your portfolio, in particular, can help provide stability when equities become more volatile, helping smooth overall portfolio fluctuations.

Within the equity portion of your portfolio, diversification also helps manage risk. Some sectors may struggle when energy prices rise, such as technology and consumer discretionary.[1] On the other hand, energy companies might benefit from rising prices, potentially helping offset losses elsewhere.

A diversified portfolio does not eliminate losses, but it can help reduce the magnitude of downturns compared to broad market indices such as the S&P 500.

It’s also worth remembering that much of your portfolio is invested for the long term. Short-term market movements can feel uncomfortable, but the assets that fluctuate most today typically are the ones you won’t need to draw on for many years. As a result, you may not need to change anything about your portfolio to respond to the current news cycle.

This year may also naturally bring somewhat higher market volatility. Historically, midterm election years have tended to experience larger intra-year declines—closer to about 17–18% on average versus roughly 14–15% in a typical year. While those declines can feel unsettling in the moment, the period following midterm elections has historically been one of the strongest stretches in the four-year presidential cycle.

A Final Perspective

In times of geopolitical crisis, it is natural for both people and markets to react quickly. History, however, suggests that these events rarely alter the long-term trajectory of markets.

One useful way to think about geopolitical crises is that markets tend to treat them as temporary disruptions rather than permanent economic changes. Denise Chisholm, director of quantitative market strategy at Fidelity, looked into geopolitical shocks from Pearl Harbor through Russia’s 2022 invasion of Ukraine. She found that, on average, U.S. equities returned about 8% over the following year, on par with their long-term annual average. Her conclusion: “It’s the exception, not the rule, that geopolitical events become sustained market headwinds.”

The chart below illustrates how U.S. equities have historically performed in the year following major geopolitical shocks.

If you have questions about how current events may affect your portfolio, don’t hesitate to reach out. We’re always happy to talk through your concerns and help you stay focused on your long-term plan.

[1] See slide 6 of the linked chart pack.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

Data sources for returns and standard statistical data are provided by the sources referenced and are based on data obtained from recognized statistical services or other sources we believe to be reliable. However, some or all information has not been verified prior to the analysis, and we do not make any representations as to its accuracy or completeness. Any analysis nonfactual in nature constitutes only current opinions, which are subject to change. Benchmarks or indices are included for information purposes  only  to  reflect  the  current  market  environment;  no  index  is  a directly  tradable investment.  There  may  be  instances  when  consultant  opinions  regarding any fundamental or quantitative analysis do not agree.

The  commentary  contained  herein  has  been  compiled  by  W.  Reid Culp,  III  from  sources  provided  by  TAGStone  Capital,  as well  as  commentary  provided  by  Mr.  Culp,  personally,  and  information independently  obtained  by  Mr.  Culp.  The  pronoun  “we,”  as  used  herein,  references collectively the sources noted above.

TAGStone Capital, Inc. provides this update to convey general information about market conditions and not for the purpose of providing investment advice. Investment in any of the companies or sectors mentioned herein may not be appropriate for you. You should consult your advisor from TAGStone or others for investment advice regarding your own situation.

Posted on

At a Glance

  • Most people have one or two of these documents in place — but comprehensive planning requires all four, working together as a coordinated safety net.
  • Each document serves a distinct purpose: financial decisions, medical decisions, end-of-life preferences, and asset distribution.
  • Estate planning failures are rarely about missing documents — they're about outdated designations, poor coordination, and plans that haven't kept pace with life.

No one likes to imagine a time when they might be sick or unable to make decisions for themselves. It ranks alongside cleaning out the garage or scheduling a long-overdue physical—important, but all too easy to postpone. Yet having the right estate planning documents in place can make all the difference.

Without a clear plan in place, the state might step in and appoint a guardian to make financial and medical decisions on your behalf. Someone you didn’t choose could end up deciding where you live, how your money is managed, or what medical treatments you receive. That's not a situation any of us wants to be in.

Incapacity exists on a spectrum. It could look like cognitive decline from Alzheimer’s or dementia, physical incapacity after an injury or illness, a sudden event such as a stroke, or a gradual decline over time.

Because these scenarios unfold differently—and at different life stages—you’ll need four key documents to address them:

  1. a durable power of attorney,
  2. health care proxy,
  3. living will, and
  4. a will or revocable trust.

You may already have one or two of these documents, but comprehensive planning requires all four. Together, these documents create a coordinated safety net. Without one, gaps can appear. It’s like living near a river and buying homeowner’s insurance but skipping flood coverage. You’re mostly protected… until you’re not.

1. Durable Power of Attorney

A durable power of attorney (DPOA) is a legal document that authorizes someone—known as your agent or attorney-in-fact—to manage your financial affairs on your behalf, including bills, banking, investments, and business interests. The word “durable” here is key: it means the document remains valid even if you become mentally incapacitated.

Choosing the right person to fill this role matters. Consider someone who is financially responsible, trustworthy, and capable of handling potential conflict if family members disagree. Many people select a spouse or adult children. If these options don’t feel appropriate, we can help you identify another trusted individual or a professional fiduciary.

It’s also wise to appoint a backup agent in case your first choice is unavailable when needed.

One related tool worth knowing about: a trusted contact person on your financial accounts. Unlike a DPOA agent, a trusted contact cannot make decisions or view your accounts, but they can serve as a point of contact for your financial institutions if something seems wrong.

For a deeper look at how a DPOA and a trusted contact person work in practice, including important tips on keeping it current with your financial institutions, see Protecting What's Yours (While You're Alive).

2. Health Care Proxy

Your health care proxy is a document that designates an agent to make medical decisions for you if you are unable to do so yourself. This covers situations where you are unconscious, severely ill, undergoing surgery, or have lost cognitive capacity.

The health care proxy is typically activated when a physician determines that you lack decision-making capacity. At that point, your agent can step in and make decisions about treatments, surgeries, medications, care facilities, and in some states, end-of-life decisions. Ideally, these decisions are guided by your known wishes or their best judgment of what you would want.

Again, a spouse or adult children are common choices. Whoever you name should be someone who understands your preferences about medical care, is comfortable making decisions under pressure, and can advocate for you with medical professionals.

It’s also common to name different individuals for medical and financial decisions. It creates natural checks and balances and helps prevent one person from carrying the entire weight.

3. Living Will

A living will complements your health care proxy. This document spells out—in your own words—the medical treatments you do and don’t want in specific circumstances, such as a terminal condition, a persistent vegetative state or at the end-stage of an illness with little hope for recovery.

You don’t need to name an agent for a living will. However, it may be helpful to come up with this document in conversation with your physician and estate attorney. Tools like the “Five Wishes” framework can serve as a jumping-off point for clarifying your preferences.

Your living will is part of a broader healthcare advance directive. We cover what that includes, and other practical tips, in Protecting What's Yours (While You're Alive).

4. Will or Revocable Living Trust

The first three documents address what happens when you're living but unable to act. The fourth addresses what comes after.

Your estate plan should also include a will or trust that addresses what happens to your assets.

A will outlines how your property should be distributed after you die, names an executor to carry out your wishes, and designates a guardian for any minor children.

A revocable living trust goes a step further. You transfer assets into the trust during your lifetime—typically naming yourself as the initial trustee so you retain full control—and a successor trustee steps in if you become incapacitated or die.

Because assets in a trust bypass the probate process, transfers tend to be faster, more private, and less expensive. There are several types of revocable trusts, and we can work with you and your estate attorney to determine which structure fits your situation.

A will or trust is just the starting point. The greater risk for most families is execution and coordination after documents are signed. We cover what that looks like in Protecting What's Yours (After You Pass) and the step-by-step process in Part 2.

Keep Your Estate Planning Documents Current

No single document covers every phase of incapacity or death. The goal is to have all four in place, kept current, and accessible to the people who may need them.

One important area these documents don’t cover is beneficiary designations on retirement accounts and life insurance policies. These designations override instructions in your will, so make sure they are up to date and aligned with your wishes.

Finally, remember that life is dynamic. Laws evolve, financial situations shift, and relationships change. Plan to review each of these documents regularly, especially after major life events such as marriage, divorce, the birth of a child, relocation, or significant changes in wealth, and update them as needed.

The Core Four documents are the foundation, but they're only as strong as the planning and coordination around them. At TAGStone Capital, we help clients build and maintain that full picture, from incapacity planning to estate execution. To go deeper on what happens after documents are signed, see Protecting What's Yours (After You Pass). Or, if you're ready to talk through where your own plan stands, schedule a complimentary 15-minute conversation.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

Data sources for returns and standard statistical data are provided by the sources referenced and are based on data obtained from recognized statistical services or other sources we believe to be reliable. However, some or all information has not been verified prior to the analysis, and we do not make any representations as to its accuracy or completeness. Any analysis nonfactual in nature constitutes only current opinions, which are subject to change. Benchmarks or indices are included for information purposes  only  to  reflect  the  current  market  environment;  no  index  is  a directly  tradable investment.  There  may  be  instances  when  consultant  opinions  regarding any fundamental or quantitative analysis do not agree.

The  commentary  contained  herein  has  been  compiled  by  W.  Reid Culp,  III  from  sources  provided  by  TAGStone  Capital,  as well  as  commentary  provided  by  Mr.  Culp,  personally,  and  information independently  obtained  by  Mr.  Culp.  The  pronoun  “we,”  as  used  herein,  references collectively the sources noted above.

TAGStone Capital, Inc. provides this update to convey general information about market conditions and not for the purpose of providing investment advice. Investment in any of the companies or sectors mentioned herein may not be appropriate for you. You should consult your advisor from TAGStone or others for investment advice regarding your own situation.

Posted on

At a Glance

  • Estate planning at higher levels of wealth is an execution and coordination challenge—not merely a legal exercise.
  • The greatest risks arise where intent, legal documents, asset titling, and beneficiary designations drift out of alignment.
  • Sophisticated families approach estate planning as an ongoing, advisor‑guided process that evolves with assets, entities, and family dynamics.

Part 2: Step-by-Step Estate Planning for Sophisticated Families

In Part 1 of this series, we addressed why estate planning matters—and why, for many families, it represents one of the most meaningful acts of stewardship they can undertake. In this follow‑up, we turn to the how.

For families with significant assets, multiple entities, or multigenerational considerations, estate planning is rarely a single document or moment in time. It is a procedural process that requires clarity of intent, disciplined implementation, and ongoing coordination across advisors.

What follows is a practical framework that reflects how sophisticated families typically approach estate planning—methodically, deliberately, and with an eye toward fiduciary, tax, and governance risk.

Hurdle #1: Deciding Who Gets What

The first step is deceptively simple: defining what should happen after you pass. In practice, this is where many long‑term issues are either resolved—or unintentionally created.

At higher levels of wealth, this exercise often extends beyond a single balance sheet. It may involve operating businesses, real estate partnerships, concentrated investment positions, family trusts, or philanthropic structures. Decisions made here can have downstream consequences for estate taxes, GST planning, liquidity, and family governance.

Rather than attempting to control every detail, sophisticated families focus first on priorities:

  • Who are the intended beneficiaries, and at what stages of life?
  • Are there second marriages, blended families, or differing levels of financial maturity?
  • Which assets are illiquid, and which are expected to fund liquid needs?

 

These questions are best addressed while capacity is intact and family dynamics can be navigated thoughtfully—often in parallel with broader lifetime planning decisions.

Who Gets What? A Strategic Checklist

  • Estimate net worth across all major assets and liabilities (ballpark is sufficient initially).
  • Identify primary beneficiaries, contingent beneficiaries, and charitable interests.
  • Consider how the bulk of the estate should be allocated, recognizing potential estate tax and GST implications.
  • Identify specific assets or heirlooms with emotional or historical significance.
  • Consider to whom or what entity you might like to leave these particular possessions.
  • Identify who you’d like to name as executor and/or trustee, to settle your estate and administer your trusts once you pass. (As described in this ACTEC article, “What It Means to be a Trustee: A Guide for Clients,” the person should be reliable to carry out their duties in a timely and responsible manner.)
  • Flag potential conflicts of interest or competing expectations among beneficiaries, such as multiple heirs each hoping to inherit the family cabin.
  • Identify individuals you would explicitly exclude, such as ex-spouses or estranged family members.

 

For many families, this stage benefits from advisor facilitation—not to dictate outcomes, but to surface blind spots before they harden into documents.

Hurdle #2: Making It Legal

Once intent is clear, the next step is translating that intent into enforceable legal structures. This is where technical precision matters—and where coordination failures can be costly.

While it is technically possible to rely on generic templates, we rarely see it hold up over time—particularly for families with layered trusts, operating entities, or long-term legacy objectives. Missing or imprecise legal language can easily undermine even well-intentioned plans. A reputable estate planning attorney does more than draft documents: they take the time to understand your family, translate intent into enforceable structures, anticipate tax and fiduciary risk, and collaborate with your financial advisors to ensure documents, asset ownership, and beneficiary designations work together. Once established, that relationship materially improves the plan’s durability and ease of ongoing maintenance.

Sophisticated estate plans often involve a combination of:

  • Will. Nearly every estate plan begins with a will. At a minimum, a will directs how assets passing through probate are distributed, names one or more executors to administer the estate, and appoints guardians for minor children where applicable. For families with modest complexity and clear beneficiary designations, a will may address the essentials. For more complex estates, the will functions as a backstop—capturing assets not otherwise titled or governed by trust arrangements and ensuring orderly administration through the probate process.
  • Revocable Living Trust (RLT). As assets, relationships, or family dynamics become more complex, many families supplement a will with a revocable living trust. An RLT allows the bulk of the estate to bypass public probate, providing greater privacy, continuity, and administrative efficiency. More importantly, it enables flexibility that a will alone cannot provide—such as supporting a surviving spouse during their lifetime while preserving remainder interests for children from a prior marriage, staging distributions for beneficiaries who are not yet ready to manage wealth, or protecting assets from a beneficiary’s creditors or spendthrift tendencies. Properly structured, an RLT also facilitates seamless management during incapacity and a smoother transition at death.
  • Specialized Trusts. Families with business interests, philanthropic goals, or multigenerational planning objectives often rely on additional trust structures to address specific risks and opportunities. These may include trusts designed to mitigate estate and GST taxes, support business succession, fund charitable initiatives, or establish long‑term family governance frameworks.

 

For families pursuing dynasty‑style planning, documents may also incorporate directed trustees, trust protectors, or successor governance provisions—structures that require careful alignment between legal language and real‑world administration.

A recurring risk at this stage is assuming that documents alone are sufficient. In reality, fiduciary risk often arises when documents say one thing and accounts, titles, or beneficiary forms say another.

Equally important is incapacity planning. Powers of attorney, healthcare directives, and trustee succession provisions should be evaluated alongside the broader lifetime planning framework, not treated as afterthoughts.

Hurdle #3: Getting It Together

This final step is where many estate plans quietly fail—not due to poor legal drafting, but due to incomplete implementation.

For trustees and executors, administrative clarity is not a convenience; it is a fiduciary necessity. Even well‑constructed plans can unravel if assets are mis‑titled, beneficiary designations are outdated, or key information is inaccessible.

Implementation and Governance Checklist

  • Maintain a detailed and current inventory of financial assets, including investment accounts, bank accounts, retirement plans, insurance policies, business interests, and any entities or partnerships in which you hold an interest.
  • Document who should receive specific collectibles, heirlooms, or personal property—typically through a separate, adjustable memorandum referenced by your will or trust.
  • Identify key professionals your trustees, executors, or beneficiaries may need to contact, such as your financial advisor, estate planning attorney, accountant, or insurance advisor.
  • Compile practical information fiduciaries will need to administer the estate efficiently: where legal documents are stored; how to access digital accounts, security codes, and devices; and contact information for household, caregiving, or pet care arrangements.
  • Confirm that revocable living trusts are fully funded with major assets so they can function as intended, with assistance from your estate planning counsel where needed.
  • Ensure homes, vehicles, business interests, and other titled assets are properly owned and aligned with the estate plan (individual, joint, trust, or entity ownership).
  • Review beneficiary designations on retirement accounts, insurance policies, and transfer on death assets regularly to ensure consistency with overall intent.
  • Reduce accumulated physical clutter and outdated records to avoid imposing unnecessary administrative and emotional burdens on fiduciaries and heirs.
  • Revisit each of these steps on a recurring basis—particularly after births, deaths, marriages, divorces, relocations, major financial events, legislative changes, or material shifts in family or trust structures.

 

For families with ongoing trusts or multigenerational arrangements, this review cadence is not optional; it is a core governance discipline as assets grow, laws evolve, and fiduciary responsibilities expand.

Security also warrants explicit treatment as a fiduciary risk-mitigation issue. Trustees and executors have a duty to safeguard sensitive personal and financial information against identity theft, fraud, and unauthorized access—while still being able to locate and act on that information efficiently when required. Poor security practices can delay administration, increase costs, and expose fiduciaries to avoidable liability. For this reason, many sophisticated families use secure digital vaults or reputable password managers to centralize account access, document locations, and critical credentials. When selecting these tools, it is prudent to designate an emergency or fiduciary contact with clearly defined access rights, so information is neither inaccessible nor overly exposed at the moment it is needed most.

How We Help

Estate planning is often described as a legal exercise. In practice, for families with meaningful complexity, it is a coordination challenge that unfolds over time—across advisors, entities, and generations.

We work with families and fiduciaries to ensure that intent, legal structures, asset ownership, beneficiary designations, and administrative execution remain aligned—not just at the moment documents are signed, but as circumstances evolve. Our role is not to replace estate counsel or trustees, but to help orchestrate the process so decisions made during life carry through cleanly after death.

For families who already have documents in place, we are often engaged to review implementation and readiness: asset titling, beneficiary alignment, liquidity planning, fiduciary access, and trustee coordination—before issues surface and before execution risk becomes visible.

Estate plans are not static. Neither are families, assets, or laws. A disciplined, advisor-guided coordination process helps ensure that what you have built—and what you intend—is ultimately carried out as designed.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

Data sources for returns and standard statistical data are provided by the sources referenced and are based on data obtained from recognized statistical services or other sources we believe to be reliable. However, some or all information has not been verified prior to the analysis, and we do not make any representations as to its accuracy or completeness. Any analysis nonfactual in nature constitutes only current opinions, which are subject to change. Benchmarks or indices are included for information purposes  only  to  reflect  the  current  market  environment;  no  index  is  a directly  tradable investment.  There  may  be  instances  when  consultant  opinions  regarding any fundamental or quantitative analysis do not agree.

The  commentary  contained  herein  has  been  compiled  by  W.  Reid Culp,  III  from  sources  provided  by  TAGStone  Capital,  as well  as  commentary  provided  by  Mr.  Culp,  personally,  and  information independently  obtained  by  Mr.  Culp.  The  pronoun  “we,”  as  used  herein,  references collectively the sources noted above.

TAGStone Capital, Inc. provides this update to convey general information about market conditions and not for the purpose of providing investment advice. Investment in any of the companies or sectors mentioned herein may not be appropriate for you. You should consult your advisor from TAGStone or others for investment advice regarding your own situation.

Posted on

At a Glance

  • Estate planning failures are rarely legal—they are usually coordination failures that surface at the worst possible time.
  • Even financially sophisticated families often delay planning, leaving loved ones to manage complex estates under emotional stress.
  • A well‑coordinated estate plan reduces settlement delays, costs, and family conflict while preserving long‑term intent.

Part 1: The Strategic Importance of Estate Planning

Fact: When you pass, you will leave behind an estate—and someone will be responsible for settling it. The size and complexity of that estate will vary, but there is no escaping death, taxes, and the operational realities that follow.

Despite widespread awareness that estate planning matters, execution remains remarkably low. As of 2025, fewer than one in four U.S. adults has a will, and only a small minority have implemented a living trust. In other words, most families still enter the estate settlement process without even basic legal documentation in place. The gap between intent and preparation creates unnecessary costs, delays, and stress for those left behind.

So why do so many families—often highly successful ones—put off estate planning until circumstances force their hand?

Estate Planning Is an Act of Leadership

Since 2015, Caring.com has tracked Americans’ estate planning behavior. While recent surveys show modest improvement following the pandemic, procrastination remains the dominant obstacle. In the most recent survey, roughly 43% of those without a will reported that they simply “haven’t gotten around to it.”

This hesitation is rarely about indifference. More often, it reflects the emotional weight of confronting mortality, paired with the logistical complexity of modern wealth. Families with multiple entities, closely held businesses, real estate, trusts, and multigenerational goals are busy managing today’s demands—until an unexpected event turns delay into disruption.

For families with meaningful wealth, estate planning is not merely an administrative task. It is an act of leadership—one that spares loved ones from having to make difficult decisions under emotional distress and time pressure.

The Real Benefits of a Well‑Coordinated Estate Plan

If you’ve been postponing estate planning, you are far from alone. But regardless of age or stage of life, proactive planning delivers tangible benefits—especially when coordination is prioritized over paperwork alone.

A thoughtfully structured and well‑maintained estate plan is one of the most meaningful gifts you can leave your family. It reduces uncertainty, minimizes friction, and allows those you care about to focus on healing rather than logistics.

According to EstateExec’s most recent data, the process of settling an estate now averages nearly 16 months, and complex or multi‑entity estates often take significantly longer—as much as 42 months for estates over $5 million. Delays are rarely caused by a single missing document; they are usually the result of poor coordination among accounts, entities, beneficiaries, and decision‑makers.

Effective estate planning delivers several critical advantages:

  • Clarity: Clearly documented intentions—supported by proper titling and beneficiary designations—make it far more likely that your wishes are carried out as intended.
  • Speed: Coordinated planning reduces administrative bottlenecks and shortens the time required to transfer assets to heirs.
  • Cost Control: Fewer delays and disputes generally translate into lower legal, tax, and administrative expenses.
  • Tax Efficiency: Thoughtful planning allows families to implement both foundational and advanced strategies to transfer wealth more efficiently.
  • Protection: Anticipating risks in advance helps shield assets from unintended recipients, creditor claims, and avoidable family conflict.

The Hidden Cost: Coordination Failure

Many families assume estate planning is complete once documents are signed. In reality, the most common failures occur after the ink dries.

Unfunded trusts, outdated beneficiary designations, unclear successor roles, and missing information can derail even well‑drafted plans. The result is often prolonged settlement timelines, increased expenses, and avoidable strain among family members.

At TAGStone Capital, we work closely with families, their attorneys, and trustees to ensure estate plans function as intended—not just legally, but operationally. Effective coordination before and after death is what transforms good documents into successful outcomes.

Step‑by‑Step Planning: What Comes Next

So what prevents families from turning good intentions into durable plans?

In Part 2 of this series, Protecting What’s Yours (After You Pass) – Part 2: The Estate Planning Process, we will walk through the three most common hurdles that stand between families and effective estate planning:

  1. Deciding who gets what
  2. Making it legal
  3. Getting—and staying—organized

Each step matters. Skipping any one of them increases the likelihood that your estate plan creates confusion instead of clarity.

Planning Doesn’t Begin at Death

Estate planning is not a one‑time event, and it does not begin after you pass. It starts with how your assets, accounts, entities, and decision‑making structures are organized while you are alive.

If you have not yet addressed that foundation, we recommend starting with our earlier post: Protecting What’s Yours (While You’re Alive).

How We Help

If your family’s legacy matters—not just in principle but in practice—coordination matters. We help families align their estate plans with their broader financial picture, working directly with their attorneys and trustees to reduce complexity, improve execution, and preserve family harmony.

Schedule a 15‑minute estate coordination call to discuss how your current plan fits together—and where it may need attention.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

Data sources for returns and standard statistical data are provided by the sources referenced and are based on data obtained from recognized statistical services or other sources we believe to be reliable. However, some or all information has not been verified prior to the analysis, and we do not make any representations as to its accuracy or completeness. Any analysis nonfactual in nature constitutes only current opinions, which are subject to change. Benchmarks or indices are included for information purposes  only  to  reflect  the  current  market  environment;  no  index  is  a directly  tradable investment.  There  may  be  instances  when  consultant  opinions  regarding any fundamental or quantitative analysis do not agree.

The  commentary  contained  herein  has  been  compiled  by  W.  Reid Culp,  III  from  sources  provided  by  TAGStone  Capital,  as well  as  commentary  provided  by  Mr.  Culp,  personally,  and  information independently  obtained  by  Mr.  Culp.  The  pronoun  “we,”  as  used  herein,  references collectively the sources noted above.

TAGStone Capital, Inc. provides this update to convey general information about market conditions and not for the purpose of providing investment advice. Investment in any of the companies or sectors mentioned herein may not be appropriate for you. You should consult your advisor from TAGStone or others for investment advice regarding your own situation.

Posted on

Why Business Exit Planning Matters

If you’re a business owner, business exit planning eventually becomes essential. Whether you sell to an outside buyer, family, or employees, the question is whether you can exit on your own terms. The reality is that most business owners don’t have a clear, documented exit plan. And if you find yourself among them, you could find it leaves you in a tight spot when it’s time for you to step down.

Delaying planning your exit risks settling for a below-market sale price, losing control of choosing your successor or rushing into choices that don’t reflect your vision. Delays also leave you with little time to take steps to boost the business’s valuation and ensure business continuity. A clear exit plan helps maximize options and value. If you haven’t mapped out yours yet, there’s no time like the present. Consider these steps:

Put a Price on Your Business

Proper valuation of your business is the first step in exit planning. Some back-of-the-envelope math can provide a decent starting point. But to really understand what your business is worth, meet with a valuation expert. Besides a healthy dose of objectivity, these professionals bring market expertise and a knowledge of valuation standards. They can identify intangible sources of value you may have overlooked and help ensure your valuation passes muster with potential buyers and the IRS.

There are three main approaches to determining value:

  • The asset approach adds up the value of your company’s tangible and intangible assets, then subtracts liabilities.
  • The income approach calculates value according to your business’s expected future cash flows.
  • The market approach compares your business to recent sales of similar companies.

 

You may find one approach is more apt than another for the type of business you own, but a comprehensive valuation is likely to incorporate all three in one way or another. Bear in mind that valuation isn’t a one-time event. As your business grows and market conditions change, you’ll likely want to update your valuation.

Clarify Your Vision

Before you can build an effective exit plan, it’s necessary to clarify your goals. Be as specific as possible as you define what a successful transition looks like to you.

Some questions to keep in mind: Do you want to maximize the sale price, selling at the highest price possible? Do you intend to keep the business within your family or pass it to a handpicked successor? What are your obligations to employees? Is it important that your business maintains a consistent set of values when you’re gone? What timeline makes sense for you? How involved—if at all—do you want to be with the business after you exit?

The answers to these questions will guide the decisions that follow. They can be deeply personal, and we’re here to be a resource as you consider what’s truly important to you.

Shape Your Exit

With valuation and goals in hand, there are a range of steps you can take to support your transition. What you do will depend largely on the type of exit you’re planning. For some owners, you might make strategic adjustments to boost the value of your business, such as reducing unnecessary expenses or diversifying revenue streams to make your company more attractive to buyers.

If your plan involves transferring the business to a family member or a long-time employee, the sooner you identify them, the better. That way you’ll have plenty of lead time to train them in the leadership skills necessary to provide a smooth handoff.

Seeking an external buyer? Preparation is equally as important. In addition to boosting your valuation, you’ll need to organize your financial records, legal documents, contracts, employee agreements and operational procedures. One thing to consider is the type of deal structure that works best for you: Would you like to be paid over time or in one lump sum? And would you like to exit the company immediately or would you be open to staying on in an advisory capacity to help the new owner learn the ropes?

Begin the process of finding and vetting buyers early. These could be industry competitors, investment groups or individual entrepreneurs who may be a good fit. A business broker can help you identify potential buyers and spread the word through their network.

Plan Your Exit with Tax Strategy in Mind

Taxes play a major role in what you ultimately keep from a sale, so it’s important to understand your options early.

Your exit is also a key moment for gift and estate planning. Be aware that gifts to family members above the lifetime gift and estate tax exemption ($15 million for individuals in 2026) might trigger gift taxes. With enough lead time—ideally a few years before a sale—you may be able to transfer interests to family members or trusts, use your lifetime gift and estate tax exemption more strategically or coordinate charitable strategies in a way that reduces future estate or capital gains taxes while aligning with your legacy goals.

Meanwhile, sales to employees could trigger capital gains taxes. If your business is structured as an S corp or C corp, you might consider an employee stock ownership plan (ESOP), which could defer or even eliminate capital gain taxes if structured properly.

If you are considering an external buyer and your business is structured as a C corp or S corp, you and the buyer will also need to decide whether the transaction should be a stock sale or an asset sale. A stock sale often benefits sellers because more of the gain is taxed at long-term capital gains rates and may avoid a second layer of tax inside a corporation. Buyers often prefer an asset sale because they can step up the basis of the assets they acquire and may avoid certain liabilities.

In an asset sale, the company sells individual assets—such as equipment, inventory, customer relationships and goodwill—and portions of the gain may be taxed at higher ordinary income rates (for example, depreciation recapture). How the purchase price is allocated across these asset categories can significantly affect after-tax results for both sides.

Because these decisions can be complex and difficult to change once a letter of intent is signed, involving an advisor, CPA, and attorney early can help ensure the deal structure supports your long-term financial plan and minimizes taxes.

Charting the future

For many business owners, exit planning rarely tops the to-do list. After all, there are plenty of day-to-day demands competing for attention, let alone the fact that it can be difficult for owners to think about the day they’ll no longer lead the company they built. Yet the most successful exits are those planned in advance, allowing owners to optimize value, identify an ideal buyer or successor, and prepare their employees for a smooth transition—and structure the sale in a way that makes sense after taxes.

If you’re starting to think about an exit—whether you’re ten years out or already in early conversations with a buyer—you don’t have to navigate these decisions alone. At TAGStone Capital, we help business owners pull all the pieces together: clarifying goals, coordinating with valuation experts, CPAs and attorneys, and designing a plan for turning a one-time liquidity event into durable, tax-efficient cash flow for the next phase of life.

If you’d like help with business exit planning, TAGStone Capital can help you design a tax-efficient strategy that meets your financial goals and protects your legacy.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

Data sources for returns and standard statistical data are provided by the sources referenced and are based on data obtained from recognized statistical services or other sources we believe to be reliable. However, some or all information has not been verified prior to the analysis, and we do not make any representations as to its accuracy or completeness. Any analysis nonfactual in nature constitutes only current opinions, which are subject to change. Benchmarks or indices are included for information purposes  only  to  reflect  the  current  market  environment;  no  index  is  a directly  tradable investment.  There  may  be  instances  when  consultant  opinions  regarding any fundamental or quantitative analysis do not agree.

The  commentary  contained  herein  has  been  compiled  by  W.  Reid Culp,  III  from  sources  provided  by  TAGStone  Capital,  as well  as  commentary  provided  by  Mr.  Culp,  personally,  and  information independently  obtained  by  Mr.  Culp.  The  pronoun  “we,”  as  used  herein,  references collectively the sources noted above.

TAGStone Capital, Inc. provides this update to convey general information about market conditions and not for the purpose of providing investment advice. Investment in any of the companies or sectors mentioned herein may not be appropriate for you. You should consult your advisor from TAGStone or others for investment advice regarding your own situation.

Posted on

At a Glance

Protecting your assets while you are alive involves planning for periods when you may be unavailable or incapacitated. Key tools include a financial power of attorney, trusted contact persons on financial accounts, and a healthcare advance directive to ensure your wishes are followed.

Protecting What’s Yours (While You’re Alive)

Whether due to disability, dementia, or simply enjoying an exotic vacation, there are many ways you can end up unavailable to make critical financial or health care choices for yourself or your loved ones. If you’ve not documented your desires in advance, it can add extra stress for everyone, plus the outcomes may not be what anyone had in mind!

One source of confusion over when and how to protect your assets is understanding which legal logistics apply during your lifetime, and which don’t come into play until after you pass.

If you’re interested in how estate planning shifts once you’re gone, we cover that separately in Protecting What’s Yours (After You Pass) — including both why it matters and how it works step by step.

Today, we’ll cover a trio of tools for protecting your interests while you are alive:

  1. A financial power of attorney
  2. Trusted contact person(s)
  3. A healthcare advance directive

I. A Financial Power of Attorney

The Basics. A financial power of attorney (POA) is a legal document authorizing someone (your “agent”) to make financial decisions on your behalf. No matter how much authority you grant an agent, they still owe you a fiduciary level of care, which means any decisions they make for you must be based on what they believe to be in your best financial interests.

When It Applies. A POA applies while you are alive, but unavailable to act for yourself. You can structure it to:

  • Begin immediately or upon a triggering event (such as a debilitating accident or illness)
  • Remain in force during a finite time period or be ongoing
  • Apply to all your financial matters, or only to specific transactions

 

Common Scenarios. A financial POA can be helpful to address:

  • Capacity: If you become incapacitated due to illness, injury or dementia.
  • Availability: If you’re unable to be present for a financial transaction, such as if you’re traveling abroad or you’re otherwise preoccupied.
  • Convenience: If you’d simply like to make it convenient for someone else to be able to make financial decisions for you – such as your spouse or a trusted sibling (in general), your parents (if you’re heading off to college), or your adult children (if you’re aging).

 

Additional Tips.

  • Again, anyone to whom you grant a POA is only your legal agent while you are alive; their authority ends the moment you pass away. Your estate’s trustees should take it from there, as we discuss in Protecting What’s Yours (After You Pass).
  • Your agent(s) should have access to the documents that describe the POA you’ve granted them. If they can’t prove what their role is, they may not be able to act on it when needed.
  • Some banks and account custodians have their own POA forms they would prefer you use; also, they may be wary of POA paperwork that is several years old. Check with the financial institutions you frequent about their policies, and consider annually reestablishing any durable POAs, to ensure they remain relevant.
  • You cannot grant a POA if you are deemed to be of unsound mind. This makes sense, since you may inadvertently name a “bad” player … or others may be able to contest the POA you’ve established. Don’t wait until it’s too late.

II. Trusted Contact Person(s)

The Basics. In 2017, the SEC approved the role of trusted contact person as part of a FINRA Rule 4512 amendment. The amendment requires your account custodians (brokers) to encourage you to name a trusted contact as an extra line of defense for your investment accounts. If the custodian feels you are being financially exploited, they then have a back-up person they can talk to about some of their concerns. The additional input may enable them to delay disbursing funds from your account “where there is a reasonable belief of financial exploitation.” [Source]

When It Applies. While the primary aim of the FINRA amendment is to prevent financial elder abuse, there are at least two scenarios when a trusted contact can be useful:

  • If you are unavailable, and the custodian believes your account may have been compromised
  • If you are cognitively impaired

 

Common Scenarios. Imagine you’re on a mid-Atlantic cruise, and your broker receives a suspicious trade order from “you.” They try, but cannot reach you to verify it’s really you. If there is no trusted contact to reach out to, they may have little choice but to execute the trade and disburse the funds as ordered. If a trusted contact can instead provide evidence that the order is likely fraudulent, your broker may be able to place a temporary hold before disbursing the funds.

Similarly, if a loved one is exhibiting signs of dementia, a trusted contact can help prevent them from falling prey to financial exploitation. What if your aging parent tries to empty out their own bank account to help a “friend” in need? If your parents have named you as a trusted contact, an account custodian who suspects foul play can reach out to you, explain the circumstances, and receive your “second opinion.”

Additional Tips. If you’ve named someone as a trusted contact, your broker or account custodian can discuss some of your relevant circumstances with them, and gather pertinent information from them. But a trusted contact cannot make any financial decisions on your behalf, nor can they view your account. Unless you grant it to them separately, a trusted contact does not have a financial power of attorney, as described in Section I.

III. A Healthcare Advance Directive

The Basics. Your healthcare advance directive can offer two types of protection:

  • Your living will provides your life-sustaining and end-of-life medical care instructions, and related healthcare preferences, in case a time comes when you cannot state them for yourself.
  • Your healthcare directive can also name healthcare representative(s), or agent(s) and grant them healthcare power of attorney. If you cannot make your own healthcare decisions, your agent can decide on your behalf, guided by your living will. Medical professionals can also more freely discuss your condition with your agent, without violating HIPAA privacy rules.

 

When It Applies. Your healthcare advance directive only comes into play if you are alive, but unable to direct your own medical care.

Common Scenarios. Accidents and illnesses can rob you of your mental capacity – temporarily or permanently. If you do not have an advance directive in place, healthcare professionals and/or key family members may have to make medical decisions for you, without knowing what you would have preferred. Also, the individual(s) you would most want to have making decisions on your behalf may not be able to do so if you haven’t named them as your representative(s) in your advance directive. This can be stressful if not heartbreaking for everyone involved.

Additional Tips.

  • Not only should almost everyone have an advance directive, it should be easy to get ahold of it when needed. Distribute copies to your primary physician and any of your other healthcare providers to keep on file. Give it to key family members. At TAGStone Capital, we also maintain a portal for storing clients’ essential paperwork – including advance directives.
  • IMPORTANT: Do you have children who recently turned 18? As soon as your child is an adult, healthcare providers may not be able to even discuss your child’s case with you unless you have a healthcare power of attorney. Also, as described in this Wall Street Journal piece, if your child is attending school in another state, it’s worth establishing a healthcare power of attorney in their state and yours.

How Can TAGStone Capital Help?

We hope our summary has helped clarify the role these protections play in safeguarding what’s yours during your lifetime. In practice, incapacity planning is only one part of a broader continuum that extends into estate administration after death. For families who want to understand how these responsibilities transition to trustees, executors, and heirs, we explore those considerations in our companion series, Protecting What’s Yours (After You Pass).

Professional legal counsel is often warranted as you work through these decisions. If helpful, we can coordinate with your existing advisors or introduce you to experienced professionals, and we can assist in organizing and maintaining these documents as part of a broader planning framework.

Need help coordinating these documents with your financial plan?
Schedule a complimentary 15-minute conversation to discuss how these protections fit into your broader wealth strategy.

Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

Data sources for returns and standard statistical data are provided by the sources referenced and are based on data obtained from recognized statistical services or other sources we believe to be reliable. However, some or all information has not been verified prior to the analysis, and we do not make any representations as to its accuracy or completeness. Any analysis nonfactual in nature constitutes only current opinions, which are subject to change. Benchmarks or indices are included for information purposes  only  to  reflect  the  current  market  environment;  no  index  is  a directly  tradable investment.  There  may  be  instances  when  consultant  opinions  regarding any fundamental or quantitative analysis do not agree.

The  commentary  contained  herein  has  been  compiled  by  W.  Reid Culp,  III  from  sources  provided  by  TAGStone  Capital,  as well  as  commentary  provided  by  Mr.  Culp,  personally,  and  information independently  obtained  by  Mr.  Culp.  The  pronoun  “we,”  as  used  herein,  references collectively the sources noted above.

TAGStone Capital, Inc. provides this update to convey general information about market conditions and not for the purpose of providing investment advice. Investment in any of the companies or sectors mentioned herein may not be appropriate for you. You should consult your advisor from TAGStone or others for investment advice regarding your own situation.