Fall has a way of bringing families back together. School schedules settle into a rhythm, calendars fill with gatherings, and the holidays begin appearing on the horizon.
Before the season becomes crowded with travel, celebrations, and year-end responsibilities, set aside time for one practical task: reviewing your estate plan.
An estate plan is not something you create once and forget. It should grow and change as your family, finances, relationships, health, and goals change. A fall review gives you the opportunity to catch outdated information before your loved ones need to rely on it.
Whether you live in Maryland or Virginia: or have family, property, or a business in both states: here are seven important documents and designations to review before the holidays hit.
1. Your Last Will and Testament
Your Last Will and Testament explains how certain assets should be distributed after your death. It may also nominate guardians for minor children and name the person you want to manage the probate process.
What to check
- Is your current spouse or partner named appropriately?
- Are your children, stepchildren, or other loved ones identified correctly?
- Are your executor and backup executor still willing and able to serve?
- Are your guardianship nominations current?
- Does the Will reflect your current wishes for personal property and other assets?
- Was the Will prepared in another state?
A Will may not control every asset you own. Accounts with beneficiary designations, jointly owned property, and assets titled in a trust may pass outside the Will. That is why reviewing your Will should always be part of a broader estate plan review.
Life changes that may trigger an update
Marriage, divorce, the birth or adoption of a child, a death in the family, a significant inheritance, or a move between Maryland and Virginia may all be reasons to revisit your Will.
If you have a Will-based plan, remember that a Will generally takes effect through probate. Learn more about the differences between Wills and Trusts in Estate Planning 101: Wills and Trusts.

2. Your Trusts and Trust Funding
If you have a revocable living trust or another type of trust, review both the document and the assets connected to it.
A trust may provide instructions for managing and distributing assets during your lifetime, in the event of incapacity, and after your death. Depending on your goals and circumstances, it may also help your family avoid some court involvement and keep private matters out of the public probate process.
What to check
- Are the current trustees and successor trustees still appropriate?
- Are the instructions consistent with your family’s needs?
- Have new assets been properly titled or connected to the trust?
- Did you buy or sell a home, investment property, or business interest?
- Are trust beneficiaries and distribution instructions still correct?
- Are any special-needs, asset-protection, or other specialized trusts still serving their intended purpose?
A trust only works as intended when it is properly funded and coordinated with the rest of your plan. A new home, refinance, investment account, or business interest may require additional planning.
Life changes that may trigger an update
A move between Maryland and Virginia, a change in your family structure, a new business, a sale of property, a large inheritance, or the death or incapacity of a trustee can all justify a review.
You can learn more about Eskay Law Group’s personalized estate planning services.
3. Your Advance Directive or Healthcare Power of Attorney
An advance directive: which may include a healthcare power of attorney: allows you to name the person you want to make medical decisions if you cannot make or communicate those decisions yourself. It may also explain your preferences regarding medical treatment and end-of-life care.
In Maryland, an advance directive can include the appointment of a healthcare agent and treatment preferences. The Maryland Department of Health Advance Directive Program provides official state information and resources.
What to check
- Is your named healthcare agent still the right person?
- Is your backup agent still available and willing to serve?
- Does your document reflect your current treatment preferences?
- Do your loved ones understand your wishes?
- Do your healthcare providers have the most recent version?
- Is the document appropriate for your current state of residence?
If you have moved from Maryland to Virginia: or from Virginia to Maryland: ask an estate planning attorney to review your documents under your current circumstances. State requirements and accepted forms may differ, and healthcare providers need clear, usable instructions.
Life changes that may trigger an update
Marriage, divorce, a serious diagnosis, a change in family relationships, the death of an agent, or a move across state lines may all call for an update.
4. Your HIPAA Authorization
A HIPAA Authorization gives specific people permission to receive protected medical information from your healthcare providers. It works alongside your advance directive and healthcare power of attorney.
Without appropriate authorization, your loved ones may have difficulty obtaining information about your condition: even if they are trying to help you or are named as your healthcare agent.
What to check
- Are the people you want involved listed by their correct legal names?
- Should anyone be removed from the authorization?
- Are phone numbers, email addresses, and other contact details current?
- Does the authorization cover the doctors, facilities, or advisors who may need to communicate with your family?
- Do your healthcare providers have a current copy?
Your HIPAA authorization should support your overall healthcare plan. The person you want to receive information is not always the same person you want making final medical decisions, so review those roles intentionally.
Life changes that may trigger an update
Divorce, remarriage, estrangement, the death of a family member, the addition of a trusted friend or advisor, or a change in your medical providers may require revisions.
5. Your Financial Power of Attorney
A Financial Power of Attorney allows you to name someone to manage financial and legal matters if you become unable to do so. Depending on the document, an agent may help with banking, real estate, taxes, insurance, government benefits, investments, and business responsibilities.
This document is especially important for avoiding unnecessary court involvement during incapacity.
What to check
- Is your primary agent still trustworthy and capable?
- Is your backup agent still the right choice?
- Does the document clearly address incapacity?
- Are the powers broad enough for your current financial life?
- Does it address real estate, tax matters, business interests, and digital assets if needed?
- Will banks and other institutions accept the document?
Older powers of attorney may not reflect your current assets or relationships. A move between Maryland and Virginia is also a good reason to have the document reviewed for current-state requirements and practical acceptance.
Life changes that may trigger an update
Marriage, divorce, a new business, the purchase or sale of real estate, a significant change in wealth, a new financial advisor, or the death or incapacity of your named agent may require an update.
6. Beneficiary Designations on Life Insurance and Retirement Accounts
Beneficiary designations are not technically estate planning documents, but they are a critical part of your estate plan. They commonly control who receives life insurance proceeds, retirement accounts, annuities, and certain payable-on-death or transfer-on-death accounts.
These designations may operate separately from your Will or Trust. That means an outdated beneficiary form can undermine an otherwise carefully prepared estate plan.
What to check
- Are your primary beneficiaries correct?
- Have you named contingent beneficiaries?
- Are former spouses still listed?
- Are deceased relatives still named?
- Have new children or grandchildren been included?
- Would a beneficiary who is a minor or has special needs require additional protection?
- Are your designations coordinated with your Will or Trust?
Do not assume that updating your Will automatically updates your retirement accounts or insurance policies. Contact each financial institution or insurance company to confirm its records.
Life changes that may trigger an update
Marriage, divorce, birth, adoption, death in the family, remarriage, estrangement, or a change in your financial or tax goals should prompt a beneficiary review.
Business owners should also consider whether life insurance and business-related accounts fit into their succession and asset protection planning. Eskay Law Group offers business planning and asset protection planning for families and business owners.
7. Your Kids Protection Plan and Guardianship Designations
If you have minor children: or provide care for a minor or dependent: a Kids Protection Plan deserves special attention.
A Will may nominate long-term guardians after your death, but parents may also need a plan for temporary care if they are unexpectedly hospitalized, traveling, or otherwise unable to care for their children. A comprehensive Kids Protection Plan can include guardianship nominations, temporary guardianship powers of attorney, caregiver instructions, emergency information, and guidance for long-term guardians.
What to check
- Are your primary and backup guardians still the people you would choose?
- Do they share your values and understand your parenting preferences?
- Are they physically and emotionally able to serve?
- Do they live in Maryland, Virginia, or another state?
- Do they know they have been nominated?
- Can a trusted caregiver quickly access important information about your children?
- Are instructions current for schools, medical care, routines, pets, and emergency contacts?
Your children may have changed substantially since you first created your plan. Their ages, needs, schools, activities, relationships, and medical circumstances should all be considered.
Life changes that may trigger an update
A new child, adoption, divorce, remarriage, a move, a change in your children’s needs, or the death, relocation, or incapacity of a chosen guardian may require an update.
Learn more about Kids Protection Planning at Eskay Law Group.

A Simple Fall Review Checklist
Before the holiday season begins, gather your estate planning documents and ask:
- Have our family relationships changed?
- Have we moved or acquired property in Maryland or Virginia?
- Have we bought, sold, or started a business?
- Has anyone we named died, moved, become ill, or become unable to serve?
- Do our beneficiary designations match our Will and Trust?
- Do our healthcare and financial agents understand their roles?
- Can our loved ones locate the documents and contact information they may need?
You do not need to solve every issue in one afternoon. Start by locating your documents, noting what has changed, and scheduling a professional review for anything that needs attention.
Refresh Your Estate Plan Before the Holidays
Fall is an ideal time to make sure your estate plan still reflects the people, property, values, and goals that matter most to you. A thoughtful review can bring clarity now and make things easier for your loved ones later.
At Eskay Law Group, estate planning is about more than preparing documents. We help families in Maryland and Virginia create personalized life and legacy plans designed to keep loved ones out of court and out of conflict, with transparent pricing and ongoing support as life changes.
Schedule a complimentary consultation with Eskay Law Group to review your plan before the holidays. This article is for general educational purposes only and is not legal advice. Because estate planning requirements depend on your circumstances and applicable state law, consult a qualified attorney for advice about your plan.

