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Matthew Sheppard-Brown CFP®, RRC

Senior Financial Consultant

Essential Guide to Legacy Planning for 2026 and Beyond

  • Writer: Matthew Sheppard-Brown, CFP, RRC
    Matthew Sheppard-Brown, CFP, RRC
  • Jan 16
  • 14 min read

As we approach 2026, legacy planning has never been more critical, with generational wealth transfers reaching record highs. Navigating legacy planning is about more than just financial assets, it’s about passing on your values, intentions, and fostering family unity.

When you plan ahead, you can minimize taxes, shield your loved ones from uncertainty, and make sure your wishes are truly honored. Why leave these important matters to chance?

Take control of your legacy today with this essential guide. Here, you’ll find a clear, actionable roadmap for legacy planning in 2026 and beyond, covering everything from foundational concepts to communicating with heirs, tax considerations, and keeping your plan up to date.

Understanding Legacy Planning: Core Concepts and Trends

Legacy planning is taking center stage as families and individuals realize that true wealth transfer is about more than just passing down money. It’s about sharing stories, values, and intentions that define a family’s identity across generations. As we look ahead to 2026, understanding legacy planning means thinking beyond the numbers and focusing on what really matters most.

Defining Legacy Planning and Its Evolution

Legacy planning is different from traditional estate planning. While estate planning focuses on distributing tangible assets like property and investments, legacy planning also covers intangible assets such as family stories, values, and charitable intentions. This shift means families are asking, “What do I want my legacy to stand for?” rather than just, “Who gets what?”

Let’s compare the two approaches:

Aspect

Estate Planning

Legacy Planning

Focus

Assets & property

Assets, values, vision

Tools

Wills, trusts

Wills, trusts, legacy letters

Beneficiaries

Named heirs

Heirs, charities, community

Intangible Assets

Seldom addressed

Central focus

In recent years, the term legacy planning has gained traction for its broader, more holistic view. Families are increasingly weaving philanthropy, ethical investing, and personal values into their plans. For example, some may prioritize ensuring the family business continues, while others focus on charitable giving or passing down unique family traditions.

Despite this shift, research shows most high-net-worth individuals have some form of estate planning, but few have open conversations with heirs about their intentions. According to Trust & Will's 2025 Estate Planning Report: Defining Legacy, only 21% of wealth transfer conversations are well-prepared, while nearly half are spontaneous or avoided altogether.

Early legacy planning is crucial. It helps families avoid lengthy probate processes and costly legal disputes. Imagine a scenario where a family business is transferred without a clear succession plan, or a philanthropic vision is lost because it wasn’t documented. These examples highlight the need for customization, since no two families have the same story or goals.

Why Legacy Planning Matters in 2026 and Beyond

Demographic changes are reshaping the landscape of legacy planning. With an aging population and the largest generational wealth transfer in history underway, families face new challenges. Complex family structures, such as blended families or international heirs, add layers of complexity.

Regulations are also evolving. Potential tax law updates after 2025 could impact how inheritances are taxed or reported. Staying informed about these changes is essential for effective legacy planning, as failing to plan can lead to probate delays, unintended heirs receiving assets, or significant estate taxes that erode wealth.

Here are some eye-opening facts:

  • Probate can last months or even years, tying up assets and causing stress.

  • According to a Northwestern Mutual survey, 50% of heirs feel unprepared when they inherit wealth.

  • Without clear legacy planning, families often face conflict, confusion, and even legal battles.

Taking a proactive approach provides peace of mind. It brings clarity to your intentions and helps loved ones avoid uncertainty. More importantly, legacy planning is about ensuring your story, values, and hard-earned assets continue to make a positive impact for generations to come.

Step 1: Defining Your Legacy Goals and Family Values

Legacy planning is not just a financial exercise—it’s a deeply personal journey. Before you can build a strong legacy plan, you must first define what truly matters to you. This means looking beyond numbers and asking, “What do I want my family and community to remember me for?”

Clarifying What You Want to Leave Behind

The first step in legacy planning is reflecting on what you wish to pass on. This includes both financial assets like property, investments, and family businesses, and non-financial assets such as personal values, life lessons, and charitable intentions.

Consider this table to help organize your thoughts:

Asset Type

Examples

Financial

Real estate, stocks, business shares

Non-Financial

Family traditions, ethics, stories

Charitable

Donations, endowments, volunteerism

Be specific: Who gets what, when, and under what conditions? Legacy planning can address concerns such as:

  • Protecting young or financially inexperienced heirs

  • Excluding individuals where necessary

  • Providing for special needs dependents

  • Setting up guidelines for family business succession

Real-life scenarios often involve complex dynamics. Maybe you’re worried about how to treat children from different marriages fairly, or how to prevent in-laws from influencing family assets. Some want to shield an inheritance from a spendthrift child. According to Northwestern Mutual, 47% of wealth transfer conversations are spontaneous, while only 21% are well-prepared. This gap can lead to misunderstandings or conflict.

To clarify your intentions, consider writing a personal mission statement or a legacy letter. These tools make your values and wishes explicit. For guidance on crafting a meaningful legacy statement, visit Creating Your Legacy. Aligning your legacy planning goals with your current financial plan ensures that your intentions are both clear and actionable.

Involving Key Stakeholders Early

Legacy planning thrives on clear communication and collaboration. Start by discussing your goals with your spouse or partner to ensure you share a common vision. This conversation can surface differences in values or expectations, which is vital to address early.

Engaging professional advisors—such as financial planners and estate lawyers—at the outset brings expertise and objectivity. These professionals help translate your wishes into a solid legacy planning strategy that is both legally sound and financially efficient.

Family meetings are another essential component. Bringing everyone to the table helps manage expectations, prevent surprises, and reduce the risk of disputes later. For example, if you own a family business, involving all siblings in succession planning ensures everyone understands their future roles or inheritance.

Early and open involvement of stakeholders uncovers potential conflicts before they escalate. It also fosters a sense of shared purpose, making legacy planning a family journey rather than a solitary task.

By proactively defining your legacy goals and values—and by involving those who matter most—you set the stage for a plan that honors your intentions and supports your loved ones for generations.

Step 2: Building Your Legacy Plan—Legal and Financial Tools

Creating a robust legacy plan is not just about dividing assets. It is about building a structure that honors your wishes, protects loved ones, and stands the test of time. In this step, you will discover the essential legal and financial tools that make legacy planning effective in 2026 and beyond.

Wills, Trusts, and Beneficiary Designations

At the heart of legacy planning are wills, trusts, and beneficiary designations. Each tool serves a unique purpose in ensuring your assets are distributed according to your intentions.

A will is the cornerstone of any legacy planning strategy. It specifies who inherits your property, appoints guardians for minor children, and can even state your wishes for personal items or charitable gifts. However, a will alone often leads to probate, which can be costly and time-consuming.

Trusts offer more flexibility and privacy in legacy planning. There are several types to consider:

  • Revocable trusts: Remain flexible during your lifetime, can be changed as needed.

  • Irrevocable trusts: Offer asset protection and tax benefits, but cannot be altered easily.

  • Charitable trusts: Allow you to support causes while providing tax advantages.

  • Special needs trusts: Protect vulnerable beneficiaries without impacting government benefits.

Updating beneficiary designations is another pillar of legacy planning. Accounts like RRSPs, TFSAs, IRAs, life insurance, and pensions bypass your will if a beneficiary is named, transferring directly to the chosen person. Review these designations regularly to avoid accidental disinheritance.

For an in-depth walkthrough of these foundational tools, see the Estate and Legacy Planning Guide for step-by-step advice.

A well-structured plan combines these elements to make legacy planning both comprehensive and adaptable. This tailored approach ensures your values and wishes are preserved for future generations.

Mitigating Risks and Protecting Your Legacy

Legacy planning is not just about passing on wealth, but also about shielding it from unexpected threats. Without a thoughtful strategy, your assets could be exposed to creditors, lawsuits, or even family disputes.

One of the best ways to protect your legacy is through trusts that keep assets out of reach from creditors or ex-spouses. Trusts also keep your family’s financial affairs private, as assets in a trust do not become part of the public probate record.

Insurance is another vital component of legacy planning. Consider these types:

  • Life insurance: Provides liquidity for heirs, covers taxes or debts.

  • Disability insurance: Protects income if you cannot work before passing on your legacy.

  • Long-term care insurance: Shields your estate from the high costs of care.

Do not overlook incapacity planning. Powers of attorney, healthcare directives, and living wills ensure someone you trust can act on your behalf if you are unable to make decisions. These documents are essential for a seamless legacy planning process.

Modern legacy planning should also include digital assets. From social media accounts to online banking and intellectual property, make sure you leave clear instructions and access for trusted individuals.

By proactively addressing these risks, you help ensure your legacy planning efforts remain intact, safeguarding your family’s future and peace of mind.

Business Succession and Complex Family Structures

If you own a business, succession planning is a critical aspect of legacy planning. Without a clear plan, your business might face legal hurdles or family disputes, jeopardizing years of hard work.

Business owners should explore buy-sell agreements, which set terms for transferring ownership if an owner retires, becomes disabled, or passes away. Key person insurance can provide a financial buffer during transitions, helping the business weather unexpected events.

Establishing family governance structures, such as advisory boards or regular family meetings, can clarify roles and expectations. This is especially important in businesses with multiple siblings or generations involved.

Legacy planning grows more complex with blended families, second marriages, or international heirs. These situations may require specialized trusts or legal agreements to ensure fair treatment and compliance with cross-border laws.

Consider two scenarios: passing a family business to children versus selling to an outside party. The first requires careful planning to balance interests and abilities among heirs. The second may involve negotiating sale terms, tax implications, and reinvestment of proceeds.

Every family is unique, so legacy planning must be tailored to fit your specific circumstances and dynamics. Collaborate with professionals who understand the nuances of family business and international estate law to build a plan that lasts.

Step 3: Communicating and Collaborating with Heirs

Open, honest communication is the secret ingredient that turns legacy planning from a paperwork exercise into a powerful family experience. Too often, families avoid these conversations, leaving heirs unprepared and relationships vulnerable to misunderstandings. If your goal is more than just transferring assets, but also passing on values and harmony, how you communicate is just as critical as what you plan.

Starting the Legacy Conversation

Starting a discussion about legacy planning might feel daunting, but it is a crucial step in minimizing conflict and ensuring your intentions are honored. Research shows only 1 in 5 wealth creators find it easy to talk about wealth transfer, yet silence often breeds mistrust and confusion.

How do you break the ice? Wise Counsel recommends these practical tips for beginning legacy planning conversations:

  • Calibrate your wishes with your spouse or partner before involving others

  • Reflect on how past family messages shaped your own views

  • Focus the discussion on the future, not past mistakes

  • Ask open-ended questions to invite input from heirs

  • Share stories that illustrate your values and intentions

Consider organizing a family meeting or writing a legacy letter to clarify your hopes and expectations. These tools can help prevent misunderstandings and ensure everyone feels included in the legacy planning process.

Here’s a quick comparison of communication styles:

Approach

Outcome

Open Communication

Clarity, harmony, trust

Silence

Confusion, resentment, conflict

Remember, effective legacy planning is an ongoing journey. Multiple, smaller conversations over time are far more effective than a single, formal announcement. For more best practices on wealth transfer and family communication, see these Wealth Transfer Planning Insights.

Preparing Heirs for Stewardship

Legacy planning is not just about dividing assets, it is about preparing the next generation for stewardship and responsibility. Many heirs feel unprepared when the time comes, with 50% realizing after legacy discussions that they need their own planning.

So, how can you set your heirs up for success? Consider these strategies:

  • Educate heirs about financial basics and your family’s values

  • Establish a family council to discuss shared goals and responsibilities

  • Involve younger family members in philanthropic activities or family foundations

  • Create incentive trusts that reward responsible behaviors, like completing education or volunteering

  • Offer mentorship, either from within the family or trusted advisors

Workshops, family retreats, or regular check-ins can reinforce these lessons over time. When you make stewardship part of your legacy planning, you help heirs feel supported and empowered to make wise choices.

Open collaboration transforms legacy planning from a source of anxiety into an opportunity for growth and connection. By preparing your heirs thoughtfully, you protect both your assets and your family’s future.

Step 4: Navigating Tax Implications and Legal Updates for 2026+

As 2026 approaches, understanding the tax landscape is more critical than ever for legacy planning. Tax rules are shifting, and the impact on what you leave behind can be dramatic. Without the right plan, taxes could erode a significant portion of your estate, leaving less for your loved ones.

Understanding Estate, Gift, and Inheritance Taxes

Legacy planning requires a clear grasp of how estate, gift, and inheritance taxes work in both Canada and the U.S. In Canada, there is no estate tax, but capital gains taxes can apply when assets are transferred. In the U.S., estate and gift taxes are major considerations, with federal exemptions currently at historic highs, but set to decrease in 2026.

If you are planning for cross-border heirs or hold assets in both countries, these differences are crucial. For example, U.S. estate taxes can reach up to 40 percent of large estates. Without proactive legacy planning, families may face surprise tax bills, or even need to sell assets to cover liabilities.

Upcoming legal updates are top of mind for many. The U.S. federal estate tax exemption is expected to be cut in half in 2026, affecting many more families. For a detailed look at these changes and what they mean for your legacy planning, see Estate Tax Changes for 2026.

To minimize taxes, consider strategies such as:

  • Annual gifting to take advantage of exclusions

  • Establishing trusts to control asset transfer and timing

  • Using life insurance to cover anticipated tax burdens

  • Making charitable donations through donor-advised funds or charitable remainder trusts

A well-structured legacy planning approach ensures your intentions are honored and your heirs are protected from unnecessary financial burdens.

Staying Compliant and Proactive

Legacy planning is not a set-it-and-forget-it task. Tax laws change, and so do your personal circumstances. Regular reviews with legal and financial professionals are essential to keep your plan current and compliant.

Stay organized by keeping detailed records of all decisions, gifts, and updated legal documents. This documentation helps prevent confusion and supports your wishes if questions arise later. An outdated or incomplete legacy planning strategy can lead to probate delays, unintended beneficiaries, or higher taxes.

Avoid common pitfalls by:

  • Reviewing beneficiary designations annually

  • Coordinating trusts, wills, and insurance policies

  • Updating your plan after major life events or legislative changes

Digital tools can help you track and update your legacy planning documents securely. Remember, the peace of mind that comes from a proactive approach is invaluable. By staying informed and adaptable, you can safeguard your family’s future and ensure your legacy stands the test of time.

Step 5: Reviewing and Updating Your Legacy Plan

Reviewing and updating your legacy planning is not a one-time task, but an ongoing commitment. Life changes quickly, laws evolve, and family dynamics shift. If you want your wishes honored and your loved ones protected, regular reviews are essential.

The Importance of Regular Reviews

Legacy planning should evolve as your life does. Major events such as marriages, divorces, births, deaths, or the sale of a business can all impact your plan. Even if nothing dramatic happens, an annual review helps you catch potential issues before they become major problems.

Outdated legacy planning documents can lead to probate delays, unintended beneficiaries, or unnecessary taxes. Imagine leaving a business or property to someone no longer in your life simply because you forgot to update a will. Or missing out on new tax-saving strategies because your plan is stuck in the past.

A practical approach is to keep a checklist for your legacy planning reviews. This might include confirming asset lists, checking beneficiary designations, reviewing legal documents, and ensuring insurance coverage is current. Staying proactive is especially important as tax laws change. With significant updates expected after 2025, resources like Planning for 2026: Trusts and Estates Tax Updates can help you understand how new rules might impact your plan.

Regular reviews can ease your mind, knowing your legacy planning reflects your current wishes and the latest legal landscape.

Leveraging Technology and Professional Support

Modern legacy planning goes beyond paper. Digital tools can streamline document management and make communication with heirs effortless. Consider secure online vaults that store your wills, trusts, and insurance information. Family portals let multiple generations access important details, while virtual meetings make it easy to bring everyone together—no matter where they live.

But technology is only part of the picture. Collaborating with a team of trusted advisors, such as a financial planner, lawyer, and accountant, ensures every aspect of your legacy planning is covered. This team can coordinate updates, spot gaps, and guide you through complex scenarios. For business owners, incorporating expert advice on Business Succession Planning is invaluable, helping you balance personal and business goals.

Using digital tools alongside professional input means your legacy planning is not just up-to-date, but also secure and accessible for your family. Together, these strategies help you turn your intentions into a legacy that lasts.

Frequently Asked Questions About Legacy Planning

Curious about legacy planning in 2026 and beyond? You are not alone. Here are answers to the most common questions people ask as they start or update their legacy planning journey.

What’s the difference between estate planning and legacy planning?

Estate planning focuses mainly on the distribution of financial assets after death. Legacy planning, however, is broader. It incorporates values, family stories, charitable goals, and guidance for future generations.

Estate Planning

Legacy Planning

Assets and property

Assets plus values, vision

Legal documents

Letters, mission, stories

Financial focus

Holistic family focus

Legacy planning ensures your intentions go beyond the numbers.

When should I start legacy planning?

The best time to start legacy planning is now. Life changes quickly, and early planning helps avoid family stress and legal hurdles. Whether you are building wealth or nearing retirement, proactive steps make a difference.

How can I talk to my family about my legacy wishes?

Begin with honest, open conversations. Schedule a family meeting or write a legacy letter outlining your hopes. Listen to concerns and encourage questions. This approach builds trust and clarity around your legacy planning.

What are the most common mistakes in legacy planning?

  • Waiting too long to start

  • Not updating documents after major life events

  • Forgetting to involve key advisors

  • Skipping conversations with heirs

Avoiding these pitfalls keeps your legacy planning on track.

How do trusts work, and do I need one?

Trusts are legal entities that hold assets for beneficiaries. They can help control distributions, protect privacy, and reduce probate delays. Many people find trusts useful for minor children, blended families, or charitable goals within legacy planning.

What tax changes should I watch for in 2026 and beyond?

Tax laws evolve, and upcoming years may bring changes to estate and capital gains taxes. For example, capital gains tax rates for 2025 and 2026 may impact how your assets are taxed when transferred. Regular reviews with professionals ensure your legacy planning stays efficient.

How can business owners ensure a smooth succession?

Early business succession planning is key. Use buy-sell agreements, clear leadership plans, and open communication with family and stakeholders. Coordinating with your legacy planning helps align family and business goals.

What role do charitable gifts play in legacy planning?

Charitable giving can be integrated through donor-advised funds, charitable trusts, or direct bequests. This not only supports causes you care about but may also offer tax benefits within your legacy planning.

How often should I update my legacy plan?

Review your legacy planning documents at least annually, or after major life events. Regular updates keep your wishes current and minimize legal or tax surprises.

Where can I find qualified help for legacy planning?

Look for experienced advisors such as estate lawyers, accountants, and Certified Financial Planners. Seek professionals with a holistic approach to legacy planning to ensure all aspects of your wishes are addressed. As you think about your own legacy, remember it’s about more than just passing on assets—it’s about sharing your values, protecting your loved ones, and making sure your wishes are honored through every twist and turn life brings. Legacy planning can feel overwhelming, but you don’t have to tackle it alone. If you’re ready to gain clarity and confidence about your future, why not take the next step? Whether you have a simple question or want a second opinion on your current plan, I’m here to help you make informed decisions that align with your goals. Get a second opinion

 
 
 
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