How and Why to Help Clients Write Legacy Letters

Nov 24, 2025 / By Debra Taylor, CPA/PFS, JD, CDFA
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You may be helping clients prepare estate plans that leave a legacy to their heirs. Your clients may appreciate more. Help them write legacy letters that can express things that might matter even more than money. Here’s how.

Perhaps a side of legacy planning many advisors overlook is the emotional legacy clients leave behind. A legacy letter is a heartfelt document in which clients share their values, life lessons, hopes, and dreams with their family members and loved ones.

Unlike legal estate planning documents that focus on material possessions and final arrangements, legacy letters allow clients to express what truly matters, their feelings, wisdom, and the personal connections they’ve built.

The concept gained significant recognition through Blake Brewer’s Legacy Letter Challenge. After his father drowned during a family trip in Hawaii, Blake discovered a heartfelt letter his father had written just days before his death. This letter became Blake’s most treasured possession and inspired him to help thousands of parents create similar meaningful letters for their children.

Read below to understand why and how to guide your clients through this exercise and when.

1. Why legacy letters matter

As financial advisors, we often focus on the technical aspects of wealth transfer: wills, trusts, and estate plans. However, the emotional aspects of legacy planning are equally important to our clients. Legacy letters offer something that legal documents cannot:

  • They cut through life’s noise to reach the heart of what matters most.
  • They provide emotional comfort during times of grief.
  • They allow clients to share values and wisdom that will outlast material wealth.
  • They serve as a powerful complement to traditional estate planning.

When helping clients prepare for end-of-life matters, presenting the legacy letter option demonstrates that you care about the whole person, not just their financial assets. This holistic approach strengthens client relationships and provides a service that transcends traditional financial planning.

For example, we recently hosted a legacy letter webinar for our clients. Among the attendees was an older couple that recently came on board and are in their late 70s/early 80s. They recently updated their estate planning documents to make sure everything is in order from a legal perspective, but they never considered writing anything personal like a legacy letter before. They were inspired and started writing the legacy letter soon after the event. A few weeks later the husband had to undergo an unexpected surgery, but fortunately was able to recover. The client was extremely grateful we had been proactive in this planning (in both technical and emotional aspects) and this helped us to build a strong foundation for the relationship early on.

Pro tip: Make it clear to your clients that a legacy letter isn’t used to divide assets, it’s meant to share something far more meaningful. This is not a legal document but rather a nice gift to leave to loved ones.

2. How to guide clients through the process

As an advisor, you’re uniquely positioned to facilitate the legacy letter process:

  • Introduce the concept during estate-planning discussions.
  • Explain the distinction between legal documents and personal legacy communication.
  • Guide clients through the process without being intrusive.
  • Provide resources that help clients organize their thoughts.
  • Create supportive environments through workshops or one-on-one sessions.

The legacy letter process gives you an opportunity to deepen client relationships while helping them address an often-overlooked aspect of legacy planning.

Pro tip: At Carson Wealth, we host dedicated webinars to walk clients through this process annually and we have a checklist resource available for all our clients. We find out clients always appreciate when we can help guide them through the realistic but more emotional parts of legacy planning as well. We are all human, after all.

3. When to introduce the legacy letter to clients

Consider introducing legacy letters during these client interactions:

  • During comprehensive estate planning discussions.
  • When clients express concerns about family communication.
  • As clients approach retirement or significant life milestones.
  • When clients are updating their wills or trusts.
  • After a client experiences the loss of someone close to them.
  • During client appreciation events as a value-added workshop.

The legacy letter concept can be positioned as either a complementary service or a standalone workshop that differentiates your practice. While some clients choose to share their legacy letters after their passing, others find value in giving them while still living. Each approach offers meaningful benefits whether it’s providing comfort and clarity during a time of grief or creating an opportunity for connection and reflection in the present.

As an advisor, you can help clients decide which path aligns best with their values and intentions.

Additionally, clients should revisit their legacy letter every year or so, or whenever major life changes occur. It’s a deeply personal document, so there’s no right or wrong way to approach it. Revisions over time can reflect evolving relationships, new insights, or shifting priorities.

Pro tip: There are different benefits to the timing of the letter. Giving the letter while living allows clients to strengthen relationships, offer encouragement, and even repair past wounds while witnessing the impact of their words firsthand. Sharing the letter posthumously can offer deep comfort to loved ones, provide lasting guidance, and help family members find peace during the grieving process. As an advisor, you can help clients choose the timing that best reflects their goals and values.

4. How to write a legacy letter

Emphasize that writing a legacy letter is an emotional experience requiring vulnerability and authenticity. Advise clients not to rush the process and to give themselves time for reflection. Clients should write the way they speak rather than trying to sound formal, share genuine emotions and thoughts, and remember that imperfection is part of authenticity.

Drawn from the outline we provide clients, here are some guidelines to help clients organize their thoughts:

  • Introduction: Explain the purpose of the letter and current context.
    • Example: “I have never been shy of saying how much I love you. I hope those words always mean something to you. This letter is my way of expressing the depth and meaning of my love for you.”
  • Apology (optional): Offer sincere apologies for past mistakes if needed.
    • Example: “Before I share with you a few important things, I want you to know that I know I have made mistakes as a parent. For those times that I’ve come up short, I’m sorry.”
  • Expression of love: Communicate the depth and meaning of their love.
    • Example: “I want you to know that I’m going to love you no matter what.”
  • Expression of pride: Share why they’re proud of the recipient.
    • Example: “I am so proud of the individual that you are. You think independently and critically. You don’t just think selfishly, but you consider others in your thought process.”
  • Positive affirmation: Express belief in the recipient’s abilities.
    • Example: “I want you to know that I believe in you. No matter what happens in life or what curveball is thrown your way, you are going to make it. You’ve got what it takes.”
  • Memories: Share four or five meaningful memories that tell a story.
    • Example: “I’ll never forget that family vacation where we…”
  • Advice: Offer three to five pieces of heartfelt wisdom or guidance.
    • Example: “I have made a lot of mistakes and learned a lot over the years. There are many things I would do differently knowing what I know now. Here are a few things I would share with my 20-year-old self if I could go back…”
  • Closing paragraph: Summarize thoughts with a meaningful “legacy line.”
    • Example: “Remember, the biggest adventure you can take is to live the life of your dreams.”

Pro tip: Address some common concerns upfront. Questions to prepare for include: Should I write by hand or type? Can I specify final wishes in my legacy letter? How long should my letter be?

Facilitating legacy letters allows you to help clients with something profoundly meaningful that extends beyond financial matters. By guiding clients through this process, you demonstrate that your practice is about more than money, it’s about helping clients create lasting legacies that reflect their values and relationships.

Plus, this practice is sure to set your business apart from the rest.

Beyond the business benefits, guiding clients through legacy letters infuses your practice with profound meaning. By helping clients create legacy letters, you’re enabling them to ensure those treasures endure for generations to come.

Debra Taylor, CPA/PFS, JD, CDFA, an industry leader and sought-after speaker with 30 years of experience, is Horsesmouth’s Director of Practice Management. She is Chief Tax Strategist and Managing Partner with Carson Wealth Management. She was the principal and founder of Taylor Financial Group, LLC, a wealth management firm in Franklin Lakes, NJ. Debra has won many industry honors and is the author of My Journey to $1 Million: The Systems and Processes to Get You There, a book about industry best practices. Debbie is also a co-creator of the Savvy Tax Planning program and leader of the Savvy Tax Planning School for Advisors. Several times a year she delivers her Build a Better Business Workshop for advisors.

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