5 Questions to Ask Yourself Before Writing a Legacy Letter

By Trilogy Financial
February 3, 2025
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Imagine a recipe box that’s been passed down from your great grandmother. It sits on your kitchen counter, full of cards containing not just ingredient lists and cooking instructions,  but handwritten notes detailing memories about each meal. It’s these personal anecdotes that transform food into feeling through stories.

That’s how a legacy letter works. It’s a way to pass on what matters most to you.

What is a Legacy Letter?

Unlike a will that distributes material possessions, a legacy letter, sometimes known as an ethical will, passes on your values, life lessons, hopes, and personal history to future generations. It serves to bridge the gap between the tangible inheritance you might leave behind and the intangible wisdom you've gathered throughout your life.

While a legacy letter can complement a legal will, it should be thought of as a personal document rather than a legal directive. You can consider your legacy letter a conversation across time – a way to share yourself with your great-grandchildren and future generations.

What are the Benefits of Writing a Legacy Letter?

Your legacy letter will benefit both you as the writer and the letter’s recipients. For the writer, it offers the chance to reflect on and crystallize what matters most in your life. We find the process often brings clarity to our clients around their deepest values and the impact they hope their assets will have on their loved ones.

For recipients, your legacy letter can help ground them in their family history, which often gets reduced to dates and basic facts. Through your letter, you give them the gift of context, understanding, and connection. Your legacy letter becomes a way for your perspective and guidance to live on after you’re gone.

What are the Components of a Legacy Letter?

Just like your life, your legacy letter is entirely unique. And while there’s certainly no required formula for one, they most often include the following elements:

  1. Values and Beliefs: Explain not just what you believe in, but why. Share the experiences that challenged or reinforced your values.
  2. Life Lessons: Discuss both your successes and failures. What decisions are you most proud of? What would you do differently? Mistakes and vulnerable moments are often more effective teachers than perfection.
  3. Family Stories: Include meaningful anecdotes about family members, especially those your recipients never met. What family traditions hold special meaning and why?
  4. Hopes for the Future: Express your wishes for future generations without being prescriptive or giving explicit direction. Share the dreams you have for your family’s future.

Who Should You Share Your Legacy Letter With?

Most people write legacy letters primarily for their children and grandchildren, but you might also consider including other family members and close friends.

Having an idea of who your audience will be before you start writing will help you strike the right tone and include the most relevant content. Keep in mind that future generations will likely read your letter as well.

How and When to Share Your Legacy Letter

The timing and method of sharing your legacy letter deserve careful consideration. Some people choose to save their letters to be read after they pass, but there can be profound value in sharing your words and story while you’re still here, particularly during significant life moments such as a child’s graduation, before a wedding, or upon the birth of a grandchild.

If you decide to share your letter while living, you have several options:

Reading it aloud in person allows you to add context and emotion to your words and can lead to meaningful family discussions that encourage others to share their own stories.

Creating individual copies for each recipient lets them absorb your words privately and return to them often. Some people include photos or other meaningful documents alongside their letters.

Recording yourself reading your letter combines your words and your voice into a powerful audio-visual legacy that can also be relistened to as often as the recipient wants.

If you prefer your letter to be shared after your passing, ensure someone you trust knows where to find it and understands your wishes for its distribution. Consider including it with your other important documents or lodging it with your attorney.

Timing isn't just about when others receive your letter; it's also about when you write it. Don't wait for the “perfect” moment or until you feel you have all the answers. Your perspective and wisdom are valuable now, and you can always edit or write additional letters as you gain new insights or want to share different aspects of your story.

How to Get Started: Five Questions to Ask Yourself

Deciding to write your legacy letter is the first step, but it can be challenging to know exactly where to begin. We’ve found these questions help jumpstart the writing process:

  1. What moments of adversity have shaped who you are? Don't just list challenges you've overcome. Dig deeper into how these experiences changed your perspective and influenced your decisions, and share what you learned from your most difficult times that might help future generations navigate their own struggles?
  2. What family traditions or values do you want to share? Think beyond the obvious. Maybe your grandfather's habit of giving anonymous gifts to neighbors in need taught you about quiet generosity, or perhaps your mother's insistence on Sunday dinners wasn't just about food, but about creating unbreakable family bonds.
  3. What parts of your story might be lost if you don't share them? Consider the small but significant moments that shaped your path. Maybe it was a chance encounter that ultimately led you to your career, or a split-second decision that changed everything. It’s these personal details that often get lost in formal family histories but can be incredibly meaningful to future generations.
  4. What do you wish you knew about your own ancestors? Reflect on the questions you have about your family history. What gaps in your own family narrative do you wish were filled? Use these curiosities to guide what you share about yourself.
  5. What misunderstandings about your life choices do you want to clarify? Perhaps you made a later-in-life career change that seemed risky to others, or your decision to end a marriage wasn't fully understood. Your legacy letter offers the opportunity to share your reasoning and the wisdom that guided these choices, but take care not to sound defensive. The goal is to help your loved ones and future generations make their own choices that are best for them.

 

Some people find the thought of writing intimidating, but your legacy letter isn’t about being the most eloquent or perfectly polished. It’s about being authentic and genuine, keeping your audience in mind, and truly reflecting on what matters most in your life.

Start today. Your story matters, and future generations will be grateful you took the time to share it.

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Rebecca DeSoto, CDFA®
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There is no shortage of information available about life insurance on the internet. A lot of it has negative connotations. From policies that historically haven’t provided what was promised, to salespeople coaxing consumers into products, and one size fits all advice. Most people come in with the base knowledge that they need term insurance if they have a spouse and children they want to protect financially if they pass away. Combine these two factors and people generally use the internet to find an inexpensive policy. However, when making a decision about life insurance there are a few important factors to consider besides simply the cost and the amount of insurance, namely living benefits or accelerated benefit riders, and whether the policy has a cash-value component.

While all policies are required to have a terminal illness rider, meaning the insured has the option of utilizing the death benefit prior to passing away if diagnosed with a terminal illness, not all policies come with a chronic or critical rider. A chronic illness rider can accelerate your death benefit if the insured is diagnosed with an illness and unable to perform two of the six daily activities of living (bathing, continence, dressing, eating, toileting, and transferring). Considering how expensive long-term care insurance can be these days, having a chronic illness rider on a life insurance policy can provide some level of affordable protection (depending on your age when you get the policy). The critical rider can apply to injuries or illness and can include things like heart attack, stroke, paralysis, severe brain trauma, and diagnosis of invasive cancer. Having these riders in addition to one that protects against terminal illness adds a much more encompassing level of protection to the insured that can provide flexibility and options in an unplanned emergency.

Life insurance can also have a cash-value component or investment vehicle in addition to providing protection. Cash-value in a permanent life insurance vehicle is one of the only ways to build non-taxable income in retirement besides a Roth IRA. Other than the tax benefits, it can also enhance your plan with diversification and stability. It generally has some level of protection, called a “floor” that assets invested in the stock market wouldn’t have, meaning there is protection against the downside while allowing the investor to take advantage of positive markets.

Whether or not you choose a policy that has all of these components, it is important to consider which benefits are meaningful to you and are worth paying for. It can be hard to determine the pros and cons without talking to a licensed professional that has your best interest in mind and it can be difficult to really understand what you’re purchasing just by browsing the internet for the least expensive policy. Just like any insurance, the ideal situation is not needing it. But if you do, you’ll be happy you did your research and understand the vehicle you chose.

This material contains only general descriptions and is not a solicitation to sell any insurance product or security, nor is it intended as any financial or tax advice. This article is intended to assist in educating you about insurance generally and not to provide personal service. Guarantees are based on the claims-paying ability of the issuing company. If you need more information or would like personal advice you should consult an insurance professional. Riders are additional guarantee options that are available to an annuity or life insurance contract holder. While some riders are part of an existing contract, many others may carry additional fees, charges, and restrictions, and the policyholder should review their contract carefully before purchasing.

If you decide to downsize after retirement and have lived in your home for at least two years out of the last five from the date of sale, you can exclude up to $250,000 in capital gains from the proceeds and almost double that if you are married.

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Diane Zing, CSA
May 18, 2018

Some people believe that one of the most frustrating words in the financial world is the word “taxes”. But it doesn’t have to be…and it actually shouldn’t be. Understanding the world of taxation takes enormous amounts of education, understanding and application. The average person doesn’t necessarily want to become an expert on taxes, but they certainly don’t want to pay more than they have to, either. Hence the reason many people and businesses reach out for help. Finding a tax professional can be complicated; hoping to find the right kind of tax professional for the services needed tends to be the number one challenge.

When starting a search to find the right tax professional, there are basically two major things to consider. Firstly, it’s important to understand the differences between the types of tax professionals. Secondly, it’s important to ask the right kind of questions to help discern if a working relationship with a particular tax professional is a good fit.

Start with having a basic understanding of a few different types of tax professionals.

TYPES OF TAX PROFESSIONALS:

Tax Preparer – A tax preparer can help individuals, families, and businesses prepare tax returns. They cannot represent clients during an audit. Their role is limited to tax preparation. A large percentage of the general population might find that a Tax Preparer is a match for their filing needs.

EA – An Enrolled Agent (EA) has passed an IRS examination that puts them in a position to not only help clients prepare tax returns, but they can also represent their clients in the event of an audit. Generally speaking, EA’s may tend to have more thorough knowledge and understanding in regards to tax preparation than that of a Tax Preparer. Individuals, families, and business owners might find that an EA is helpful due to the complexities that their tax preparation needs may entail.

Tax Attorneys – Tax Attorneys can not only prepare tax filings, but they can also represent their clients during an audit, as well as represent clients in court proceedings. Tax attorneys play a significant role in helping their clients through complications with tax liabilities, responsibilities, and other issues that may arise.

CPA – Certified Public Accountants are tax professionals who have a degree in accounting or a related field. They have passed the state CPA exam, and are able to perform a myriad of services for their clients. They can prepare tax filings, represent clients during audits, prepare and certify audit statements. They cannot, however, represent their clients in court.

There are additional types of tax professionals, but the above mentioned tend to be the most widely sought after by individuals, families, business owners, non-profit entities, and others.

Secondly, it’s important to ask questions that are relevant for finding a professional that might be best suited for the specific needs at hand. Here are a few questions to consider when interviewing a tax professional:

QUESTIONS TO ASK:

  1. What is your designation, or professional title?
  2. What industries or types of clients do you have?
  3. How many years of experience do you have?
  4. How many people do you have in your organization, and what are their roles?
  5. Do you help clients with tax planning strategies, as well as tax preparation?
  6. Do you work in collaboration with financial planners and other professionals?
  7. What kind of ongoing service model do you have?
  8. What is your fee structure?

When discerning which tax professional to work with, having a basic knowledge of the types of tax professionals might go a long way with helping to build a productive relationship, and subsequently, possibly more favorable tax solutions. Taxes are a major part of life, and having a strategy around how finances are built, managed, and maintained could possibly help significantly. It’s important to be responsible with taxes, and having a professional that can help discern taxation with efficiencies could have significant importance to overall financial planning.

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