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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By
Diane Zing, CSA
June 11, 2018

Paying taxes is inevitable. The key to being as efficient as possible about how much one pays in taxes requires careful consideration of the big picture. And while many people simply want to know if they can have a tax-free retirement, it really starts with being clear about how and when taxes get paid…and to defining what a “tax-free retirement” actually means. For example, if someone is striving to have income during retirement that is tax-free AT THAT TIME, then there are a plethora of investment and insurance products out there that could help defer taxes on earnings, and potentially, have tax-free withdrawal benefits for some types of accounts. But that doesn’t mean retirement is “tax-free”.

Let’s clarify what a few of the most common types of taxes are:

Income Tax – taxation on earned income can occur on many levels; local, state and federal. The amount a person would have to pay varies greatly on their situation. And, there are various types of tax credits that could affect the amount of taxes that would be paid on income. Any earned income that is deferred into a qualified retirement account generally means that taxes on that income won’t get paid at the time it is earned, but when that income is taken at a later date, during retirement, taxes are paid at that time. The idea that paying taxes on income later, when one might be in a lower income tax bracket, might prove more beneficial. But a) there is no guarantee what the tax rates will be in the future, and b) there may be several other factors with a person’s overall taxation that could affect what is perceived as a benefit. A tax professional is the best person to help folks evaluate what kinds of strategies are best for their overall situation. At the end of the day, SOME form of income tax will be paid, either when it is received upon earning, or when it is withdrawn from a qualified plan “down the road” in retirement.

What can be done to possibly reduce these taxes? Speak to a tax professional about what tax credits might apply, and also review with them if itemized deductions can play a role in reducing taxation.

Sales Tax – taxation occurs on state levels for various goods and services that get purchased. The percentage of taxation is usually based on the price of said goods and/or services. But that percentage charged can vary greatly from state to state, or even within different municipalities. There are a few states that don’t have any sales tax on most goods and services.

Excise Tax – taxation that is applied to specific types of goods; gas, cigarettes, beer, liquor, etc. These are typically nicknamed as “sin products”. Taxes received for these particular products are generally used to help raise money for bringing awareness to the potential dangers of these products.

What can be done to manage sales and excise tax? Not much. These types of taxes are very hard to “manage”. Changes in lifestyle; consumption of goods that fall within this category, will obviously affect the amount of sales taxes paid.

Property Tax – taxation that is applied to property owned. Taxes received tend to go towards local municipality needs. The amount of property taxes charged is usually based on a percentage of the value of the property.

What can be done to manage or alleviate property tax? Renting instead of owning might prove beneficial with alleviating property tax. However, there may be tax benefits also lost by being a renter instead of an owner. Again, a tax professional is best for helping to calculate what the tax benefits are for both scenarios.

It might not be possible to have a completely tax-free retirement, but by working with a financial professional and a tax professional, the ability to strategize investments and manage how taxation occurs could prove very beneficial. It’s not just about saving and investing…it’s about being as savvy as possible with the decisions along the way.

By
Mike Loo, MBA
June 13, 2018

Retirement is one of life’s most significant milestones. Not surprisingly, it’s both an exciting and worrisome prospect for many Americans nearing those Golden Years. According to a 2016 Gallup poll, 64% of Americans are worried about not having enough for retirement, 51% worry they won’t be able to maintain the standard of living they enjoy, and 60% are concerned they won’t be able to pay the medical costs of a severe illness or accident. One of the best ways to alleviate uncertainty is planning ahead.

What Will I Do with My Time and With Whom Will I Spend it?

Just as you would plan for the financial elements of your retirement, it’s equally important to plan how you will live out your retirement years. One of the biggest decisions you will make when you retire is where you will live. For example, maybe you want to live near your children part of the year and vacation a portion of the year somewhere else. Or perhaps you can’t imagine leaving the home you’ve spent years building and improving. Your housing will affect your finances, spending, and daily activities.

Next, address how you will spend your time. No one entirely escapes a daily schedule. Your daily retirement schedule doesn’t have to confine you, but it will help you fill your day and plan ahead. Start by establishing a balance of short, medium, and long-term goals. Short-term goals could include cleaning up the house, going to the gym, planting a vegetable garden, taking a vacation, or visiting family. Medium-term goals may be redesigning your yard, remodeling your home, taking a class, or planning for an extended vacation abroad. Long-term goals could be learning a foreign language, mastering a musical instrument, obtaining a new degree or certificate, writing a book, or building a vacation home. Whichever goals you define, the idea is to identify an extensive list of options so you can stay busy, maintain some control of your daily schedule, and have different activities to which you can look forward. Additionally, consider with whom you will be spending your time and enjoying these activities. If you and your spouse are not used to spending a lot of time together, know that there may be an adjustment period as this newly found together time can create tension in your relationship that hasn’t existed in the past.

How Much Will I Need in Retirement?

While it will differ for everyone, research from Fidelity shows that most people need to replace between 55% and 80% of their pre-retirement, pre-tax income after they stop working, to maintain their current lifestyle. After working hard throughout your career to save for retirement, now comes the critical decision of determining how much you can safely withdraw to replace your income while still having enough to last through your retirement. When taking withdrawals from your portfolio during retirement to pay for expenses, there is a risk that the rate of withdrawals will deplete the portfolio before you reach the end of retirement. Since you may know that stocks have historically earned an average of 8% a year, you may erroneously assume that you can afford to withdraw 8% of the initial portfolio value each year, plus a little more for inflation. However, 8% is an average, and while in some years, the numbers may be higher, in others, they will also be lower – and in some years, much lower. To protect yourself from the uncertainty of the market, you may want to consider limiting your withdrawals to 3 or 4% initially.

Ultimately, choosing a withdrawal rate means weighing your desire for increased spending in relation to your willingness to reduce spending. This relies partly on your attitude towards spending, and partly on your risk capacity. If you have Social Security and a substantial pension that is payable for life, then you have more capacity for risk in taking withdrawals from your portfolio. If not, you may need to reexamine your goals and expense categories to make sure they line up with the funds you have available.

Which Retirement Fears Could Prevent Me From Retiring?

A Retirement can be both exciting and terrifying for some people, as it’s such a significant transition in one’s life. As you plan for your retirement, it’s important to consider any fears you have that may prevent you from retiring. Through working with my clients, I’ve found there are a few common fears. First, some who have spent so many years dedicated to their career may fear they’ll lose their identity. Often, lawyers, doctors, teachers and other professionals may wonder what their purpose is if they’re no longer serving others. This is where it’s essential to return to the first question here and identify how you can find meaning in your new schedule. Second, many worry they could run out of money. While it’s impossible to predict the exact amount of money you will need, a financial plan can provide a roadmap that gives you probabilities of how long your money can last. Working with an advisor to review different scenarios may offer you more confidence. Lastly, another common fear is high taxes. While there’s no avoiding Uncle Sam, there are legal ways to mitigate your tax burden and make the most of your earnings. Consult with a tax advisor to give you an idea of how much of your withdrawals you’ll take home versus paying in taxes.

How Will I Address the Issue of Long-Term Care?

While some expenses go down once you retire, others can increase, such as healthcare costs. On average, a couple both age 65 can expect to spend between $157,000 and $392,000 on healthcare costs alone throughout their retirement years — a 29% increase over the past 10 years. This estimate assumes enrollment in Medicare health coverage but doesn’t include the potential added expenses of a nursing home or long-term care that a retiree may require. Long-term care insurance covers the cost of services that include a variety of tasks you may need help with as you age. For the past 20 years that long-term care insurance has been available, cost was the most significant hurdle for most people. Today’s long-term care policies offer more flexibility and benefits than in the past, and there are now more options and affordable choices that are designed to fit almost any budget. The most well-known option is a standard long-term care insurance policy, where you pay a premium in exchange for the ability to receive benefits if you need them. This is a “use it or lose it” policy, so won’t receive any benefits or money back if you don’t end up needing longterm care. If you don’t like the idea of a “use it or lose it” policy, you may consider a hybrid product, such as buying a life insurance policy with a long-term care rider. With this type of policy, you invest in a standard cash value life insurance policy and select your long-term care coverage terms in the rider. If you end up requiring long-term care, there are available funds. If you don’t need long-term care or if you don’t spend the total benefits available, your beneficiaries receive a death benefit payout upon your death.

Next Steps

Taking the first steps for retirement planning can be overwhelming, but you don’t have to face it alone. An advisor can help you create a personalized retirement roadmap, work, through various retirement scenarios, and help you identify what you will do during retirement to make the transition less stressful. As an advisor who works closely with many couples and families, I want to help you address your retirement questions and feel confident about your future. Take the first step by reaching out to me for a complimentary consultation by calling (949) 221-8105 x 2128 or emailing michael.loo@trilogyfs.com.

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