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
David McDonough
July 2, 2019

Words are power, and each word has its own weight and energy. Words have inspired people to stand up for what they believe in or hang their head down in defeat. Therefore, choosing the right words to describe that which you want to manifest is very important.

For example, when speaking of aspirations for the future, there are those who use the words dreams and goals interchangeably. However, they ae distinctively different in definition and performance. A dream is boundless, fueled by your passion and imagination. However, it is akin to fantasy, with no immediate call to bring it to life. When someone tells me they dream of owning a sports car or starting their own business, I know most of the work to make that dream a reality hasn’t taken place and probably won’t for the foreseeable future.

A goal, on the other hand, is the mapwork to that dream, concrete and behavior-driven. When you have a goal, you have markers, measurements and steps to get to the destination. Setting the right goals, especially when it pertains to financial goals, can have a significant effect on how and when you achieve them. In fact, a guide to good goal-setting has long been to make it S.M.A.R.T.1:

Specific: if we are truly making a map towards our goals, telling ourselves to go in a general direction or for an undefined distance is most likely only going to get us lost. Steps towards our dreams have to be detailed and specific.

Measurable: When a goal is measurable, there is a way to track your progress to stay motivated or identify issues that may need problem-solving.

Attainable: It is admirable to be striving for something grand and lofty. However, it’s imperative that we have feasible goals that we can accomplish to keep us motivated and actually accomplish said goal.

Relevant: Having impressive goals are fine and dandy, but if they don’t move you closer to your overall goals or work against other goals you may have, it may be time to rethink them.

Time Bound: Once something has been stated as a goal, the stop watch has started. There is an expectation of completion, which is necessary to keep us moving forward towards that goal. It may not get completed in the expected timeframe, but just by having a deadline, we can stay accountable.

Based on this description of a S.M.A.R.T., you can see that there is a difference between, “I’m going to start saving money for a house,” and “I’m going to put 15% of my paycheck into a savings account specifically designated for my eventual down payment, and I should have enough saved after 3 years.” One expresses a desire while the other one lays out a concrete plan to achieve the goal.

If one seems to be fueling the other, how can a dream inhibit a goal? Well, one way is when your lifestyle fits with your dream rather than your goals. To achieve many financial goals like saving for retirement or buying a home, one needs to save and stick to a budget. However, if you fail to save and incrementally work towards the goals, it will take longer and longer to see results. Worse is if you choose to skip the incremental steps and live your dreamer’s lifestyle by using credit cards. The debt you accumulate will take you farther and farther from your goals and possible put you in an unfortunate and stressful predicament.

Sometimes when we haven’t developed a goal for a dream, it’s vagueness can work against an already established goal. Perhaps a good friend asks you to go into business with them. If you choose to pour funds into this new endeavor without any parameters, you may find yourself taking funds away from saving for retirement or depleting savings you already had. Of course, if you had outlined your goal on how to contribute to your friend’s business, with specific and timely parameters, the situation could be completely different.

Please understand that I’m not asking you to stop dreaming. In fact, quite the opposite. I happen wake up every day saying, “Dream Big! Work Hard! Laugh often!” I sign letters and thank you notes and end employee meetings with those very words. Dreaming is important.

So please know I want you to dream big and bold. At the same time, I want you to buckle down and create some S.M.A.R.T. goals to propel you closer to your dreams.

https://www.mindtools.com/pages/article/smart-goals.htm

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

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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