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
Zach Swaffer, CFP®
February 19, 2019

Let’s talk about employer loyalty. For much of the 20th century, Americans (by and large) followed a standard script: enter the workforce and work for a single company for decades, then throw a retirement party at 65 and cash in a pension – a reward for years of company loyalty. This pension provided retirement income; usually, a percentage of the yearly salary the employee earned while working. American Express established the first corporate pension plan in the US in 1875. By 1960, about half of the private sector employees had a pension. Of course, in 1960 the average life expectancy was 67, meaning that if you retired at 65 (standard at the time), the average pension only had to provide income for two years.

Since 1960 there have been many advances in modern medicine raising average life expectancy to 79. Suddenly, plans designed to cover a few years of post-retirement income were expected to cover retirees well into their 80s and 90s. Companies offering pensions began to realize that their retirement plans were becoming increasingly – sometimes prohibitively – expensive to fund. As pension expenses continued to rise towards the end of the 20th century, many companies were forced to design new systems to ensure their employees were financially secure come retirement.

The 401(k) plan hit the streets in 1980. The employer-sponsored retirement plan was rolled out as a replacement to traditional pensions and has since become the most common retirement savings mechanism in America. In essence, the 401(k) provides a tax-deferred way for employees to set aside wages for retirement. Employees elect to divert a certain percentage of their income each year to a 401(k) account. The diverted funds grow tax-free in that account until the employee retires.

In addition to providing the account, most companies offer a savings-match system. For instance, in a 3% match system, the company would match up to 3% of an employee’s elective contributions to their 401(k) account. The employer match provides a strong incentive for employees to start planning for retirement. If an employee doesn’t divert AT LEAST the match threshold into a 401(k) they miss out on the employer match – in other words, they lose out on free money from their employer.

Let’s talk about the benefits. Funds in a 401(k) account are able to grow tax-free. Because growth is not disturbed by capital gains taxes, accounts are able to grow faster than a standard individual account. Of course, there’s always a catch: money in employer-sponsored plans – like a 401(k) – cannot be withdrawn prior to age 59 ½ without paying penalties. Most plans offer options for the participants to increase their contribution rate on an annual basis, and small increases in contribution rate (even as small as 1%) year over year can make a huge difference by the time you retire.

Contributing to employer-sponsored retirement plans such as a 401(k) or 403(b) – the non-profit version of a 401(k) – is a vital part of preparing for retirement. The money is automatically deducted before your paycheck is cut, making it easy to budget and painlessly save for retirement at the same time.

Contributing to employer-sponsored retirement plans is an essential step towards retirement planning – but it is only the first step.

Please contact me at zach.swaffer@trilogyfs.com if you are interested in discussing the next steps you can take to ensure retirement security.

By
Ahmed Ghulamali
September 26, 2017

What does retirement actually look like? Some people might say they will literally “turn in their papers”, go home, then putz around the house and tinker with projects for the rest of their life. Others might say they want to travel the world. Some might say they don’t actually want to “retire”, but would rather transition to work they are passionate about, without having to worry about what kind of income they receive. The bottom line is that we tend to have some idea of what we dream it to be. The problem is, there are factors that can contribute to turning our dreamy retirement into a complete nightmare.

Trying to predict that our retirement will end up being exactly as we have planned it to be is like shooting an arrow towards a bullseye as we are blindfolded. It COULD happen, but there are a lot of “what ifs” circling around our idea of a perfect retirement. For instance, what if we retire and expect to putz around the house doing projects for the rest of our life, and find that by week three we are bored out of our mind, yet we didn’t prepare or invest in doing anything different? What if we expected to travel the world, but before retiring, develop health issues that prevent us from being able to do so? The “what ifs” can be a real game changer, not only to what we get to do, but how we would be prepared to pay for it.

Here are some tips to consider when thinking about how to prepare for retirement:

Retirement vs. Financial Independence. Trying to decide now, at our current age, what retirement has to be can be quite stressful. Maybe we don’t have a clue what it should look like in regards to activities and how we will spend our time. So instead of trying to define what retirement might look like, maybe focus on working towards financial independence. Financial independence means over the course of a long-term, disciplined effort, we work with our advisors to help us make financial and protection planning decisions that lead to financial strength over time. Disciplined effort and long-term commitment are key factors when trying to build financial security. This might prove helpful with preparing for whatever retirement ends up looking like.

Planning before Investing. There are thousands of licensed financial professionals whom would love nothing more than to manage our assets by investing in the market. Many go into this with the sole goal of simply “growing assets”. They tend to focus on returns, and believe that we only want to hear that our investments are “going up” consistently. Seeing our account values “go up” is all the satisfaction they think we desire. And with that, they tend to feel like we are on track for retirement. BUT, this is not a guarantee. We can’t predict or control the markets, so this is an example of shooting that arrow blindfolded, hoping we land in the middle. Instead, consider focusing on what your assets need to DO. What job do our assets have? Knowing what the job is upfront will help us make more informed decisions not only on how to invest, but with what kind of risk we can afford to subject ourselves to. Risk management might prove just as critical as growing assets.

Start NOW! Financial planning for retirement could prove far more difficult if we wait to the last minute, vs. making effort starting now. It might seem daunting to think we have to “do everything at once”, but focusing on our future needs is just as important as focusing on our current needs. It might seem difficult to do everything at once, but that’s why working with a financial advisor who values planning prior to investing blindly might prove helpful.

We are all unique in what our lives and dreams are. And whether we are focused on exactly what we want retirement to be, or simply have no idea, the common theme is that the closer we are to having financial independence, the better chance we have of being more prepared. Financial independence shines the light on our options, which might help to make our dreams come true.  And just like when we were kids in a dark room, the nightmares tend to not go away until we turned on the lights!

Get Started on Your Financial Life Plan Today