Working On Dying: Crafting a Legacy Today

I’ve been thinking about dying lately.

Not in a depressed, morbid kind of way – more in terms of financial planning and values based lifestyle design.

Join me on a thought journey, as I plan, as an early-retiree, to work daily on both living and dying! Hopefully, you’ll get some ideas for crafting your own life and legacy.

Why Am I Thinking About Dying?

First off, I have elderly parents, now in their late 70’s. They would both rebel at being referred to as “elderly” and hopefully still have many more productive, healthy years ahead of them. They’re both in okay financial shape, but I still can’t help but worry.

I worry about long term health care costs, or that they could fall pray to a financial scam – generally just worry about them in the typical “tables are turned” kinda way that seems to happen with children and parents as they age.

Then, this week I happened upon a podcast where the inspiring Tiffany Aliche, otherwise known as The Budgetnista shared her very personal experience with death. She lost her husband recently, who died suddenly at a young age.

She said something I couldn’t get out of my mind. “Make it so your loved ones only have to worry about missing you when you’re gone.” I thought that was just about the the most perfect way to sum up end of life planning! Master class material, for sure.

And then, to top it all off, I went and had a sort of “near death” experience myself to really ensure that dying was top of my mind. But I’m prone to be a bit hyperbolic.

I was in a public crowd situation that got out of hand. There was pushing and shoving, with nowhere to go. People were freaking out, crying and screaming.

The tragedy in South Korea on Halloween in 2022 did come to mind, but I stayed calm and came out unharmed. It was just a little reminder for me at how quickly something can go from just fine, to totally f*cked.

It wasn’t my first experience like this, nor even close to the worst. Not like the time I flew through a windshield when I was 16! But I was due for a reminder, I guess.

Maturing Life Goal

With the universe seemingly determined to make me face mortality, and heavily influenced by the Tiffany Aliche interview, I decided it was time to set a new overarching life goal. I had previously been focusing more on the living side of life, and decided it would be good to focus equally on the dying.

The new goal: Live well, leave people only missing me.

What living well means to me is using my time, energy and money, as best I can, according to my personal values.

Currently, those values are people, growth and experience. So, building strong relationships, growing and challenging myself, and traveling the world to experience all the abundance it has to offer. I have a special emphasis on “will it get me outdoors,” as well.

What “leave people only missing me” means is taking care of myself and my finances so that no one is left burdened in any way. That means money to cover my expenses, things organized and easy for an executor, and physical possessions dealt with.

It also means having said everything I needed to say. No one should wonder how much I loved and appreciated them, they should all know, because I told them – often. And it would mean contributing something of value to those around me.

And this should be the state of things on any given day!

Goals Needs Systems

From my corporate days in operations, I’m apt to try and turn everything into a repeatable, well documented system! So, I’ve been working on a system for “living well” for a while.

First, I had to get clear on my values. Seems like our values should be “obvious,” but come to find out, it does take a little work.

Sometimes, we actually have competing values battling it out in our heads. We need to step in as judge and actually set them in a particular order. Also, values do evolve and change over time. We all need to check in with ourselves from time to time and do a values check!

So, I intentionally set and review my values periodically.

Then, everything I do, every decision I make, should be run through my “values” filter.

Will this build or strengthen a relationship in my life? Will this lead to personal growth and development? Will this give me a memorable experience, expose me to something new, or get me outdoors?

Last piece of the system is to build the habit of actually using the filter! Its imperfectly implemented, of course. But trying to be intentional and reflecting on the processes, I do get a little better all the time.

As the articulation of the “leave only missing me” as a goal, however, is new to me. I don’t really have a system for that yet – guess it’s time to build one!

The Financial Assessment

As an early retiree at 45, I purposely traded time during my “prime” physical years for some financial security. Of course, in assessing if I was able to leave my corporate job, I considered having the financial resources to cover me for the rest of my days.

But to be honest, because I’m retiring so early, and think that my retirement could turn into more of an extended sabbatical, or career change, I was comfortable with a less “safe” likelihood of success.

By that I mean, the retirement calculators, depending on the assumptions, may say something like I have an 85% chance of covering my costs to 90. I’m comfortable with that now, because I feel relatively certain that I will make some money in the future.

If I were 70 and felt that I would never earn another dollar, I would probably want to have that likelihood much closer to 100%!

But, with more emphasis on my legacy goal, I thought I should do another financial review.

Facing the Numbers

Some of the numbers I looked at were pretty bleak. Somewhere around 50% of Americans will die broke or in debt, says Motley Fool. Single women in old age are the most likely Americans to live in poverty – too poor to afford a luxury like having a cat. And says people with less money, in general, seem to die earlier.


And what will it set me back to age comfortably, if I want decent medical care and need a high level of assistance – nearest I can figure from scouring the internet is in the vicinity of 100k a year.

Not exactly affordable. Add that level of spending for 5 to 10 years into the retirement calculators and its not pretty.

And then there’s life expectancy, well…those numbers are just ridiculous. Statistical averages are meaningless when its your death. The Bankrate life expectancy calculator says I should expect to live to 83.6 years old.

But, according to the National Safety Council, I also have about a 1% chance on any given day that I engage in driving, biking, walking or canoeing – all activities that I do almost every day! So, if I do all 4 in a day, am I engaging in “high risk” behavior?

I know statistics don’t exactly work like that. But fact is, any given day, we all have at least a chance of dying!

All my review of the “numbers” led me to conclude was that death will come for us all, ready or not, no matter our bank balance!

Fear Factor

Will I change much of how I’m living, allocating resources because I fear running out of money at 75, 85, 95? Should I go back to work immediately? Blow my budget buying insurance against everything under the sun, hoping they will actually pay if the time comes?

Probably not! It is simply too far away for me to spend a ton of mental energy on. With the money and plan I have right now, I think I’m good for a while.

And when you dig into the actual financial models behind the retirement calculators that say I have a 15% chance of outliving my money, there are many circumstances in which I die at a very old age a multi, multi, multi millionaire.

That would also be a failure, to me. I do not want to hoard wealth and would prefer to spend it while alive. I’m aiming for the Die with Zero end, a la Bill Perkins.

But its just too far away to start “preparing the gear” for landing, in my opinion.

I already do a financial review annually, its part of my “system” – but some of the statistics on elders living in poverty did affect me. I might end up being a bit more conservative with projections going forward.

I definitely want to be able to afford not only a cat, but a dog, and maybe a bird. Who knows!

Are Your Papers in Order?

Beyond being a financial burden, “leave only missing” means not leaving people a physical or paperwork mess to deal with. As part of my preparation for early retirement, I did prepare a will, Power of Attorney, and medical directives. I also made sure all my beneficiaries were up to date.

I have few possessions, as I’m currently nomading around the world. So, right now I would not leave anyone with a house full of knick-knacks to feel guilty throwing away.

Things are fairly well organized, but have already thought of a few things that need tightening up as I write this article. I will add them to the “actionable items” on my agenda. And I will add “review insurance needs” to the parking lot area of my to-do list where I keep things I’m considering.

So, for this part of the system, I think I will add to my financial review to “double check beneficiaries”, and “update instructions to executor.”

And going forward, if I open a new account, buy a car, a home – I will consider the best way of passing it along. Such as add intended inheritor to the title, for example.

Bringing Death into Today

What I discovered was really lacking in my system to address my new goal was bringing it into my every day. So, I have added a new question to the daily decision filter: Will this contribute to or take away from the “only missing” legacy I wish to leave?

To flesh that out further, I plan to interrogate decisions with questions like:

Is what I’m doing today likely to contribute to healthy aging, like eating well and exercising? Does everyone I love know it because I’ve told them recently? What have I done today for somebody that is worthy of missing?

That last question is especially resonating as being more needed in my life. I want to ensure that every day I have an eye for providing value – giving, helping, bettering someone or something around me. Maybe something as small as making someone smile, giving a compliment, or lending a helping hand.

But hopefully also something larger – like transforming other people’s lives, through sharing my knowledge and experience! I want to not only save myself from dying, cat-less in poverty, but as many others as I can, as well! But I also don’t want to miss out on living, and I don’t want anyone else to, either.

So now, its just up to me make this a habit. Rinse and repeat and see what happens!

I’m hoping that it will not only help me and my loved ones when I die – hopefully many, many, many years from now. But also that it will lead to a better, more fulfilling life today. Hopefully, my obituary will be filled with tales from a life well lived, and my funeral will be well attended by many people who have good reason to miss me.

A Perfect End?

Stories are powerful teachers, and all this ruminating on death made me consider some of the “final chapters” I’ve come across in my life.

One story came to mind that I found inspirational and applicable:

I grew up a farm girl, surrounded by “a bunch of old dirt-farmers,” as my father would say. One of them, Woody, was a very soft spoken man, with a slight build. He said few words, most of which you couldn’t understand because of the toothpick that perpetually dangled playfully from his mouth.

In his life, Woody had cared for, and helped to their own deaths, not one, but two wives. He cared for his family, he cared for his farm, he cared for his community. He volunteered his time, and was quick to sneak a dollar into whatever cause the jar on the counter at the local coffee shop was collecting for – a band trip for a needy kid, or someone struggling with an illness.

Well into his 90’s, he died slumped over behind the wheel of his old pickup. He was in his neighbor’s driveway, there to deliver the fruits of his farming – a watermelon. He’d been out delivering several of his homegrown fruits that day, and it was, literally, his “last stop.”

Now, I’m not sure, but I like to imagine that he had a smile on his face with a toothpick still in place.

One might say it was not the most dignified of ends, dying in a dusty old pick-up truck. But in my mind, it was downright perfect.


I’d say Woody lived a truly prosperous life, characterized by care and cultivation. No amount of planning at the age of 45 could have orchestrated such a precisely perfect end for him.

He never needed the dreaded expensive living assistance. Didn’t have to burden a loved one, either. Maybe it was just luck? Undoubtedly luck was some part of the equation!

But I can’t help but think that it was the way he lived everyday, that set up the conditions for his happy ending. He was active, he gave more than he got, lived simply not chasing the new pickup.

How Will You Die?

One thing is for sure, having your finances in order is key in any life. If you’re not motivated to manage yours, maybe consider doing it for your ones?

Hopefully, you have gotten your own ideas about what a life well lived means to you, and are empowered to start crafting your desired legacy. Feel free to copy my system, if you need somewhere to start. Find your values, set your goals, build your systems – and let me know how it goes!

I would love to hear your thoughts, plans, fears. This is a difficult subject sometimes, but hard conversations are often worthy ones!

Respond if you’d like to hear an update from me on how implementing my new system goes. It will give me some needed accountability.

I love and appreciate you for reading this article. 🙂

Master Your Money, Live a Truly Prosperous Life!

Want to live a truly prosperous life? Don’t waste time. I can help!

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