Three Questions

Ask yourself these three questions, right now.

If you died right now, in your final moments, what would upset you that you hadn’t taken care of?

If you knew you had only one more day to live, what would you do with that day?

Why aren’t you taking care of those things right now?

I don’t know about you, but when I look at those three questions, I cringe a little, and I’m a person who feels like I’ve taken a lot of steps towards answering those questions.

Let me be brutally honest about my own situation for a second by answering each of these questions about myself.

If you died right now, in your final moments, what would upset you that you hadn’t taken care of?

I’d be upset that I would not be there to give my children advice and to be their father as they grew older. That would be my biggest disappointment.

I feel as though my children would be fine financially if something happened to me, which is a relief. I know Sarah would take care of them and, if something happened to Sarah, there is a wonderful couple that we have designated as guardians to take care of them.

Sarah is a very strong woman and I feel that, once her period of grief was over, she would be able to get on with her life. It’s one of the things I cherish about her – she is strong and reliable.

I’d be upset that I have a lot of paperwork and other items that aren’t as organized as I’d like them to be. To get everything in the order I would like is a pretty daunting task. I do feel somewhat organized, but not strongly organized.

I’d be upset if I left anyone I really loved without having the chance to tell them that I loved them. I’d be incredibly upset if my final words to them were not kind ones.

I’d be upset if anyone had any difficulty putting my affairs in order. I could certainly document things better than I have, though all of the information is there.

If you knew you had only one more day to live, what would you do with that day?

I’d spend most of it with my wife and children. I’d probably invite some of my closest friends over for a while, but not for the whole day, and I’d give them each some mementos and things I want them to have. I’d probably make some videos and some mementos for my children to remember me by.

When they were all asleep, I’d try to take care of organizing my affairs so that they have less to deal with after I passed away. Mostly, I’d simply make some lists of how to clear out accounts and how to get access to life insurance policies. Mostly, this would just make things easier for them.

Why aren’t you taking care of those things right now?

The truth of it comes down to two things. One, these kinds of tasks are clearly in the “important but not urgent” camp. They’re practically the poster child for these kinds of tasks. Clearly, these are important things. They ought to be done. They need to be done. At the same time, they’re not urgent at all. Completing them is basically irrelevant until the very end of your life. Completing them doesn’t help you in any direct way.

The other factor is harder. The truth is that it’s really hard to face your own mortality and to think about your family moving on when you’re not a part of it. It’s not a comfortable or happy thought. I don’t like thinking about my own mortality at all and neither do most people.

Taking on these tasks basically requires you to think about your own mortality. At the same time, it’s not an urgent task, either. Because it’s uncomfortable and it’s not urgent, it’s really easy to put off tasks like this until it’s too late.

For me, I’ve found that tackling these questions in an organized fashion has been the key to moving forward at all. Even though I’m still not where I want to be, I have made a lot of progress in the last few years – and especially in the last few months – by doing such things as securing a life insurance policy for myself, drawing up a will, and so on, and without a good process in place, I wouldn’t continue to move forward on these things.

Here are three specific things I need to keep doing – and you need to be doing – to make sure that you have good answers to these questions.

Think About These Questions – Even If They’re Hard

If you died right now, in your final moments, what would upset you that you hadn’t taken care of?

If you knew you had only one more day to live, what would you do with that day?

Why aren’t you taking care of those things right now?

You probably have some gut reactions to those questions – and that’s a good thing. You probably have a small flood of ideas of things you’d like to do, and perhaps you feel a bit guilty for not having done them yet. Again, that’s a good thing. You might not feel perfectly comfortable thinking about them, either – again, normal, and probably a good thing.

Give It Time – But Not Too Much

I find that, whenever I’m thinking about a difficult or deep life question, it works best if I let it marinate in my mind for a while. I’ll revisit it every day or two, and then I’ll let it rest for a bit.

As I turn a major question over and over in my mind like that, I begin to see things that I didn’t see before, and those insights are often really useful.

Sometimes, I go so far as to schedule thinking about an important issue. I’ll add it to my calendar for, say, Wednesday and Sunday. “Think about things you need to do to prepare your life for others.”

I usually take gradual notes on my thoughts, writing down the good ideas I have as they come to me. A lot of times, with questions like this one, they turn into a rough “to do” list of really big steps to take, along with some really specific steps, too. It’s a disorganized but still useful brain dump, a diamond in the rough.

However, there comes a point where the new ideas stop coming and instead it needs to turn into action. For me, that comes when I realize I’m not coming up with anything new when I turn that core question over and over in my head. It’s time to turn thought into action.

Make a Checklist

For me, the end result of really turning over an idea in my head is a rough list of ideas that’s partially written down and partially floating around in my head. Unless I do something with that jumble of ideas, that’s where it will stay. Those thoughts need to be refined a little bit or else they’ll remain wishful thinking.

Write It Down – Don’t Just Keep It In Your Head

My first step is to just write all of it down. I usually try to do this as I go along, spending a few minutes every few days jotting down my thoughts on the topic, as indicated above.

If this is done well, it ends up being a really disjointed list of actions and ideas. They often aren’t in any realistic order. Some of them are reasonable tasks, some of them are enormous projects, and others don’t really mesh at all.

That doesn’t really matter. Just get it all down on paper (or in electronic form).

Once I have all of those ideas out of my head, I make a few passes through the list, tossing out bad ideas and grouping together similar ones.

For example, as I’ve been running through this very process with the questions about the end of my life, I have several pieces written down. Here’s a sampling:

Leave cards for my children for key life milestones
Record some videos for them
Leave some journals for them to explore
Make sure life insurance up to date
Organize filing cabinet and office
Update documents and make sure copy in safe
Leave cards for Sarah too

As I said, some of these ideas are good ones, some of them are mediocre. Some are big projects and some are little tasks.

Break Down Bigger Actions Into Littler Ones

For all of the tasks that are too big to knock off in half an hour or so, I try to break it down into smaller pieces. It is far easier to complete a series of difficult tasks if you can take on those tasks in easy-to-understand bite-sized chunks.

For example, I have an item of “leave cards for Sarah” on that list. That sounds nebulous – and it is. So, I try to break it down by thinking about it further.

What kind of cards would I want to leave for Sarah? I’d like to leave her a card to read when she falls in love again, letting her know that I want her to open her heart to someone else if I’m gone. I’d like to leave her a card to read on our next anniversary after our passing, reminding her how much I loved her, but also encouraging her to find a new journey in her life. Mostly, they’re just simple things to remind her that, yes, I loved her deeply, but that I want more than anything else for her to have a joyful life that’s filled with love even if I’m not a part of it. Those individual cards are things that I can pull off in half an hour or so by simply writing down my thoughts on a blank card, putting it in an envelope, writing Sarah’s name and when she should open it on the back, and putting it with the others in a bigger manila envelope in our safe deposit box.

It may seem trite or unimportant to you, but it’s important to me. Not doing this would leave me feeling devastated in my final hours of life.

Likely, you have your own ideas of what you would want to take care of before you die. Maybe you want to have a life insurance policy. Maybe it’s something as simple as being sure that an old friend knows how much you care. Maybe you want to leave behind a master information document, listing all of your passwords and account information, so your survivors can pick up the pieces.

Whatever it is, break it down into individual pieces – things you could tackle in a half an hour or so. Add all of them to an ongoing checklist.

Make Continual Progress on That Checklist

At this point, you should have a real list of things that you’d like to take care of. The next step is to simply do them. Start knocking those items off your checklist, one at a time. Here are a few strategies for doing just that.

Devote Several Minutes a Day to the Next Specific Item

Make this checklist a part of your day. If you’re like me, you already have a big running to-do list, so just add a new daily item to that list. “Take care of a life planning task.”

This is exactly how I handle every major project in my life. I just add an entry to my daily to-do list that says “Take care of a task related to [project],” where [project] is just whatever project I happen to be working on and have already developed a checklist for.

So, as I said above, right now I have a “take care of a life planning task” on my daily to-do list (I use Todoist to keep my to-do list). To check off that item, I look at my other checklist – the one full of the tasks I came up with in response to those three questions – and I either knock off one of those items or take care of the next step for one of those items.

Sometimes, I can knock a whole item off my list. Other days, I don’t have the time – or the spirit – for it. In either case, I try my best to devote at least a handful of minutes to taking care of whatever task is on top of that list.

Think About and Add the Following Step Whenever You Complete Any Step

If I can’t quite finish off the top item on that list, I’ll add a new item to the top of the list that explains what yet needs to be done.

To continue with the card example I’ve been using (which is really relevant right now, because it’s what I’ve been working on lately), I might choose to start on a task of writing a card for Sarah to read when she falls in love again. I get off to a good start, but maybe I find myself having a hard time writing it, or maybe something else comes up.

So, what I’ll do is check off the old task – “write a card for Sarah for when she finds love again” – and add a new task to the top – “finish the card for Sarah on your desk.”

That way, the next day, when I find my way to the checklist, I know exactly what I need to do first.

Add “Monolithic” and Time-Specific Tasks to Your Calendar as an Appointment

Some tasks can’t really be broken down like that. Perhaps they require the time-intensive help of someone else. Maybe they can only happen at a specific time.

For those tasks, just add them to your calendar at the right moment. It’s easy.

The Indirect Benefits

So, why go through all of this? Why face those end-of-life issues so directly? Isn’t it morbid and depressing?

Actually, I’m finding it to be quite the opposite. Here’s why.

Peace of Mind

More than anything else, this entire exercise is bringing me substantial peace of mind. I sometimes worried about what issues my family would have to deal with after my passing, but I never realized how much I worried about them, both directly and indirectly.

With each item I knock off of my checklist, I find myself with a little more peace of mind. I know that my children and my wife will be financially secure if something happens to me. I’m beginning to feel that my children will have a chance to know me as they grow into adulthood as well as have an opportunity to hear my advice and know of my family’s history when they want to hear of it. I’m also beginning to feel that I’ll be able to leave behind a whisper in Sarah’s ear when she’ll need it in her life.

Knowing that feels good. It feels really good, in fact; far better than I would have imagined.

Better Choices

Another valuable part of my response to those questions is how it has really encouraged me to make better choices each day in terms of my money, my health, and many other things.

As powerful as it has been to take care of these steps and as much peace as completing them has brought to me, I realize now more than ever that I don’t want these things to ever have to be used, at least not for a very long time.

Staring my own mortality in the eye makes me want to secure this wonderful life I have physically, financially, and emotionally. Questions like this, when you really process them and put effort into solving them, can provide real motivation for making your life better.

The Power of Reflection

Another valuable part of all of this has been the opportunity for reflection. It’s given me a chance to think about what’s genuinely important in my life and what gives my day-to-day life real meaning.

In a way, this list has become really life-affirming, not just in completing it, but in the thought that went into making it and the thought that went into completing each step. It has reminded me what really matters in my life and what brings me lasting joy and meaning. All of that goes far beyond simply checking something off of a checklist.

The Full Circle

When I was younger, one of the most powerful experiences I can remember is reading through my grandmother’s little journal after she passed away. It wasn’t anything elaborate. Most of it was just notes about the weather each day or about something she learned.

Yet I loved leafing through it. I still love pulling it out and looking at it whenever I get a chance, and I hope to be able to retrieve it after my parents pass away and we decide what to do with their belongings.

Why did that experience feel so powerful to me? It brought to life – and still does bring to life – a woman who is somewhat faded in my memory. I can see her in my mind’s eye, but she’s something like a sketch rather than a full person. It leaves me feeling whole and complete and hopeful.

When I think now to my wife, my children, and my potential future grandchildren, I see myself in that role of my grandmother. I want to leave some fragment of myself behind so that they can discover it and feel that connection that I feel to my own grandmother.

In this, it all becomes something of a completed circle. By consciously leaving some things behind for them, I can hopefully be a bit more “real” to them and help them through life’s trials in some small way after I pass, much like my grandmother (perhaps unknowingly) did for me.

In some way, this entire checklist I put together is about completing some circle in my own life.

Final Thoughts

It all starts with three simple questions.

If you died right now, in your final moments, what would upset you that you hadn’t taken care of?

If you knew you had only one more day to live, what would you do with that day?

Why aren’t you taking care of those things right now?

Yet, it can lead to so much more. It can lead to a huge sense of relief and peace of mind. It can lead to some real revelations and deeper understanding of your life. It can lead to better financial and personal choices in the here and now.

All in all, those are three incredibly powerful questions.

Loading Disqus Comments ...