The Most Reliable Way To Avoid Deathbed Regrets (And It Can Be Done During Your Morning Coffee)

Can I let you in on a little secret? I think about death a lot.

Like… a lot. It’s become one of my primary frames, and I believe, has been one of the greatest contributors to my joy. I have a decades-long practice that I have never made public before.

Before spending time with a loved one, I imagine they are dying and that this is the last time I will see them. I lean into this, hard.

I’ve done this outside my parents’ front door every time I visit. I will do this before entering the super bowl party with friends this weekend. I will see and feel their death – because it will allow me to see and feel their presence.

I do this not because they are dying, but because I am. When? Not sure. But it’s coming, and I hold each day as that miracle, that defensible space, between myself and the inevitable.

We have a reminder to this effect on our living room wall:

I’m on the left, my wife is on the right. Each week we check off another box, forced to ask ourselves, “how did we use our time?”

What’s Essential?

I’ve recently found the works of Greg McKeown on Essentialism, learning the skill to “distinguish the vital few from the trivial many.”

Here’s some irony for you: when I subscribed to the Essentialism newsletter, someone hacked their system, subscribing me to thousands of other newsletters and completely obliterating my inbox with the nonessential. Cudos, you bastard, whoever you are.

I’m studying Essentialism in my constant quest to boil my life down to its simplest terms, to ensure I don’t miss this life. In this attempt, I have reduced my life’s complexity down to a single notecard, which sits on my desk:

To be fair, this is still too much. Having multiple priorities quickly becomes having no priority. But for the sake of my world today, in this season of life, this is sufficient.

This has become a very simple filter through which I assess my world. If a proposed event – a task, a phone call, an event, a book – brings me closer to one of these goals, it’s a “yes”. Everything else is a “no”.

Most of the world’s “opportunities” fall into that latter category. With this clarity, saying "no" to the trivial is easy. What’s more challenging is saying no to the beautiful.

Some Major Life Decisions

In my recent curation of the works of Tim Ferriss, I came across the following question:

“What can I categorically and completely remove, even temporarily, to create space for seeing the bigger picture and finding gems?”

I’ve been auditing my calendar (read: my life) to see how it stacks up to my notecard. This has led me to stop doing some things I don’t want to do, which is wonderful. Harder still, it’s led me to stop doing some things that I love doing.

To that end, I’m committing to not officiating any weddings in 2024 and 2025. I will revisit this at the end of 2025.

Here’s a few reasons why:

• There are only a couple hours each day to practice creative works. These hours are spent aiming at the second item on my card, writing books that help millions of people. (lofty, yes, but I believe I’ll get there.) A good wedding ceremony requires a tremendous amount of writing and public speaking practice. In the two months or so preceding a ceremony, nearly all my creative time is spent working on that ceremony. One wedding a year requires 16% of my writing time for the year. Two weddings requires 33%. The math adds up quick.
• I can’t phone it in. With the honor to lead the most important day of loved one’s lives, I’m going to bring it, leaving no room for error. This requires tremendous focus. If I’m in, I’m in – which means I’m out for everything else.
• And if I did still fulfill my personal writing, while writing the ceremony, those hours will invariably be withdrawn from time spent with my wife and soon-to-be-here son. With that being at the top of my notecard, this is a trade I just cannot make.

This is one of the many things I’m saying no to so I can say yes to my notecard. It’s not easy – the weddings I have been a part of were some of the most beautiful days of my life - but it’s necessary.

When Saying “Yes” to yourself becomes saying “No” To People You Love

The hardest part about decisions like this is saying no to people you love. My experience has taught me that these conversations are more difficult in imagination than reality.

The people who don’t understand you or your decision get upset, make it personal, and will attack your character, directly or indirectly. They value their preferences over yours and will hold this decision against you. The good news: these aren’t the people on your notecard.

The people close to you, the ones who understand you, support you, and root for your success, will applaud your clarity. They don’t make you feel guilty; they celebrate your conviction. They value you and your relationship with them more than their request.

The people on your notecard honor your notecard.

There’s an old quote that rings true here:

“Nothing real can be threatened. Nothing unreal exists. Herein lies peace…”

The Exercise

1) DEFINE: Fill out your notecard. What’s most essential? What are the “vital few” that are the greatest source of life within your life? What must be prioritized and protected amid modern chaos?

2) CREATE: Create your list of “no’s”. What are the things you have been doing, which you will no longer do, because they don’t line up with your notecard? Make premade decisions that will simplify addressing the requests of the world.

3) REVISIT: Revisit your notecard daily. Leave it somewhere you will see it. This single tool will remove stress, confusion, and laborious decision making. This card is your freedom.

And remember:

When you say "no" to all the things that are not on your notecard, you are saying "yes" to the few things which are. On a long enough timeline, that will become a life you are proud of and grateful for.

But What About Regrets?

What about all the things we’ll miss out on? Won’t I regret not officiating my friends' weddings for the next couple years (or longer)? Yes, I will. I will regret this tremendously.

But I will not regret giving my second highest priority in life – writing - my best shot.

“In life, we must choose our regrets.” – Christopher Hitchens

We will regret many things in this life. That’s how the game works. Our opportunity is to ensure we don’t regret anything on our notecard. That’s how the game is won.