Contemplating Death – Stoicism, Deliberate Practice, Planes, Last Time, Calculating Days, Gratitude, Enough

Do you have life insurance?”

This was the opening question from my neurosurgeon. My mum and dad were sitting on either side of me.

10 minutes earlier, I’d been in the bathroom trying to compose myself while we were waiting for the appointment.

A day earlier, I’d been at home waiting for my MRI results after a concussion wakeboarding. As the referring GP, my mum was faxed the radiologist’s report.

It said I had a brain tumour.

No driving for 3 months… no exercise… scan in a fortnight… decision about operating… referral to a neurologist…

The neurosurgeon’s instructions blurred.

In hindsight, and now with my own children, I can’t imagine what that appointment was like for my folks.

As I buckled into the back seat of the car on the way home, I completely lost it.

I couldn’t believe this was happening.

I was 25 and terrified.

12 months later it turned out, unbelievably, that it had been a misdiagnosis.

All the testing, scanning, appointments and second opinions ultimately drew the conclusion that it was an unusual myelination pattern in my brain and not a tumour at all.

That outcome still blows my mind. I was so incredibly fortunate.

But that experience didn’t exactly trigger an awakening. I kept moving.

Fast forward 11 years and Mum had two thirds of one lung removed to clear out a growth dangerously close to her heart. All clear thankfully.

The following year dad wasn’t so lucky.

A brain tumour too, but real this time. The diagnosis and treatment sparked questions, forgiveness and shared experiences. 6 months later he was gone.

When Dad died, along side the grieving, I was rocked by the thought that I might be two-thirds of the way through my own life. Dad’s parents had died at ages 98 and 93. He’d been 66.

Genetics hadn’t meant a thing.

And all along the way, there have been so many other reminders of mortality.

Cancer, accidents, suicide, sick children, aging parents and grandparents – all in my immediate circle of friends and family.

The only certainty is that you have your own stories like this. We all have. And if you’re in the thick of it right now, I feel for you and wish you all the best. They can be times of real trial and suffering.

So why contemplate death? Why would I write about it at all?

Because while the death I was terrified about at 25 has become no more desirable, it has at least become more useful in guiding my actions.

And that change has been nearly entirely due to my growing understanding of a school of philosophy called Stoicism.

Stoicism & Contemplating Death

For those who aren’t familiar with it, Stoicism is a philosophy founded in Athens by Zeno in 300 BC.

I first began exploring it in 2009 when I read an article by author and Stoic practitioner Ryan Holiday: Philosophy As An Operating System For Entrepreneurs. (If this sort of thing interests you, I strongly recommend Ryan’s books.)

That sent me down the rabbit hole.

My reading began with Lucius Seneca’s *Letters From A Stoic.*

Seneca’s advice was digestable, actionable and relevant. It was hard to believe that it had been written 2,000+ years ago. It appears we humans haven’t changed much.

In one of his most famous essays, On The Shortness Of Life, Seneca counsels **that we should contemplate death to appreciate life and make the most of the time we have.

As I’ve become increasingly aware of my own mortality, I’ve created more deliberate practices to derive meaning, focus and prioritisation from contemplating death.

Deliberate Practice

Here are three practices that I’ve found incredibly useful for course correcting – overall and in the moment.


Each time I jump on a plane, I ask myself the following.

If this “tin-can-in-the-sky” goes down:

  • Do the people I love know I love them?
  • Am I satisfied with what I’ve done, what I’m doing and who I’ve been along the way?

I’ve found it a quick check-in point. The answers aren’t always comfortable but it’s a useful time and place to “look in the mirror”.

What if this is the last time?

Another practice I’ve been trying to cultivate is asking myself this single question.

What if this is the last time?

I first heard it in a mindfulness exercise by Sam Harris.

It also turns out that Roman Emperor, and most famous of all Stoics, Marcus Aurelius used to say something similar to himself as he tucked his children into bed.

Don’t rush this. This might be the last time you do this. There’s no guarantee that either of you will make it through the night…

In his book The Meditations (also a great read), Marcus reminds himself:

“You could leave life right now. Let that determine what you do and say and think.”

This question is an immediate prompt for me to engage fully in the present and an exercise in gratitude, whether it’s truly tasting a slice of pizza, putting my girls to bed, sipping a coffee, spending time with a friend or going for a swim.

If I can bring that question to mind, it at least gives me a shot at being present and taking action in order to be the person I’d like to be.

[At the moment I’m trying to practice it when my children go to war at home… and often failing. If you have any other questions/prompts you’ve found useful for that specific instance, I’d love to hear them in the comments!]

Calculating days

Another way I’ve found to make contemplation of death more tangible is to calculate the shortness of life with these two numbers.

Calculation 1: Days I’ve Been Alive

I find this number particularly useful as a proxy to understand time as an ongoing process. It’s recognition of the days already gone.

Just like a software program, I’ve had many “versions” already. It means that I have the power, freedom and responsibility to bring forward the best of those past versions and remove what hasn’t served me. I can make changes right now that can make a difference.

Calculation 2: Days Left To Live

  • How many years do you expect to live? (I use 80 as the average lifespan for someone like me.) Enter that into your calculator.
  • Multiply it by 365. That answer might be the number of days you’ve been given.
  • Now, subtract your Days I’ve Been Alive number.

My two numbers

  • Days I’ve been alive: v15,816
  • Days left to live: 13,384 (80 x 365 – number above)

The reality is I may have more, I may have fewer. Ultimately there’s no way to know.

But I check these numbers most days as a part of my daily practice to help me keep focussed on what truly matters today.

It helps remind me that time is limited and not renewable.


Even if science and tech manage to solve aging as a technical problem, there are always accidents.

Anyway I cut it, time is finite.

But, as Seneca says: “Life is long enough.”

Long enough to try to make the choices today that move me towards purpose, values and the people and things that matter most.

Not in an attempt at perfection, because I’ll inevitably fail along the way, but in the recognition that the work is never finished.

Because finally, when my time does run out, hopefully the people I love will know I love them and I’ll be satisfied with what I’ve done, where I am and who I’ve been along the way.

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