Chapter 4 – Contemplating Death: The Unexpected Path To Personal Commitment

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Do you have life insurance?”

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

10 minutes earlier, I’d been in the bathroom trying to compose myself.

A day earlier, I’d been at home waiting for my MRI results after a wakeboarding concussion. 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 parents.

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

As I shared in chapter three, he had a brain tumour too, but real this time. The diagnosis and treatment sparked questions, forgiveness and shared experiences. 6 months later he was gone.

Dad’s parents had died at ages 98 and 93. He’d been 66. Genetics hadn’t meant a thing.

Alongside the grief, I was rocked by the thought that I might be two-thirds of the way through my own life.

And over the years, 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 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 that terrified me at 25 is no more desirable, it has become useful in guiding my actions and driving commitment.

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


Stoicism is a school of philosophy founded in Athens by Zeno in 300 BC.

I first began exploring it in 2009 when I read an article by author Ryan Holiday titled Stoicism 101: A Practical Guide for Entrepreneurs. (If Stoicism interests you, Ryan’s books are excellent.)

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 must contemplate death to appreciate life and make the most of the time we have.

It’s time to bring that counsel to life.

Create your Reinvention Note

Before we go further, I’d like you to pull out your phone.

Open up a new note in your favourite app and title it: Reinvention. (Keep this note close. We’re going to build on it for the remainder of the book.)

Add a new header in your note: Commitment.


My favourite way to make death tangible is two quick calculations.

Calculation 1: Days Left To Live

The calculation is straightforward:

  • 80 – your age = your years left to live
  • Multiply that number by 365 = your days left to live.

Enter that number into your Reinvention note under the heading Commitment:

  • Days left to live: ………

Calculation 2: Days I’ve Been Alive

  • Your age x 365 = days you’ve been alive.

Add that number into your Reinvention note too under the heading Commitment:

  • Days I’ve been alive: ………

Why these numbers matter

The “Days Left To Live” number is critical as a concrete reminder for us that time is finite. You may have more, you may have fewer but once it’s gone, it’s gone. We never get it back.

The “Days I’ve Been Alive” number serves a different purpose.

I’ve started a number of different businesses in my life. The first was a digital marketing company in 2005. 13 years later, having been through my crucible period in 2016, I finally made the call that marketing was no longer for me and resigned.

I then set out to build a tech company around the science of psychological flexibility. 3 years later we hadn’t been able to bring a product to market. So again, I resigned.

Both were painful experiences. To let go of something that I’d committed so much time and energy to was hard.

After the second resignation, a great friend of mine asked me: “How’s Toby 2.0 going?”

While I answered their question, I couldn’t help but feel that surely I was past version 2.0.

That led me to calculate the Days I’ve Been Alive number.

I find it a useful proxy to understand that time is an ongoing process. It also helps us to recognise that we have already made many, many changes in our lives and that we can make more.

If we were a software program, we’ve already had many “versions”. And, just like software, we can recognise that in every moment, every invisible increment, every choice we make, we have the power, freedom and responsibility to bring forward the best of those past versions and remove what hasn’t served us.

The only time for those choices is right now.

Enough & Commitment

Because even if (and that’s a big if) longevity science manages to solve aging as a technical problem, there are always accidents.

Any way I cut it, time is finite.

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

And this is where commitment comes in.

It’s the commitment to do the work to reinvent your mind and build your psychological flexibility.

To become the trampoline that can absorb the hits and bounce back rather than the brick wall that cracks.

So reflect on your two numbers and make the commitment.

Because it’s going to require you to take action.

Even the time you spend reading this book you will never get back.

There aren’t many exercises in this book. I’ve stripped them back to the absolute minimum effective dose required to get you started.

To personalise the toolkit of psychological flexibility.

To define your infinite game.

To take your first steps towards it.

To put the science here into practice.

My promise is that, just like the yin yang symbol, it will include the full spectrum of experience.

And it will be the one thing you learn to practice over and over and over.

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

Finally, it’s important to recognise that this is not a commitment to me or anyone else.

This is a commitment to yourself to make the change only you can make.

Let’s get after it.

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