“Remembering that I'll be dead soon is the most important tool I've ever encountered to help me make the big choices in life. Because almost everything—all external expectations, all pride, all fear of embarrassment or failure—these things just fall away in the face of death, leaving only what is truly important.”

- Steve Jobs

Let me be clear: I don't want to die anytime soon.

I want to live a long, enjoyable and impactful life.

There’s still a bunch of on my bucket list I want to check off.

I exercise regularly, don’t drink, and eat well.

I'm committed to getting in the best shape of my life this year and just completed VO2 Max, RMR testing and joined Function.

But wanting to extend my life and being aware that it will end aren't contradictions.

They're actually complements.

The awareness of death is precisely what makes me want to live well.

It's what makes me want to live more.

There's a basic principle in economics that applies to valuing assets:

Scarcity creates value.

And time is our most valuable asset.

Being aware of my death, helps me make my time more valuable, not less.

And there’s one person that helped me adopt this mindset; Steve Jobs.

Back in 2005, he gave the Stanford commencement speech. It’s widely considered one of the best commencement speeches in history.

At the time, he had cancer, but it wasn’t public knowledge. No one in the audience knew.

He talked about dropping out of college, getting fired from the company he founded, and the importance of having the courage to follow your intuition.

He mentioned how all those negative things became the foundation for so many positive things that happened in the future.

He called them dots, that could only be viewed in retrospect, not preemptively:

“…you can’t connect the dots looking forward. You can only connect them looking backwards, so you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well-worn path. And that will make all the difference.”

He also reflected on the importance of using death when making big decisions:

"Remembering that I'll be dead soon is the most important tool I've ever encountered to help me make the big choices in life."

I first heard those words in 2008 during one of the lowest points of my life.

I’d moved across country to Charlotte, NC to launch a company that failed.

It was a really dark time for me, and many others.

The Great Recession was in full swing.

Fear was at an all time high. So was unemployment.

My Plan A failed, and as a back-up, I found myself working a job that I hated.

I felt stuck.

Every morning I woke up dreadful.
Every evening I came home drained.

I knew this job would never to get me where I wanted to go.
It was taking a toll on my life, and the costs exceeded the benefits.

It wasn't a stepping stone.
It was a holding pattern.
And holding patterns have a way of becoming permanent if you let them.

Here I was, 25 years old, with my health, an engineering degree, and my whole life ahead of me, but all I could think about was fear. Fear of the unknown. Fear of failure. Fear of judgement. Fear of being homeless. The fear of fear.

Thankfully, Steve’s words helped me think of a different fear.
A fear bigger and more important than the other fears.
I feared wasting my life trapped in a job that I hated, and never having the courage to pursue the life that I wanted.

I feared dying with a heart full of regret and resentment.

That speech gave me the courage to quit.
To leave the safety net and move back to California.
I took the leap of faith.

In the short term, I took a couple steps back.
I had to move in with family. I dipped into my savings.
But in the long term, everything worked out, and much better than expected.

Steve was absolutely right.

The dots are connecting beautifully.

And that’s why I love to remind myself that I’m going to die every week.

A couple of years I learned about the book 4,000 Weeks: Time Management For Mortals.

The premise is we get 4,000 weeks (or about 77 years) to live.

The book inspired several people to create online calculators that visualize the estimated amount of time you have left to live.

You enter your date of birth, and it spits out a color-coded grid.

Each tiny square represents one week of your life.

The red squares are the weeks you’ve already lived.

I have 2,153 weeks left to live.

There’s something about seeing it laid out like this, that really hits me.

It’s simple, directionally accurate and profound.

The Stoics had a phrase for this practice: memento mori—remember that you will die.

Marcus Aurelius, the Roman Emperor and philosopher, wrote in his journal:

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

Seneca, another Stoic, put it even more bluntly:

"Let us prepare our minds as if we'd come to the very end of life. Let us postpone nothing. Let us balance life's books each day."

These weren't morbid men obsessed with death.

They were people who understood something we've largely forgotten: that awareness of death is not a burden but a gift.

Death isn't the enemy of a good life, but forgetting about it is.

It's the frame that gives the picture meaning.

Here's your reflection for the week:

How closely did last week’s actions align with what you want your obituary to say?

Think about the life you want to be remembered for. Now look back at the last 7 days. Did your time go toward the things that would be mentioned at your funeral—the relationships, the meaningful work, the moments of real presence? Be honest with yourself. The gap between how you spent last week and how you want to be remembered is trying to tell you something. Listen to it.

Here's your challenge for the week:

Calculate your number. Look at the visual representation of your remaining time. Then choose one thing—just ONE—that you've been postponing. Take the first step toward it this week. Send the email. Make the call. Start the project. Have the conversation.

You don't have unlimited time. None of us do. Let that truth move you.

With courage,

Jonathan