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There’s a Latin phrase that’s been haunting philosophers for centuries:

Memento Mori — “Remember you must die.”

Morbid? Maybe. But also… motivating. If you’ve been waiting for the “right time” to make a change, to start, to leap, to do the thing you’ve been putting off, here’s your reminder: time is the one thing we can’t earn back.

This week’s issue is about facing that reality head-on, by not fearing our own mortality, but instead using that knowledge as leverage to focus on what matters.

What’s inside:

• A wake-up call from the stoics

• A not-so-fun data point on regrets

• A mindset flip to overcome procrastination

• Tools to explore Memento Mori further

• A challenge to stop waiting and start living

Main Idea

You probably don’t want to think about death in general. Let alone your own. That’s normal. Our culture has done everything it can to avoid that discomfort — with anti-aging everything, toxic positivity, and distractions designed to help us forget how fleeting this life really is.

But the many of the great stoic philosophers believed the opposite:
By facing death, we live better.

Marcus Aurelius wrote,

What does death have to do with a finding career purpose or getting off the ladder?

It’s about shaking off the illusion that you have unlimited time to “someday” chase your dreams or fix your misalignment or do what actually matters.

Because “someday” isn't guaranteed. But this moment is.

We all are only gifted so many revolutions around the sun, and most of us will get little heads up of when we’ve reached the end. So ask yourself:

• What if you only had a few years left — what would matter most?

• What are you postponing that would make life feel more meaningful?

• What are you willing to stop tolerating today?

You don’t need to spiral. You just need to get honest.
The clock is ticking. And that’s not something to be afraid of; it’s something to build from.

Memento Mori. Remember you must die, but a powerful motivation to start living.

Ditch the Metrics

Burn the business scorecard – focus on what matters!

The Metric: 

The Top Five Regrets of the Dying - A Life Transformed by the Dearly Departing is a 2011 book by Bronnie Ware inspired by her time in palliative care. As recorded by Bronnie, these regrets are:

1. "I wish I'd had the courage to live a life true to myself, not the life others expected of me."

2. "I wish I hadn't worked so hard."

3. "I wish I'd had the courage to express my feelings."

4. "I wish I had stayed in touch with my friends."

5. "I wish that I had let myself be happier."

Ditch it:

At the end of life, most people don’t say, “I wish I’d earned more,” or “I’m glad I spent extra hours at the office.” Instead, they regret the time lost, the authenticity sacrificed, and the experiences never had. Let’s stop playing by someone else's clock. You don’t get an extra life for working overtime. If the ladder is costing you presence, purpose, or joy, it’s time to reframe success on your terms.

Reframe This

 A quick thought-flip to help shift how you see your work, your worth, or your path.

Old Belief: I have time to figure it out. I’ll get to it someday.

New Perspective: I don’t know how much time I have. But I know I can start today.

Rung Breaks

A curated mix of tools, links, books, and ideas to help you step off the ladder and into your own path.

📚 Book: Four Thousand Weeks by Oliver Burkeman — a grounded, existential look at time management through a philosophical lens.

✍️ Read: Memento Mori: The Reminder We All Desperately Need – from Ryan Holiday’s The Daily Stoic

🛠️ Tool: Death Clock – an eerie, but effective reminder of how precious each day is

✍️ Read: Your Life in Weeks - Tim Urban’s visual breakdown of the life of an average American

🎨 Inspiration: Memento Mori painted by graffiti artist Piombu in Borgo, France

Your Move

A reflection and challenge to help you break out of autopilot and make real change.

Reflection Prompt:

Challenge:

Until Next Time…

Time is our most precious, non-renewable resource.
You don’t need to fear death to honor it.
You just need to stop assuming there will always be more time.

I’ll leave you with another favorite quote of mine on the subject, not from a historic philosopher but modern American rapper, J. Cole, in the lyrics to his song Mr. Nice Watch:

Live like it matters.

See you off the ladder.

— Sean Sirianni
Founder, Off the Ladder

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