The Deathbed Regret Test

Will you let this happen to you?

Steven Yates
5 min readJan 20, 2023


Photo by Kinga Cichewicz on Unsplash

Imagine this scenario. Warning: it’s not going to be comfortable.

You’re on your deathbed. The specifics of how you got here don’t matter. It could have been something sudden and unexpected. Shit happens.

The point is, you’re going to die, and soon.

It could be tomorrow, the next day, or even tonight. You don’t know, and your doctor(s) can’t tell you anything for sure, because they don’t know, either.

Let’s assume your mind is still sharp.

What are you thinking about?

What do you regret doing — or more likely, not doing?

You could have started that business on the side, but you procrastinated, and when push came to shove, you didn’t do anything.

Now it’s too late!

You could have written that book, but you told yourself you didn’t have time.

Too late!

You could have taken that vacation — your family was ready — but you didn’t want to spend the money.

Can you take your money with you?

You’re looking back at all these should’ves, would’ves, could’ves, and all you can do is close your eyes and wish you couldn’t remember it…



Steven Yates

I am the author of What Should Philosophy Do? A Theory. I write about philosophy (especially the Stoics), health and systems, and the future if we have one.