by Jay 

Dreading Regrets? This Powerful Exercise Reveals The Brutal Truth About What Matters Most in Life

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Morgan Housel Reverse Obituary Exercise

Imagine your life as a book, its pages slowly filling with the choices you’ve made. 

Now, think about the last chapter.

What do you want it to say?

What story do you want to leave behind when your time here is done?

This is the heart of the "reverse obituary" exercise Morgan Housel talks about—a way to step outside the hustle of life and ask:

What really matters? 

It’s not about what you’ve earned or acquired but about the moments and relationships that define you.

The exercise is simple, but its impact? Profound.

What Do You Want Your Life to Say?

Morgan doesn’t care if his obituary mentions his book sales or career accolades.

What he hopes it says is this:

  • He was a good father.
  • He was a loving husband.
  • He left his community better than he found it.

That’s it. Simple, right?

But here’s the catch: we spend so much of our lives chasing things that would never make the cut.

A bigger house, a faster car, a promotion at work.

These are the things we think we need to feel happy or successful.

But when it comes down to it, they’re not the things we’d want written about us when our story ends.

What We Leave Out

The reverse obituary isn’t just about what we include—it’s also about what’s missing.

Imagine a eulogy filled with lines like these:

  • “She worked long hours and missed her kids’ milestones.”
  • “He bought a bigger house every year but couldn’t make time for his friends.”
  • “They left behind a fortune, but no one to remember them.”

No one wants that.

And yet, how often do we find ourselves living as though these things matter most?

Morgan shares the story of an obituary he read once—a brutally honest one. 

It described a man who prioritized money over love and left his family feeling relieved, not grieved, when he passed. 

It’s the kind of cautionary tale that makes you stop and ask: What am I really working toward?

The Mirror Test

Here’s where the reverse obituary gets interesting.

It’s not just about imagining what your life might look like decades from now.

It’s about holding up a mirror to your life today and asking:

If I were gone tomorrow, what regrets would I have?

Most of us wouldn’t wish we’d worked harder or earned more.

We’d wish we’d forgiven someone, reached out to an old friend, or spent more time with the people we love. 

The real regrets aren’t about what we didn’t achieve—they’re about the connections we didn’t nurture.

The Spectrum of Wealth

One of Morgan’s favorite stories is about Derek Sivers, who once said he didn’t feel rich when he sold his company for millions.

He felt rich when he had saved $20,000.

That was enough to give him the freedom to live the life he wanted.

We often think wealth is a finish line, something we’ll achieve “someday” if we just work hard enough.

But Morgan reminds us that independence is a spectrum. 

Every dollar you save gives you a little more control over your future. 

It’s not about reaching some elusive destination; it’s about finding freedom, bit by bit, along the way.

A Life Without Wasted Time

David Cassidy’s final words were haunting: “So much wasted time.”

Think about that.

A man who achieved so much—fame, success, fortune—looked back and saw only the moments he had missed.

It’s a sobering reminder that the real currency of life isn’t money or status. It’s time.

And yet, time is what we squander most.

We chase after things we think will make us happy, only to find that the things that truly matter—love, health, connection—were within reach all along.

Writing the Life You Want

The beauty of the reverse obituary isn’t just in imagining the story you want to leave behind. It’s in using that vision as a guide to live differently today.

Ask yourself: 

What small choices can I make now to create the life I’ll be proud of later?

Maybe it’s spending an extra hour with your kids, calling a friend you’ve lost touch with, or saying no to a project at work so you can say yes to dinner with your partner.

These aren’t grand gestures, but they’re the moments that add up to a life well-lived.

The Story That Lasts

In the end, the reverse obituary isn’t about pleasing anyone else.

It’s about finding clarity in what matters most to you.

It’s about making sure your days reflect the values you want your life to stand for.

Because when the book closes, it’s not the possessions or achievements that will define your story.

It’s the people you loved, the lives you touched, and the moments you truly lived.

This post was inspired by Dr. Rangan Chaterjee's interview with Morgan Housel.

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Jay

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