The Two People I’m Trying to Make Proud…

And why the real question is whether the life I’m living today honors them both.

There’s a quote floating around the internet that I’ve seen in one form or another for a few years. It goes something like this:

There are only two people in this world you need to make proud: the eight-year-old version of yourself and the eighty-year-old version of yourself.

It’s a great quote. Perfect for Instagram. Put it over a black-and-white photo of an old man holding hands with a little boy, add some inspirational music, and you’ve probably got yourself a viral reel.

I do actually like the idea, but I think it leaves someone out. A pretty important someone…

You.

The person standing between those two versions. The one actually living your life. The younger version of you can’t change anything anymore. It’s out of their hands. The older version can’t change anything… at least not yet.

You can.

Which makes me think the more powerful hook isn’t:

Would my younger and older selves be proud of me?

Maybe it should be more like:

Is the way I’m living today honoring both of them?

That question has been following me like a shadow lately and, the more I noodle on it, the more I realize I’ve actually been exploring it for the past year now without officially putting those words around it.

A Little Experiment I’ve Been Running

On every episode of The Story of Us: From Cosmic Dawn to The Depths of Being, I ask every single one of my guests two questions without fail.

I do it very intentionally.

These aren’t questions I throw in because we have four minutes left and I need to land the plane. Nope. I’ve been secretly collecting the answers. I guess the cat is officially out of the bag. The jig is up.

I created these two questions from the jump because I kind of suspected that if I asked enough different people the exact same two questions, eventually patterns might emerge.

At the end of our conversation, I ask each one of them:

If you could go back and whisper something into the ear of a younger version of yourself, what would you say?

Then I flip the script because I realize traveling back in time is total science fiction. Going forward isn’t.

These conversations are being recorded. They’re floating around somewhere in that mysterious “cloud” we all talk about as though we understand what it is. Ten years from now, twenty years from now, a future version of that guest could actually listen to the episode.

• They could hear their own voice.
• They could remember who they once were.
• What mattered to them.
• What they were afraid of.
• What they hoped would happen next.

So I ask:

What message do you want to send today to that future version of yourself?

I’ve been paying attention to what people say. And, as I hypothesized, something beautiful is taking shape.

Nobody Wants to Give the Kid Stock Tips

Think about the first question. You get one miraculous opportunity to travel backward through time and spend a precious few seconds with the younger version of yourself. What do you say?

• You could tell them what career to choose.
• Which mistakes to avoid.
• Which relationship won’t work out.
• You could tell them to buy Apple.
• Then Amazon.
• Then Bitcoin.

(And for heaven’s sake, eight-year-old Jeff, stocking up on baseball cards is not a retirement plan).

But that’s almost never where people go.

They don’t try to make the child more successful. They try to make the child less afraid. Again and again, the answers sound remarkably similar:

You are loved.

You’re going to be okay.

Trust yourself.

Trust life.

You have everything you need.

Stay the course.

Stop worrying so much.

Have a little faith.

Think about that… Imagine possessing an actual time machine and deciding that the most important thing you could send backward wasn’t information.

It was reassurance.

These people know how their story unfolded. They know about the heartbreak. The wrong turns. The losses. The mountains of mistakes. The people who came into their lives and vanished. The things they stayed awake worrying about that somehow worked themselves out.

And after all of it, they don’t usually tell the child: Work harder.

They say: Relax.

They don’t say: Get ahead.

They say: Trust yourself.

They don’t say: Be more impressive.

They say: You are loved.

Maybe adulthood eventually teaches us something our younger selves desperately needed to know:

Most of the things we’re terrified won’t work out somehow do.

Not necessarily the way we planned. Not without pain. Not without battle scars. Not without our share of suffering. But… life certainly does keep unfolding.

We spend an extraordinary amount of energy worrying about chapters whose endings haven’t even been written yet.

The Podcast Time Capsule

The second question creates a different kind of silence. You can almost see the guest shift perspective. They stop looking backward. The wheels start spinning and they begin searching for a crystal ball that doesn’t materialize. They struggle to envision someone who doesn’t exist yet.

Ten years older. Twenty. Hell, maybe thirty (if they’re lucky).

Somewhere out there is another version of themselves. Older. Hopefully wiser. Certainly different. I often have to step in and remind them: That person may actually hear this.

What do you want them to remember? And once again, patterns emerge.

Keep going.

Keep evolving.

Stay curious.

Keep finding joy.

Relax.

Remember what matters.

I hope you’re happy.

I hope we did it.

That last one has appeared in several different forms, and I think there’s something important hiding inside it.

Not: How much did we make?

Not: How many followers did we end up with?

Not: Did everyone finally realize how important we were?

Something closer to: Did we get it done?

Did we make the life mean something? Did we help someone along the way? Did we create anything cool? Did we remain curious? Did we love people well? Did we ever become more fully ourselves? Did we use this strange, brief experience of being alive reasonably well?

Doug Brouwer imagined looking backward and realizing how much anxiety had been unnecessary. His message to himself?

Relax.

I suspect eighty-year-old Jeff may have a similar complaint. He’ll probably look back at fifty-year-old Jeff and say: Dude, you spent an alarming amount of time worrying about emails.

Fair point, old man.

The Child Wants Safety. The Elder Wants Meaning.

That may be the clearest pattern I’ve found. The younger version of us seems to want reassurance. The older version wants to know that we actually lived.

The child asks: Am I going to be okay?

The elder asks: Did we do okay?

The child needs to hear: You are loved.

The elder hopes to discover: You loved well.

The child worries about everything still to come. The elder looks backward and wonders whether we paid attention while it was actually happening.

And then…there’s “Us”.

You and Me

Right here.

Livin’ in the glorious middle lane of our lives.

Which brings me right back to the question: Is the way I’m living today honoring both of them?

That’s Why These Reflections Are Letters From the Middle of It All

I’ve been calling these essays “Letters from the Middle of It All“.

Until recently, I thought of that title as a catchy little description of where I’m writing from. You know, not from some mountaintop ashram. Not after I’ve figured everything out. Not as some wise old sage who finally cracked the secret code.

I’m writing from the middle.

• Middle age.
• Middle of raising a family and watching that family change.
• Middle of a career.
• Middle of questions about meaning, faith, purpose, identity, aging, love, and whatever all of this is supposed to be.

But now, I recognize the title means something much deeper to me.

We’re all writing from the middle.

Behind us is the person we once were. Ahead of us is the person we’re becoming. And here we are. Right smack dab in the middle of it all.

We are the only version of ourselves who can ever see both sides.

The present moment is all that is real. The past no longer exists. The future doesn’t yet exist. Our younger self and our older self can’t affect any sort of change. But…

We can.

That’s what the Instagram quote leaves out. It gives us two judges, but there are actually three people in the courtroom.

Three Chairs

Imagine them.

Three simple folding chairs placed on the empty stage of your life. Maybe some spotlighting and a dim, smoking background.

In one sits the younger version of you. You choose the age. 5, 10, 16, 30…

• A time in your life before most of the titles and responsibilities landed.
• Before the mortgage payments.
• Before LinkedIn profiles.
• Before anyone convinced you what success was supposed to look like.

What would that kid think was cool about your life?

Maybe some of the answers would surprise you. Eight-year-old Jeff would probably think it was “rad” that I take adventure trips around the world and that I built a podcast studio and spend my free time talking to interesting people. Maybe not.

But I’m certain he would be significantly less impressed by how many meetings I attend. Lame.

Fair again.

But that kid might also be carrying things I don’t want to lose.

• Curiosity.
• Imagination.
• Playfulness.
• Wonder.
• The ability to become completely obsessed with something simply because it was fascinating.
• The willingness to dream without first creating a spreadsheet explaining the ROI.

Maybe our younger selves aren’t just people we’re supposed to make proud?

Maybe they’re carrying pieces of us we should have protected like treasure?

Ok, now look at that third chair. Eighty-year-old you. That person has something the child doesn’t.. Perspective (and far less hair)

• Time is no longer theoretical.
• The number of summers remaining matters.
• The ordinary Tuesday afternoon matters.
• The people sitting around the dinner table matter.

I can’t imagine eighty-year-old Jeff saying: I really wish we’d put in some overtime hours. I think he’ll care about different things.

• Did we stay curious?
• Did we keep creating?
• Did we travel?
• Did we keep meeting people who challenged the way we understood the world?
• Did we become more peaceful instead of merely more successful?
• Did we tell people we loved them?
• Did we spend enough time with Jessica? With Brady and Peyton?
• With whatever grandchildren hopefully appear someday and completely destroy whatever remaining authority I believe I possess?
• Did we leave anything useful behind?
• Did we have the courage to change when life asked us to?
• Did we laugh enough?

And maybe underneath all of those questions: Are you proud of us?

Not because we did everything perfectly. (God knows we’re already disqualified from that competition). But, because we tried to live a good life.

And then there is the middle chair. That’s Ours.

The one sandwiched between the other two.

The only chair from which anything can still be controlled.

Somewhere Between Reassurance and Regret

There’s another thing I’ve noticed in the answers I’ve been collecting.

When people talk to their younger selves, they rarely want to erase everything difficult that happened. Even the painful parts.

Somehow, looking backward, they understand that removing every scar might also remove part of the person they eventually became.

So they don’t necessarily want to rescue the kid from life.

They want desperately to sit beside them while life happens and whisper:

You’re safe.

You’re loved.

Keep going.

This isn’t the whole story.

Then they look toward their older selves and seem concerned about something different… Regret.

They don’t want to reach the end having stopped living somewhere along the way.

Don’t stop learning.

Don’t stop building something

Don’t lose your childlike sense of wonder

Don’t let fear make the world smaller.

Don’t wait so long for the perfect moment that you wake up and discover there aren’t many moments left.

Find peace. Find joy. Let go. Love people. And please…

Don’t arrive at that final chair carrying a suitcase filled with all the things we were always going to do someday.

Maybe that’s the real conversation happening across the stage. The child reminds us what we shouldn’t lose. The elder reminds us what we eventually will. And those of us sitting in the middle get to decide what happens next.

So again: Is the way I’m living today honoring both of them?

Two Questions. And Then One More.

I’ve asked the first two questions to every guest who has sat across from me. Today, I’d like to ask them of you.

First, look backward – Picture that younger version of yourself. I mean really picture them. Sit with that image for a moment.

They don’t know what happens next. You do.

• You know what they’re going to survive.
• You know the mistakes they’ll make.
• You know the people they’ll love.
• You know the nights they’ll believe everything is falling apart.

You get to lean down and whisper one sentence. What do you tell them?

Now look ahead – Picture yourself much older. Maybe you have an elderly parent and that becomes the image you create for yourself.

You don’t know exactly what their life ends up looking like. But you’re building it for them right now.

Every choice you make today becomes part of the life they will inherit. Every decision today provides you with an opportunity to serve your future self.

You get to record one message that person might desperately need to hear.

What do you want them to remember?

Maybe:

• Remember how much you loved these people.
• Don’t take any of this too seriously.
• I hope you found peace.
• I hope you didn’t carry too many regrets.
• I hope you’re proud of us.

And then comes the question the Instagram reel left out. The question directed right at the only person who can actually do anything about either answer:

Is the way I’m living today honoring both of them?

That’s the question I’m wrestling with. Here. In the middle of it all.

I can’t go back and reassure the scared little boy.

I can’t skip ahead and ask the old man how everything turned out.

But I can honor both of them. And I can do something right now. Today.

• Call someone.
• Begin something.
• Stop something.
• Create.
• Rest.
• Forgive.
• Travel.
• Pay attention.
• Say I love you.

Take one small step toward becoming the kind of old man that younger Jeff would think was pretty damn cool. Maybe that’s all any of us really get.

A child behind us quietly asking: Am I going to be okay?

An elder somewhere ahead asking: Did we really live?

And the person in the middle answering both questions with the life we choose to live today.

These are, after all…

Letters from the Middle of It All.

And this is exactly where they’re supposed to be written from.

Hit reply and tell me: what would you whisper to your younger self? I read every one, and with your permission, a few may show up in a future Letter.

If someone forwarded this to you, you can get a Letter every Thursday, free: thestoryofusproject.com/blog

This Sunday on The Story of Us, I read this Letter aloud and keep going where the page stopped. New here? Start with thestoryofusproject.com/start-here