#54 I Met My Younger Self for Coffee Today

Here's what happened.

There’s this trend going around on Instagram and TikTok where people are posting what they’d say to their younger selves over coffee. A mix of nostalgia, self-reflection, and a bit of humour, it started with a poem by Jenna Cecelia, author of Deep In My Feels. The idea is simple: If you met a younger version of yourself, what would they order? What would they be worried about? What would you tell them?

In one TikTok video, jackiecamardo shared her version:

Most of these posts follow a familiar pattern—listing what’s changed (music taste, career goals, friendships) and what’s stayed the same (personality quirks, lifelong dreams, maybe an embarrassing obsession with a certain band).

But they point to a deeper idea that we can look back on who we were and see how far we’ve come.

At the heart of this trend is self-compassion. These kind of posts flip that cringe script. Instead of self-criticism, they invite kindness. They remind us that our younger selves were just doing their best with what they knew at the time.

Just looking at photos of myself as a teenager makes me glad that Social Media was not yet a thing! It’s easy to look back and cringe at who we were—to judge our past selves for the mistakes we made or the things we didn’t know. And yes, I do wish someone had told me to get a better haircut.

What if we could meet our younger selves with encouragement instead of embarrassment?

So, I’ve been thinking—what would I say to my younger self?

I met my younger self for coffee today.

Both of us were on time.

He ordered a massive milkshake, loaded with chocolate sauce and flakes.

I went for an oat milk latte. He asked how you milk an oat, fully expecting the whole café to erupt in laughter. Nobody did.

He showed up in cheap supermarket jeans and a Ralph Lauren Polo Chaps hat—bought on a Friday, somewhere between art college and a shift at Toys R Us.

I showed up in cheap supermarket jeans but no hat.

He was listening to Bart Simpson “Do the Batman” on his Portable CD Player.

I was listening to Taylor Swift on my AirPods but I told him it was worship music because I was too embarrassed to admit I was a secret Swiftie.

He told me he wanted to be a cartoonist.

I told him that one day, we’d get to see a cartoon Santa we created on a town centre billboard—he loved that. I told him we’d run a graphic design business, the first step in a career built on pioneering new things.

We talked about girls.

He wasn’t sure if he’d ever find someone who truly loved him for who he was.

I told him he’d marry the worship leader

Leah Boden

he fancied on stage at Youth Camp. That one made him smile!

He told me he wanted to help young people like him—lost, searching, trying to figure it all out—find their identity and purpose in Christ.

I told him he’d point many young people to Jesus... He’d lead a summer camp, helping hundreds of teenagers just like him. He’d launch a video series for teens that would be used in thousands of churches worldwide. He’d lead an organisation impacting thousands of young people. He’d write books for the next generation—the kind he wished he had when he was younger. And one day, he’d even get to raise the most incredible teenagers himself.

He asked me if it would be hard.

I told him, you’ll probably never fully stop feeling like that teenager—but you will always find your way through.

I hope we meet again for coffee soon.

Of course, we can’t actually meet our younger selves for coffee.

But we do have people in our lives who are younger than us— the next generation who are still figuring it all out. And that’s where real impact can happen beyond just a trip down memory lane.

In Psalm 145:4, it says:"One generation commends your works to another; they tell of your mighty acts."

God’s design has always been for wisdom and experience to be passed down, not kept hidden. We aren’t meant to be mysteries to the next generation.

I was struck by a recent instagram story from

Amber O’Neal Johnston

where she shared a quote from Viola Davis speaking on Brené Brown’s podcast in relation to this very thought:

"I will not be a mystery to my daughter. She will know me, and I will share my stories with her—the stories of failure, shame, and accomplishment. She will know she’s not alone in that wilderness."

That hit me hard. Because isn’t that what we all needed when we were younger? Not just answers, but stories. Proof that someone else had been there, made mistakes, struggled with doubt, and found their way through.

So while I can’t sit across from younger version me and tell him everything’s going to be just fine, I can do that for someone else now. I can share my stories—the failures, the lessons, the wins. I can make sure the next generation doesn’t feel alone in the wilderness. I can help them find their purpose.

And maybe that’s the real reason this trend resonates so deeply. It’s not just about looking back. It’s about looking forward—and making sure the young people in our lives don’t have to wonder what we would have told them, because we’re telling them now.

So, tell me below: What would you say to your younger self?

PS: Credit to Julian and Kate Boden for going into the coldest part of their house and finding some old pics to scan over to me.