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Why I Still Cry on Airplanes (And Why That’s Okay)

There’s a hush in the sky that you can’t replicate on the ground.

Thirty-some-thousand feet up, when the world below blurs and the seat belt sign hums steady, I finally hear the things I’ve silenced. The things I didn’t have time to process when I was nodding my head at Summer of Loud, listening to Parkway Drive crack the sky wide open.

I don’t cry because I’m falling apart.
I cry because it’s where I’m finally allowed to feel.

Just like I wrote in The Immortality Equation — concerts and travel aren’t just entertainment. They’re sacred. So are the pauses between them.

And airplanes? They’re altars in the sky.

Not because of the tiny cup of ginger ale or the overpriced Wi-Fi that never really works — but because up there:

  • I’m not anybody’s bodyguard.
  • I’m not the guy with the clipboard.
  • I’m not the steady presence with the steady hands.
  • I’m not reading the crowd.
  • I’m not calculating risk.
  • I’m not “on.”

I’m just… there.

Unseen. Untethered. Un-busy.

And maybe that’s what sadness needs to come to the surface — not attention, but space. A few inches of legroom, a slow song in the headphones, and a window view that doesn’t expect anything from you except honesty.

There’s something about that kind of stillness — that liminal quiet between cities, between roles, between versions of yourself — that turns your own heart into a confessional booth. Not with shame. Not with guilt. But with gentleness. With grace.

I’ve come to believe the sky is where the weight I carry finally loosens its grip.

Down below, I’m always catching something:

  • A bag
  • A vibe
  • A meltdown
  • An expectation
  • A curve ball

But up here? My hands are empty. And my eyes are open. And every once in a while, my chest tightens — not from fear, but from memory.

That’s when the tears come. And they don’t ask permission.

They don’t need a dramatic soundtrack or a life-shattering moment. They don’t even need a reason. They show up because my body remembers what my brain buried beneath the noise.

A conversation I never got to finish.

A goodbye that still feels like it’s echoing in my chest.

A version of myself I thought I was over — until a lyric drags him out of the shadows and into the aisle seat beside me.

And maybe this sounds like a lot for a five-hour flight from Nevada to New Jersey. But healing doesn’t check the departure board.

It comes when it wants.
It lands when it’s ready.
And for me, it usually chooses altitude.

Because up here

  • I’m not performing
  • I’m not problem-solving
  • I’m not pretending I’m fine 

when I’m running on fumes and forgiveness and a playlist that understands me better than most people do.

I’m just a man in a hoodie with his head against a scratched-up window, quietly unraveling at cruising altitude.

And for once, that’s enough.

The Quiet That Breaks You Open

Back on the ground, my life is a war drum of noise.

From guarding entrances at sold-out wrestling events to flying for hours half-asleep while GQ texts me about coffee and sunrises — the chaos doesn’t clock out.

I once wrote that Executive Protection is the “invisible job.” That’s still true. I’m the calm in the middle of someone else’s storm. The steady hands. The eyes that never blink. The one who holds the weight while others get to be loud, be free, be seen.

But on a plane? Nobody needs me.

And that’s when I let go.

It doesn’t happen all at once. Not like in the movies. There’s no dramatic soundtrack or slow pan to my face as a single tear rolls down. It’s quieter than that. Slower.

It starts with noticing how sore my shoulders are.

Not from working out.
But from bracing.
From always being ready.

  • Ready for the shove in a meet-and-greet line that turns into something more
  • Ready to step between someone and the chaos
  • Ready to de-escalate a crowd with nothing but body language and breath control

Ready to make sure the person I’m protecting gets home safe — even if it means I don’t

That kind of readiness lives in your bones. And it’s loud, even when you’re silent. Especially when you’re silent.

But once I’m in the air, once the cabin lights dim and the hum of the engines wraps around me like a blanket made of white noise, something shifts.

The tension doesn’t scream as it leaves.
It sighs.

And when I hear it — that almost imperceptible exhale — I know I’ve crossed some emotional border. That’s when the quiet breaks me open.

Not violently. Not like a shattering glass.

More like thawing.
More like a river that’s been frozen for too long finally cracking open under spring sun.

Because even though I live in chaos, I’ve made peace with it. It’s the stillness that unnerves me.

Stillness means there’s space to feel.
And I’ve gotten very good at not doing that.

There was a night — somewhere over Texas — when I realized I hadn’t been touched in weeks. Not affectionately, anyway.

  • A firm handshake
  • A nod from a crew member
  • A pat on the back from a stagehand after load-out

But nothing soft. Nothing human.

I sat there, suddenly aware of how skin-hungry I’d become. Not for sex. Not for performance. But for presence. For the kind of contact that says, you’re here, and I see you.

It hit me so hard, I had to excuse myself to the lavatory just to breathe.

That’s the kind of moment that only rises in the quiet.
And once you’ve tasted that kind of truth, you can’t go back to pretending you’re fine.

It’s in the quiet that I remember the kid I used to be.

The one who memorized every lyric of James Taylor in his bedroom with the door locked and the lights low, just trying to survive the night

The one who used to write poems in the back of notebooks and dream of being something other than a ghost in the background

He still lives in me. But on the ground, he gets buried under duty.

Up here? He comes back to life.

Not loud. Not attention-seeking.
Just a whisper. Just a presence.

A reminder that softness is not the opposite of strength.
It’s the proof of it.

The Weight They Never Notice

Most people only notice the burden when it drops with a thud.

They don’t see it in the small silences. The thank-you that never comes. The fact that I’ve worked more meet-and-greets than most people will ever attend, and not once has someone asked me how I’m doing.

It reminds me of what I wrote in Cardboard Cowboys & Life Bans from Walmart — how even absurd joy has a weight when it’s always carried for someone else.

On one flight to Japan, the ache caught up to me. I had just finished protecting someone who never acknowledged my presence. Not out of malice. Just… assumption.

And as I sat in seat 17F, playlist humming low, I asked myself: When’s the last time someone saw me as more than a silhouette?

See, the tricky thing about carrying weight well is that people start thinking it isn’t heavy.

And when you’re good at holding the line — not just physically, but emotionally — they stop asking if you need anything. They assume your silence is strength. That your stillness means peace. That your nod and “I got it” means you’re built different.

But that’s not strength.
That’s choreography.

That’s years of learning how to tuck the ache into your spine and keep moving.

Because in this job, in this life, there’s rarely room for pause.

  • You don’t cry when the tour bus is late.
  • You don’t process a breakup between call times.
  • You don’t ask for a moment during load-out because your heart’s heavy.

You just tighten the laces, scan the perimeter, and press on.

And after a while, that becomes normal.
Until one day, it doesn’t.

One day you’re mid-flight, looking out the window while the clouds float by like ghosts of things you never said, and it all lands at once.

The weight.

The unpaid emotional labor.

The apologies you never received.

The countless moments where you held it all together, not because you wanted to — but because there was no other option.

And here’s what no one tells you:

If you carry something long enough without naming it, it doesn’t go away.
It just becomes part of your posture.
And people start calling it confidence.

But inside? You’re tired.

Not in a “need a nap” way.
In a “don’t know where to set this down” kind of way.

I think about that often — about how the strong ones, the “unshakables,” are usually the ones no one checks on. Not out of neglect. Just assumption.

  • You seem fine.
  • You seem strong.
  • You always handle it.

And maybe that’s true. But even the guy who always carries the weight deserves to be asked how his back is holding up.

Because sometimes? It’s not.

The Gospel of the Middle Seat

I think middle seats were designed for emotional unraveling.

Once, flying to St. Louis, I sat between two strangers who shared stories, baby pictures, belly laughs — all while I quietly wept into my hoodie.

Not from sadness.
But from longing.

From wondering whether fatherhood passed me by, or whether I was too scared to reach for it in the first place. From that uncomfortable truth that sometimes our dreams don’t die — they just get quieter. They wait in the corner, politely, until a stranger says the word “seven” and suddenly your whole rib cage cracks open from the inside.

Middle seats don’t let you escape.
No lean to the window.
No aisle to stretch into.

You’re held in place

  • by armrests
  • by strangers
  • by everything you haven’t said yet.

It’s funny how a three-hour flight can feel like confession.

The woman next to me wore a sweatshirt that said “Be kind to your mind.” I don’t think she saw the irony when she started scrolling Instagram, liking beach photos and baby announcements, as I sat beside her trying not to fall apart.

She smelled like lavender and road trips.
He smelled like aftershave and fatherhood.

And between them, I sat in my wrinkled hoodie, listening to Gregory Alan Isakov sing about ghosts and gardens and whatever else manages to make the world feel both tender and temporary.

I think what made me cry the most wasn’t the baby pictures or the laughter. It was how comfortable they seemed.

Like the world had made space for them.
Like they knew — with certainty — that someone would be happy to see them get home.

That kind of comfort… that kind of rootedness… it’s hard to explain when you’ve lived your whole life on standby.

  • Always packed.
  • Always braced.
  • Always in motion.

I’ve moved through so many places with a borrowed sense of belonging — hotel rooms that never learned my name, backstage areas where I was known but never known deeply.

And the middle seat? It doesn’t let you pretend you’re okay. It holds you still long enough for the ache to catch up. It whispers all the things you’ve been too busy to feel.

That St. Louis flight reminded me of something I used to write in my high school notebooks: “I think I’d be a good dad… if someone would just show me how.”

I’d forgotten I ever wrote that. Forgotten I ever believed that.

But up there, somewhere above the clouds and behind two strangers talking about birthday candles and ballet recitals, I remembered.

And that remembering wrecked me.

Not in a hopeless way.
But in a holy one.

Because grief is rarely about loss alone. Sometimes it’s about recognition. About seeing the part of you that still longs. That still hopes.

And middle seats — those cramped little confessionals with bad elbow room — they know how to take that hope and hold it without judgment.

  • They don’t offer solutions.
  • They don’t ask questions.
  • They just give you a place to ache in peace.

And sometimes? That’s all you need.

Soundtracks for the Things We Don’t Say

Music doesn’t knock. It just lets itself in.

I’ve played “Body in a Box” by City and Colour on so many flights, it ought to earn me seat upgrades. It’s not dramatic. It’s not desperate. It’s true.

And if you’ve read Volume 1 of Backseat Benedictions, you already know — truth, when it finally shows up, is the only thing that keeps me breathing steady at 36,000 feet.

I’ve always said grief lives in playlists. Alphabetized, timestamped, waiting in shuffle like an emotional ambush. My most honest therapy sessions have taken place midair, through glitchy earbuds, while a lyric did surgery on something I hadn’t touched in years.

And I stand by it.

Because when you’ve spent most of your life behind the curtain — always the one scanning the exits, always the one holding the line — finally standing in the crowd, watching Seether in Seattle rip through an encore that could’ve cracked the sky…

You don’t just hear the music.
You feel what it means to belong to a moment again.

Music gives that back to me. For three minutes and forty-two seconds, it says: You don’t have to hold it together right now.

And I believe it.

Some people need journals.
Some people need church.
I need playlists.

I’ve got a folder on my phone called “Don’t Hit Play Unless You’re Ready.”

Inside are the songs I only let myself hear on long drives, late nights, or — most often — when I’m floating over some stretch of American sky, disconnected from everything but the hum in my chest and the ghosts in my headphones.

There’s one track — a deep cut from an album that never charted — that brings me back to a parking lot in Baltimore, where I said something kind to someone I never saw again. He overdosed that same night.

Another song smells like sunscreen and sweat, and somehow takes me right back to that outdoor show in Salt Lake City, where a lyric made a stranger beside me cry, and I didn’t know whether to say something or just let it be sacred.

Because that’s what music does when you’re really listening.

It turns memory into muscle.
It bypasses explanation and dives straight into embodiment.

You don’t remember the facts — you remember the feeling.

  • The inhale that came too fast
  • The tear that blinked before you could catch it
  • The lyric that felt like it knew your name

And sometimes, on these flights, I wonder if the people around me can hear it too — not the song, but the ache behind it.

  • The way my eyes close tighter on the bridge
  • The way I press pause before the final verse
  • The way I turn my head toward the window like it’s a shield

It’s strange — how music knows the doors you’ve locked and still finds the key.

I’ve written entire emotional timelines in my Notes app, just tracking what came up with which track.

  • Sometimes I’m 8 years old again, hiding behind the couch during an argument I wasn’t supposed to hear.
  • Sometimes I’m 21 and sitting in the driveway with the car running, too ashamed to go back inside.
  • Sometimes I’m just… this version of me, older and exhausted, praying to whoever’s listening that the people I love know it.

And the soundtrack? It doesn’t judge.
It just plays.

The Cities I Never Tasted

There are cities I’ve technically “been to” that I couldn’t find on a map.

New Orleans broke me once. Not because of what happened. But because nothing did.

I was there for a show. I guarded the doors. I kept people safe. But I didn’t dance. I didn’t laugh. I didn’t live.

And that plane ride out of Louisiana? That’s when I cried for all the places I’ve ghosted.

I wrote about this in The Front Row in My Own Story. How we confuse proximity with presence. How you can live just outside the magic and start believing that’s enough.

But it’s not.
And the air reminds me.

There was a night in Portland when I could hear the city calling me. Not in some metaphorical way. Literally — street musicians on the corner, laughter echoing off the bricks, a jazz bar tucked under the glow of an old neon sign. It was all there, waiting to be stepped into.

But I didn’t.

I sat on a folding chair backstage eating a protein bar and scrolling hotel reviews, wondering which one had the quietest air conditioning.

I wasn’t tired. Not really.
I was disconnected.

Like I’d built a life that touched everything but didn’t taste anything.

I’ve seen sunrises in Cincinnati, but only through tinted windows.

I’ve walked through Times Square in a black hoodie, head down, not because I was famous — but because I was invisible.

I’ve stood on rooftops in Nashville with some of the most talented people in the world and felt lonelier than I ever did alone.

And I know that sounds dramatic. But if you’ve ever lived a life of utility — of being useful but unseen — you know what I mean.

You start to lose track of who you are when you’re not needed.

There was a moment once — after a festival in Chicago — where I walked past a wedding on the hotel lawn. Everyone was dancing. Shoes off. Laughing like they meant it. Some guy in a wrinkled dress shirt singing “Tiny Dancer” into a beer bottle like it was gospel.

And I just stood there, behind the hedge, watching. Not out of envy. Not even regret. But a kind of quiet grief.

The grief of witnessing a life you haven’t allowed yourself to want.
A life that doesn’t require a lanyard to belong.

I’ve lost count of how many cities I’ve technically visited. But I remember the ones that made me feel something.

The corner in Seattle where someone handed me a warm coffee and didn’t ask what I did for a living.

The quiet bookstore in Austin where I read the first two pages of a novel I never bought and still think about.

The night in Atlanta when I walked past a blues bar and stopped, just for five minutes, to listen.

That music? It cracked something open.

Because it didn’t need me to do anything.
It just needed me to be there.

And maybe that’s what I’ve been missing all along.

Not just the flavors and the sights.
But the stillness. The belonging. The being.

Finally Sitting Front Row

Most of my life, I’ve stood just outside the spotlight.

But when I fly? I’m not backstage. I’m not anyone’s fixer.

I’m the guy with the playlist, the window seat, and the tears I’ve been holding in since Albuquerque.

This is what I meant in The Cry That Keeps Me Whole — when I said that tears aren’t breakdowns. They’re evidence that we’re still tender. Still reachable. Still here.

And I don’t know about you, but I’d rather cry mid-flight than lose my softness on the ground.

When you’ve spent years keeping your head on a swivel, you forget what it’s like to look inward. You memorize everyone else’s entry points and escape plans, but you lose track of your own.

Your needs become background noise.
Your feelings get rerouted — a flight perpetually delayed, never canceled, just pushed back to a later, more convenient time that never comes.

So when I sit on that plane — no matter how cramped or delayed or half-lit — it feels like the only space in the world that doesn’t demand anything from me but presence.

  • No itinerary.
  • No earpiece.
  • No responsibility tethered to someone else’s emergency.

Just me.

Not the protector.
Not the plan.
Not the anchor for everyone else’s storm.

Just… the man I forgot I was becoming.

I’ve spent years holding other people’s moments.

Moments of joy.
Moments of crisis.
Moments of transformation and tenderness and televised triumph.

And I was proud to do it. Still am.

But the thing about holding space for others is… you start to shrink yours.

You start believing that bearing witness is enough.
That proximity to the sacred makes you part of it.
That showing up for other people means you’re showing up for yourself too.

But it doesn’t always work that way.

Sometimes it just leaves you feeling like the ghost of your own story. Like you’re in every picture — but always blurry, always off to the side, always holding someone else’s coat.

That’s why I cherish these flights.

Because up here, no one’s asking me to be anything but honest. No one’s watching to see if I’ll flinch. No one’s checking if I’ve got the right answers, the right posture, the right awareness at all times.

I get to be uncertain.
I get to be cracked open.
I get to miss people I’m not supposed to miss and dream about things I’ve convinced myself I’m too old or too tired or too something to want.

And that front row seat?

It’s not about luxury.
It’s not about status.
It’s not about being seen by the world.

It’s about seeing myself.

Really seeing.

The grief. The joy. The loneliness that doesn’t always feel lonely. The tenderness that survived the armor.

I used to think I had to earn the right to sit front row in my own life. Had to protect everyone else’s show first. Had to be strong. Had to be quiet. Had to be needed.

But now I think maybe the seat’s always been there.

Waiting.
Window open.
Tray table down.
Space made.

All I had to do was claim it.

And I’m claiming it now. Not perfectly. Not every time. But more often.

Because there’s music playing.
And a story unfolding.
And I’ve got a seat — finally — with my name on it.

And Maybe You Do Too

Maybe you’re reading this in gate B24 right now. Maybe you’re in the middle of your own unspoken grief.

If so — welcome.

You’re not alone in the sky.
You never were.

Just like I wrote in The Ones We Let Go Of, healing isn’t linear. It’s melodic.

So let it come.
Let the lyric land.
Let the ache breathe.

You don’t need a reason to cry up here.
You just need the courage not to stop it.

Maybe the heartbreak that’s pressing on your ribs tonight isn’t the kind you can explain to your friends over drinks. Maybe it’s the quiet kind — the slow-dripping ache that nobody notices because you’re still showing up, still smiling, still forwarding memes and answering texts and asking how they’re doing.

Maybe your grief isn’t loud.
Maybe it’s polite.
Well-dressed.
Under control.

And maybe — just maybe — that’s why it’s so dangerous.

Because it’s easy to ignore what doesn’t scream.

But let me tell you something: There’s no bravery in pretending you’re fine when your soul is unraveling beneath the surface. There’s only delay.

And you deserve more than delay.

Maybe you’re sitting in your car right now — parked outside the apartment you no longer feel at home in — scrolling this on your phone, just trying to make it to bedtime without crying in front of someone who wouldn’t understand.

Or maybe you’re mid-air, same as me.

Hood up.
Song playing.
Flight attendants whispering about the weather.

And that lyric — the one you’ve always skipped — lands differently this time.

Suddenly you’re not in row 22. You’re back on that porch. Back in that driveway. Back at that birthday party you didn’t know would be the last one with them.

And the ache isn’t nostalgic — it’s cellular.
It’s not “remember when…”
It’s “I never got to say…”

And that’s okay, too.

Maybe you’re in between relationships. In between jobs. In between identities. Or in between versions of yourself — the one they knew and the one you’re still becoming.

And you don’t quite recognize your reflection anymore, but you know enough to trust the ache is telling you something true.

Here’s what I believe:

Crying isn’t the sign that something’s wrong.
It’s the sign that something matters.

That you’ve lived.
That you’ve loved.
That there’s still tenderness under the armor.

And no matter how high you fly, how far you run, or how much you try to keep it together — that tenderness is the most sacred part of you.

So protect it.

Not by hiding it.
But by honoring it.

You’re not too sensitive.
You’re not too emotional.
You’re not weak for missing them.

You’re human.

And being human — fully, messily, beautifully human — is a privilege not everyone gets to keep.

So if your tears come quietly at 36,000 feet or in the middle of a crosswalk or while making coffee before dawn… let them.

They’re not breaking you.
They’re reminding you.

You’re still here.
Still healing.
Still becoming.

And maybe, like me, you’re finally learning that you don’t have to hide the parts of you that feel too much.

Maybe those are the parts the world needs most.

Pack the Bags. Don’t Forget the Tissues.

Writing this emotional independent music blog was never just about tour stops or t-shirt memories.

It’s about truth.

The kind that lives in aisle seat confessions and whispered lyrics.
The kind that finds you somewhere between Baltimore and Tijuana.
The kind that lets a bodyguard drop the armor and just be.

So yes — I cry on airplanes. And I’m not sorry.

Because in that altitude, I remember who I was before the earpiece.
Before the silence became routine.
Before strength became costume.

And if the sky is where I feel most like myself… then maybe I’ll keep booking flights, just to remember.

I’ve started packing differently now.

Not just clothes and chargers.
Not just snacks I probably won’t eat or backup deodorant that always ends up in the hotel trash.

I pack space.

Not physical space.
Emotional space.

  • Room for the memory that will sneak in during turbulence.
  • Room for the lyric that will bring me back to that version of me I swore I outgrew.
  • Room for grace — for the parts of me I still haven’t made peace with.

I pack the tears, too. Because I know they’re coming. Not every flight. But enough to plan for.

I used to pretend it was just the altitude. That my sinuses were acting up. That I must be dehydrated.

But the truth is… I cry because I need to.

Because in the rush of life down below — the work, the worry, the wondering if I’m doing enough — there’s never time.

But up here? There’s nothing but time.

So I make music-for-a-road-trip like lifeboats. I carry songs the way some people carry prayer beads.

I don’t always know what’s going to hit me — a single note, a closing line, a voice that reminds me of someone I lost — but I let it. And I don’t apologize for it anymore.

Because crying isn’t what ruins a trip.
It’s what makes it sacred.
It’s what baptizes the journey in something real.

When I land, I try to carry that softness with me. Not always well. Not always gracefully. But I try.

  • I try to be gentler with the strangers who rush past me at baggage claim.
  • I try to smile at the TSA agent who probably hasn’t been seen all day.
  • I try to call the people I’ve been “meaning to call.”

Because the flight reminded me: There’s no reward for waiting until you’re less tired, more composed, more together. The people who matter just want you real.

So yeah… pack your bags.
But pack the tissues, too.

Not because you’re weak.
But because you’re awake.

Awake to the ache.
Awake to the healing.
Awake to the fact that this strange, brutal, beautiful life is worth feeling all the way through.

Even if it unravels you somewhere over Kansas at 2 a.m.

Catch you in the chaos,
Haha

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Written By Haha Bailey 

Haha Bailey has spent thousands of miles finding himself between verses

Haha Bailey has spent thousands of miles finding himself between verses. His Music Travel Repeat series Backseat Benedictions turns long drives into emotional pilgrimages — where forgiveness hums quietly through the speakers. Listen to The Backseat Benedictions: Music For A Road Trip.