You Shouldn’t. You Will: Thrill, Crash, Regret, Repeat… Release
There’s a feeling I want to talk about.
It’s subtle, but once you spot it, you can’t unsee it. A tightening in the chest. A whitening flash behind the eyes. A flicker of electricity that whispers:
You shouldn’t.
And right on its heels, almost overlapping:
But I will.
That’s recklessness.
Not risk. Risk is calculated. Risk involves weighing the odds and making a choice. Risk says: I understand the stakes, and I leap anyway.
Recklessness doesn’t weigh. It lunges.
It says: Screw the odds—I want the feeling.
It’s the half-second rebellion. The dopamine-drenched dare. A thrill for the sake of the thrill.
It’s the moment you go all in… on a bluff.
The Glass Bottle
Not long ago, Louis and I were out with Obi on one of our favorite trails—the one we call the Mountain Laurel Trail. A sacred little stretch a Goffstown friend told us about years ago: dappled sunlight, rustling pines, birdsong, and that hushed hug of the forest. We walk there to breathe. To reset. Sometimes, to swim across the watering hole, past the old rope swing and back.
That day, somewhere along the path, I spotted a discarded Smuttynose bottle—glass, brown, out of place. I picked it up. Litter triggers something in me, some deep desire to restore order, so I grabbed it without thinking.
“Just toss it,” Louis said—meaning, off-trail, out of sight, no big deal.
Now, I knew he didn’t mean smash it. But in that split second, seizing his patriarchal permission slip and waving it like Ron Swanson gif, something twisted in my chest. I knew I shouldn’t. I knew it would shatter.
And I wanted to anyway.
I wanted to smash that fucking bottle.
Not to litter. But to destroy. To hear that sharp, satisfying crack. To break something. For the giddy, childish, naughty joy of it.
I held both thoughts in my head like live wires:
“I shouldn’t.”
“I will.”
And before either voice could win, my arm had already flung it at the rock that juts out beside the pond.
The bottle shattered—loud, final, violent. Louis flinched and pulled Obi’s leash close. I felt the rush.
Then the shame.
That’s it. That’s recklessness.
The split-second where your higher self stands by, mouth agape, while your shadow self dances gleefully on the shards. I want you to notice that feeling. Because once you can name it, you can do something about it.
Legal Recklessness
The Romans had a name for it: temeritas. Acting without regard for the consequences. Not ignorance. Not malice. Just… carelessness cloaked in desire.
In American law, recklessness lives in a similar gray zone. It’s not quite intent, but it’s a whole lot more than accident. If you act with wanton disregard—for human life, for truth, for safety—you cross the line.
It’s the line where free speech becomes defamation. Where an oops becomes a charge. Where “I didn’t mean to” stops being enough.
Legally, recklessness is a choice you could have prevented. And deep down, you knew it.
Which makes it personal. Moral. And hard as hell to face.
Because if you admit you’re reckless, you have to ask: Does that make me cruel? Or just careless? Or maybe something worse… like empty?
Childhood Loops and Landmines
For some of us, recklessness isn’t rebellion—it’s adaptation.
If you grew up in chaos—where rules changed daily, where love came with strings, where discipline dropped from the sky like a surprise anvil—you might have learned to leap before looking.
“I’m going to get in trouble anyway…”
“…so I might as well.”
That logic becomes a loop. A weird kind of safety. A preemptive strike against punishment. You light the match before they can burn you.
And then… it becomes addictive.
Not always to substances—sometimes to chaos. To the surge. To the flash of being bad. To the little hit of dopamine that says: you did something.
The sugar. The cookie. The angry comment. The smashed bottle.
The narrative you build afterward to justify it.
Before I got sober, I was stuck in that loop. Not just with booze, but with everything. I negotiated and renegotiated with myself constantly:
Eat the thing.
Say the thing.
Buy the thing.
Burn the bridge.
I told myself it was freedom. It wasn’t.
It was compulsion cosplaying as choice.
The Gift of Clarity
Quitting alcohol didn’t erase the impulses. It exposed them.
Sobriety handed me clarity. And clarity gave me space. And in that space, I started to see the split.
The leap-before-looking reflex. The flinch disguised as boldness.
I could finally say: Ah. There you are again.
Now, I rarely negotiate with myself. Not because I’m perfect—but because I’m mostly aligned. My thoughts, words, and actions hum in tune.
And when they don’t? Oh, I feel it.
I feel the old circuitry start to warm up. The craving. The itch. That familiar moment when chaos puts on a sexy little outfit and calls herself fun.
But now I can choose.
I can still throw the bottle—but I know which part of me is reaching for it.
Learn the Pause
This is what I want you to take from all of this:
If you find yourself constantly bargaining with yourself—
“Just this once.”
“It’s not that bad.”
“I’ll be good tomorrow.”
—pay attention. That’s not freedom. That’s a loop.
That’s the signal.
Start tracking that flash. That greedy thrill. That moment of reckless glee right before the regret.
If you can pause there—just for a breath—you can change everything.
You can become someone who stops, then acts.
Someone who chooses, not chases.
Someone who lives in alignment… instead of aftermath.
Because real freedom isn’t doing whatever you want.
It’s wanting what you do.
And waking up without having to explain yourself to yourself.
Because you know—and I know—the worst loop is when you don’t even agree with you.
Is it true that Sinead o’Connor’s “Nothing Compares to You” (which I believe was a Prince song?) was directed at her mother, i.e. that she saw it as a song about the mother wound–her mother had thrown her out of the house?–rather than a romantic song. I recall hearing that in a clip but not sure I’m remembering correctly
Yes, you’re recalling correctly, though the story is nuanced. Sinéad O’Connor’s “Nothing Compares 2 U,” written by Prince, was interpreted by O’Connor as deeply personal and tied to her relationship with her mother, Marie O’Connor, rather than solely a romantic song. In interviews, Sinéad explained that the song resonated with her due to the profound loss and pain she felt after her mother’s death in a car accident in 1985, when Sinéad was 18. She had a tumultuous relationship with her mother, marked by abuse and being thrown out of the house at a young age, which contributed to her sense of a “mother wound.” In a 1990 interview with *Rolling Stone*, Sinéad said the song was about her mother, specifically the void left by her death and the complex emotions tied to their relationship. She felt the lyrics captured her grief and unresolved feelings, beyond the romantic context Prince originally intended. While the song’s lyrics are framed as a love song, O’Connor’s raw emotional delivery and her personal interpretation shifted its meaning toward her experience of maternal loss and trauma. So, while the song is a Prince composition about romantic love, Sinéad’s performance and perspective imbued it with a deeper, personal layer tied to her mother. Your memory of the clip aligns with this narrative she shared publicly.
Nothing Compares to You (Even If I Told Myself It Did)
My mom died in late February. I haven’t said that out loud much, because the sentence feels… unfinished. Like a placeholder. Like I’m just repeating what the timeline demands, not what the soul knows.
Because the truth is: Ma (and Pa) kinda died for me when I was ten. She just finished in 2025.
When I was ten, I was sent to boarding school. All of us pretending them moving to another continent and leaving us in Africa was No Big Deal. “No crying, m’kay?” “Stiff upper lip, what, what.” Just me, in my old school’s uniform, blinking in the sunlight. “Don’t watch them leave,” my sister had warned me. “It makes it worse.” So I didn’t. I turned and walked into the brick building, head hung, but thinking, You’ll need to pull your shoulders back soon.
The Grumps—The “Grown Ups,” which all the Diplomat Brats shortened to The Grumps—explained it away. “We’ll talk to you on the weekends.” For less than five minutes. And no one knows what to say on such calls when you’re carrying so much abandonment.
“Yes, it’s sunny.”
It’s fucking South Africa, Pa. It’s almost always sunny.
My child-brain filled in the blanks the way children do—eventually settling on: Just think of them like they’re dead.
So I did.
(My sister did too.)
(Figuring out how you were still speaking to your dead parents every other week is another essay.)
At sixteen, with the whole family living together for the first time in four years, Ma had a stroke while packing to move to Rio de Janeiro.
I.e., they were leaving again.
And this time, my sister and I would share an apartment in Sunnyside while we attended the University of Pretoria.
Like real Grumps.
Paralyzed on her left side. Unable to walk, talk, or smoke anymore.
They still left.
“She’ll get great treatment in Rio.” And, through pure perseverance, she did indeed learn to walk and talk again. She was still there—but sideways. But also, thankfully, with her incredible sense of humor intact. To the end, the spark in her eyes remained, like everyone in her presence was permanently sharing a joke. And truly, if the joke is life, we were.
When she died this year—after the ailing health, the falls, the forgetting, the shoulder hanging too far from its socket—I didn’t fall apart.
I reassured my sister and father. I booked the flight. I cried while delivering her obituary at the memorial.
I wore the “looks good but is also comfortable during all times of the month” black dress—the one every woman owns.
The one I was wearing again months later, for the same reason, my period on the road (a literal curse in my life, meaning I couldn’t wear the outfit I actually wanted. Of course).
This time, I was at the Ron Paul 90th birthday bash in Texas, with a large Free Stater contingent sharing Airbnbs and rental cars.
Grief is a shapeshifter.
There I was, in a convention center full of celebritarians and free-marketeers, talking to Keith Knight—not making small talk, because we don’t do that.
Keith and I bonded years ago over quitting carbs and reclaiming our bodies.
Our conversations are always meat and no potatoes. No filler. Just truth.
And that day, the truth ambushed me.
I was trying to explain something—how the bond between me and my mom had stretched too thin when I was sent away to boarding school as a child. How then after, the stroke had changed her. How I had built a scaffolding around all of that so I could function. And suddenly, I was about to cry. Just—a couple of tears. Raw, uninvited. The kind that makes other people pretend they didn’t see.
Later, we were driving back to the Airbnb—Jason Sorens was behind the wheel, his wife Olga up front. I was in the back, riding shotgun to my own emotional unraveling, surrounded by volunteers half my age, like a kid again. Not in charge. Not in the driver’s seat.
And that’s when it happened.
Sinead came on the radio.
Nothing Compares 2 U.
Now, I had always filed that song under “first heartbreak”—Stephan, final year of ‘Varsity, who left me for a prettier blonde (who, by the way, is now fatter than me—sorry, transcending the pettiness of being dumped is beyond my capabilities). I used to play it in my room, wallowing. Thought it was about romantic loss. Melodrama and melancholy. First love’s broken heart. The hardest part.
But I had seen a clip years ago—Sinead saying the song was really about her mom. About the wound. About being thrown out. Exiled. About her mother dying in a car crash before they could heal. About that hollow ache that follows you, even when you’re thriving.
And in the backseat of that car in Texas, her voice cracked open something in me. The lyrics shifted. The context clicked.
This wasn’t about boyfriends.
This was about mothers who left and mothers who stayed broken.
This was about the grief I’d been too strong, too resilient, too busy to feel.
Nothing compares.
Nothing compares to you.
Like in her iconic video, a single tear slipped down my cheek. I swallowed hard.
Then I saw a seagull. And remembered not to be sad.
Because, in that moment she died—and that bird landed, framed in the window I was staring out of—I decided something.
I decided I would no longer miss her like she’s alive but dead.
I already did that, for too long.
What I choose to feel now is something else.
Something closer to… loving her like she is alive around me. Because I decided, as I gazed at that bird, to see her—everywhere.
In all the birds.
In New Hampshire, I walk in the woods every day. That’s my church.
And there, on my path, she appears. A flash of wings. A silhouette in a pine. A call I recognize in my heart.
I see her in cardinals, in blue jays, in herons with their long necks and better posture.
I see her and I smile.
I choose to see her.
And in that choice, something softened.
Maybe it’s forgiveness.
Maybe it’s grace.
Maybe it’s that she’s finally free of her handicaps, her body’s betrayals, her decades of pretending everything was fine.
Maybe that pretending destroyed her soul in ways I never understood—until now, as I grow into my own womanhood and feel how heavy that mask can be.
So, no. I didn’t fall apart when my mother died.
But I did drop a tear at a libertarian conference.
I did remember the girl I was: How alone.
And, for that, I let Sinead sing me home.
In that moment, I understood something that took this whole lifetime to learn:
Nothing compares to the mother you lost before you ever had a chance to love her whole.
But nothing compares to the woman you become when you stop needing her to be anything other than what she was: half-whole, but now, forever streaking across the sky.