Michael Sebastian

New York

Editor-in-Chief at Esquire

News Director at Hearst

Editor @esquire.

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Articles

The System Doesn’t Feel You, But It’s Listening Anyway

2 weeks ago | medium.com | Michael Sebastian

Dr Michael Sebastian·Subscribe16 min read·--A woman is sitting on the floor, her back against the washing machine, clutching her child’s onesie to her chest. She’s not speaking. Just breathing in heaves, somewhere between sobbing and silence. The caption says: “It’s been a year since he died. I still smell him in the fabric.”The video is 27 seconds long. It has 4.6 million views. People respond with broken hearts and fire emojis.
Street Wisdom

2 weeks ago | medium.com | Michael Sebastian

Dr Michael Sebastian·Follow29 min read·--It’s 6:15 p.m. in a trendy co-working space in Fortitude Valley, Brisbane. Around you, exposed brick walls and filament bulbs frame a sea of faces, illuminated by the bluish glow of laptop screens. You watch as a young entrepreneur – let’s call her Jess – furiously types on her keyboard. She’s 27, fiercely intelligent, and ambitious. Her espresso, untouched, has long since grown cold.
You’ll Regret This, and That’s the Point

2 weeks ago | medium.com | Michael Sebastian

Dr Michael Sebastian·Follow3 min read·--You’re stuck. Not because you’re lazy. Not because you’re indecisive. You’re stuck because deep down, you think the right choice is out there – the one where no one gets hurt, you don’t lose anything, and your future self gives you a standing ovation. But that choice? It doesn’t exist. Søren Kierkegaard – philosopher, truth-teller, soul surgeon – said it plain: no matter what you do, you’ll regret it. Marry, and you’ll suffer. Stay single, and you’ll suffer.
The Lie of Freedom

2 weeks ago | medium.com | Michael Sebastian

Dr Michael Sebastian·Follow3 min read·--You think you’re free. You wake up, go to work, come home, stream some distraction, sleep, repeat. You pick your coffee, your phone case, your political opinion. You believe freedom is having options. But deep down, you feel stuck. Trapped in a loop. Like life’s happening around you, and you’re just getting through it. And that’s not entirely your fault. Most of us were taught freedom was the absence of rules, the ability to choose what we want. But real freedom?
The Lie of Smallness

3 weeks ago | medium.com | Michael Sebastian

Dr Michael Sebastian·Follow3 min read·--You’ve been fed a story your whole life: that you’re just one person, one body, stuck on one rock in space. That your value is tied to your resume, your body fat percentage, your ability to fit into a routine. Go to school. Get a job. Pay your bills. Smile when it sucks. Die quietly. You know the script. You feel it every time you stare at the ceiling wondering if this is it. That weight? It’s not just exhaustion.
You’ve Been Lied To About Success - Here’s Why You Still Feel Empty

3 weeks ago | medium.com | Michael Sebastian

Dr Michael Sebastian·Follow2 min read·--You did everything they told you to. Went to school. Got the job. Checked all the boxes – mortgage, promotions, meal prepping on Sundays. And yet, you wake up one day, stare at the ceiling, and think, “Is this it?”You’re not broken. You’re not ungrateful. You’re just waking up to the fact that the version of life you were sold doesn’t deliver. Alan Watts called this out decades ago.
You’re Not in Love - You’re Just Not Alone

3 weeks ago | medium.com | Michael Sebastian

Dr Michael Sebastian·Follow3 min read·--You think you’re in love, but really, you’re just afraid of being alone. You’ve got someone who checks a few boxes – maybe they’re attractive, they don’t treat you horribly, and they laugh at the right jokes. But deep down, something’s missing. You feel it. And if you’re honest, you know this thing won’t last. What you’re really chasing isn’t romance. It’s connection. The kind that still means something when the spark fades and the world quiets down.
The Voice in Your Head and the One Who Hears It

1 month ago | medium.com | Michael Sebastian

Dr Michael Sebastian·Follow33 min read·--It’s early morning and a young lawyer named Ashley is getting ready for her first big case. Even before she opens her eyes, a running commentary starts up in her mind. “You should have woken up earlier,” the voice chides. In the bathroom mirror, it gasps: “Look at those circles under your eyes. You’re going to mess this up today.” On the train to court, it’s still with her, analyzing every possible mistake in advance.
The Success You’re Chasing Is What’s Holding You Back

1 month ago | medium.com | Michael Sebastian

Dr Michael Sebastian·Follow3 min read·--You’re tired – not just physically, but existentially. You’re doing everything you’re supposed to do. You’re chasing goals, hitting deadlines, checking the boxes. And yet, something feels… off. You’re not lazy. You’re not lost. You’re just stuck in a loop. You think if you can push a little harder, control a few more variables, maybe then things will finally click. Maybe then you’ll feel the peace, clarity, and freedom you’ve been grinding toward.
The Ache of Potential

1 month ago | medium.com | Michael Sebastian

Dr Michael Sebastian·Follow3 min read·--It creeps in quietly. You’re in a conversation, doing laundry, halfway through a workday – when it hits. That subtle, sinking feeling that something’s off. Life isn’t bad. Nothing’s falling apart. But it’s like you’re living slightly out of tune with yourself. You sense it deeply: you were made for something more. Not in a flashy, “change the world” kind of way – but something that feels more you. More real. More alive. The hardest part?