Morning Meditation: Try Again. Fail Again. Fail Better

A morning meditation with Lloyd Dobler—yes, from Say Anything—all grown up and trying (imperfectly) to become a dissident sorta-guru.

This is a repeatable ~10-minute practice for mornings when you woke up tired, hit snooze too many times, or you’re already commuting to the capitalist timeclock circus.

Built around four “sacred questions” (popularized by Deepak Chopra):
Who am I? What do I want? What is my purpose? What am I grateful for?

Expect breath cues, monkey mind interruptions, cultural critique, and permission to meditate badly—because not all of us can disappear to a silent retreat with catered vegan breakfast and hot rock massage lunch.

Try again. Fail again. Fail better.
From the edge of empire and the center of self—this is The Tao of Lloyd.

Transcript

My name is Lloyd Dobler, and this is a morning meditation you can come back to whenever it actually helps.

[Bell chime, meditative music]

Get comfortable.
Find yourself sitting in the lotus position.
Or in a chair—
or lying in your bed after hitting snooze for the third time
or MAYBE you’re late to work already and you need to pop this on while you commute to that soul sucking capitalist timeclock circus you call a job.
Wherever you are.
Get comfortable.

Close your eyes and start the journey within.
…Or don’t.
I’m not here to turn waking up into some of middle management performance review.
But really, unless you are unredacting the Epstein files or finally organizing your mismatched Tupperware container drawer- both things which just might just take priority over the invitation to meditate with Lloyd fucking Dobler, then why don’t you just close your eyes to start the journey within. 

Let’s start with what we have in common.

Today, we woke up.

A lot of people did not wake up today.
So it goes.

You’re still here.

And that’s enough to try again.
To fail again. 
To fail better. 
And yes, I just stole from Becket and Vonnegut and I’m about to ask you four sacred questions popularized by Deepak Chopra. Do you want to clock my fucking footnotes here, or do you want some meditation practice?

Okay. 

About those four sacred questions. 
I’ll lead you through them, one by one, and your only job is to repeat them silently in your head, like a little mantra. 

Your mind will wander
this is normal
we call this monkey mind
and I’ll be right there with you,
In fact, I’ll give voice to my monkey mind. 
My stray thoughts. 

Unorthodox meditation protocol you say?
Maybe. But maybe we have to practice keeping calm in the eye of the storm. Not all of us can afford a three-day silent retreat in the Berkshires with catered vegan breakfasts and hot rock massage lunches. Some of us need to navigate the shit storm of Trumplandia sloshing through the gig economy door dashing chicken McNuggets to rich teenagers at a boarding school.

so with that, take a long, slow, deep breath in through the nose
and let it go
breathe out like you’re trying to keep warm in the chill of a dying democracy

And keep breathing in; breathing out.

First question.
Who am I? or What am I?
keep silently repeating that as a mantra: Who am I? or What am I?

I am… a middle-aged mixtape with opinions.
I am an unpaid intern in my own life, hoping this eventually turns into something with benefits.
I am trapped somewhere in the aspic of your nostalgia, still holding up a boom box outside Diane Court’s window?

I am—
okay, wow, that’s a lot of metaphors.
Right.
That’s not an answer.
That’s a performance.
I’ll do better next question.

Second question:
What do I want? What do I want?
Keep silently repeating that: What do I want?

I want a new class war
where we take back
what the billionaires stole from us.

I want a good cup of drip coffee
Hot.
Strong.
Reliable.

I want an end to the genocide in Gaza.

I want my hamstrings to be as flexible as they were in my twenties.

I want one day where my inbox doesn’t feel like a threat assessment.

And I want universal healthcare
so nobody has to decide
whether to ignore a pain
or risk financial ruin.

And I want my kids—
and your kids—
and the kids we haven’t met yet
to inherit something better than a Mad Max future.

I want the impossible to seem inevitable. 

And you keep silently repeating: What do I want? What do I want?

Third question:
What is my purpose?
and you keep silently repeating to yourself: What is my purpose?

I used to think my purpose had to be big.
Visible.
History Book material.

Like make the one piece of quote content unquote that would topple the pillars of the evil empire. 

But quote content unquote is entwined with those pillars, isn’t it?

I know purpose is supposed to feel like a mission
or just something you keep doing
even when no one’s watching
and it’s not trending
and it doesn’t scale.

Yeah.
This question scares me a little

I mean, I’ve lived a life of relative privilege into my mid-fifties. Shouldn’t I have an answer to this question?

Lloyd repeats:
What is my purpose? 
What is your purpose?

Final qustion:
What am I grateful for?

Lloyd monkey mind #4 (koan):
I’m grateful for this opportunity—
to try again.
to fail again.
to fail better.

[Soft inhale / exhale cue]

Take a slow breath in.
And as you exhale,
let all of the questions
let all of the answers
yours and mine, let them all go, and let the universe sort it out for itself.

[Bell chimes]

You can open your eyes.

Take whatever surfaced —
and turn it into an intention.

Then take that intention out into the world today and throw it like a Molotov cocktail at the Overton Window. The Overton window is the cage that decides which thoughts get called “reasonable” and which ones get called “crazy”—and history only changes when someone rattles the bars.
What if you are that someone?
what if we are that someone?

Go on now.
Then try again.
Fail again.
Fail better.

And come back here tomorrow. I’ll be here. 

From the edge of empire
and the center of self—
this is The Tao of Lloyd.