Boulevard of Broken Dreams' Analysis

Alleviating lifelong suffering through a single dream

Hellooo Life Examiners,

I’m coming off a men’s retreat last weekend with a bunch of dudes where we do hard physical labor then talk about our feelings, beat each other up then open up emotionally, you know, that kind of macho masculine energy married with that grounded, embodied man willing to be vulnerable.

I can’t stress enough the importance of this kind of work. I think everyone should spend 1 week out of the year away from their normal life in an intentional setting focused on themselves (very different from a vacation).

But what surprised me most was that the most impactful moment came when I wasn’t even awake…

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I wake up from a vivid dream. It’s one I’ve had hundreds of times before, differing in setting but always ending the same way.

I’m doing whatever it is I do in my dreams, usually with intent to go somewhere. This time I’m in a hotel, waiting outside the elevator with anxious anticipation as I’m late for a flight. The door finally opens and I take a step when I run into something. An invisible barrier prevents me from moving forward. Everyone around me is unphased by it, continuing as normal, while I can’t move a single inch ahead.

I try to dig my heels in, with every ounce of strength I labor to push through to no avail.

Trapped in this stasis I know this force is impenetrable, yet even so, I try and I try.

It’s frustrating. Fear-inducing. Paralyzing.

Normally I wake up with an elevated heart rate and a sense of dread. But this time I’m alert, full of energy that I sense has a purpose. Before I even have a chance to process being awake, my journal and pen are in my hand as I’m heading to the roof of this retreat center in Vieques to sort out this recent illumination.

I’ve made a connection between the dream and my life. It feels disingenuous to call it a metaphor because the association is so strong it feels more like a literal manifestation of the most persistent form of suffering I’ve experienced in my life.

For years I’ve grappled with the idealized version of myself that shows up entirely authentically, uninhibited by external pressures, able to express myself freely, but feeling blocked. Feeling like I need to think through how to do it, feeling like there’s a right way and I need to figure it out, feeling like there’s repercussions for not doing it the right way, feeling like I’m different from everyone else, like every other human on earth is in on how to do things the right way while I’m alone on this island scouring to find a way off.

I’ve been trying to brute force my way through it. Pushing through despite the intense resistance. Yet time and time again, I’m left stuck in this frozen state, dejected and despaired.

As I’m watching the sun rise over this picturesque Caribbean island I realize this barrier has been my greatest gift. It’s what has shaped my entire lifestyle. It’s why I’ve spent so much time meticulously designing it, critically analyzing my present state, getting clear on who I am and what I want. It pushed me to take radical action with my job early on, it’s what led me to leave NYC for a more aligned life in Puerto Rico. It’s what guided me towards writing to further understand why I feel these things, what I can do about it, and how to share those learnings with the world.

That said, I can’t just give up and let the barrier win. I still need to get on that elevator. I have a flight to catch and digging in my heels any more won’t get me there.

So what happens if I stop struggling, ceasing any further efforts to break through and instead recognize I’m dreaming? If I’m dreaming then that means I’m in complete control. I’m the architect who designed this dream world, therefore, I can dictate what happens next. If I want to talk forward, I can walk forward. If I want to fly out the window, I can fly out the window.

This doesn’t just apply to my dream. It applies to my reality, which I’m realizing is a lot like my dreams. The barriers in my life I construct have little to do with objective reality, they’re not tangible walls in front of me impeding my progress.

The story I tell myself about why I shouldn’t compliment that cute girl at the park, the perceived backlash from my boss if I ask for a raise or the awkwardness from telling my best friend a harsh reality they need to hear - none of that is real. They’re simply invisible barriers that I created.

I can try to brute force my way through them. But it will be a lot easier if I just realize I’m dreaming and watch them dissipate.

In Hindu philosophy, there’s this idea maya, or cosmic delusion that shrouds the ultimate higher truth. The Toltecs have mitote, the internal mind chatter that clouds our thinking and judgment. What these ancient traditions recognized was that much of what we experience is illusory in nature, not fundamentally grounded in reality. By viewing it as such, it’s possible to transcend the restrictive confines of the mind and live a freer life.

It’s only been a week since this sunrise epiphany and yet there have been countless times when I sense a desire to do something but feel held back, I hear the inner voice whispering excuses, I feel the barriers starting to form, and I pause, reminding myself I’m starting to dream, and I watch it dissipate as I seamlessly continue through the day.

Thought of the Day

I can’t believe I just found out about

Ted Gioia

. I want to pause time for a year and read everything he’s put out. Fascinating guy.

From his State of Culture 2024

The tech platforms aren’t like the Medici in Florence, or those other rich patrons of the arts. They don’t want to find the next Michelangelo or Mozart. They want to create a world of junkies—because they will be the dealers. Addiction is the goal.