Starting Over With Nothing: When Staying Becomes More Dangerous Than Leaving

It started with a text about snow that made the sweat on my brown run cold in an instant.

I was mid-shift full sprint at the nightclub, working my second job after already putting in hours at the factory my cousin managed all week. Chicago winter had unleashed a plan to dump several inches, and it was already coming by the time I was getting ready to leave a few hours earlier. I'd planned to shovel in the morning, or later that night when I got home to his basement where I'd been crashing for a few months.

The text came through around transition from dinner to party on the floor: "Why haven't you shoveled?"

Blasphemy of the highest effin' order

Not "Hey, can you handle the driveway when you get back?" Not "When you get a chance." Just blunt accusation wrapped in a question mark.

I stared at my phone between orders and hot plates, trying to formulate a response that wouldn't escalate things. Before I could even understand what was going on, another message. Then another. Each one angrier, more disrespectful, spiraling into the kind of unhinged energy that makes you realize someone's been waiting for an excuse.

I left him on read and did what I had to to wrap my shift. I dropped 2 pieces of glassware and bumped into a guest that night. Slept at my girlfriends place.

The next morning, I called him. Same energy. I worked to begin explaining myself; calmly, rationally, the way you do when you're trying to keep the peace in a situation where you have no leverage. He quadrupled down. The disrespect wasn't an accident.

It was the point.

That's when I knew: staying had become more dangerous than leaving.

The First Wake-Up

I'd been on autopilot since arriving in Chicago. Summer 2021, fresh out of the Marine Corps, convinced by family that moving back home was the smart play in the wake of a recovering world. They'd help me get back on my feet, they said. There was an apartment my cousin was renovating, they said.

What they didn't say: the apartment wasn't ready. What they didn't say: there was no gorydamn plan at all.

I left my job in New York, my apartment, my friends. Used my credit card to fund the move. Showed up to find my cousin's basement instead of the promised renovated apartment.

But I made it work. That's what you do, right? You adapt. You overcome. I got the factory job through my cousin. Added the nightclub gig when the factory pay wasn't enough. Started dating someone. Kept my head down, my backwoods rolled, and I set in to grind through it.

Until that night.

Until the snow shovel text woke me up to what I'd actually been doing: surviving in a space that was never meant for me, waiting for conditions to improve in a space where such was impossible.

I moved out the same day, and onward. My mother's living room, third floor of my grandparents' building. Not ideal, but better than a basement where I'd outstayed a welcome I never actually had.

The Loop

It's 2022. I quit the factory job after a coworker attempted to escalate an argument into violence. Been building a while, but fight club rules are different when the uniform you're wearing isn't government-issued. Walked out mid-shift. Proudly. Dropped my tools, collected my things. Heard my manager shouting for me to stop and come back. Didn't.

I had my gig at The Vig, my wits, and my laptop. "All you have is all you need" says Marcus Taylor, so I started planning. Working in a place like the Vig also has a way of making you want to make more money. I too, wanted to have "My Cut".

No. 2 on my Top 3 Most Impactful Jobs Ever List: The Vig Chicago

The offers came in once I put my skillset out there. Sales positions, good money, the kind of opportunities most people would jump at. But the more I thought about it, the more I realized I didn't want another structured job. I liked the chaos of nightlife because it wasn't really a career, it was just a wild, seductive, survival mechanism that gave me (desperately needed) space to think...and relieve stress...

What I actually wanted was to build something of my own.

So I pulled from every piece of experience and knowledge I'd ever gained and started planning what would one day become the Legion v1 model of My Digital Empire. Business books. Educational YouTube. Goals, graphs, and game plans. Every hour I wasn't at the club, I was glued to a screen, slaving dutifully over a hot keyboard.

The relationship ended when my girlfriend got pissed off about an ALUX podcast episode I was listening to; some such about harsh truths low value people need to hear. I found that episode truly impactful, and it literally helped me rewrite the entire basis and operating system to my life.

That breakup was another wake-up call. I'd been operating on autopilot in my romantic life too. Random inputs, random outputs. I needed to become the kind of man the woman I wanted would actually want to be with.

Then my car got repossessed, which gave me more time to notice the building I was living in was falling apart. I discovered my mother had no retirement plan. None. Just "I'll retire in a few years" with no money saved and no strategy beyond working until her body gave out.

So I got to work trying to fix that too.

Captain Sayvohoh, at service! o7

Imagine a clown emoji right ^ yonder

The Attempt

My mother used to send daily emails to massive friend groups; her scripture devotionals were also typed out and launched out in unruly text groups. Little messages of encouragement. I pitched her a blog. She was receptive at first, then resistant. We switched to newsletters. She became defiant.

"I don't understand how technology works," she'd say, while spending hours on YouTube and the phone talking to everyone about everything except this one thing that could actually help her.

It's 2023. My grandparents are declining both mentally and physically. My uncle lives on the first floor of their building. He has a roommate. Neither of them could be bothered to walk upstairs and make brekkie for the old folks, and especially not sit with them for a while.

"absolutely not", was the exact phrase used, actually.

So my mother and I did it. Multiple times a week, we'd drive over with food, spend time with them. We fumigated the place at our own expense when we discovered the bed bugs. I know smooth brain 1 and 2 on the first floor knew about it, but accusation without proof or whatever it is they go on about in "courts of law".

I was going insane

Then my grandmother got violent. Started calling me out of my name, attacking me with full intent to harm. That's where my physical displays of love stop. When someone tries to hurt me, I can only do so much to prevent the literal muscle memory that's been ruthlessly drilled and trained into me. She was never really a grandmother to me anyway. She mothered the man who adopted and abandoned me. As far as I'm concerned, that line can end.

But my grandfather came with us. We smoked together back when that was the favored pastime. He'd laugh at movies while I worked on my laptop and my mother was on the phone in her room. He'd sleep while she repeated, over and over, that she simply couldn't understand "the speed of technology these days."

I'd cry, alone, in my basement apartment.

We'd been having the same argument from the beginning:

"You need a retirement plan."

"I'll retire in a few years."

"How much money do you have saved?"

"A little chunk..."

"Enough to last at least 10 years?"

"Well..."

"This can be your retirement plan. The blog, the newsletter can be a means of income; you're already doing this for free. Just monetize it."

"I don't understand how this works."

Round and round. She could watch YouTube all day, talk on the phone about every topic under the sun, but couldn't...mayhaps wouldn't...learn this one thing that could actually change her situation.

The Breaking Point

By March 2024, I woke up to the fact that I'd been in the same spot for years. To my absolute horror, I was actually getting fat. Using substances to cope. Trapped in an inescapable loop, circumnavigating the same problems endlessly until I started spiraling into the darkness of nihilism.

There was lashing out. A binging bender. Explosive outbursts. A lot of crying. And finally, what I call an "environmentally forced total mental collapse and hard reboot."

My mother had started avoiding me entirely. Not even acknowledging my presence in the room. The core of the argument that finally broke me isn't for public consumption, but the flavor, was lack of accountability.

She'd told me multiple times to "just go live your life and not worry about her, because she'd figure it out."

"How can I be content knowing you're struggling?"

"I'm not struggling."

"Look around. You have no plan. No savings. What happens when you can't work anymore? You literally can't even afford this place by yourself."

"I'll be alright."

Misdirection. Avoidance. Mental gymnastics. Gaslighting me into thinking I was the problem, the reason she couldn't move forward. Meanwhile she's struggling to care for my grandfather and refuses to ask for help when it's desperately needed.

This final argument was the same. So I decided to give her what she wanted.

I found La Sirena on Craigslist in California. $4,000. I'd only had positive experiences in California, so why not? It was an impulse decision made of quiet acceptance and born from true desperation, but it felt right in a way nothing had felt right in years.

There was nothing for me in Chicago. Nothing for me anywhere in the States, really. Why should I stay when I felt more at home in Japan during deployment? Why settle in Japan when there's a whole planet out there?

To hell with dying within 50 miles of where you were born. My aim is to not die on the same continent.

I reached out to the owner. We talked on the phone. I broke down and shared everything with this complete stranger, and he prayed for me. Amazingly, wasn't till then that I became Jesus curious.

I told my mother I'd be gone for a few days. The next day, I was on a plane to California with $4,000 scraped together from savings, spartan living, emergency sales, and extremely lucky circumstances. My sales skills from Recruiting weren't "fresh", but they were "timeless". Effort, planning, execution. I was out of the plane at that point, and in controlled freefall toward an entirely new life.

Confacimus Navegemus, yo'

The Escape (And Failure, And Escape Again)

Everything was great for about three days. I reconnected with old friends, one of whom was living on his own sailboat in North Carolina... Then I discovered La Sirena's engine was inoperable.

Rather than figure it out alone in an unfamiliar place, my friend suggested I come to "the right coast" and start over. One more time. For the last time.

I donated La Sirena to a nonprofit charity.

I flew back to Chicago to pack my things for storage. When I arrived at the apartment, on a night I expected my mother to be at work, imagine my absolute state when I found the doors barricaded.

I was in the process of successfully making the door un-barricaded (oorah) when she finally removed the barrier and allowed me entry. I was willing to have a conversation. She wouldn't speak to me like an adult.

So I gathered my affects, and closed that book.

Apartment to storage. Storage to train station. Amtrak to Raleigh, where my friend picked me up and let me crash on his boat until I could buy my own.

In January 2025, I found Matilda on Facebook Marketplace. $4,000. (lol?) Made payments to the previous owner. We're homies now, actually.

I moved aboard in February, and today, this boat is my Home.

What It Cost, What It Gave

I am not in communication with anyone with whom I share a blood or marriage relation. I am not in communication with anyone who I feel did not help me along my journey, or support me in my darkness. I am not in communication with many people who refuse to be honest with themselves as to why that might be. That's the price. The entire bloodline, severed. Countless former relationships, ended in the same silence that I've received over this long and dark night that descended upon my soul.

Some people hear that and think it's tragic.

I think it: Necessary, because I desire a clean slate.

You can't rebuild while standing amongst the wreckage. You can't evolve into someone new while surrounded by people invested in you remaining stagnant.

The basement decision wasn't just about leaving my cousin's house. It was about recognizing that staying anywhere that diminishes you, anywhere that asks you to be smaller, anywhere that punishes you for trying to help...is more dangerous than the uncertainty of leaving.

Remember that you have SURVIVED 100% of all previous experiences that you THOUGHT would take you out of the game ENTIRELY.

I've lived in three places that weren't mine, tried to help people who didn't want help, and burned through every conventional option before accepting that the only way forward was to build my own path entirely.

Now I live on a 31-foot sailboat. I'm enrolled in a boat manufacturing course. I'm building my Internet Thing in public. I have a plan that's mine, a life that's mine, a future that's mine. Come January, I'm setting sail.

It took several lifetimes, three wake-up calls, two failed boats, and one complete mental collapse and reboot to get here.

But I'm here.

And for the first time in years, I'm not on autopilot.

Per Aspera Ad Astra

Through Hardships to The Gorydamn Stars

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This is Week 1 of a 12-week series documenting my journey from the void beneath hell to ground zero just above the pit, and the frameworks that got me here. Next issue: "How to Identify Which Bridges to Burn (A Tactical Guide)" . Next Week: "The System Behind the Chaos" If you're reading this at 2am wondering if starting over is even possible...it is. I am your proof. Don't drift in darkness, build a way out. If you need some inspiration, check out my publishing hub. I believe in you, frfr, yo'.

- Isaac