Starting Over After The Military: How I Became Ronin
- Isaac Lester
- Aug 7
- 5 min read
The only way I can best describe my life is "a series of eventful lifetimes, 4x speed, back to back. I hit some time dilation, and at some point I detached from the mainstream timeline all together. This is more or less, how we got here.
Sometimes life chooses not unfold in neat chapters but to erupt in a blur of lifetimes, each one stacked in rapid succession, each demanding its own reckoning.
The Foundation
My story begins in the inner city of Chicago, where I learned early that survival requires both grit and adaptability. After my adoption, it was just granny, mom, and me. In 2013, I made the decision to enlist, and in November I was born again in the cloth and tradition of the Marine Corps. Over eight years of service across three different units, I discovered discipline, brotherhood, and purpose alongside encountering the weight of deployment, the pain of divorce, and the slow erosion that comes when the world starts looking gray around the edges.
By the end of my contract in 2021, I was operating on alcohol fueled, nicotine fueled autopilot, moving through days that felt more like combat fitness tests than life itself. When I finally removed my uniform for the last time, I sat in my disgrace and the wreckage of everything I thought I knew about myself and the world.
The Drift
What followed was a period I can only describe as necessary chaos. I found work stocking shelves at my favorite liquor store, built a circle of friends who helped me party away the silence, and scraped by huffing cope in a small apartment in upstate NY. I was barely surviving, but I WAS surviving. There are days when weathering the storm is sometimes enough of an amazing and brave accomplishment.
When family convinced me to move back home with promises of stability and support, I thought I was making a smart move. Finally, a chance for Isaac, future Captain of Matilda, to show his quality. Instead, I found myself touring an unlivable apartment, and a family member's basement shortly after. Often I cried while watching my savings evaporate into drinks and smoke as the Chicago winter settled in around my diminishing hope and sanity.
The reality check came with the snow. I found one job, then another, wrestling with those stubborn ends that refused to meet. I transitioned from the basement to my mother's living room, attempting to reposition myself as a boon rather than a burden. Bedbugs and crumbling walls forced us into a larger space, and the costs kept climbing. My grandparents were ailing. Despite countless discussions about moving forward as a family, I felt increasingly invisible.
Here I was, a trained Marine with skills I knew were valuable and the will to move the world after rewriting the heavens given a place to stand, yet unable to create stability in my own life. The shame was crushing. The disconnect between my capabilities and my circumstances felt like a daily reminder that something fundamental within my mind and very being was broken.
The Calling
After four years in Chicago I arrived at a breaking point. Four years of my life had flown by, spent trying to help others move forward while falling further behind myself. More shame.
The air became impossibly thick and I was suddenly baptized in a feverish cold sweat. The mass of emotion boiled in contrast to the ice in my tingling fingers. It descended from my core to the pit of me, before boiling over into grief for the countless versions of myself that I vividly remember so brutally snuffing out in order to force this dream to work.
It came during yet another discussion gone wrong, but this time something different happened. In an instant, like receiving an update directly from the heavens, I realized I was in the wrong place, doing the wrong thing with my life.
Have you ever felt that? That sudden, crystal-clear understanding that you simply *must* completely reposition yourself?
It didn't feel impulsive. It felt right. There is another book of experiences between then and when I eventually found and purchased my sailboat. My 1981 Bangor Punta Cal 31 saved my life, and her name is Matilda. I'd always dreamed of having a large boat someday and traveling with a cohort of found family, and even though I knew absolutely nothing about sailing the idea resurfaced and took permanent root immediately, growing with an urgency that matched my circumstances.
Starting Over | The Ronin
Today, I find myself estranged from family and technically homeless, though I prefer to think of myself as a modern Ronin. My contract has ended and now I am free to wander as I wish with purpose I am free to define and pursue. I have been trained by, served for, and devoted myself to masters who have now released me, and with no home or family to return to in the traditional sense, I drift.
But it's not really drifting when you have a destination in mind.
Not all who wander ... or some such, you know the quote.
As crazy as it sounds to write, let alone say out loud, I've accepted the way of delusional self belief, and I believe I'm destined for great, adventurous purpose. My goal is to circumnavigate the world while sharing my story. I have endured pain and have stories to tell to those who may learn something from them. No one should have to suffer in a vacuum, and no veteran should feel alone in a rapidly changing world. I want to share hope.
What's Next
I own SV Matilda now as a full time cruiser learning how to sail, and I'm planning the next chapter of my life. From here, as I approach my 30th lap around the local yellow star, I embark on Campaign: The Way Forward. Every day brings new stumbles and challenges to unravel, but that's part of the journey. Through this blog and the letters I write, I want to share what I learn about restoring sailboats, transitioning into this lifestyle, and navigating the practical realities of unconventional living.
Beyond the sailing content, I'll be diving deep into the philosophical questions that occupy my mind during long hours of boat work, sharing insights from the documentaries, podcasts, and audiobooks that fuel my thinking, and exploring topics that range from science fiction to personal growth.
For now, this blog will serve as my home base and a place to go deep on the topics that matter to me. Here I will build my archive, to document this journey for my future children, and to connect with others who might be navigating their own course corrections.
An Invitation
Life and the modern world have mastered the art of leaving us reeling and grieving from the rapid succession of change. If you're in the middle of one such course correction, a major pivot or just the daily work of trying to make ends meet, I hope my stories might offer some companionship along the way as you work to find your own peace. Cups up and hats tipped to the doers, for they will obtain their wildest ambitions because life is about how well you walk the fire. This is just the beginning. The real adventures lie ahead, and I'm grateful you're here to share in them.
From the watch post of SV Matilda, Bob & Rob shout to you:
Per Aspera, Ad Astra
Go now, Through your Hardships,
To The Gorydamn Stars
Move Forward Always, and
find Light out of the Darkness, yo'
- Isaac Lester
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