About Living Large by Living Little
Hi, I’m Matt Ray — a writer, sailor, and cybersecurity consultant.
This is my primary writing home.
Living Large by Living Little is where I explore the overlap between tech and travel, memoir and misadventure, systems and creativity — and what happens when you choose to live deliberately instead of on autopilot.
Over the past decade, I’ve sailed around the world by crewing on other people’s boats (a journey I call Global Hitchhiking), worked in cybersecurity, and returned to writing as a way to make sense of it all.
This publication sits at the intersection of those worlds.
Here, you’ll find:
Stories from my sailing journey and the Latitude Longings podcast
Practical cybersecurity and tech guides
Reflections on writing, AI, work, and reinvention
Memoir, essays, and occasional poems
Some posts are technical. Some are personal. Most live in the space between.
If you’re interested in creative reinvention, learning in public, or building a meaningful life one small, intentional decision at a time — you’re in the right place.
Books
Global HitchHiking: How I Sailed the World Without Owning a Boat
If you’ve ever thought about sailing the world—or crewing on someone else’s boat—this book shows how it actually works in practice.
Buy the PDF direct: Gumroad link
Or get it on Amazon: Amazon link
(More projects will appear here as they’re completed.)
Subscribe to follow the ongoing work and receive new posts in your inbox.
Welcome aboard.
— Matt
