Hi, I’m Matt Ray — a writer, sailor, and cybersecurity consultant.
This 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.
Here, you’ll find, stories from my sailing journey, 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.
A practical crewing guide built from three years and 30,000 miles of real-world sailing across the Atlantic, Pacific, and Indian Oceans — without ever owning a boat.
Top Writer in Travel, Photography, & Poetry.
