I tried writing about all this a few months ago, when I first set out on this fiasco. I published a single post on my primary site, a post that was pure, pretentious horseshit. It was self-indulgent, clunky, and reeking of a sad middle-aged man taking a poetry class at the learning annex to meet single moms. It might have been that writing about something other than tech was, and is, far outside my usual stomping grounds, or maybe I was overwhelmed with optimism and did not know how to wear it without sounding ridiculous. Anyway, I give you my word I will do my very best to suck less this time around.
To get started let us review the basics: I am a dude, 43 years old as of this writing. I own and operate a small software consulting company that does well all things considered. I am in decent health that I know of - I don’t make it to doctors often, so hopefully what I don’t know won’t kill me. I live aboard my sailboat, a 35-foot Ericson sloop built in the late 1960s. Onboard with me is my football-sized dog. This month marks six months of living aboard, and six months of lifetime sailing experience. We have been docked in Philadelphia since August, making repairs and preparing to head south, hopefully setting sail in the next few days if all goes well.
What I write here will mostly be about living aboard and working truly remotely, likely a bit on sailing as I learn, and some color commentary on things from my view out on the water.
Prelude
Lots of people sail. Most of the people who sail grew up on boats, joined the Navy, or maybe were among the thousands of extras in WaterWorld earlier in life. I did none of those things and had no interest in boats as a kid. Instead, I was obsessed with motorcycles; they were fast and dangerous and loud and flashy; sailboats are mostly not those things. Young me went to a SUNY college (primarily to meet girls and party, which was the core curriculum at most SUNY schools around the turn of the century), and graduated with a mostly worthless degree in foodservice administration. This higher education qualified me for a management trainee position at a shoe store in Van Nuys CA, my first shirt-and-tie adult job post-college.
My career slinging shoes lasted a few months until I bought my first motorcycle, and then promptly quit to go sling motorcycles instead. Over the next few years, I worked like a dog selling bikes, sacking away a ridiculous amount of money for a kid in his early 20s. All I did was work and ride motorcycles - more of the latter at first, but eventually almost all of the former. I invested all that money into a sure thing - California real estate. In 2005.
After the Great Recession, I found myself back in New York, broke. I Learned to write software, began freelancing websites and applications for small businesses, and then some larger corporate clients through connections I had in the security industry. I liked what I was doing but I missed motorcycles and the surreal, vulgar insanity of motorcycle shop culture. And then, I discovered a proxy for that culture in a small Philly tech startup. It was brewing typical 2000s startup Kool-Aid: work mad hours, devote yourself completely to the thing “we” are building together, and you too will reap that life-changing big exit in a few years. Of course, those big exits rarely come, and by the 2010’s most of the people drinking that Kool-Aid were surgically excluded from them when they did. Still, I spent the next decade chasing that dragon at various startups, stopping at some mid-size and even enterprise companies along the way. I picked up a master’s degree and a sizable chunk of new education debt. I amassed a pile of worthless stock options that could be used as kindling or toilet paper, not much else.
I realized that the only way to win the startup game is to play your hand. So I brought together smart people and founded a startup that failed. Then I founded another. And another. Finally, I founded the company that was sure to be my unicorn; the customers got it, the investors got it, we had IP, and we had working software. We just needed runway - so I pitched to investors tirelessly while pitching in every cent I had. When the music of zero-rate stopped suddenly in 2023, my startup was left without a chair; our platform looked more like something you would cut from the budget than a new expense you’d take on.
Clawing for some semblance of that startup hope and excitement, I signed on as the first employee at a well-funded, bleeding-edge AI startup. But the Kool-Aid was gone, and all that remained were the brutal hours, non-existent job security, and risk; even the illusionary pot-of-gold startup carrot was painfully absent.
By the time it was over I looked like shit, and felt like microwaved shit. I had worked myself nearly to death for a decade and a half, along the way destroying all my relationships, abandoning my hobbies, and sacrificing my health. I had enough cash on hand to cover me for two months, and enough in a 401k to cover my retirement provided I died within a month of retiring.
In my career I have walked into more than a few stuck and failing projects, recussitating them as part of a day’s work. I realized that my adult life was not that unlike those projects. I had lost sight of my core measures of success, fallen down a rabbit hole that was leading me away from the things I wanted and towards a false idol. And so, I broke out post-it notes. Lots of them. I covered the table, the counter, the walls. I moved them around, debated them, crumpled them up, replaced them, consolidated them, until a plan had formed.
Shortly thereafter I sold my motorcycle, my truck, my furniture, my firearms, my spare computers. Then I drove a friend’s very old car to a small town in Virginia where all the sailboats are, spent $14,000 cash on a 55-year-old sailboat, and moved the dog and myself aboard. Of course, that process was more complicated than I’m making it sound and had its roller coaster of events, and there are amazing people I met throughout that saved my ass repeatedly - I will write more about these things later.
Why 301?
A 301 Redirect is how a server responds when an address has changed. For example, if your self-help website used to be www.anustart.com and after several awkward misunderstandings you update it to www.a-nu-start.com, you would send a 301 telling the requestor that your website has changed direction. A 302 would indicate the change of address is only temporary, but a 301 makes it clear that this is forever.
Setting sail is my forever change in direction, so Project 301 seemed only fitting.