Near-Death, New Tattoos, and How I Accidentally Became a $2K Weekend Hooker (for Boats)
Well, to update everyone: I passed my PADI Instructor Exam. Yup — I’m now officially a dive instructor. Sounds glamorous, right? Until you realize it also comes with:
$1,000-a-year insurance (apparently saving people’s lives isn’t free)
Annual dues to PADI (PADI = Pay All Dues Immediately)
And the promise of making “tons of cash” teaching people how to breathe underwater… which basically covers my rum habit and boat repairs.
The perks? Discounts at dive shops, tax write-offs for gear, and a backstage pass to some of the coolest people you’ll ever meet in flip-flops.
And… I Got Inked
To celebrate, I did what any rational sailor does when life gets exciting: got another tattoo.
As with my Ohana tattoo, this too has meaning:
Placement: Forearm, sailor-style — highly visible so I don’t have to awkwardly roll up my sleeve every time someone says, “Show me your tat.”
Design: Anchor + compass. Very nautical. Very me.
Symbolism: It’s my personal GPS — from my old, traditional life in Woodbine to the completely unhinged, fun, rum-fueled adventure I’m living now.
Bonus? Tattoos are conversation starters. At bars, at the helm, even at church (don’t ask). If nothing else, it’s a good excuse when someone grabs my arm to “see the ink” and I get to say, “Careful — that leads directly to bad decisions.”
Rebuilding the “Friend Network”
Lately, it’s been all about building a new friend network. For 20 years I managed the entire U.S. — which sounds impressive until you realize local friends? Zero. The ones I did have were:
Parents of my kids’ friends
My late wife’s friends (a.k.a. “the moms”)
And, post-Donna, my girlfriend’s friends… who usually vanish when the girlfriend does.
Now I’m meeting people through charters, taking them out on Ohana, showing off my favorite Annapolis bars, or just DM’ing random Instagram followers offering sunset sails (which, shocker, no one ever takes me up on).
I used to joke with Old Lisa about my lack of local friends. New Lisa (yes, there’s a new Lisa) has been chatting with me lately. Might actually meet her soon. Still not sure if she’s real or just a sophisticated AI who loves boats and occasionally ghosts me.
Lightning Didn’t Strike Ohana (This Time)
Let’s clear up a rumor: No, Ohana didn’t get hit by lightning. That was a charter boat I was captaining — a 45’ Leopard cat owned by a super nice couple in Florida. (Side note: When a stranger calls and says, “Hey, want to captain my yacht?” …you say yes.)
So, picture this: We’ve been dodging storms all day. First one passes — family’s in the water, lightning cracking nearby. They ask if they should get out, and I’m like, “Yeah… climb out and stand next to the lightning rod mast. Totally safe.”
Second storm rolls in — didn’t look bad — and we’re only a mile from the marina. I think, let’s just go for it. Cue: biblical downpour. No visibility. I hear a crack, see debris falling, look down — no instruments, no radio, no lights.
I spot another boat and start tailing him like a drunk Uber driver. He keeps slowing down, probably thinking I’m stalking him. I send a customer forward to yell, “WE GOT STRUCK — NO RADIO — NO ELECTRONICS — FOLLOWING YOU IN!” Finally, rain eases, land appears, and we limp into Back Creek.
The two husbands onboard? Absolutely thrilled. “We thought this was gonna be a boring family day!” they tell me. Nothing like near-death to spice up a marriage.
Captain Life = 3-Day Work Weeks + $2K in Tips
Here’s the upside: I only work Fridays through Sundays. I literally move my house (Ohana) to Annapolis for the weekend, anchor out, dinghy to the charter boat, run three- to four-hour sails, and walk away with $1,800–$2,000 in tips and fees. Stress-free. Sunshine. Zero corporate bullshit.
Was I in the wrong career before this? Absolutely.
The only catch? Crew. Single guys don’t have a built-in +1 for sailing, so I’ve been using Jake and Joe. Jake’s basically my apprentice — wants his captain’s license, pilot’s license, motorcycle license… probably a license to thrill at this point. It’s like teaching my kids to drive again, except now it’s 45 feet of fiberglass and me praying, please don’t hit that million-dollar yacht.
Ohana Drama
Ohana herself? She’s good. (Mostly.) Lightning didn’t hit her, but yesterday while beefing up my batteries, the generator threw a “high exhaust temp” error. Never seen that one before, but I’ll figure it out. Boat ownership: 20% bliss, 80% WTF-is-this-alarm. My guess? Saltwater impeller not circulating water.
That’s the latest: new career, new ink, new friends, new Lisa (maybe), and one lightning strike to keep life interesting. If you’re reading this thinking, “Wow, this guy’s life is insane”… you’re right. But also? It’s fun as hell.
Now excuse me while I go pay PADI another fee and Google “how to fix high exhaust temp errors” with one hand while holding a rum runner in the other.
