Pimping My Retirement: How a Broke Captain Hustles in Board Shorts
From Winter Woes to Summer Whoas
All winter, I was crawling up the walls—craving sun, salt, getting use to being alone AGAIN, and looking for something to do. Be careful what you wish for. Now it’s summer, and I’m busier than a squirrel in a peanut factory. Between charters, renovations, instructor training, and financial gymnastics, it’s officially the Season of Doing Too Much.
Let me take a break from my studies (yes, I’m back in school!) to catch you up…
Captain, Instructor… Bookworm?
In a twist no one saw coming—including me—I’m training to become a PADI scuba instructor. That’s right, I'm back in the books like a college sophomore… but older, slower, and more easily distracted by shiny objects (snacks and writing these BLOG posts).
Luckily, scuba isn’t new to me. I’ve been immersed in it since 1985, thanks to Donna and her dad—both instructors who basically raised me with fins on. And over the years, I’ve had the privilege of working alongside one of the greats: John Kiser, a bona fide PADI Examiner. Not just an instructor. Not just a course director. A PADI Examiner—one of only 17 in the world qualified to certify the people who certify instructors. Yeah, he’s that guy.
John’s dive résumé reads like a Hall of Fame plaque:
Former PADI East Coast Regional Director
Recognized by PADI for certifying the most Open Water students in the world
Had dinner with Jacques Cousteau (yes, that Cousteau)
Deeply involved in environmental restoration with Donald Schaefer and Chesapeake Bay projects
Oh, and he’s also a 100 Ton Master Captain, having run Sea Colony’s dive boat out of Ocean City—the same one Donna and I used to head out on together.
In short: when I do something, it’s always with the best. That’s been my M.O. from the Ocean City Beach Patrol to Johns Hopkins, Lumenis Lasers, Topcon, Thermo Fisher, and now… back to the water.
Here’s my path to being an instructor:
Finish eLearning (without falling asleep).
Survive Zoom sessions.
Head to Key Largo for pool & ocean dives.
Pass the final two-day exam in front of the scuba Jedi council.
Easy, right?
It’ll all be worth it. From what I’ve heard—from folks who’ve worked in Key West, local dive shops down there, and even my own instructor—having both my USCG Captain’s License and a PADI Instructor Certification means I can basically write my own ticket. Any dive shop in the Keys would want me on their roster.
Charter Chaos and Twerk Trauma
I recently captained a charter for a group of 22-year-old inner-city party girls celebrating a birthday. Picture this: perfect weather, deafening music, and nonstop twerking—recorded, of course, for their social media empires.
Every time we cruised past another boat—especially down Ego Alley—it turned into a live dance-off. Twerking became the official signal for “We’re having more fun than you!” I had to maneuver Ohana like I was dodging cannon fire just to avoid traumatizing the tourists on the Woodwind and Harbor Queen. Luckily, the center-console crowd seemed happy to ogle and wave.
Then there was the birthday girl’s 52-year-old boyfriend (yes—52), swaggering around like a washed-up reality TV star. He kept bragging to me and my son Jake (who was working as my crew) about his “hot young skank” (his word, not mine). Jake and I just exchanged that father-son look that says, “We are way too sober for this” and “This guy is disgusting!”
Note to midlife Romeos: if your back goes out faster than your girlfriend does on weekends, maybe cool it with the flexing.
This Old Dad: DIY Kitchen Edition
Back on land, I’m in the thick of a kitchen reno at the boys’ house. So far:
✅ Demolition done
✅ Outlets: installed
✅ Ceiling light: moved, patched, and still dropping drywall dust on my head
✅ Wiring: ready for under-cabinet low voltage lighting (yes, it will be glorious)
✅ Walls: painted (and the boys did it all!)
Next up: hang cabinets, setting counter, and re-plumbing sink, garbage disposal, dish washer. Which means at least one obligatory trip to Home Depot—formerly known as Donna’s job while I stayed under the sink yelling, “Honey, you back yet?!”
Board Meetings & Boat Wiring
Because I clearly don’t have enough going on, I may soon join the Piney Narrows Board of Directors. Because nothing says “relaxing summer” like marina politics and HOA drama.
Meanwhile, Ohana’s solar upgrade is full steam ahead. I’m headed back to Bert Jabin’s for the crane install of the new arch with:
Solar panel wiring
Starlink hookup
Dinghy lighting
Iridium Go antenna
Once done, I’ll have a floating off-grid fortress. My lithium upgrade (in the works since March) will finally be complete, making Ohana beefier than 90% of boats out there. After spending near $100K including dock fees in NC and Annapolis, fuel getting to/from NC, and adding a chain counter and the Zeus plotter in the nav station, I am looking to do a whole separate Blog on what was done w/ a page added to Ohana’s Adventures under “About Ohana” Highlighting everything about this upgrade.
Disability, IRAs, and Tax Kung Fu
Now for the grown-up stuff: finances.
With the recent “X” in the rearview, I’ve taken a deep dive (pun absolutely intended) into early retirement funding—especially now that I’m on Social Security Disability Insurance (SSDI).
Like most people, I thought I couldn’t touch my IRA until age 59½ or until the year I turn 59½. Turns out, if you’re officially disabled, you can—no 10% penalty start drawing from it NOW. Just pay regular income tax. Better still:
IRA withdrawals don’t count as “earned income,” so SSDI isn’t affected
SSDI isn’t needs-based, so they’re not watching my bank balance
And I’ve got decades of disciplined saving behind me
I maxed out 401(k)s and IRAs every year from my first day at Hopkins in ’89 to my last paycheck in 2022. After Donna passed, I kept stuffing tax-deferred accounts full while living like a hermit—no Game Stop addiction to support, no wine cellar to restock, and no clothing/linen obsessions to fund. (Just my gadget, electronics, boat device addiction to support!🤪)
Now, I’ve gone from having saving for two to retire in comfort living in a 4,000 sq’ million-dollar home + 6 car garage w/ fitness center + 8 acres + 1:1 basketball/tetherball court + dirt bikes + a tractor + zero turn + RV and expenses galore… to a saltwater minimalist life ALL BY MYSELF. And (thanks to “Old Lisa”) kinda learning to love it…. returning to the life I had wanted to live before meeting my Donna. Just when I met her all I wanted to do was provide for her the life she wanted to live and family she wanted to have. So now goal is to find a first mate who can compliment my “estate”—providing a “brick and mortar” home to match Ohana and have some kinda retirement savings.
Income Streams & Lifestyle Hacks
People ask how I afford this. Here’s how:
✅ Dock rental from owning my slip at Piney Narrows
✅ Charter income (sitting out on a yacht while others party = genius)
✅ Teaching scuba (paid to do my hobby as well as talk, swim, socialize and stay fit)
✅ SSDI for baseline income
✅ Strategic IRA taps for big-ticket upgrades
Figure that if I could manage $100M corporate budgets, I can manage my minimalist floating budget with an Excel sheet, a side hustle, and a screwdriver.
Tax Shenanigans: Florida vs. Maryland
Since Florida doesn’t tax income, I’m reestablishing Florida residency (hello, Key West). I need to see if I still have a Declaration of Domicile on file with Florida from when I had the RV. Since I will spend 6 months a year down there, it will be easy to proove I am a local. When my plans were delayed by the recent “X” I don’t think I ever changed it back to Maryland… I just got a MD driver license again, so I believe I am still recognized as a Florida resident!
No need for a new license—just a little bureaucratic salsa to keep the IRS from becoming a pen pal.
Final Thoughts from the Floating Circus
Yes, I’m busy as crap. But everything is working on Ohana, the compass is set, and (mercifully) the twerking has stopped. (no really—though fun to joke about, it was sad and disgusting to see how “the other ½” are raised & brought up.)
If you’re dreaming of a simpler, sunnier life—whether it’s on land or at sea— just know it takes hustle, humor, (a decent understanding of IRS & SSDI loopholes), and being task focused with the perseverance that got me from being a OCBP beach bum to where I got with my career running global service operations!
Until next time, may your wiring behave, your marina neighbors keep their shorts on, and your retirement plan work as hard as you did.
