The Slip, the Survey, and the Freedom to Sail

What I'm Telling You is Not About a Boat. It's About Recovering from Your Breakup

As soon as I bought the boat that was perfect for me and my budget—a 1981 Cape Dory Cutter, a small, true bluewater sailboat that can take me to any common cruising spot on the planet—I hit a snag:

I needed insurance for the sailboat. Without insurance, I couldn’t even get a marina slip.  Naturally. It makes sense. And without a slip, I couldn’t move forward, couldn’t make this new chapter of my life work.

One big-name insurer—you’d know them for their sweet, nostalgic mascot with the interesting accent—told me I’d need every single tiny item on the boat survey checked off, before they’d even consider insuring me. New rigging. New lifelines. New through-hulls.

Even a new cockpit support pillar that the surveyor incorrectly flagged as being rusted out when it just had an orange patina of rust.

I was down with the new rigging and new lifelines. They weren't terrible, but this amazing boat was originally from British Columbia, only as recently as 2019, and there was no record of when the rigging was last redone. I want to know my standing rigging and lifelines are new and solid

But there were all kinds of unimportant odds and ends on that survey report.

So it was like being told, “We’ll support you... as soon as you’ve fully healed. ”

The quote? $900 a year.

I'd be willing to pay it, if they'd only sell me the insurance. I just wanted to get started on this new chapter of my life after that brutal breakup.

Another company—famous for an annoying animal and a  guy with a 70s fake mustache—told me they’d insure me… after the survey was 1,000% satisfied ... For $2,000.

I laughed. And not the happy kind of laugh.

I was stuck. The anxiety kicked in. The "What if I can’t?" started whispering inside. "What if I screwed up, forced by my budget to buy a bluewater boat built in 1981 instead of 2001?"

Real-World Based Options

But then—I took a breath, and considered other options of finding the info. Nowadays we think, "Just Google for an insurance quote. That's how you get fast info, and how lucky we are."

But pausing, I remembered life before the Internet. (Yes I'm almost 60, and I live as if I'm 35, as should you all, no matter your age from 18 to 80. Live and think and act as if you're 35.)

And remembering what life was like back then—and it was pretty damn awesome, talking to people so much more often—I stopped trying to Google better insurance. Stopped trying to do it on my own. 

So I asked real sailors, people who’d been here before. There are scores, if not hundreds, of boats beyond 40 years old in Oriental, NC. 

I talked to the woman who owns the boatyard doing the refit of my boat. A long experienced pro.

She pointed me to a specific insurance agent. Just like it was 1981, the year the boat was built and I was a freshman in high school. Good times.

It was so old school. Sure, she emailed me the info. But as she gave me the name I wrote the name in a paper notebook. (I rely on digital info to keep and organize my life as much as anyone, but I also use paper notebooks, because they make information and ambition and direction physical in the world, which keeps it from disappearing in the cloud.) 

And get this:

One phone call later: $303 for the year. Immediate coverage. Done.

It was exactly what I needed—just enough coverage to meet the marina’s requirements, keep me safe, and let me get on with it.

No overkill. No endless checklist. No gatekeeping. No shunting me through computer phone options and treating me like a data point. 

I'd been connected with a solution by one real human interaction. 

Why am I telling you this?

Because most problems to solve, including one big thing I write about here, recovering from betrayal and breakup and heartbreak, are solved in the same way.

Some  search engine optimized “experts” will tell you that before you can feel good again, or start on your new life, or love again, that you need to fix every scratch in your hull.

Clean up every lingering fear.

Check every emotional box. 

(Oftentimes this wrong advice comes from women, or from a feminine-principled man. Or a man who hasn't been through it, who has only read about it and talked about it.) 

Then they’ll approve your worthiness to move on. And this can cause you to doubt yourself, and delay your recovery for months, years, or decades. 

But they’re wrong. 

What you really need is this:

• A simple reality-based structure that gets you moving.
• A realistic plan that cuts through the emotional red tape of your mind.
• Just enough stability to dock your soul somewhere safe while you heal.

Sometimes, that means talking to people who’ve been through it.

Sometimes, it means trusting the quiet expert inside yourself.

Either way: when you stop spinning and start asking better questions, you find a way.

You don’t need perfection.

You don’t need full closure. (It doesn't exist in the form anyone would prefer; you'll never get full answers or explanation or justification or expiation.)

You just need a slip to pull into. A shelter from the storm. 

And a simple steadily liberating solution based in real people and real methods that work, one decision at a time.