Might or Might not have made the biggest Mistake of my life

[Colorado Jim]

I think you're in an enviable position. You have an incredible opportunity ahead of you - a fine boat, decent amount of savings, regular monthly income (as long as you're within WiFi range) and the freedom to explore the seas. Of course there is some anxiety during life-changing phases; that's to be expected. The evening before I opened my restaurant business I had a panic attack - what was I thinking? But it was the best decision of my life and has put me on a course that I would never change, if I had to do it over again.

My wife and I are currently traveling (sold the business four years ago) with less savings then you have. We have spotty income from her work. We just don't sweat it. If we have to stop and work, we'll do that. We try to control our spending and hope to prolong our traveling lifestyle as long as possible. We chose not to wait until "retirement age", when health or financial issues for us or our family might derail our plans, to see the world. You have that chance now. Maybe in a year, or two, or six months you'll change your mind and head back to land for a steady job and another relationship. But you'll have chased your dream.

[Sea Dreaming]

It's not really my place to advise you. I've lived my entire life on less money than you have invested in your boat alone. My point is that "enough" money is proportional to how you choose to use it and a "mistake" is directly proportional to how well you use your money to meet your expectations.

The question is: have your choices so far set you up for meeting your real desires and plans?

From my financially humble perspective, I would sell the boat you have now, buy something smaller but we'll founded, and invest the rest with an eye to living off dividends. Your money would take you very far for a very long time and you would still have enough to revise your plan if needed. But this idea means accepting that your travels will not be in high style, but not lacking in comfort.

[Stillwater1]

Beautiful boat. You are so ahead of the game. Make the most of it.

Do what others have been doing. Plan on the boat being your new life. Hire a captain (if you need too) to spend a couple of weeks on a shakedown cruise to get you comfortable with how she sails.
Then work on getting your captain's license, and take on crew, and sail the world, or at least the Caribbean. Many people your age and younger or older will want to sail with you on that boat. After some years doing the exploring thing you can always downsize to a more manageable boat if you want to continue on.

Man, to be in your shoes at that age. Wow. Go for it.

And call me when you are ready to make your first voyage south.

[rmlarson1098]

Thats a LOT of boat, but other than that I don't see the problem. It's never too early to 'make the jump' and get out of the rat-race. IMHO living debt-free is the key. Whether ashore or on the water. Put your money away and try to live on your income. Set the yacht up for living on the hook (solar & wind) and stay out of the marinas. Learn to cook and avoid dinners ashore except for special occasions. Sail rather than motor the boat! And cruise where the living is cheap.
Again, put yourself in a debt-free position, and go from there. Keeping up that Little Harbor is gonna be pretty pricey, can't offer any advice there. We consider 30' a big boat.
Cheers.Lot'

Originally Posted by jaygatsby

Long story short, got a divorce (no kids) age 33 last year, I got the cruising bug and spent about 6 months searching for a good boat without a budget in mind.

I lived on and worked on private yachts from age 18 - 25 where I met said ex wife.

Got lucky with a company I helped start and sold it late last year (said ex wife got nothing, thanks lawyers far and wide)

I made a few hundred thousand south of 7 figures and cashed out 2 weeks ago decided to pull the trigger compulsively on a 1989 Little Harbor 53 FSBO for about 390k, she is loaded and was recently refitted including new teak decks, standing, running rigging, sails, full electronics package, topsides repainted and interior all stripped and varnished. She was repowered in 2014 and also rewired. In 2015 had all her canvas and upholstery redone.

Surveyor convinced me I was getting the deal of a lifetime and the boat would easily list at 550 - 600k on the market as is.

I have about 410k left total with a income of about 3100 - 3500 a month I get from part-time (remote) consulting I do for the company we sold off.

Everything works and the boat is dry as a bone having been taken care of by a professional (full-time) Captain for the past 10 years.

Now I'm having buyers remorse. Ex-wife got the house, I have no assets right now. I'm thinking of selling off the remainder of junk I've acquired over the years. Leaving my place in Texas and just taking off cruising.

My worry is the money I have left is not enough to keep me sustainable for the long term cruising life. Now contemplating maintenance + dockage expenses (will need wifi to keep consulting/income) ect.... other expenses, unkowns ect... ect... ect....

I don't know what to do now. I think I've bitten off more than I can chew. I have a lot of life left at the age of 33 - no where near retirement age. I'm sure I could sustain cruising for a few years with what I have left plus the consulting income. But I'm afraid once I come to the end of that what will I do next..... work wise to maintain such a vessel... lifestyle .... ect....

What position are people at in life when they make the leap...? The questions and anxiety running through my veins is crippling me right now. My family thinks I've lost my mind completely but I have no real desire to do anything else at the moment. I know I'm very lucky and have a good opportunity with what little finances I have left but I don't want to be that guy... 5 - 7 years from now looking back and saying to myself (broke) (unemployed) living on a giant liability at age 40 saying what in the **** was I thinking!

Suggestions? Advice? heard of similar experience or had one like this? How dumb was I?

I've been sitting at my computer all day contemplating calling a broker.

Thanks in advance for any advice, suggestions ect...

[Juho]

The size of the boat seems to be your only problem. If you have no plans for dry land right now, why not check if sailing life could be your future. Since you got your big boat with reasonable price, you could as well start with it, and change it later to a smaller one if that feels like the right thing to do. CF member Kenomac sails a large boat, and he says his expenses are low. Maybe he has something to say about the costs.

[pathlesschosen]

Ok folks, the OP admitted he was a troll.

[PYV58]

CALL THAT BROKER !

[Cadence]

Originally Posted by pathlesschosen

Ok folks, the OP admitted he was a troll.

I wish I had sold something a couple of hundred grand less than 7 figures at 33. Sure sounds like a fairytale. I certainly wouldn't be crying pour me.
Granted something around 800k isn't what it used to be. At 33 I would settle for a 150K boat and invest the rest to supplement the supposed residual income of some kind.

If he isn't a troll, I wish him well.

[charliehows]

Quote:
Originally Posted by Ann T. Cate
Jay Gatsby is the name of a character in a book by David Carroway: "The Great Gatsby," which is why I suspected it was a troll.

A.

Originally Posted by jaygatsby

One of my favorite novel characters of all time. As for being a troll ironically enough I am a troll. The business I helped build and sold was basically teaching people how to be profitable internet trolls. Not in the negative, take advantage of people kinda of way though. We charged money to teach people how to avoid being trolled and intern trolling the trolls.

???!!! Seriously?? c'mon you guys, americans have so few literary icons!

[charliehows]

F Scott Fitzgerald ring any bells?

[TrentePieds]

@PYV58, post #82:

Always, always check the date of the post your are responding to!!! The tread you are reviving is TWO YEARS old and was OBVIOULY started by a troll.

Post #1 has an unmistakable whiff of trollery about it. Leave the trolls under the bridge, and we common goats will go about giving wholesome milk and cheese :-)!

TrentePieds

[JPA Cate]

Trente Pieds has the right of it, and when there is a troll, the milk goes off, and the cheese doesn't set!

Ann

[Pelagic]

Originally Posted by JPA Cate

Trente Pieds has the right of it, and when there is a troll, the milk goes off, and the cheese doesn't set!

Ann

Wow!... an Olfactory Troll [emoji87]

[heron237]

• The only thing folks regret is what they didn't do, not what they did.
• If not now, when?
• you can make plans but you can't plan outcomes
• Overcome you fear.

[GrowleyMonster]

That's too big a boat for singlehanding, particularly newbie singlehanding. Maintenance costs might be surprisingly low, for the first few years, but you could get blindsided. OTOH, you have a very very roomy and comfortable boat to live on. Who needs a house when you got THAT? I lived on a 20 foot plywood sailing skiff at one time. Just sayin. Last boat I lived on was 27' and I still own it, just live with my GF now. Present boat is 44' and I only upgraded that big so the two of us could have the space we need. For myself alone, I need a boat bigger than 35' like I need a hole in my head.



So you have a very nice 53'er and nobody to share it with, worried that your consulting fees won't cover your expenses. And you are quite new to sailing. And the surveyor swears up and down your boat is work a hell of a lot more than you paid for it. I would say that you have some serious decisions to make, but you are fixed up a hell of a lot better than half the members here. Way better than me.



My idea of a good way to handle your "unfortunate" situation is to first of all, find a mentor, even a part time hired skipper, and take the boat out! Go sailing. That's what it is for. You will either hate it (unlikely on that boat) or like it somewhat, or love it passionately. If you find yourself forgetting your troubles and grinning ear to ear as soon as you get used to the idea that the boat is NOT tipping over but IS going crazy fast through the water without even burning a drop of diesel, then you love it passionately and you need to stick with it for a while. Get that wheel in your hand and learn how to keep those sails filled with wind, and nothing on the beach really matters any more, at least for a while, if you have the calling. I would keep that boat for six months or so while you figure things out. You don't know the answers to your questions yet. You don't even really know the questions themselves, yet.



THEN


List that boat, for about half the difference between what the surveyor values her and what you paid for her, keep it listed for about 6 months, and see if you get any nibbles. Meanwhile, enjoy the boat. Learn enough that you can manage her yourself, with volunteer crew. Surprising how easy it can be to recruit a couple of people, when you have a sweet boat like that. Learn to do routine maintenance like checking, watering, charging, equalizing batteries, changing pump impellers and engine oil and filters and belts, how to troubleshoot electrical problems, do simple rigging tasks like replace halyards and sheets, navigate... ACTUALLY navigate, not look at some silly screen, and other skipper stuff. Learn about radio. Wood work. Sail repair. Maneuvering in difficult situations. Stuff like that.


After owning the boat for a year, figure out what she cost you to own for the year. And drop your asking price to what you paid for her. Hold that price for a few months. Should sell. No? Drop it some more. End of second year, figure out what it cost you so far. Maybe keeping the boat is a good idea? Probably not, but maybe, yeah.


So, let's say you sell. Let's say you get $350k for her. Put $300k into mutuals and forget about it. Go shopping for something between 25' and 35' that with your newly acquired knowledge, you can singlehand nicely if you want to. Figure on spending $10k or so for a nice but heavily loved fiberglass boat with a running diesel and plenty of sails. Figure on spending $20k to fit her out the way you want, and make it yours. You will have chopped your ownership and operating costs to about a third of your old 53'er. You will have an easy boat to handle solo, or with a single crew person. You will have something big enough to live aboard with a small office nook where you can work. You will meet some fascinating neighbors, and find that your pier is sort of a small neighborhood, where crime is low and most everyone looks out for one another and their boats. Your slip will probably cost 1/4 of what a decent apartment would cost. Your taxes will be stupid low. I think you would ultimately be a lot happier with a smaller boat.


Now if you want to cruise, and consult, you will have another major expense... internet, likely via satellite. Even coastal cruising will necessitate this, because lots of times you will be out of range of the nearest cell tower.



You realize, of course, that if you keep your expenses low, you can retire right now? Assuming sound investments of course. But expenses, yeah. You are probably used to having a lot of disposable income, though likely you never regarded it as such. GOT to have this. GOT to have that. Can't be seen driving a $400 car, or wearing walmart t shirts or cheap sunglasses or eating at the $6.99 Chinese buffet. What kind of watch do you wear? Shoes? $60 haircuts, or cut your own? Seriously. A lot of liveaboards literally live on less than $1000/month. Some, way less than that. And when I say $1000/month I literally mean $12k/yr, no big extra, "necessary" purchases that "don't count". Get my meaning? Live poor now, while you are young, and let your substantial nest egg work for you and grow. You will need it more when you get old. And meanwhile you will have your not so big but cheap and easy to own and manage boat, that will still take you anywhere you want to go, whether it is across the bay or across an ocean.



Let's say you take the boat out and decide you HATE sailing. Okay. Take what your boat cost you, add all expenses to date and anticipated expenses for the next 3 months, and list the boat at that price. If you get the full price, you can go "Whew... that was a close one... I almost lost a couple thousand dollars!!!!!!!" but if she doesn't sell quickly, reduce aggressively. Hate sailing? Then the boat is 100% a liability. Dump it. Your goal should be to sell in less than a year, and call it a lesson learned. Ebay it after a year. Get rid of it. Before stuff, expensive stuff, breaks, and stuff on a boat breaks just from being on a boat. It is the nature of it. But you NEED to use the boat a little. Really use it. That is the only way to decide whether you will be getting your moneys worth of enjoyment out of it. Then figure out whether you want a big boat, a small boat, or no boat at all.