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

[Pelagic]

LIVE, LAUGH, LOVE. !

Just think of the boat as another wife (mistress)... Laugh and get on with enjoying your Life.

Your smart and ambitious, so the money side will take care of itself as your preferred lifestyle provides you with inspiration to keep on living.

[Don C L]

Originally Posted by jaygatsby

Yeah, pretty much, did not think before I purchased, hindsight is 20/20. My purchase does not reflect my overall goal which was just to escape and get some clarity for a period of time.

Can I have the boat?

[89zorro89]

Touche`, I couldn't agree more. It is unfortunate that the majority do live their lives as you stated. It is a great model for financial independence and if you look deeper into the statistics of the "average" you will see their retirement portfolio is practically non-existent causing the rest of us to ponder the future of our society and economic outlook.

As for me, I can say when I was in my early thirties it was a struggle to get over the hump to purchase my first house. I'm doing okay now but I can certainly relate to what the mass are going through. Today's economy is even more difficult. "Millennials" are forgoing home ownership even longer than we did and either continuing to live with parents or renting/leasing. That said, even the best at managing their own finances are having a tough time getting started. But when they get there look out. In the mean time it's tough to manage what you don't have.

[Three Sisters]

Originally Posted by jaygatsby

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...

Just took part of your info from the first post. But you are in Texas with terrific marinas at terrific prices. Just one thing though, an internet connection beyond wifi. Something like broadband. Some marinas may offer it or allow you to install it, as your business depends on it.

Had to look up what a Little Harbor is. It's designed and built to run from the cockpit, singlehanded. Unless I'm on the wrong page. A big Congratulations to you.

Taking from your quote above, I guess there are not many celebrations through your family on this decision...and at a time when you may need some reassurances the most. Reading of your time spent in the previous years, I'd be exhausted and have difficulty relaxing.

This calls for a video of you sailing her.

Whadya Say ?

[David B]

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...

Understand the confusion, and self-questioning.

My suggestion is to just settle for a while. Live on the boat, sort out how you can continue to earn money into the future from various locations (developing your consultancy perhaps?).
Then go on 'holiday' for a month or so. Take that boat and go sailing. After a month, you will have a much better idea if this purchase was a knee-jerk reaction to your divorce, or something you really want to do for a year, or three, or ten.

Settle - just settle, and look forward. You now have in front of you a brand new chapter - all the pages are blank, and you have so many exciting possibilities ahead of you.

Can you do it? Of course you can - look at all these people younger than you, who go and buy a boat with pretty well all that they have saved, and then one way or another, spend a year, or many, living their dreams.
You are already in a much better position than many of them (and with that income, many retirees !), so if that is really what you want to do, just go for it. There is nothing to stop you changing direction down the track.

I hope that helps,

David

[captlloyd]

You are in your mind, a dangerous quagmire. Stop thinking and enjoy your boat. Your biggest concern should be deciding where you want to take it.

[ozdigennaro]

Go sailing! For a year or two, and then make your plan.
You'll be in great condition to liquidate your assets or to sail on.

[Alastair A]

Please keep this site nice with "NO TROLLS", as you admit.
Best wishes when you settle down from the divorce and $ world. You need some real sailing times behind you. Cheers A.

[millstone]

My two cents you have had some major life changes Slow down with a 53' boat you could be sitting on your new business, people love to go and hang on a nice boat for the weekend. Partner with a GOOD captain and do day charters. When you're up to speed on the whole sailing thing either head off into the adventure or sell it. A boat/business might be easier to recoup investment. In the mean time kick back and enjoy life is too short to sweat the small things

[jimbunyard]

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.

My oh my, what a double-edged sword, the joys of the internet...now my curiosity runs rampant. What an interesting and instructive way of teaching, if what you have done is your last 5 posts has been 'teaching by example". ( and of course disregarding the potential for an 'infinite regression' of gullibility)

If not, my apologies, and I hope you've solved, or are further on your way to solving, your 'dilemma', though I personally still find it kinda a 'non-dilemma'. But far be it from me to compare my life history's tales-of-woe with yours...talk about an exercise in futility...

[Rorzech]

[QUOTE=jaygatsby;2272792]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.

Wow Would I love to be in your shoes.
First thing I would do is down size my life style. Learn to live on 1500 $ monthly immediately.If you do that you can enjoy retirement for the rest of your life. If you can't do that, then you'll have to go to work like the rest of us saps sooner or later. It all boils down to the star that burns the brightest has the shortest life span. Being 33 means you got maybe another 50 years ahead of you ,give or take. Just do the simple math for what you need, to get you there.if you like the life style of cruising , you'll always have choices like the expensive way or the inexpensive way. If you like entertaining people to show them how opulent you are and how lavish you can live, then you better pull out now. If you like reading books researching the internet, diving ,fishing , Boat maintenance , then you stand a good chance of having a happy life cruising . Only you know what you want. You have a great start. Looking back at my life, I wish I had my youth the enjoy this life style instead of starting it at 60. Nobody has a lease on life. you could drop dead 5 years from now for dozens of reasons. I say go for it and live your life. Every day above ground is a good day.Forest Gump says life is like a box of chocolates . Yada Yada Yada. I hope you get something out of this rant.Cheers

[waterman46]

Jay, man, sell that big boat quickly before you get used to the luxury! You can't reasonably afford even one year's maintenance and taxes on 36K a year income and have enough left over for having fun.

One definition of internet trolling is posting off-topic, personal information that seems intended to elicit attention or sympathy. I'd say much of JayGatsby's posting here falls into that category.

[SKG56]

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...

I went thru about 3 pages of this thread, not going any farther, you say you've got 410k with 3100-3500 coming in monthly with a boat you could get, lets say 350k quickly, and you have a problem,my response, you've got to be kidding, this is absurd to say the least, " with what little finances I have left" come on

[Alastair A]

Mr Gatsby. How dumb do you take the "Cruising Forum" sailing community to be? Is this your best way of starting a constructive dialogue on line for sailing? Oh dear me. Just go sailing yourself, anywhere, please. It will give you some space and help you "wise up" and share more nicely threre after. Regards. Alastair

[manawatuman]

Join crewbay.com and get yourself some experienced sailing company