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tonforty 21-01-2011 10:48

Buy Big (and Cheap) - Go Now ?
Been in the insurance business for 8 years with my wife and 2 teens 17 boy 18 girl. Totally burned out with health care reform and general business climate. The only passion I seem to have these days is living adventurously on a sailboat.
My intial plan was to do the 10 years to 100% vest in the company stock and have some sort of residual. I just don't have any passion at all to suffer till Jan 1 2014. I know ya gotta do things you don't want to do to be successful sometimes.
I have a couple grand coming in (gets smaller a little each month) 40k in stock and 20k in debt.
Definately not burned out on life,just feel totally stuck.
Currently ,We are exiting out of the big rental house and Bec and kids are going to Spokane Wa (freezing) to stay with family. In the mean time I will stay and hold out for my not so liquid stock and squeek out a few policies.
I think I'm at the point of getting the money,pay off debt, and buying a cheap sailboat in Florida to live and learn on.It really seems doable.
I'm tired of dreaming and lurking.
I think we would meet some cool people ,get some connections,and set up a catalyst to a renewed passionate lifestyle.
I just find it really hard to believe we would regret it.
Our stuff is already in storage and it's freezing out. Maybe now is the time.
I was thinking a serious "don't want anymore" seller for the 10 to 15k range. Bigger the better.All 4 of us unless a family member bags it cuz they hate it.
We could learn and build confidence for the Caribbean escape.
I'm actually very good at helping people with insurance considerations so I could fall back to it. I'm also very mechanically inclined. I was an auto parts salesman for 10 years.
Do i have the "bug" or what?

Skabeeb 21-01-2011 12:43

Go for it my friend!

I own a sales company and have been in sales for 20 years. Have the huge home and all the toys one could want (except a sailboat).

I am conditioning my wife to do the same thing eventually.

Although we live in Florida only 600 yards from the ICW and only 1 mile from the Gulf of Mexico, I still want to learn sailing, buy another yatch and cruise all over the world!

Good luck!

chadlaroche 21-01-2011 12:47

do it. I feel your pain. go for it

bljones 21-01-2011 12:54

tonforty, you might want to skip this post...
You've been in the insurance business for 8 years, and your commissions are getting smaller each month and you gave up a rented house because you couldn't afford it????????? Sure you could drone it out for another 2 years and pick up the residuals, but, speaking as somebody who manages salespeople, if you're bringing in less business every month, you won't last another 2 years, and even if you do, your residual income is gonna be nominal at best.
Quit. Now. find something you are good at that makes you happy and bank some coin, THEN think about buying a boat, cuz right now you appear to be doing more sinking than swimming.

Or, if you really think living on a boat is gonna solve your problems, buy a plane ticket to florida and find a boat you like- lay down a 20% deposit with a 90 day closing (if you can get it), go back home and doorknock your ass off. close like you have never closed before, build up your kitty, cuz paying for a boat you have already bought is a HELL of a motivator. Take that newfound confidence and sense of freedom and build a rep as a closer instead of a sandbagger, and then you have created a portable career while putting more money in your pocket. Closers have value, in any business, in any region. bew the kind of cruiser who is living on his boat by choice, not living there because he has no other choice.

tonforty 21-01-2011 14:47

Good Stuff
Great post BLJones...really.

These are constantly the pondered thoughts you have outlined.

I also ask myself ..."Can I close living on a sailboat?"

Feral Cement 21-01-2011 15:11

Tonforty --

You don't mention anywhere how your wife and kids feel about this. They may be OK with moving and a change in income, vocation, and lifestyle, but they might balk at living on a boat 3000 miles from where they are used to living. Ever been to Florida in the summertime?

If this is what all 4 of you want to do, then do it together. If this is what dad alone wants, then there is a high risk of dad getting just that - what he wants, alone.

Good Luck, in every way!


atoll 21-01-2011 15:21

go for it go now,your kids are at the right age to really appreciate the university of life,get any boat,30-35 ft is fine for a family of four if you can manage the 90 miles to the bahamas from florida,you will have achieved what some people work their whole lives to do. ....then take it from there... get the kids doing stuff,boy cleaning hulls,girl baby sitting,wife,learn to varnish or cut hair,you mechanic,you wont starve(there is allways conch and rice and beans)
whaterver happens you are sure to end up better people for it.......

Noname1 21-01-2011 15:39


I know ya gotta do things you don't want to do to be successful sometimes.
That may be true but why not try to find something your heart is in?

The cheaper the initial price vs other similar boats means you need a bigger repair kitty.

Ask yourself are you "house" oriented or "away from the house" If you are the kind of people that go home to sleep but otherwise are on the go then a smaller boat may do that is a little easier on your wallet. AFTER you have a sound boat AND you can do your own maintenance you really can't live any cheaper than on a boat.

tonforty 21-01-2011 17:52

Why not find something my heart is in!

The family loves the adventure. They always believe in me and would be great for it.
My son would sorta balk at 1st but I'll think he'll be into it.
Even if hes not ,It's OK Ill make it cool for him.

Also I'm thinking like ALL the responses. I could do it for one year then have a spiritual awakening and rejoin the rat race.

I think my idea is flexible enough to keep some latitude.

However....It is definately hot hot in Florida. We'll just have to get away from the boat or hybernate in the AC or get use to it.

Or....quit after the 1st month and go rebuild an awesome business of some sort.

The flexibility is there for once in our life.

If I dont do it then I can say ....."someday"..."I shoulda".

Man...Believe me. I really really tried to make my goal in this business.It woulda been an amazing boat in 3 years. I would have changed sooner but didnt wanna give up 5 minutes before the miracle.

Khagan1227 21-01-2011 18:38

If you are looking for sunshine and roses, skip this post.

I am of the opinion that too many people feel like life is rushing by them and if they donít jump now, they will regret it later in life. Most don't think, or worry about what happens after they make the big decision....

Let's face it, the economy sucks, so unless you have a guaranteed income that you can live on AND keep your boat up, you are likely to end up as ďone of thoseĒ cruisers that cities run off as an eyesore.

I AM living the American dream, but I had to take the bad with the good. I wonít bore you with details, but there were MANY times I wanted to chuck my responsibilities and run away. Looking back, Iím glad I didnít. I have an annuity that will pay me for the rest of my life, and I can live on it if I want to walk away right now. But I want to ensure that I donít have to eat kibbles in my golden years because I made a single ill thought out decision.

So, if you are looking for me to tell you to grab for the golden ring and go for it, forget it. What I will tell you, is what a friend of mine told me about buying stocks, writing covered and uncovered options and trading options. ďThe level of risk you are willing to take should be at a level that allows you to sleep at night.Ē

Incidentally, I buy and sell stock, and I write and sell covered calls. :whistling:

tonforty 21-01-2011 23:43

Sometimes I'm such a chump

atoll 21-01-2011 23:57

there are a lot of south african families,who left with only a yacht,and not very much money since 1990,most of them have done okay.

not all are still cruising,but there are a lot doing okay living and working all over the world.............

ps listening to jimmy buffet helps to get the right mind set!!!!!!

SouthernHiker 22-01-2011 02:49


Originally Posted by atoll (Post 602232)
ps listening to jimmy buffet helps to get the right mind set!!!!!!

Made me laugh. That's exactly what gets me motivated to finish out my work projects before buying the boat, but that's only b/c I'm less than a year out from cruising now. Listening to JB and Kenny Chesney last year had me quitting my job and setting down this path.

I'm probably much too young and a dreamer to give much advice on the subject, but if your whole family is into this liveaboard dream, go for it. It may not be easy or the attractive "yachty" lifestyle some imagine, but hey..there are McDonald's in Florida that I'm sure are hiring. Just make sure you family wants to share in this dream, and knows what it will entail. I'd suggest laying out a realistic plan of detailed costs and sacrifices to them (full disclosure in otherwords).

If yall want a boat to live on, what is the worst that can happen in reality. That is the question I always ask before undertaking a decision. What is the absolute worst thing that is most likely to happen. I run out of money, have to work at some minimum wage job while my boat is at a $200=300 a month marina, and is waiting to sell to give me any small equity out of it to get back on my feet. Could I live like that, SURE, there's a lot worse out there for others.

One thing I would say is that a boat should probably not be bought on credit. Boats, like most personal property depreciate, leaving you upside on it and stuck with it. Sometimes major sacrifices have to be made in order to pursue the dream, it's a question whether your family and you are willing to make them. People all around the world live on a lot less than a stock option, it's just a question of what you and your family want and how badly you want it. No one can make that decision for you, but there are folks out there cruising on less than you could probably imagine.

Hudson Force 22-01-2011 03:22

It's far more likely that you could be successful moving aboard and cruising with an established income than escaping to the boat in Florida without economic prospects. I would expect that you could take the move from renting in the cold north while employed, to renting in the warm south while employed and begin searching for the boat after the move. Why put all at risk simultaneously? This would allow you to do some longer term and wiser shopping for the vessel and allow you to adapt to live aboard before cruising. If you take the geographic move, the boat purchase and the cruising as separate tasks; I would expect that your family would be better at adapting too. Good luck & skill!

David_Old_Jersey 22-01-2011 03:47

errrrr, kids are 17 and 18? How them going getting jobs? either to chip into the "family dream" or to set up on there own. Can always get more education later, under there own dollar - if they value it enough they will.

If you are broke at the moment you are going to be broke on a boat. and unlike the rental house you will (highly likely) be married to your new home, and the bills that go with it.

Fair enough get out of your rut, maybe even move to Florida - but if you cant get sorted ashore then buying a boat (whether to sit on at the dock - or sail off into the sunset) ain't gonna provide a magical solution.

But we each tread our own path :thumb:

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