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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:

Pete7 22-01-2011 04:19

There is a French exchange officer with a family whose yacht is moored opposite me, its a large and very scruffy Jeanneau about 40 feet. The yacht looks like its been 10 rounds with Mike Tyson, but most of it is purely cosmetic. Do they care, nope and more to the point is they use it every weekend. Over on the posh side of the marina there are dozens of newish white European yachts that never move whilst there owners are slaving away at work to pay for them.

I suspect the hard bit is making the final decision, but if you go then good luck and safe seas :thumb:


Wand 22-01-2011 05:04


Originally Posted by tonforty (Post 601662)
Do i have the "bug" or what?

Don't forget the old saying that the problem with holidays is that you've got to take yourself along.

Same applies here I think with the proposed move south. Florida won't solve the problems you've outlined; no 'other place' can. You live in your head; get that right and the rest will fall into place.

Seems to me you're far too young to become a boat bum. I'd recommend getting into a line of work that interests you. If you're interested in boats, and you've got sales and mechanical background, look for work in the industry. There's always work for enthusiastic people, and there is a boating industry in most corners of your country.

Real pleasure comes from your interests and your achievements in your working life; sitting under a palm tree watching sunsets gets very boring very quickly.

David_Old_Jersey 22-01-2011 05:07


Originally Posted by At sea (Post 602291)
Real pleasures come from your interests and your achievements in your working life; sitting under a palm tree watching sunses gets very boring very quickly.

Wise words Buddha :thumb:

Doodles 22-01-2011 05:15


Originally Posted by David_Old_Jersey (Post 602278)
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:

As a retired (mostly) CPA who's done a bit of financial advising, I'm very much with DOJ here. I'm also concerned about two kids that should be getting ready to go off to college. Any plan there? With only $20K in net assets you are going to have a tough time looking for a boat for basically 4 adults to live on and still have something left for monthly expenses. If you were single it would be a different story, but have you sat down and tried to figure out how you are going to afford this, even for one year? Somebody has got to work and if sales is your field you are going to have to stay put somewhere which gets expensive. I hear a lot of frustration but not much of a concrete plan other than buy a cheap boat and sail off ...

Feral Cement 22-01-2011 07:20


Originally Posted by SouthernHiker (Post 602270)
if your whole family is into this liveaboard dream, go for it.....Just make sure you family wants to share in this's a question whether your family and you are willing to make's just a question of what you and your family want and how badly you want it.

Key word: family

If they are on board (pun intended) with this idea, it could be the adventure of a lifetime. If not, I wouldn't bet on a happy outcome.

BTW, Southern hiker - you nailed it, You may be young, but you've got great vision for a pup.


gettinthere 22-01-2011 07:49

so you have $40k in stock & $20k in debt.

You want to buy a boat big enough to accommodate 4 adults for $15k. Any boat over 35' will cost a lot more than $15k. A boat ready to go will run well over $50k and a boat selling for $15k will need a TON of work and not likely suitable for living until repaired.

Capt Force gave the most practical advice. Walk before you run.

Liam Wald 22-01-2011 07:58

"What would you choose, richness of purse or richness of life?" Quote Sterling Hayden.

Someday we will all be lying on our death bed and breathing our last breath. When that day comes will you think, "I wish I would have worked more and earned more money for me and my boss." or will you think, "I wish I would have done more of what I wanted to do in my life and had more adventure".

Which do you think is most likely? For me, thinking either of those things would be a tragity.

If you feel trapped or imprisoned by your situation break free. Life holds an endless number of choices and opportunities. We all leave here with nothing except for our experiences and we live on in the memories of those who knew and loved us. Give them something grand to remember!

Tia Bu 22-01-2011 08:22


Real pleasure comes from your interests and your achievements in your working life; sitting under a palm tree watching sunsets gets very boring very quickly.
Actually, neither of those sentiments rings true for me. At the age of fifty-two, I've settled into a new career teaching at a college (one of those dreams people sometimes have like sailing off into the sunset or finding high-paying work:)-- which I've also done in the past). The work part was fun at times and awful at others. The sailing into the sunset (cruising) was the same way. Neither really brought a strong sense of fulfillment for me-- although I still enjoy sailing very much and like my new job.

It seems to me that being a loving, patient, caring father and husband (hard as that is and as poorly as I did it) was the more worthwhile and important activity- in hindsight. You seem to still have that going on. If you can keep it up and still go sailing, then bon voyage. If not- then I say do what they want you to do.

I doubt everyone else has that same opinion.

For what it's worth, I get the impression Florida is not a very friendly place for liveaboards these days. The Bahamas are prettier and more interesting. I've met some families and couples who seem to have a grand time moving back and forth between the Bahamas and the Northeast U.S. coast with the seasons.

Kimarah 22-01-2011 08:28

Buying a boat to learn on sounds like a plan. Getting a job in Florida before buying the boat sounds like a realistic plan.

17 and 18 are tough ages to move kids unless they've both finished high school.

kenny chaos 22-01-2011 10:03

If you're older and can't work much anymore then I guess a pension of sorts to live off of might help.
On the other hand, I remember a story about a couple who raised 11, yes, 11 kids in a van. They were all very well adjusted and HAPPY. Sure it wasn't easy or even fun often. So what?
When I bought this farm I wanted to use draft horses and all my new farming friends scoffed. One old timer I'll never forget told me if that's what I wanted to do, that I should do it because we don't have a lot of time here. He seemed to understand something that younger folks don't and he died a week later. I did farm using the horses, got a wife and two kids, never made a nickle, but oh what experiences. People called me a lucky man (?). Now I can sell the farm and finance my final chapter. Maybe my second final chapter.
Good luck-

tonforty 22-01-2011 10:33

perplexed only for a moment
I guess my thinking is really a rare opportunity to go for it with the timing and all.

Another point is that I just don't feel that just simply working harder and all that just won't necessarily get me ahead...maybe just more in debt.

Maybe it's just time to keep it simple for a bit. I'm 44.

However , I know I am beieng a little outta the box on my thinking right now.

Never know...My cash could be alot more than I think in a month or 2.

I could pull it off for a year and see what happens.

Daddy needs a break...A real one.

I need to find that cracker jack cool sales leader I use to be.

tonforty 22-01-2011 12:43

Yep...You are exactly right Doodles...No concrete plan.
I think 20 -40 grand is chump change for what I need to do.

You are helping me with the great responses formulate one.

I am a get it done kind of guy...just not lately.

I have to fix "my part"...can't control anything else I guess.

cabo_sailor 22-01-2011 13:54

I feel for you tonforty,

I too finally got so sick of my job that it was causing health problems but the difference was I was 58 and had saved for retirement since I was in my mid-20's. So while I have to watch my spending a bit, it is not a major pressure. But I think you might need to rethink what you will have to spend to achieve your desire.

There are several liveaboards at my marina, most are either single or just a couple. Only one boat I know of has kids and I'm uncertain of their age, they're off trying to make enough money to repair their boat. As others have suggested, not all marinas will allow liveaboards and most communities make liveaboard anchoring a very large hassle. Our marina has a definite limit on how many at any one time. A liveaboard slip for around a 40 ft boat goes for around $500-600/mo plus electricity.

There are a couple of boats here that might meet your requirements but they are definitely project boats. In their present condition they are not going anywhere. Two lack engines, several lack sails, all would need new running rigging, one came in with no dock lines. The marina supplied them and will charge the owner a premium. Also, the larger the boat the more expensive it will be to maintain. Sails will cost more, lines need to be larger and cost more, etc. A friend is on a 34 ft boat cruising the Bahamas right now on a boat he paid $7k for. He probably put another $3k-4k into it and none of that was for cosmetics. I helped him break down and splice 600 ft of 5/8 in nylon three strand into two anchor rodes and a set of dock lines. We also did additional repairs to his rudder that was seriously cracked. But that is just him and his dog.

Sorry to be so long winded but the point is, there is a lot more than the cost of the boat. Saltwater is a harsh environment and the more you use the boat the more repairs you will be making. Doing a lot of your own work will help but even so, the guys that came out to repair my refrigerator charge $90/hr plus parts.

I do wish you and your family well but perhaps in the interim move to Florida if that's your desire and see what kind of work you can find that's related to boating. Sales, repair perhaps.

Good luck,

chris_gee 22-01-2011 15:55

Times are difficult. It sounds like you are down to it and have decided it is too hard. Much easier and more pleasant to think of boating. I guess some watch porn, and others buy lottery tickets or take drugs. Go cold turkey and start working to a future instead of looking for a quick fix.

Doodles 22-01-2011 16:08

Here's another idea. Since it sounds like you are just burned out and looking for a break for a year or so, and would like it to be an adventure of sorts, why not just get an old RV and cruiser around North America for a while? The learning curve will be a lot shorter, the family might be more inclined, costs of maintenance, slips, etc. is less, you still get to see lots and enjoy the outdoors, its an adventure too, and well I could go on but you get the idea. Just a thought.

I feel your pain though. Life is short, so don't give up just keep planning and something will work out. Yea, don't give up ... never, never, never give up!

atoll 22-01-2011 16:31

you guys make me want to puke.....i left south africa with nothing apart from a boat,36 ft and $2000 dollars,best decision of my life,now 25 years later have two teenage kids and a 63 ft boat sailed 2 1/2 times around the world,and still got the original $2000 dollars.

all you need is guts and determination,plan the sail, sail the plan,we used to dream about being able to work legally in the usa, land of the easy buck.

if it's not happening at home you got to go out there and make it happen.
most salesmem are born oppertunists,and you know what they say about oppertunity..............

zeehag 22-01-2011 16:39

i was working from age 16--even went to a few colleges before becoming a nursee.. but i was working at age 16. kids CAN and DO pay part or all of their own way when families are becoming destroyed by economy. there are ways to afford to live. there are ways to afford a boat.
all depends on what you reallly WANT to do.. goood luck, smooth sailing

bljones 22-01-2011 16:39


Originally Posted by atoll (Post 602732)
most salesmem are born oppertunists,and you know what they say about oppertunity..............

It's spelled with two "u"s? :)

I'm with you, atoll. If one wants to make it happen, one will find a way to make it happen.

atoll 22-01-2011 16:44

yeah i left skool at 15 ,swowwy abat th spellink

zeehag 22-01-2011 17:38


Originally Posted by atoll (Post 602745)
yeah i left skool at 15 ,swowwy abat th spellink

is all rite..i send kat to skul so h ekan typo bwtter than i kan. after skul, he goe to wurk so someone can make income hear. i mene-- they wont let the kat miss joory dootty, so he has to wurk too

i bought big, and now, 2 1/2 yrs after purchasing, i am gettin gto be able to think abou thaving a crew ND ESCAPE TO SAILING. we leave mar 1.... or thereabouts.....with size comes pricyness of repairs. is only drawback of big.

atoll 22-01-2011 17:40

dikslkeksia wools ko

kenny chaos 22-01-2011 17:55


Originally Posted by atoll (Post 602784)
dikslkeksia wools ko

Dislexics, untie!

atoll 22-01-2011 18:01

!ah !ah

zeehag 22-01-2011 18:09


boatman61 22-01-2011 18:15

Driad threft....:popcorn:

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