My New Hobby, Investing (to Sail/Cruise)

Sep 8, 2014
2,551
Catalina 22 Swing Keel San Diego
That is welcome information, since my wife has left her administration position at a local hospital after 30 years and we are trying to build a homestead business for the next 5+ years. Our goal is to retire onto a cruising boat and travel. The last thing either of us wants to do is fall back into the world of office politics.

- Will (Dragonfly)
Will, you seriously need to read that book I mentioned above, "The Simple Path to Wealth", by J.L Collins
He is from New Hampshire!
 
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Oct 19, 2017
7,973
O'Day Mariner 19 Littleton, NH
Will, you seriously need to read that book I mentioned above, "The Simple Path to Wealth", by J.L Collins
He is from New Hampshire!
I will look into it, thank you. My wife read one years ago by a guy named Givens. His first piece of advice was, pay yourself first. Somewhere in there, he points out that more wealth has been made from real estate that any other path. Last I heard, years ago, he'd been arrested for fraud.
That, of course, doesn't mean he didn't give good advice, just that I have less faith in it than before.

- Will (Dragonfly)
 
Jul 20, 2005
2,422
Whitby 55 Kemah, Tx
A few things I want to point out:

1) If I remember correctly, you are counting on 18% APR. That may work now but doubt long term, especially as your money grows.

2) The markets, including housing, is going to be in the dumps in 5 years.

3) It is 100 times easier to make money when the market is going up; it will not keep going up all the time. Most expect it to tank just before or during the primaries for 2020 and some think it can be worse this time around.

My advice: make money while you can and have a goal and plan, but keep it private. By stating an aggressive (some may say far fetched) plan publicly, if it doesn't pan out you will feel like a fool.
 

jssailem

SBO Weather and Forecasting Forum Jim & John
Oct 22, 2014
23,037
CAL 35 Cruiser #21 moored EVERETT WA
One recommendation start a HSA as soon as you can. It will be a valuable tool in your adventure.
 
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Feb 21, 2008
413
Hunter 33 Metedeconk River
A little late for you maybe, but every kid once he gets an allowance should read and ocassionally re-read the book
"The Millionaire Next Door" by Thomas J. Stanley. It does not tell you how to make the money, its more of a treatise on what millionaires have in common in their livestyle. It is very interesting and timeless.
 
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Oct 10, 2011
619
Tartan 34C Toms River, New Jersey
So here comes the ugly part... and I'm throwing this out there because I want everyone to know I a flawed human being like the rest of us and maybe this will help others avoid these pitfalls.
Here is what I did wrong, mostly in the past, which has motivated me to correct my course;
#1. I wasted a CRAP LOAD of cash... As a young officer in the military I was living like a Rockstar. I partied and chased women, bought expensive toys, and din't think about the future much when I had the discretionary income that could have really grown.
#2. I missed a HUGE opportunity to invest 10 years ago. Not the kind of 'oh if I had known Netflix or Bitcoin would have blown up I would have invested'... not like that. None of us have crystal balls to see the future, so I don't beat myself up about that. I do kick myself because in 2006 I sold my condo in Hawaii and made a cool $125K tax free. I SHOULD have invested all of it, but I didn't. I paid some debt down and I also made a down payment on my new house plus about $20K in necessary landscaping upgrades (retaining walls and other concrete work). The investment in my home was good, but the rest of the cash was burned up over several years of buying race bikes, partying in Vegas, and other such debauchery.
#3. I was saving in my 401K at the time, but only 10% of my income. I had not considered a Roth IRA and wasn't investing elsewhere either. I also could have funded a 'rainy day' cash reserve and 'hidden it' in a Vanguard money market account at 3%: This a cash account that is relatively easily to access in an emergency, but not as easy or tempting if it were in a savings account. Had I put about $15K in such an account, years later when I was laid off from First Solar I could have used that instead of cleaning out my 401K! Doh!

These were HARD lessons in retrospect; what is even more bitter is that I understand them now but had no clue about such things when it mattered (I would have made better choices). So looking at this played out in my life has motivated me to move in the right direction. I'm just under 40 and I still have time to steer the right course.
So basically you did what 90% of young guys do.(myself included) The question is did you have fun? I did.:yeah:
 
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Sep 8, 2014
2,551
Catalina 22 Swing Keel San Diego
One recommendation start a HSA as soon as you can. It will be a valuable tool in your adventure.
Excellent point... Using an HSA is a strategy that is mention in the book I cited above and in several of the financial management blogs I read. I am looking into it, but at the moment I do not use a High Deductible Health Insurance provider, so to start one would cost me some money. I have to do the math on what it will cost to fund the account and what it's long term benefit will be vs. other tax-sheltered investments that I could possibly make.
 
Sep 8, 2014
2,551
Catalina 22 Swing Keel San Diego
A few things I want to point out:

1) If I remember correctly, you are counting on 18% APR. That may work now but doubt long term, especially as your money grows.

2) The markets, including housing, is going to be in the dumps in 5 years.

3) It is 100 times easier to make money when the market is going up; it will not keep going up all the time. Most expect it to tank just before or during the primaries for 2020 and some think it can be worse this time around.

My advice: make money while you can and have a goal and plan, but keep it private. By stating an aggressive (some may say far fetched) plan publicly, if it doesn't pan out you will feel like a fool.
1) I certainly don't think I'm getting 18%, If I made a typo somewhere please point it out. I use 7% as a conservative growth estimate for my long term accounts.
2) I agree, the markets will dive at some point and I'm prepared for that. The majority of my holdings are long term, 20 to 30 years before I expect to tap into them. History has proven that over long periods the markets always recover. On the housing market, I plan to sell if I catch the right window. If I don't, I will stay put and re-align my plan. If the housing market takes a dump and I will still want to leave I can rent my property for a small profit, even if the rental averages slide a bit too. I will just have to wait to tap into the equity until a later time.
3) Agree and totally expect markets to slide post 2020, also post this years mid-terms. Old adage "when there is blood in the water, buy more". Again, all of my stock holdings are Dividends that Drip Invested. After markets slide I will by more shares at a handsome discount, they will recover in price eventually.

I don't see how I could look like a fool if the markets fluctuate, as they always have and always will. This is long term investing, not really different than most people do with managed retirement accounts. I haven't stated any specific funds or stocks (other than category types) or what percentage of my diversification I hold them in. So how is it that I will look foolish? The lessons I am trying to share with others are 1) have a plan and track the plan. 2) Pay attention to your Net Worth and the percentage of disposable income you invest or 'savings rate', and 3) This isn't about getting rich quick, it's about getting rich SLOW with mitigated risk.
 
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Jun 2, 2007
404
Beneteau First 375 Slidell, LA
2) The markets, including housing, is going to be in the dumps in 5 years.
IMHO, these are exactly the kinds of statements that prudent investors should avoid. NOBODY knows what might happen in the future, be it next month or 5 years from now. Just be assured that there will be bumps in the markets at some point, and have a plan to ride them out. Forget the timing part.
 
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pateco

.
Aug 12, 2014
2,207
Hunter 31 (1983) Pompano Beach FL
@CloudDiver ,

I did some satellite internet work for a cruiser in the Bahamas many years ago. He was paying his way through the Caribbean night trading the currency markets in Asia. He set up an alarm to get him up an hour before the Asian market opened. He then studied the numbers from the overnights, made his trades at market open, and then went back to bed. I set up a portable Vsat broadband system for him so that he could have high speed internet as he moved from marina to marina.

He had a nice 60'+ sailboat, so his method must have been working for him.
 
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Sep 8, 2014
2,551
Catalina 22 Swing Keel San Diego
@CloudDiver ,

I did some satellite internet work for a cruiser in the Bahamas many years ago. He was paying his way through the Caribbean night trading the currency markets in Asia. He set up an alarm to get him up an hour before the Asian market opened. He then studied the numbers from the overnights, made his trades at market open, and then went back to bed. I set up a portable Vsat broadband system for him so that he could have high speed internet as he moved from marina to marina.

He had a nice 60'+ sailboat, so his method must have been working for him.
I don't think I'm skilled enough to be day trading on the currency markets, LOL! As far as working while sailing goes, I've heard you can make a nice little bit of pocket change by editing academic papers for non-english as first language students. Depending on the length and importance of the paper, how much grammar/structure/format editing you have to do, it appears you can make up to a couple hundred bucks per paper for about a day's work on a laptop. Only low bandwidth required to download emails with MS Word attachments.
 
Jan 7, 2011
5,527
Oday 322 East Chicago, IN
I've recently learn that social security benefits are based upon earning from the last 5 years before applying. This means, if you have cut back on hours or taken a more modest job before retirement, you won't get back what you've been paying all your life. Quitting work early my net you no SS income when you reach retirement years.

- Will (Dragonfly)
Speaking of SS, CloudDiver, assuming your defined benefit plan is through a US government job, does that mean you are not eligible for Social Security? My dad worked for the Us Forestry Service pretty much all his life, and I thought he said he was not eligible for Social Security. He has since passed away so I can’t ask him.

Defined benefit plans are very hard to come by these days, so it sounds great. But if it replaces Social Security, then maybe not.

Also, does it include lifetime health insurance? That is probably my biggest obstacle to retiring too early. I am 56, married to a wife with some medical issues. I will retire early, planning g on 62 at this point, but health insurance / medical costs are keeping me from getting out of the rat race earlier.

Also, I don’t think you mentioned if you were married or not...that makes a huge difference in how much $$ you need to retire.

Interesting discussion. You have started here!

Greg
 
Sep 8, 2014
2,551
Catalina 22 Swing Keel San Diego
Speaking of SS, CloudDiver, assuming your defined benefit plan is through a US government job, does that mean you are not eligible for Social Security? My dad worked for the Us Forestry Service pretty much all his life, and I thought he said he was not eligible for Social Security. He has since passed away so I can’t ask him.

Defined benefit plans are very hard to come by these days, so it sounds great. But if it replaces Social Security, then maybe not.

Also, does it include lifetime health insurance? That is probably my biggest obstacle to retiring too early. I am 56, married to a wife with some medical issues. I will retire early, planning g on 62 at this point, but health insurance / medical costs are keeping me from getting out of the rat race earlier.

Also, I don’t think you mentioned if you were married or not...that makes a huge difference in how much $$ you need to retire.

Interesting discussion. You have started here!

Greg
Greg... no, not married. Pretty sure that is the only way I am able to achieve a nearly 40% savings rate, LOL. Yes, my defined benefit portion is for Federal service (combined military/civilian GS @ 20 years). I still get SS, but I am under the newest version of the FERS plan. I'm not sure, but under the old CFERS I think you didn't have to pay into SS so you didn't get SS (maybe, someone of that generation would have to speak up). I do know that CFRS was way too generous, thats why it tanked. You could serve 20 years on active duty and get your normal military pension @ 50% of your base pay, then you'd get a Federal GS position and you'd be credited with 20 years of service for your military time, work until 57 (12 to 15 years avg, depending on age you ret from military), and then retire again with a credited 30 to 40 years under the CFRS plan... they called that 'double dipping'. For me, I have 'buy' back my 10 years of active duty service which was $14K for me (still paying for it, but worth it).
 
Jan 7, 2011
5,527
Oday 322 East Chicago, IN
Greg... no, not married. Pretty sure that is the only way I am able to achieve a nearly 40% savings rate, LOL. Yes, my defined benefit portion is for Federal service (combined military/civilian GS @ 20 years). I still get SS, but I am under the newest version of the FERS plan. I'm not sure, but under the old CFERS I think you didn't have to pay into SS so you didn't get SS (maybe, someone of that generation would have to speak up). I do know that CFRS was way too generous, thats why it tanked. You could serve 20 years on active duty and get your normal military pension @ 50% of your base pay, then you'd get a Federal GS position and you'd be credited with 20 years of service for your military time, work until 57 (12 to 15 years avg, depending on age you ret from military), and then retire again with a credited 30 to 40 years under the CFRS plan... they called that 'double dipping'. For me, I have 'buy' back my 10 years of active duty service which was $14K for me (still paying for it, but worth it).
That sounds about right...I don’t think my dad paid into SS.

How about health insurance?

Greg
 
Oct 19, 2017
7,973
O'Day Mariner 19 Littleton, NH
does it include lifetime health insurance? That is probably my biggest obstacle to retiring too early. I am 56, married to a wife with some medical issues.
Tally Ho,
Since my wife left her job and we are trying to build a business to become self-employed and self-sustainable, we currently have zero income (I think we have had a rough total of $2000 gross income and much much much more than that in expenses this year). We have been doing little but spending money on infrastructure. My wife's benefits ran out and we had to apply for healthcare on the marketplace. Because we have no income, the price of insurance went from unaffordable, even if we still made our old income, to almost free. There is a sliding scale for determining how much it will cost. There were a few hoops to jump through, but it wasn't that bad. The hardest part is learning to ask the right questions because information isn't always forthcoming. When we start actually making money again, that will change. I don't know what the future will bring in health insurance, but for now, it can be found for an affordable rate.

-Will (Dragonfly)
 
May 1, 2011
4,964
Pearson 37 Lusby MD
but under the old CFERS I think you didn't have to pay into SS so you didn't get SS
CSRS didn't pay into SS. FERS does, but you knew that. I get no credit for my military time - I retired from the Navy with 20 yrs and a few months, so get retainer pay. It would be too expensive to buy that back, but I was able to buy my 4 yrs as a midshipman. Half an Ensign's pay from '74-'78 wasn't much, so cost less than $500.
 
Sep 8, 2014
2,551
Catalina 22 Swing Keel San Diego
That sounds about right...I don’t think my dad paid into SS.

How about health insurance?

Greg
Health insurance I have covered for life, pretty lucky in that respect I guess. In the future I will try to find some type of 'international' coverage plan if such a thing exists because I doubt I will always be able to fly back to the U.S. if I need some medical care. On the flip side, in most travel videos I have seen that discuss health care while traveling or living abroad, you can pretty much afford to pay cash for most general healthcare needs in any country but ours! Also, fingers crossed that my general health remains in good condition so I won't need any consistent high level of procedures or care outside of normal bumps and bruises until I am at the age where I should retire to shore anyway.
I've been looking into starting a Health Savings Account, but I don't have a high deductible health insurance plan. Nothing is stopping me from getting additional health coverage, but it would cost me $75 a month just buy the insurance so I could contribute to the HSA. At this pint it isn't feasible since its already a challenge for me to make the maximum allowable contributions to my 401K and IRA each year plus Drip Invest and buy boat stuff... I'm kinda tapped out after that, LOL. If my salary were to miraculously double in the next three years I would definitely start an HSA.