Any early retirees turned cruisers with big careers have regrets?

[Sojourner]

Originally Posted by ol1970

Just curious if there are any people out there in this camp with wisdom to provide:

- Retired 55 or earlier - meaning zero paid work, only living on investments
- Highly compensated in their profession (arbitrarily picking $250k or higher)
- Enjoyed their career, loved their work/people
- Substantial assets that allow for a comfortable life at sea
- Paid for boat, no other debt
- Meaning $100k or much greater budget that is not a stretch
- Means to transition back to land life no problem
- Ability to park the boat and take a 3 month break or greater
- Married happily with no underlying issues (basically extremely happy already)

So with that, anybody regret going, regret walking away from a gig that you enjoyed. Any marital tips for the cruisers to be?

While I won't share financials on a public forum with a bunch of strangers, I got very lucky after a few years of hard work with a series of investments that let me 'retire' very young. Not because I'm rich (EDIT: of COURSE I am rich compared to a lot of the world, very very privileged and thankful for it...I meant to say I'm not RICH rich by US standards), but because I decided what I had was enough, and sustainable through my lifetime. A decent amount of very well diversified investment assets leave me with a modest monthly income (nowhere near 250k PA but enough to buy and live fulltime on a nice sailboat and satisfy all of the other things on your list)(Second EDIT: but in perspective, we cook 6 nights a week, anchor out much of the summer, and spend 1200 bucks for the whole of our winter livaboard harbor. So, we live on the cheap.). I could have rolled it over and over into more, leveraged and sweated and risked, but that seemed like a waste of time since I already had enough to live okay.

As for relationships, I happen to have two wives (actually, we're all married and in relationships with each other, but anyway). People tend to think poly relationships are all about the bedroom. Nah. It's all about COMMUNICATION. Poly people have that down in spades, I'm tellin ya. When we were open in the past, without communication all would have been lost, but with good, honest communication, it was a blast. Now that we are closed these last 3 years, it's no less important. Talk to your wife, and really really listen to her answers. Encourage her to talk. Often. All the time. Before you go, and after. About her feelings. Her reactions. Talk to yourself. That's fun too (if you ain't fit company for yourself, how can you expect to be fit company for anyone else? )

On a boat, there is an infinite list of things to do, to learn, to plan, to explore, to try, to cook, to read, to sew, to stare at, to fish, to fix.... you'll never be bored if you don't want to be. For me, I was used to life without a 'meaningful gig', but the boat sure became one anyway. It was sort of what I had been missing Us three had been living together 24/7 in a land based apartment for years, so spending all that time together wasn't a new thing, but I've heard for couples retiring, it can be devastation to be together all the time. Somehow you should test how you two do 24/7 for a few weeks if you don't already know. Again, talk about it, see what's what. And then fix it if you can.

As usual, too many variables. Some people love the intimacy of a long life confined 24/7 with the one or ones they love. We sure do. But to others, they'll be tearing their hair out in a week. Only you can tell which you two will be. Hopefully before you buy the boat

[valhalla360]

We don't quite hit the income bracket but otherwise, we are similar, happy with healthy relationship and still make pretty good money.

There are other options beyond chuck it all and set sail. We've done a variety of them. They key is to be flexible:
- Can you work remotely part time? This is what we largely do.
- Can you work in stings? ie: 3 month on/3 month off or similar. We did find that once we got below 2 months, we tended to just hang out and do occasional day trips.
- Take a 1yr sabbatical.

Relationship wise...be ready to change what you are doing if it's not working. If you want to anchor out and she wants to be able to go out...split time between anchoring and marina. Maybe one of you is uncomfortable with the idea of long passages...keep it to coastal cruising until (maybe never) they are comfortable. At least you each get some of the dream.
- The people we've seen who broke up one of them had a dream and there was no compromise to ...until eventually, their partner had enough.
- It's a drastic change in lifestyle. You probably spend 3-4hr a day with your wife right now (not counting sleeping)...it will immediately become 24/7 in a much smaller space. Be prepared to be considerate and give each other room to do things apart (you'll still likely wind up spending a lot more time together).

[heliotrope]

We retired 26 years ago (43 and 37), and did not regret one day.
130000SM, and still a happy couple.
But we are not the norm.
N.B. We did not understand your budget:
100k will last only for 2 years!!!

[B23iL23]

I'm in my mid fifties and retiring in the new year and starting cruising. Was supposed to be two of us but unfortunately my wife passed away in June.

Last kid is almost in college so I would have an empty house so cruising is a much better option for me. Always think would I prefer staring at 4 walls in an empty house or living on a boat (Amel 50 on the way) and all the daily challenges it will bring. Cruising should add years to my life.

Will sail solo most of the time, including across to the Carribbean next Nov. Kids will join me for some winter sun once I get there.

I don't think I'll regret leaving work for 1 second. Can't wait until the only thing in my mind is passage planning or the SOC of the batteries.

[daletournier]

I retired young, didnt really have a job, had a business, it absorbed my life and I liked it that way, never looked at the clock.

Cruising now absorbs my life, dont miss the business, I miss the money , cruising is what I do now until I dont and then something else will absorb my life. I dont divide my life.

It depends on ones personality, I cant make myself interested in something, I am or I'm not , all or none.

Knowing oneself is where the answer lies, we all have different personalities.

[Jackz]

Individual question. To each their own. My only contribution is that if you are unsure, don't go all in. Take your time and it will become clear to which direction works for you.

[Augi]

Originally Posted by Jackz

Individual question. To each their own. My only contribution is that if you are unsure, don't go all in. Take your time and it will become clear to which direction works for you.

Best, most succinct response of the entire thread! As the cliche goes, "Life is what happens while you are making plans", anyway.

[boatpoker]

In 94' at the age of 42 I got out of hospital after a session with duodenal ulcers and collapsed lung from stress and exhaustion. My wife told me to quit and I refused. She collected all my suits in garbage bags and set them at the curb.
Sold the house as is ..... all furniture, paintings on the walls, classic car and motorcycle collection and moved onto the boat. I will be forever grateful to that wonderful woman who has since passed.

PS. Retirement lasted two weeks til' I went back to school and started a new "career" doing something I absolutely love.

[B23iL23]

Well said and what a great woman. Like is short and time passes in a flash - do what you love doing.

Originally Posted by boatpoker

In 94' at the age of 42 I got out of hospital after a session with duodenal ulcers and collapsed lung from stress and exhaustion. My wife told me to quit and I refused. She collected all my suits in garbage bags and set them at the curb.
Sold the house as is ..... all furniture, paintings on the walls, classic car and motorcycle collection and moved onto the boat. I will be forever grateful to that wonderful woman who has since passed.

PS. Retirement lasted two weeks til' I went back to school and started a new "career" doing something I absolutely love.

[44'cruisingcat]

My only real regret is the money I wasted buying new cars. Could have retired earlier than I did. (40)

[belizesailor]

Originally Posted by 44'cruisingcat

My only real regret is the money I wasted buying new cars. Could have retired earlier than I did. (40)

Yes, most first worlders waste a lot of money on dramatically depreciating assets. Ive bought 2 cars for myself in my adult life (since I finished grad school in my early 20's around 1983). Both used...at a grand total of $21K combined. The second one was mostly paid for by a generous insurance settlement of about $10K for the 1st one, which was worth maybe $4K. It was totalled big time, and I was exceptionally lucky to not be badly injured or killed, due to the negligence of another driver. Their insurance co opted to over pay me in exchange for not suing. So, my net outlay has really only been about $11K! [emoji3]

The last one was my good old '89 Jeep XJ, which Im still driving. I bought it in about '95. I recently started restoring it. My build thread is at the link below if interested:

https://www.jeepforum.com/forum/f177...build-4378801/


This does not include the cars Ive bought for women. [emoji849]


More related to this thread, while not spending much on cars etc, I lived on about 40% of my income most of my career and shoveled money into savings/investments...its amazing how fast you can accumulate freedom chips that way...esp in an era when any idiot could make money in the stock market/tech industry. Thats how I was able to punch out early w no regrets.

[daletournier]

Originally Posted by belizesailor

Yes, most first worlders waste a lot of money on dramatically depreciating assets. Ive bought 2 cars for myself in my adult life (since I finished grad school in my early 20's around 1983). Both used...at a grand total of $21K combined. The second one was mostly paid for by a generous insurance settlement of about $10K for the 1st one, which was worth maybe $4K. It was totalled big time, and I was exceptionally lucky to not be badly injured or killed, due to the negligence of another driver. Their insurance co opted to over pay me in exchange for not suing. So, my net outlay has really only been about $11K! [emoji3]

The last one was my good old '89 Jeep XJ, which Im still driving. I bought it in about '95. I recently started restoring it. My build thread is at the link below if interested:

https://www.jeepforum.com/forum/f177...build-4378801/


This does not include the cars Ive bought for women. [emoji849]


More related to this thread, while not spending much on cars etc, I lived on about 40% of my income most of my career and shoveled money into savings/investments...its amazing how fast you can accumulate freedom chips that way...esp in an era when any idiot could make money in the stock market/tech industry. Thats how I was able to punch out early w no regrets.

Financial regrets, ex wife and her fake boobs!, dumbest financial decision of my life by far.

[sailorboy1]

been 39 months now cruising and living on the boat, not once have I wished I was back at work

[Group9]

I retired at 52, at the peak of my earning potential, to go cruising (I made $165,000 my last year with an additional 5 per cent put into a retirement account for me every year). I have calculated that it probably cost me somewhere between a million and two million dollars in lost income and investment returns.

And, I admit, sometimes, I think about what if. But, my best friend, who did a lot of commuter cruising, and always planned to retire and go cruising full time (he helped me bring our boat back from the Bahamas one year). He dropped dead, two years ago, at sixty years old, while changing the lower gear case oil on his outboard motor. At least he died doing something he enjoyed. But, he left a pot full of money in the bank when he went.

So, what price do you put on experiences and memories? I think the ones I have are worth more than a couple extra million dollars. I know which is more likely to give me pleasure when I am too old to do anything but sit on a couch or lay on a bed.

[thomm225]

There's always the alternative of doing both......working and cruising.

Some jobs allow you to take off for extended periods while with others location is the most important thing so you can sail/cruise after work, on long weekends, and vacations. Plus visiting the boat most days .....

For some, this allows you to quench that thirst to sail/cruise and to escape the working/city life until such time as you retire full time say in your mid to late 60's or at 70 years of age while also giving you something to look forward to and to plan for

In this area and some others, you can be totally away in a few hours sailing.....