Any early retirees turned cruisers with big careers have regrets?

[goboatingnow]

Originally Posted by thomm225

Nice, I'm glad you enjoy it, but as I have mentioned before that slow of a day/lifestyle for me would be tough to handle.

I'm thinking though when I retire at 69 or 70 years old (if I'm lucky enough to stay healthy that long) it might be just about right to relax on my boat like that

why would anything work for you at 69 , or 59 , or 49 , theres no magic " line"

To some extent you either have the personality or lifestyle outlook that suits living on boats for long periods , you have to accept its not a continuation of your shore based life.

Nobody says you have to like sailing at all. You might just like one or two specific aspects , Hey dont sweat it , maybe spending lots of time on a boat isnt for you , thats fine

Mind you I do find the title pejorative, surely whether you have a " big career" has nothing to do with it, someone might have quite a modest job that they are very fond of and are reluctant to give up. I dont think the money is a factor

[theDangerz]

Originally Posted by thomm225

Sometimes work allows you to learn things you wouldn't if anchored out on a boat someplace.

Today I walked out of my office and checked on the two cruising boats anchored in the small bay there.

They hadn't moved since a few days before but their dinghies were tied up behind their boats. One of them was a boat about the size of mine and the other was a larger ketch.

I'm not sure how they are passing all the time.

Afterward, I went for a long walk then a workout in the weight room in our building.

Let me get this straight... you're now trying to somehow suggest that the boats currently in your bay aren't "really cruising" because they decided to anchor for a couple of days without bothering to let you know why??

I'm not sure how they pass their time either.
It's none of my business and I have no time to care... but apparently, they also find themselves busy enough to not go check in on you at the end of each day (or asking/wondering why you're still there).

Maybe there's a lesson in there somewhere you didn't learn at work that you may have figured out if you decided to go out and anchor somewhere new rather than sailing out and back again each day.

You talk a good game about being so busy at work/home and not making the leap into cruising because you're afraid you be bored... but in reality, the first place you go when leaving the office each day is to stare longingly at the cruisers in the bay and wonder what they're doing.

"Me thinks the lady doth protest too much"

[thomm225]

Originally Posted by goboatingnow

why would anything work for you at 69 , or 59 , or 49 , theres no magic " line"

To some extent you either have the personality or lifestyle outlook that suits living on boats for long periods , you have to accept its not a continuation of your shore based life.

Nobody says you have to like sailing at all. You might just like one or two specific aspects , Hey dont sweat it , maybe spending lots of time on a boat isnt for you , thats fine

Mind you I do find the title pejorative, surely whether you have a " big career" has nothing to do with it, someone might have quite a modest job that they are very fond of and are reluctant to give up. I dont think the money is a factor

The magic line has to do with getting the country house paid off and finishing up the flight sim contract.

I've hire a bunch of guys and gals born in the 90's! so I want them to get trained properly before I leave.

Then the plan will be sail to the Dry Tortugas then Pensacola after I do my shake down cruise in the Chesapeake Bay Bridge to Bridge and round the outer banks. Then decide from there

[thomm225]

Originally Posted by theDangerz

Let me get this straight... you're now trying to somehow suggest that the boats currently in your bay aren't "really cruising" because they decided to anchor for a couple of days without bothering to let you know why??

No, that's not it.

Somehow you have created a scenario in your brain that you can make an argument out of. Enjoy!

I just enjoy seeing how the cruisers spend their time since I only sort of half way watched the ones that were hammered drunk by noon back in the day in Florida.

Usually we have a few big Cats in that bay but since the night temps now are getting down in the 30's and 40's most have gone South already.

[LauraleeG]

All the bickering here aside.... it has been my experience when one has spent their adult life working at some career, the transition between retiring and the “ next chapter” should not be taken lightly. It’s a “ thing”.
My identity as a career person was teacher then department head, then principal- then retired. It took me a while to find my groove but that’s fine. I figured it out...and now I would NEVER go back to a school even though they are crying for staff due to the plague. The art of doing “ nothing” and finding the joy in the day has to be cultivated... that’s why so many people on lockdown or quarantine struggle with all that down time. We tend to need distractions. Hence the crowded mall parking lots!! ( what are people buying???!!!!!) . Retiring with a full pension is a blessing and allows me to live my dreams in full - but transitioning from the job I loved to finding joy in an unstructured day took time. Now though I wouldn’t trade it for the world. Cruising/ living on my boat/ land travel when we are allowed beats “ working” any day of the week- but only because I have the means to pay for my joy.

[thomm225]

Originally Posted by LauraleeG

All the bickering here aside.... it has been my experience when one has spent their adult life working at some career, the transition between retiring and the “ next chapter” should not be taken lightly. It’s a “ thing”.
My identity as a career person was teacher then department head, then principal- then retired. It took me a while to find my groove but that’s fine. I figured it out...and now I would NEVER go back to a school even though they are crying for staff due to the plague. The art of doing “ nothing” and finding the joy in the day has to be cultivated... that’s why so many people on lockdown or quarantine struggle with all that down time. We tend to need distractions. Hence the crowded mall parking lots!! ( what are people buying???!!!!!) . Retiring with a full pension is a blessing and allows me to live my dreams in full - but transitioning from the job I loved to finding joy in an unstructured day took time. Now though I wouldn’t trade it for the world. Cruising/ living on my boat/ land travel when we are allowed beats “ working” any day of the week- but only because I have the means to pay for my joy.

Absolutely agree which is why I have been "practicing" becoming a cruiser instead of "I have to win racer guy" since 2011 and slowly but surely I'm getting there.

I plan to use my "starter boat" which is actually my 12th boat and 6th sailboat for my first cruiser before possibly getting a larger boat.

A friend of mine has a Westsail 32 that he sometime wants to sell so maybe I'll buy that one day if cruising seems to work.

I certainly enjoy sitting below on that Westsail at the table which feels sort of like visiting a friend and sitting at his kitchen table as the boat is that stable.

[Simi 60]

Originally Posted by thomm225

I just enjoy seeing how the cruisers spend their time since I only sort of half way watched the ones that were hammered drunk by noon back in the day in Florida.

.

Thats a very myopic view of a very small % but I bet they were laughing at the ones chained to a desk thinking they were doing something important or making a difference

[SalingSue]

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)

We aren't planning on leaving in the next year or two, just enjoying life right now at what I'd call a very low stress pace. I do read about couples who've gone and failed, or worse yet end up divorced...I can't imagine that being us, but I would imagine most people were like that starting out.

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

Also, I understand this is the internet and people like to say shitty things, but I've interacted with some great people on this forum and legitimately looking for people who have blazed the trail before us and what they might be able to share.

For one I doubt I’ll ever retire, just not my thing.

But more important what’s your sailing background and your wife’s?

That’s going to make a biiiiiig difference in the answer

[sailorboy1]

I retired at 56 and NEVER have wished i was still working. While cruising isn't like my dreams I still like it a a lot more than working.

If you are more a “don't see myself retiring” type why are you wasting time on this thread?

[goboatingnow]

I’ve always had the view that most people have money or time but rarely both

Only a very few end up with both

For me , time in way more valuable then money as it’s fixed. Quite happy to live frugally to release access to time.

[LauraleeG]

Originally Posted by goboatingnow

I’ve always had the view that most people have money or time but rarely both

Only a very few end up with both

For me , time in way more valuable then money as it’s fixed. Quite happy to live frugally to release access to time.

Watched a documentary on Netflix about Bill Gates. When asked if he was ever late for a meeting his response was something like- never- money is a resource I can gain or lose, time is a resource that I can never get more of, so I can’t waste it ( pardon the paraphrasing).

[thomm225]

Originally Posted by Simi 60

Thats a very myopic view of a very small % but I bet they were laughing at the ones chained to a desk thinking they were doing something important or making a difference

Why would someone who isn't working or that has retired early be concerned with what others that are working are doing and much less be laughing about it?

[LauraleeG]

Originally Posted by thomm225

Why would someone who isn't working or that has retired early be concerned with what others that are working are doing and much less be laughing about it?

Cause it makes us feel smug and validates our choice...obviously

[thomm225]

Another thing to consider is type of job and where it's located.

I have lots of freedom in my job whereas others do not.

A guy at my dock works 56 hours/week on an assembly line at a factory. I'm not sure I could do that for one week! He is late 50's.

We here are also at a perfect spot for sailing. We can be on our boats on a Friday afternoon and sail totally away from all city life and be anchored on a river or up a creek in 3-5 hours most times alone.

So there's no real need to retire early and sail say to Florida and anchor or get a slip at a marina for months on end waiting out hurricane season or some such.

We have about 150 miles of bay to the North with tons of small creeks and rivers to explore, several thousand miles of ocean to the East, and the ICW to the South. Not many places offer this many choices for the working cruisers/sailor.

[theDangerz]

Originally Posted by goboatingnow

I’ve always had the view that most people have money or time but rarely both

Only a very few end up with both

For me , time in way more valuable then money as it’s fixed. Quite happy to live frugally to release access to time.

So very true...
but we tried years ago to stop considering them as equals (though life often makes us think they are).


You can always make more money, but the one thing you can never make more of is time.

https://www.youtube.com/watch?v=lqVd3q3CdrY