Any early retirees turned cruisers with big careers have regrets?

[ol1970]

Thanks for all of your great responses! I get that the financial aspect puts us in a very fortunate position (mostly from a decade of 80-100 hour work weeks through my 20's and early 30's building a business, that part was hard and stressful). I actually "retired" from that gig 6 years ago and now have a consulting business in the same industry that takes up about 20 hours a week with a great revenue stream. One of the options we are contemplating is just going cruising for 3 month stints. I keep the business churning along remotely for about that period of time, much longer and it would be problematic.

We currently sail about 4-6 weeks a year and vacation another month or so beyond that, no issue with not taking time to do fun stuff. We absolutely love the water and being on board going places we've never been, and the excitement of having to just figure stuff out in new locations. The thing that we (probably mostly me) think about is that no time is guaranteed and the intensity of the experience is amazing when we are on our adventures...I wonder that even though things are so cushy and great now, we may not have the chance later from a health perspective even though we are in great shape now.

First world problems I understand, but I see a lot of people out there in really nice boats that must be in similar situations. That is why I'm really interested in the social aspect and wondering if people miss the challenge/professional interaction of a job.

(I attached a pic from our last anchorage in October...so many beautiful places to go see!)

[Foolish pleasur]

I am in my senior years have owned power boats, have limited sail boat
Expérience presently in Palm Springs Ca. I am searching for a captained boat
to some what assist as a crew member, in a limited capacity.For that reason
i am willing to pay my fair share plus to experience an extended sailing trip
going to South America , originating from any where practicle . I am flexible
and can leave at a drop of a hat after April 30, 2020 .
I have sailed the BVI and enjoyed tremendously, I am opened to any other
Location you may suggest as long as it is safe and

Thank you
Gilles

[JoeRobertJr]

Hi, Foolish Pleasur, welcome to the forum

I recommend starting a new thread, perhaps in the Crew Positions forum. You'll get plenty of recommendations on how to proceed.

[Paul L]

Originally Posted by ol1970

Thanks for all of your great responses! I get that the financial aspect puts us in a very fortunate position (mostly from a decade of 80-100 hour work weeks through my 20's and early 30's building a business, that part was hard and stressful). I actually "retired" from that gig 6 years ago and now have a consulting business in the same industry that takes up about 20 hours a week with a great revenue stream. One of the options we are contemplating is just going cruising for 3 month stints. I keep the business churning along remotely for about that period of time, much longer and it would be problematic.

...

There are many cruisers who do 6 months on, 6 months off. This is a much more practical sched than trying to do 3-3-3-3. The 6 months matches up witn cyclone/hurricane season well. Don't underestimate the amount of effort and time to find a place to safely store the boat, lay the boat up and then recommision it. You could suck up more than a month of each of your 3 months just in preparations.
Also 6 months is long enough to get in the groove to try and figure out if the lifestyle really matches eith your combined needs. The upsides, mechanical downsides, weather dependencies, people you connect with, crappy internet, etc.

[Martin S]

Originally Posted by tkeithlu

I don't qualify, given having been an academic (money) or totally happy in my career (loved parts of it) and age (quit at 66, but still hopping over fences at 74).

But....

That's such a complex question that votes among people who have done it are not really going to help you. I can make a recommendation. Start doing what you want to do in retirement while still in your career, assumedly cruising with your spouse. The tragedy would be cutting your bridges to your career, setting out cruising, and finding that one or both of you don't like that life.

Some career regret I should think is always there, unless you hate it; I certainly miss teaching undergraduates. Realize that retired life is also unstructured. My wife asked me what I plan to do today, I could not tell her, and a 11:00 AM I'm still pecking away at the computer.

Good luck with your dream.

Good advise above.
You are asking way too personal questions to get full answers which may or may not translate/gel with you.
Figure out what you want to do by sailing more. Admittedly getting time off work is a major obstacle. If you are convinced you want to dive into cruising in a bigger way then don’t leave it too long and have a plan B. Life is not a rehearsal.
Good luck.

[PaulvR]

In 1990, we were cruising pretty much penniless on my Muira. We met Barry and Candy in a remote anchorage near Paratii. He was 53. I was in my twenty's then, and thought him mighty old!

His favourite saying was, "Do it now Baby!"

[AZUS]

I would suggest taking it in steps.

We took a 1 year sailing sabbatical at about that age for me and three months in my wife said, "would you sail around the world with me?" I love sailing but love my business, so.... I said yes, of course. Three years later, I have the reins just about handed off in the company, and will be leaving behind a business and people I love 5 months from now.

I have real trepidation about it, but am doing it. However, sailing for a month is nothing like sailing for a season or a year. It's the difference between a vacation and a life. I'd take a sabbatical for a very extended period to ensure that it is what you both really want to do.

[Maple Leaf]

Very interesting post. Although this not my exact situation, I can certainly relate to some of the issues. I am 55 years old and sold my business one year ago. I have one more year in the sales contract to assist in transitioning my business. We have been chartering cats in the eastern Caribbean for 10 years.
There is no turning back for me. I began searching for that ideal cat recently and hope to sail 6 months on / 6 months off. I will commit to a minimum of 2 to 5 years but will not return to my high stress, high pressure work. Life is too short. Live life. There will always be somebody with a bigger boat. Enjoy what you have.
Good luck with your plans.
Fair winds.

[Augi]

Originally Posted by ol1970

Thanks for all of your great responses! I get that the financial aspect puts us in a very fortunate position (mostly from a decade of 80-100 hour work weeks through my 20's and early 30's building a business, that part was hard and stressful). I actually "retired" from that gig 6 years ago and now have a consulting business in the same industry that takes up about 20 hours a week with a great revenue stream. One of the options we are contemplating is just going cruising for 3 month stints. I keep the business churning along remotely for about that period of time, much longer and it would be problematic.

We currently sail about 4-6 weeks a year and vacation another month or so beyond that, no issue with not taking time to do fun stuff. We absolutely love the water and being on board going places we've never been, and the excitement of having to just figure stuff out in new locations. The thing that we (probably mostly me) think about is that no time is guaranteed and the intensity of the experience is amazing when we are on our adventures...I wonder that even though things are so cushy and great now, we may not have the chance later from a health perspective even though we are in great shape now.

First world problems I understand, but I see a lot of people out there in really nice boats that must be in similar situations. That is why I'm really interested in the social aspect and wondering if people miss the challenge/professional interaction of a job.

(I attached a pic from our last anchorage in October...so many beautiful places to go see!)

Sounds like a good course of action is gradually increase the amount of time cruising and keep the consulting gig going and see how it goes. Maybe the optimum is do both (work and cruise), as long as possible maybe take on less consulting work but keep your options open to increase the consulting work. Plus if you decide to full time cruise and stop working you are well off enough to keep a house to either spend time while cruising, or rent out and have available when you don't want to cruise any more. In addition the house you potentially keep sounds like it can be in a less expensive location and perhaps a smaller, less is more kind of place. Another way to go is you can rent the house out full time and "airbnb it" when you need a beak from the pirate life.

[inchcailloch]

Wishing to leave a dream job working with kids and spending much time on Scottish lochs and up mountains I wished retirement for 50. Loved the job so much at 53 thought if I don't go now I never will. Had invested on the stock market, properties and pension have had enough for the last 9 years and income enough each month both for living, yacht expenses and some to put to one side. Biggest expenses, yacht up keep, storage if returning home and such times ie Panama canal and occassional marina. No electric bills, no council tax, no expensive holidays as constant "holiday", no heating bills....follow the sun. Maybe £1 a week for gas. Diesel as little off as much as you wish, under £5 a day for food, no car expenses road tax or car insurance. A great life no regrets whatsoever! Never leave it too late, have a smaller less expensive yacht rather than work another 2 to 3 years for a more expensive one. You'll be seeing the same views as those in a £500.000 vessel.

[Captain Puget]

I pulled the trigger at 59 1/2 (irs rules on retirement access without penalty).... and then life happened😉

GRANDKIDS- I now only cruise for a few weeks at a time in the summer with fair weather winter trips (pacific nw). No regrets as grandpa is the best job title I have ever held! I hope that the kids will join me when they are old enough, as I single hand most of the time and will probably need the help in a few years.

Bottom line - family is the deciding factor for me. I choose a smaller boat and lesser scope of travel for family. If I didn’t have that incentive I would go far and long ... maybe will in the future, with a young crew😉

[a64pilot]

Life can and does happen, we were one year into it and never got further than Vero Beach Fl. That was when we got the call that our Son had been run over and left for dead by a hit and run driver, who has yet to go to court, but that’s another story.
We spent I’d guess the next six months in rehab. And obviously incurred many unexpected expenses.

So I guess the point is no plan ever survives contact with the enemy or maybe Murphy has a vote to, so plan on it, maybe then it won’t happen.

[Stewie12]

Dońt leave it until it is too late.

[Chotu]

Speaking of busineses for sale, I'm looking. Just in case anyone here is trying to transition out of something.

I'm in a unique position in that my other businesses pay for my life expenses, so I can devote your entire current net to paying off acquisition debt.

I'd sign a formal contract to prohibit me from making changes to management, employees or the company in general, so it would safely run as you have been running it all along. No risk.

A great way to go sailing now and keep your income level where it is.

Serious post. Please DM me if you have something you'd like to transition out of.

[Telemark43]

"Different people are different. Each one of us has to figure out who we are and what we want out of life, and then live it."


The test for marriage was to buy a 19' sailboat in Maine, sail it to Florida during hurricane season, and see if you two were laughing or ready to kill each other... new experiences test each individual uniquely, and one learns more about each other as the stress increases.



Best of luck, your past successes are not relevant to all new experiences.