Any early retirees turned cruisers with big careers have regrets?

[Bangorang]

We left at 51. Spent 6yrs cruising the Pacific. Definitely a bucket list experience. No regrets.

When to go is a tough call and kind of a leap of faith, but life sometimes pitches curves, so don’t wait too long.

Finally, cruising can be a great marriage builder, but it’s not a marriage saver... Listen to your partner.

[gregfreed]

I was a Senior Captain at a major Airline, well compensated, always happy to be working.
At the tender young age of 59 I decided to quit and go sailing.
I already lived on my boat and it was ready to go, so off I went leaving Seattle in my wake.
That was 5 years ago.
My boat is in a “Cyclone Pit” in Fiji till May. I have a small Camper Van in New Zealand, and a list of campgrounds as long as my arm to visit.
It’s not for everyone, and when the adventure includes a significant other it is absolutely imperative your both on the same page.
As for my former career, and life, I’ve never looked back for a minute, my past is behind me. I’m currently in Florida with my Grandkids for Christmas .
I’ll head back to NZ in a couple weeks, with a short stop off in Fiji to check on the boat and lighten my load of newly acquired spare parts.
Your asking all the right questions, just understand it’s not an easy life, sometimes fun, always an adventure.

[ttex]

My wife and I are in our 30s. We both have peasant jobs that pay less than 60k a year.

I don't think a person could be anymore opposite to you than I am.

We worked our fingers to the bone to buy our fixer upper and we are working our fingers to the bone to fix it up. Once we start cruising in a year or so we will work our finger's to the bone to not starve until the day we die.

And I can't imagine anything I want more than that.

[theBigKahuna]

The one recommendation I would have (we're a bit in a tax bracket lower, but very happy w/ our luck in professions).

Identify some type of income generating work you can do remotely... definitely helps keep the gears going upstairs (and helps keep each of you out of each others hair a bit)! I'd also recommend doing it well BEFORE leaving. I'm doing it a bass-ackwards and that part I do regret.

Cheers and good luck!!!!

[KLo]

My replies in CAPS, not yelling:
Retired 55 or earlier - meaning zero paid work, only living on investments COMPANY I WORKED FOR BOUGHT, I WAS LET GO AT 55...
- Highly compensated in their profession (arbitrarily picking $250k or higher) YES
- Enjoyed their career, loved their work/people LOVED EVERY MINUTE OF THE WORK DAY
- Substantial assets that allow for a comfortable life at sea WE SAVED UNTIL IT HURT
- Paid for boat, no other debt PAID CASH FOR LARGE MOTORY YACHT
- Meaning $100k or much greater budget that is not a stretch
- Means to transition back to land life no problem STILL LIVE ON LAND BUT USE BOAT A LOT
- Ability to park the boat and take a 3 month break or greater YES
- Married happily with no underlying issues (basically extremely happy already) FORTUNATE THAT WIFE LOVES MARITIME LIFESTYLE

WE'RE NOW GOING ON 4 YEARS LATER..... ALL IS FANTASTIC. LOVE THE BOAT, LOVE WORKING ON IT AND MAINTAINING IT, ALWAYS NEW THINGS TO LEARN, OBTAINED CAPTAIN'S LICENSE, LOVE THE PEOPLE IN THE BOATING LIFESTYLE, MY ADULT CHILDREN LOVE IT, THEIR FRIENDS TOO, NEW PLACES TO DISCOVER, PARTIES ON THE BOAT, SOLITUDE ON THE BOAT, FEEL BLESSED TO BE ABLE TO EXPERIENCE IT ALL. MY BROKER/FRIEND I BOUGHT THE BOAT FROM SAID, "IF YOU WAIT UNTIL YOU THINK YOU HAVE ENOUGH MONEY, YOU'LL BE IN YOUR 70'S, HAVE A KNEE REPLACEMENT, OTHER HEALTH ISSUES (CANCER IN MY FAMILY)....THEN IT'S TOO LATE. LIVE THE DREAM, DON'T JUST WAKE UP FROM IT."

I'M SO GLAD I WAS LET GO FROM WORK BACK THEN. SOMETIMES WE NEED A JOLT TO FORCE US DOWN THE PATH WE ALWAYS DREAM OF.

GOOD LUCK AND HAPPY CRUISING TO YOU AND YOUR WIFE.

[taxwizz]

I am 73 and doing my cruising on cruise ships.
Other people make my bed, clean my cabin, cook fantastic meals, and I still get the travel.
I am out spending my kids' inheritance.

[VickiW]

I think this question completely relies on each individual or couple that is thinking of dropping their careers earlier than is socially the norm to go cruising. My husband and I are considering a similar choice and when thinking about regret, the biggest regret I can think of is not following our dreams and taking a risk to open up new opportunities for ourselves. I realize there is a real risk that it might not work out and we just might regret it, however we will definitely regret it if we never tried.

[daletournier]

Originally Posted by ttex

My wife and I are in our 30s. We both have peasant jobs that pay less than 60k a year.

I don't think a person could be anymore opposite to you than I am.

We worked our fingers to the bone to buy our fixer upper and we are working our fingers to the bone to fix it up. Once we start cruising in a year or so we will work our finger's to the bone to not starve until the day we die.

And I can't imagine anything I want more than that.

Awesome mate, well done.

[ol1970]

Okay, so I'm the OP and wow this thread had definitely got some great insightful posts to it. Definitely helpful for learning the mindset of other cruisers out there. I did want to add/clarify a couple of items, but mostly wanted to say thank you to everyone for commenting!

Additional info:
-This is not really a financial question, without sounding like a jackwagon (which I'm sure I do anyway), I've done very well, and living on $100k+ a year is very modest for my means. This is because I realize that a life well lived doesn't take a whole lot more than that. I will donate more to charity than I will have spent in my lifetime more likely. I was Financially independent at 33, and "retired" the first time at 43 with enough to last our lifetime.
-My wife I met after I retired, because I wasn't working my ass off and could be doing what I love at 10AM on a Tuesday. She is a Swede, grew up on the ocean on boats, and we are both all in and on the same page with sailing. We spend nearly every waking hour with one another other than the 8 days a month she works. If we could spend 26 hours a day together we would.
-We have a ridiculously too large home that we use as our home base now, the plan would be to sell it to have a small home base on land someplace tropical. Small but spectacular, that along with a well built catamaran to cruise on and go back and forth. So far of all the places we've traveled we like the Bahamas, and I like the idea of being able to sail home and have it docked in our back yard. But we are still actively searching for where the "forever" home base will be, it will be someplace tropical though!
-My wife is in the airline industry and will be able to retire with flight benefits for life for the two of us. This is part of the dilemma because we love traveling to land based destinations as well. In the past 24 months the list of places we've traveled to for fun for free is ridiculous and I'd just upset people if I rattled the list off.
-I work purely for the fun and challenge of it. I'm and engineer by trade and have a couple of inventions that allowed me a nice income. I now get to do the creative problem solving part of my former career, without the managing of people. There is zero stress. I would irresponsibly speculate that over 95% of the people on this forum have come in contact with a product(s) that my ideas were used on/in. The satisfaction of solving a technical issue that nobody has done before it a lot of fun! That being said, everybody thinks what they do is super important, and I fully realize I'm the only goofball who really cares what contraption I dreamed up. They don't write stories about engineers who monetized their ideas, but they write a lot of them about people who do adventurous stuff.

On the other hand, I am succinctly aware that we are not guaranteed anything in this life, and some days I wake up and say to myself, you've got a beautiful loving wife, a healthy body, and the means to leave and never come back or have to worry about it. I really loved the truthful responses from people, and in the end it is really a personal decision. My crystal ball says we will continue to charter for a couple more years building our sailing skills and home shop for our eventual landing spot. We will then transition into 3 months on cruising for a season or two then pull the trigger. In the meantime have a hell of a lot of fun and figure out if I want to even bother finding a way to stay involved in the professional side of things.

Thanks CF community, I'll keep you posted!

[Hopefull]

Great question and yes I kind of fit the bill.

Rather than just a big and sail away, I decided to buy the right boat and do a full time refit. It’s taken just over a year working with a very experienced Shipwright.

Having been a desk jockey for 35 odd years, I’ve really enjoyed working with my hands and head. The advantage is I know my boat inside out. It’s not often in life that you have an opportunity to do something completely different...not cheap but exceptionally satisfying.

[MVDarlin]

I retired at age 56 from a wonderful job. I never made $250k but boat and houses were paid for. Divorced, no kids
I have a 52 foot motoryacht in the Sea of Cortez and a 34 ft sailboat in Ketchikan, AK. I keep a small studio apt for a home address in Seattle. Summers in Alaska and winters in Mexico. Travel and time in Seattle spring and fall. Motoryacht goes on the hard in the summer. Sailboat is in a well protected marina with brackish water. I'm now 66 and facing back surgery for a chronic problem.. Working friends have stress related problems, heart issue stroke while I spent the last 11 year's cruising. I have not spent my retirement nest egg and it is now 4x as valuable. People ask me what I do, I have 4 rental properties and 2 boats. Lots of maintenance and upgrades. . Iced cruised the West Coast to Alaska and back twice in the powerboat. It has all the amenities, w/d, freezer, 2 staterooms. Kayaks, 11 ft whaler skiff. Beautiful vessel with reliable twin diesels. Cruise at 8 knots. I'll probably keep boat in Mex for a few more years. Check my blog page. Mvdarlin@ wordpress.com for years of cruising info.

[zabbaskeema]

My brother died in 2015 and I quit at the end of that year.

Last year I bought a Wharram cat and I foolishly thought I had about 10 years of cruising life ahead of me with the money I had.

One year after this is down to a bit less than 4 year of cruising.

Sure the boat I now have has been completely refit but at a dire price.

Don't ever believe what a seller/surveyor tells you and agree to pay for destructive investigation - the best "investment" you will ever make.

Lesson learned a very high cost.

[nofacey]

If you or your wife encounter a dehibiltating condition tomorrow, would you regret not stepping out of your comfort zone, and sailing over the horizon?

- alternative to chartering (which isn’t all that much like ocean passages) is to go to something like Oceancrewlink and crew on passages - some pretty nice boats out there to try.

Fit profile, did 5 yr circumnavigation - would repeat in a heart beat. Heading off sooner would only have made it better.

[AuroraGH]

I never made that kind of cash. But I do OK.

I am lucky to have a job I can do anywhere I have internet. My boat is paid for and wrapping up a long refit to prepare to do this.

I am 55 living in Baja not far from San Diego (halfway between Ensenada and San Diego) with my boat still in SD.

I'm planning to start cruising half time while working some. During the off season I will work full time. Planning to just hang around Baja, Sea of Cortez, and west coast Mexico->south for a couple years to see how I and the Mrs like it.

[petegasson]

I’m 50, wife, 2 kids and I set sail from New Zealand May 2020, main difference for me is I’m not retiring just taking 5 years off - or maybe longer??? Thing is I don’t see myself not working again as I enjoy it.
Everything’s paid off so why wait. As for the rest, will let you know in 12 months