Any early retirees turned cruisers with big careers have regrets?

[KorinaSublime]

We matched to you also except early 60’s. We chartered about 10 times, owned a monohull early on, ended up on a catamaran. Husband was more experienced sailor, and very handy... you must be able to fix your own stuff! Things break etc. We are a happy couple, truly but I can say it hasn’t been easy at times. I don’t like overnight sails, a lot😬 but have to overcome things together...not a fan of bad weather either 🙄. We have a lot of wonderful times but honestly it can be really trying too, especially when things aren’t perfect. On land, you can get a break from each other, in your tiny house on the water, not so much. You only live once, if you don’t do it now you never will... you don’t want to be that guy that’s 80 with regret. If you don’t like it, sell the boat!!! It’s a sellers market!!! But at least you did it...my montra

[xtream]

I think your best bet is to figure out a way to take off and go cruising for 30 to 60 days, I believe this will answer all your questions before taking a leap.

For me I thought I wanted to sell everything, cash out on my career, buy a big serious blue water boat, and sail off into the sunset. After doing what I'm suggesting to you, after 30 days all my questions were answered and my plans totally changed.

I found I didn't enjoy sailing the type and size of sailboat I thought I needed, and my wife found she would not be happy living only on a boat. So the answer for us was buying 35 to 40 performance cruiser that is a joy to sail for me and a cute little patio home.

[surf_km55]

Originally Posted by ol1970

- 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)

Your qualifications are not likely to be met by the majority and those who do qualify 100% are not likely to be respondents to your query, invasive as it is. But the kids who never picked me for volleyball at gym class always regretted their decision, so I'll play here too.

- 54
- Don't qualify, 'only' ~$100K/year
- I loved I.T. and the people who (mis) use it. I quit working to get a handle on care for my 86 year old mother with dementia/Alzheimer's...a story of its own.
- Not cash rich, but 2 houses & boat paid for.
- Zero debt.
- Don't qualify, only ~$18K/year allocated for boat time.
- Haven't really left land. Boats are most fun in bitesize chunks.
- Bingo! Actually living on a boat full time sucks. Always maintain options.
- Happily married & wife wants nothing to do with the boat. I do passages with friends, while she flies in. She's exclusively a day & fair weather sailor, no wine spilling allowed.

Regrets? Zero.

If you actually meet every requisite on your list, one has to wonder why you are so reticent to give it a go without external encouragement. It sounds like you have it made to me... you have a spouse willing to fully participate, after all.

Was that too much to share on the Internet? Probably, but I am definitely a smaller fish to chase than you, LOL. Now go get em tiger!

[Frank60]

I don't think anyone ever lies on their death bed thinking 'I wish that I had worked more' even if they liked their job. Make the leap. I don't know about you, but the most fun I've ever had was getting outside my comfort zone and doing something new. It's not like it's an irreversible decision. If you decide that you don't like it, you can move onto something else and never regret having not tried it. There are some good books on the live aboard lifestyle and cruising that can give you some perspective and what to expect and things to consider. Search on Amazon. I would say that you and your spouse need to be equally excited about doing this and truly enjoy spending time together, or it's unlikely to be as much fun as you hope. Good luck!!

[thomm225]

Originally Posted by 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!

Some folks here really love it when the OP responds!

Btw, feel free to tell us about your inventions.

There are a lot of tech/nerd/engineer types here that enjoy that sort of thing just check out some of the solar and battery threads or fix it/repair advice threads

Also, at times many of us have had to "invent" things just to get us back home on our short and/or long cruises but unfortunately we couldn't make money from our ideas

[PLANET EXPRESS]

Mid life crisis haha yes there is more to life. With that income get a nice boat and have it moved from place to place. Then you take time off and spend it on the boat.

[lornolsen]

Originally Posted by Shrew

Who would admit such a thing at the the risk of sounding pretentious? Exposing monthly expenses is one thing. Exposing ones portfolio is another thing entirely.

I love the idea that you included a reference to your assets. Anyone objecting to this is just plain jealous.

I am 76 and still don't have enough money to retire. I do love my job. I live in Detroit and keep my cat in New Bern, NC. The season is 10 months long in Pamlico sound. My goal is to drive(of fly) to the boat every 2 months and stay on it for 10 to 14 days. This amount of time is just right for me and I am ready to get home by then.

I did sail from Kemau Tx to New Bern, NC when I bought it in 2018.

My boat is a 36' cat.

[Mauruuru]

Original plan to retire at 55 not realized but by 59 had had enough of a good thing. Left the C suite life, bough a new boat and never looked back. But my advice, don't wait till you're "finished" you don't have to jump into the water over your head wade into it a bit at a time.

[GGamble]

I don’t post much but his caught my interest. I meet/exceed the requirements. Retired at 47, 7 digit income, been cruising for most of the time. I’m currently in my 60’s. I still have my home and go back and visit it. My partner in crime still has her home and visits it too. I think expectations are the greatest enemy. Living on a yacht is not always fun. The AC quit and it took a while to get the part to fix it. It was hot and sweaty for a bit. We also take lots of side trips. We get a rental car and explore inland. We don’t travel on the cheap, we eat out a lot, we stay in nice marinas. And most importantly, we move the boat constantly. In the last 3.5 years we have crossed the Atlantic twice, covered all the med and hit every island in the Caribbean. We are both avid divers and dive constantly. This is our third time of doing the Atlantic Loop. If I was just sitting in a marina and never moved I would get bored I’m sure. We get along fine most of the time. Living in a small fiberglass tube can really wear on you. But, she loves as much as I do. We joke that if we parted ways I’d have to find a new women to sail with and she’d have to find a new man with which to sail. But, we would both still stay on a boat. Our current boat is 55 feet long, six years old and has served us well. But, we are moving to a new (to us) boat. Giving up sails and living at 15 degrees of heel. Going to a expedition style motor yacht with 5000 mile range. A new adventure awaits! But, first we will sail from Panama to Florida and enjoy the last leg of this voyage.

[CatExplorer]

Can you cruise part time like us. Contract/consult when you return.
My partner mid 60’s has a business and we are fortunate it is well managed whilst we travel. So we are part time cruisers leaving the boat on the marina in the med. We spend approx 3-4 months cruising a year over 2 or 3 trips. Yes the flight prices are expensive from NZ to Turkey (renting our house more than covers it)
We are having a ball and all our friends back home say ‘Whow you are living the dream, inspirational etc’. They comment how relaxed, content, happy we are, most want to join us, but never get around to it.
Truth is everyone has a choice, dream it, research, make it happen. Join a yacht club, wander around a marina, visit boatshows, speak to as many boaties/cruisers as poss, get a feel for their passion.
We did a med charter with friends 2017. We were hooked & followed the dream, researched during 2018/2019 and bought a 2 yr old catamaran in the Med end of 2019. We never plan our trips too far ahead. This life suits us perfectly.

[SSgtPitt]

I manage a very successful construction /remodeling company in Denver. Absolutely LOVE what I do. First time we left for 6 months but had to go back early due to poor leadership. Left again for 6 months and am back for a year and a half but leaving again....maybe for good this time.
Every time I leave it’s a huge cry-fest. I’m leaving what I love to be with who I love.
My Dad died at the kitchen table with a ton of unfulfilled dreams.....I can’t do that. Better to die old and broke with a ton of great memories than rich with as many regrets.

[MLC101]

I qualify. I was "C-suite". Fortune 100 Chief Technical Officer. Enjoyed my job immensely. However, on my bucket list was to go cruising. Lin and Larry Pardey's books weighed heavily in my youth. So, at age 53, as soon as the last kid entered college, we cast off lines and went cruising. Obviously we had been preparing for this for many years. We had purchased a 43' boat, paid it off, paid off the house (and kept it), no debts. Sold one car, put the other one in storage. cast off lines and went cruising. It was definitely worth it and would do it again. We were financially comfortable, not "rich". If there was any regret, it is that a few more years would have padded the financial nestegg. We cruised for 6 years and then got tired of it and returned. By then I was obsolete and age discrimination had set in, so no opportunity to reenter the old career. A good tradeoff. We found that by early 60's, we were approaching the age where the work associated with a sailboat would have exceeded our ability to do it with comfort.

[Tatenda]

This is a serious question!


I had a very successful career in the pharmaceutical industry, and retired at the age of 55 to pursue the dream. For us, money itself is not an issue, yes, we have been blessed. But I can tell you there is a sense of belonging that can not be replaced when you leave your career - we get validation from our life's work, and there is a sense of loss and purposelessness when you leave the office for the final time. It's real and you must expect it. Best advice is to remain active, and sailing is certainly one way to go.


For us the bigger issue was a lack of shared dream: We hit the ocean, sailed to the Caribbean as a starter, but it turned out the dream was more mine than a married couple's. So we have had to adapt. The dream of sailing to the Pacific and beyond is gone; no point worrying about what might have been, the point is to make a new plan. So the 45 foot Island Packet is gone, and a diesel hungry trawler is on the cards to explore the Great American loop.


If your career is amenable to periodic consulting, it's a good way to transition. You can keep a sense of professional attachment, work from the boat, and earn a few dollars just so that you don't worry about the mega-outflow that is inevitable with any boat. Doesn't matter how much money you have in your bank, it always hurts to shell out another 5 or 6K unexpectedly!


If you want to chat at a more personal level, reach out to me at sail.pajarito@gmail.com. I suspect we may well be in very similar circumstances.

[Tatenda]

I posted a longer reply, but let me add this: I'm an Oncologist. Yes, a cancer specialist. I've been with a lot of patients' facing end of life discussions. I never met a patient who, in the face of imminent mortality, wished they had spent more time at work before they died. There were often regrets - should have spent more time with family was the most frequent. Or more time exploring. Or more time pursuing a dream. Never more time working.


Take that for what it's worth, and don't wait for tomorrow if you have the means to make today count.


Carpe Diem!

[JimmyDarci]

We are mid 50s with a paid off 46' catamaran. Happy marriage, working 250k grind, but "low stress" is mythical to me. Upon deciding whether to leave now or stay a while and enjoy local waters, the one question we asked: If the world stopped tomorrow, what would you miss most? Do that. For us, it is sailing for a few more years in New England and Caribbean for now, then jump across the pond for longer range fun. This lets us enjoy both lifestyles a bit longer.... and perhaps leave the kids a party favor when we die.

Health is THE big variable. Fortunately not our issue today but, my dad was extremely healthy until he suddenly dropped dead at a young age. Wife's dad also died younger than usual. This reminds us that each day is a gift. Perhaps you know others that had life dialed in one day and lost it all the next, so why wait?

My 250k job is not "low stress" and that is why I need sailing in my life. If you are that fortunate to have a "low stress" job (or trust fund) pulling in more than 250k, you should be able to take a full year off an come back to reality IF you choose to do so. Nothing is permanent, even sailing.