Any early retirees turned cruisers with big careers have regrets?

[Dooglas]

Originally Posted by Paul L

the low stress Colombia River Bar pilot, .....

I understand your point, but your post still made me smile. I began to wonder about the difference between piloting large commercial vessels over the Columbia River bar and piloting my way around the many bars in Colombia.

[sailorboy1]

If i were the OP i would find this thread too much trouble to keep up on. I would have my crew do it and write me a short summary note about it later.

[Paul L]

Originally Posted by Dooglas

I understand your point, but your post still made me smile. I began to wonder about the difference between piloting large commercial vessels over the Columbia River bar and piloting my way around the many bars in Colombia.

I only have experience on the Cartegena side Surprisingly I didn't feel the stress.

[double u]

U...now finally a thread with intelligent, relevant (well except this one), self-reflected & insightful posts! Well done, gentlemen!

[belizesailor]

Boy, thats a lot of qualifying requirements the OP lays out...I think those eliminate most of the cruising community...and most of humanity for that matter.

I had an intense career, very dead line driven, near full time travel, 80 hour work weeks were the low end...I often had 40 billable hours in by Wednesday AM...max was over 400 billable hours in one month. I enjoyed it until the last few years with more hassles, more responsibility, and less fun work. I was thuroughly burnt out by the time I fired myself.

No regrets, it was time, and it was also my plan all along to punch out at 40.

[CassidyNZ]

To the OP, I suspect that the “criteria” you listed do not describe 80% of the cruising population. It certainly doesn’t describe us although I’m sure there will be folks on this board that it does.

My wife and I both retired for no reason other than we got tired of the daily grind. Our cruising desires form only a part of that retirement and we mix it with “ordinary life” in more ways than one.

We sail a lot around our home where conditions are excellent for short (week or less) trips within 30nm of where we live. We also do trips of 4 to 6 months, all to the South Pacific island groups to the north of us. But we also get to spend the rest of the time in our home with friends and family, hobbies, projects (including boat maintenance) and those things that “normal” families enjoy.

Longer term cruises are also a compromise to suit us both. My wife is the classic reluctant mariner who doesn’t enjoy passagemaking (to be honest it’s not my favourite form of sailing either, just a means to an end) so when we go to the islands she’s sails there and back with Air New Zealand, I take the boat with crew. In the island locations we both enjoy the local sailing and foreign cultures and our friends and family are invited to share that with us.

This way we both get to do the things we want to/can and avoid the things we don’t.

@ Anne Cate: Your absolutely correct, people should not be encouraged to go cruising - they need to motivate themselves. We made the mistake of encouraging life-long friends to cruise with us. They spent a lot of money buying a boat and all the gear and then realised they were not emotionally equipped or confident enough to manage a boat at sea. Their beautiful boat now languishes on a mooring in our bay, seldom used and just costing them money. We’ll not make that mistake again. Happily they can easily afford it and don’t blame us for wasting their money - we’re still very good friends

[HBrew]

I had a job that completely consumed my life for a long time. Unlike you, I didn’t have to choose to leave it to go sailing, the decision was made for me . But now I am five years into the cruising life and completely happy with my choice. Here are a few of my observations:

1. Cruising takes a lot of time. I have met people who snatch 4-6 weeks every now and then to go sailing and it seems to me that they are always struggling trying to balance their cruising life with their work life (very concerned about having high speed internet access so they can deal with work problems all the time). As has previously been said, take it in small steps. Try three months, then six months etc but recognize that if you really set off on a major voyage (e.g. circumnavigation) then you’ll have to make it your priority or I think you’ll create a lot of stress for yourself (and maybe your spouse too).

2. Cruising, for me, includes taking pleasure in running and maintaining a boat. That is my hobby now because I always have a long list of things to do. As mentioned above, many jobs are frustrating, but once you’ve got them done, the satisfaction in knowing your boat well and overcoming some (occasionally sh**ty) problems is part of the real joy of cruising for me. Are you ready for this? I think that just getting other people to do all your boat work for you would mean missing out on a lot and unlike in business, where most people tend to be very service oriented, getting boatyards to do stuff in a timely manner is the exception rather than the rule. They are generally very amateur in the way they operate their businesses in my view and that can be quite frustrating. So, doing it yourself if you can is much more predictable.

3. Sounds like your life has included a lot of interaction with interesting people. Well, there are lots of really interesting and often very likable people cruising from all walks of life. I don’t think you’ll regret leaving behind one type of social interaction for the cruising life. Just remember that in business, you tend to deal with your financial peer group mostly, and you are all likely following the same financial path if you are successful - nice house, fancy stuff, cool car, exotic vacations etc. In cruising, your peer group is people who love to sail and talk about sailing. Some have big fancy boats and others don’t have a fridge onboard, but they all have interesting sailing stories to tell.

4. I would not want to do this without my spouse and as mentioned above, yours may not like the cruising life as much as you. So just be mentally prepared for what you’ll do if that turns out to be the case - i.e. get your priorities in order so you make wise trade-offs

5. One day, going cruising will no longer be an option for you because your health will prohibit safely operating a boat at sea. Make sure you don’t wait too long to take the plunge and see if it’s right for you. If you’re not in good shape then get fit before you start or you might hurt yourself and once you start sailing you’ll find it keeps you in pretty good shape without having to live the Peloton life

[Larimar450]

Well we just did this last year and into our first year.
No regrets to this point. We had a business and worked all the time, I see the transition as no problem, fixing and finding your next adventure keep me busy enough.

Good luck and you won't know until you try, but work will always be there to go back to, but sailing won't.

[ramblinrod]

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.

Well, anyone who did what you are planning and hated it, wife left, kids became socially inept from not having a stable friendship through tough times, sunk the boat, etc., are prolly not following this forum to talk about it, so chances are, you will only get, “we would do it exactly the same but earlier” responses.

We were one of 3 couples from our yacht club to go cruising. The other 2 planned on cruising indefinitely (one couple sold all of their 3 properties). We have yet to go (2022) and plan for 1 year (adding more if we are part way through and decide not to return yet).

Of the other couples, one lasted 2 years. They have sold their boat and bought Ontario and Florida properties. The other couple lasted a year. They are living in a rental in Ontario, until the boat sells (in Florida).

Both couples commented that it was a terrific experience, but a lot more expensive (Bahamas) and a lot more work than they expected.

Another guy where I used to work, after many many years of club sailing, retired young (40 something) to take his family on an open ended cruise. They lasted 3 months, making it to Chesapeake Bay. She left with the kids, the boat went up for sale, no idea what happened to him.

We are still working and have been sailing for 25 years. We have taken trailerables all over the Great Lakes and several spots on the eastern seaboard. and both sides of Florida.

We are very cognizant that right now cruising is a temporary escape from our working lives. When we retire and. take off on our extended cruise it will not be a short vacation (couple a greatweeks) it will become normal everyday life; just with different activities and geography.

We plan to be very careful to ensure “the cruise” doesn’t wreck sailing or our marriage for us.

My advice; if your marriage isn’t rock solid, and you don’t enjoy being in each other’s company constantly, even during hardship, give this a great deal of thought.

[belizesailor]

Originally Posted by ol1970

....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.



...

That was an option I considered too...and even tried once. However, for me, it created somewhat of the oppossite problem posed in your post...after several months of sailing, I had little interest in returning to work!

In my case, I was a partner in a business. I had good partners to keep things running while I was gone so that part was easy. The plan was that I would sail 3-6 months of the year then be back involved in the business the rest of the year. The work environment was intense....110% throttle all the time...after several months of cruising, I really struggled to get back up to speed...and I never did. I finally fired myself for poor performance! [emoji6]

That was 18 years ago...

[denverd0n]

Originally Posted by JPA Cate

...recently have begun to think people should not be encouraged at all. You either have the gumption to make it happen or not.

This has been my feeling for quite a while. If someone asks, "should I go?" then answer should almost always be "NO!"


If they are really ready to go they will ignore the negative responses. If a few "NO!" answers, from strangers on an internet forum, are enough to stop them, then they were nowhere ready to go in the first place.


Bottom line, if you have to ask, you are not ready. When you ARE ready, you won't have to ask, and you won't really care what sort of answers you get if you do decide to ask.

[Rorzech]

YES I agree with your plan about the cruising attitude.

[Red Sky]

Recently saw a 2 year old version of a boat my wife and I are interested in for sale. Did some research through broker contacts. Early retirees, 30’s, open ended cruising plans, $650,000+ new, less than 1 year of actual use, just sold for less than $500,000. One or both decided they didn’t like cruising.

[kev_rm]

This is essentially where I am. +1

Originally Posted by Sailshabby

We hit some of your criteria, and found the biggest change is going from “0-60 in five minutes at work on Friday” to “Retired at 5 knots on Monday.” It was a little discombobulating and took a few months to transition into the new mindset. If you defined your life by what you did in the office, it might take longer. I now do a bit of consulting (on site) which fills the kitty and reminds me of why I retired.

[Desertroseii]

I retired at 50. That was 11years ago. I thought that my time is worth more than the money I was selling myself for.
I had to drag my wife with me to cruise. It is always the same. Once on the boat she is very happy.
Went back to work for 8 months after two years to find out that working for big corporations is a waste of time. Even they paid me a lot with almost no responsibility.

Someone said to me how many good memories will you have from your job? I have none. However I remember every single place we visited in Indonesia.

A year ago my wife was diagnosed with brain cancer at 58.
I she waited for her retirement she would have missed it all together. This gives me some comfort now.

The longer you work the more you get paid. So it is harder to quit. You will also get older so your risk taking will diminish.
You won't be able to buy back your time.

I made more money when I retired at 50. When you are working you pay taxes. When investing you are not or pay less.