Retirement "What If"

[SoSound]

Last things first. For the next seven years, don't take your foot off the 'retirement' gas! Continue to save, plan, manage, invest, and explore your post retirement 'work' options. Continue to work on setting yourself up for not needing the extra 'icing' income, and for identifying work that you don't care whether you get paid for, or not.

My wife and I were lucky enough to become what I thought of as corporate 'drop-outs' a while back. During our planning stage, we thought that we'd need to operate a small business of some sort to make ends meet. But at the very last minute (OK, six months before our scheduled retirement date) we lucked into a windfall that allowed us to be able to live the lifestyle that we wanted without working. Both of us found things to do that filled up our weekly schedules at a part time level. And I still work, seasonally, to keep replenishing MY toy budget.

For the pre and post retirement stages, there are plenty of blogs and forums out there to help with the financial side of things. Start spending time reading about and researching what others have done to accomplish what you hope to. But, I wouldn't plan on a huge reduction in personal spending if you expect maintain both your current lifestyle and a sailing one.

WRT work; my big epiphany came when I realized that the people who I knew, who were the best at what they did, would be doing their same jobs whether they were getting paid for it, or not. If it wasn't their job, it would have been their hobby. What, specifically, do you want to do with your sailing interests after you retire? Is it on the water? Is it fabricating? Is it using your skills and knowledge to help others accomplish their goals and dreams? For me, I 'work' during the winter at something that I used to spend a couple thousand dollars a year on. With what I earn, I keep up with my hardware habit for both my winter activities and our summer sailing.

After quite a while at this, we are now starting to talk about what it is that we will do when it's finally time to actually "retire"...

 

[Will Gilmore]

"Motivational speaker"
Only
You exclusively do venues near a marina you can sail to.
Travel, excellent pay, short hours, zero responsibility.

YOU CAN DO IT.
JUST VISUALIZE YOUR GOALS.
And follow these four easy steps:
Save
Aquire
Install
Leave

-Will (Dragonfly)

 

[Jim26m]

"Motivational speaker"
Only
You exclusively do venues near a marina you can sail to.
Travel, excellent pay, short hours, zero responsibility.

YOU CAN DO IT.
JUST VISUALIZE YOUR GOALS.
And follow these four easy steps:
Save
Aquire
Install
Leave

-Will (Dragonfly)

Good for artists, politicians, sports figures, and con-artists. We engineers can't seem to grasp the concept. Wish I could, though. It can be lucrative.

 

[Will Gilmore]

Good for artists, politicians, sports figures, and con-artists. We engineers can't seem to grasp the concept. Wish I could, though. It can be lucrative.

Ah yes, if your an engineer and you want a high paying job with no responsibility to retire into, then consulting is the career for you.
Get hired to suggest things a company can do to be more efficient. Spend a few weeks just interviewing and walking around at $200/hr, read and rewrite the company's protocols and ask the guys who actually do the work how they think it should be done, then produce a report a couple of weeks later, at $10,000, that uses all those ideas. If and when the company reports back that they experienced no benefits from your work, just point out that they did not successfully follow your outlined plan of action and they need to concentrate on their record keeping and goal setting discipline.
It's also good to suggest a key employee get promoted (instant ally) and several extraneous upper middle positions (there are always those) get cut/consolidated (Instant short term cost savings). This is new CEO SOP. Cut jobs so the end of year financials show a net gain. A CEO can ride on that for two more years before the board realizes he's killing the company. A consultant can ride that wave forever because any future failure is the fault of the CEO.

-Will (Dragonfly)

 

[Sailm8]

I retired at 55 and moved to Florida so we could sail full time. My wife, who is the accredited teacher, had been hired to teach High School said I couldn't just be retired while she worked. So I got a job teaching High School too. They were looking for someone in my field and got hired on the spot. Worst year of my life, but after that, I had it figured out and lasted 7 years. We have the boat behind the house and can leave almost anytime we want.

Funny thing is, we don't really sail as often as we did up north but we sail for weeks at a time now.

 

[dlochner]

Worst year of my life, but after that, I had it figured out and lasted 7 years.

That would be true for you and every other first year teacher.

 

[Sailavie1]

Will, I think you just summarized exactly what’s wrong with corporate America and Canada. Not that I care as much now.
During my career, I have seen these consulting “experts “ come and go. The only results were heads scratching and asking why the hell did we hire them.

 

[Jim26m]

Ah yes, if your an engineer and you want a high paying job with no responsibility to retire into, then consulting is the career for you.
Get hired to suggest things a company can do to be more efficient. Spend a few weeks just interviewing and walking around at $200/hr, read and rewrite the company's protocols and ask the guys who actually do the work how they think it should be done, then produce a report a couple of weeks later, at $10,000, that uses all those ideas. If and when the company reports back that they experienced no benefits from your work, just point out that they did not successfully follow your outlined plan of action and they need to concentrate on their record keeping and goal setting discipline.
It's also good to suggest a key employee get promoted (instant ally) and several extraneous upper middle positions (there are always those) get cut/consolidated (Instant short term cost savings). This is new CEO SOP. Cut jobs so the end of year financials show a net gain. A CEO can ride on that for two more years before the board realizes he's killing the company. A consultant can ride that wave forever because any future failure is the fault of the CEO.

-Will (Dragonfly)

Not my style. Like @Sailavie1, I watched "consultants" come and go, leaving death and destruction in their wake. I wasn't brought up that way.

I've had offers to do consulting work along the lines of what I did for my career, but I need some down time before I would want to get back into it - if ever.

One of the consultants projected a workload downturn, and management cut our engineering staff in half accordingly (while actually creating middle management positions). The downturn was short term and very slight, leaving those of us who remained, on constant overtime/overload. The organization was still understaffed when I retired, virtually drowning in workload.

And, I didn't mean to say that all motivational speakers are con men. I just meant that you don't find many engineers who are good motivational speakers; or who can speak in public for that matter. I just threw con men in for artistic flair. Maybe I see why I shouldn't speak in public either...

 

[kloudie1]

I did a little consulting when I retired (at 60), but it was the kind where the question was "Can you get that machine to run longer than 6 months?" or something to that effect.. It is the same job I did when I was having the most fun at work.. like an engineering puzzle with failure analysis thrown in.. Worked out fine until I remembered how I hated other people's deadlines.. I am happily really retired now..

 

[dlochner]

Worked out fine until I remembered how I hated other people's deadlines..

One of very pleasant experiences of being retired is no rushing, no deadlines. Want to drink another cup of coffee in the AM, go ahead. See a cool YouTube video, the lawn can wait.

One of the hardest adjustments in retirement is knowing that is OK to spend some of the money I had been saving since I was 16. And feeling guilty that after saving money for 50 years, I wasn't saving money.

 

[MikeHoncho]

Dab nabit! Being the OP and inquiring about sail specific side hustles, I’ll allow the engineering banter because I always thought I would have made a good one but I’m throwing out the retirement planning (my LE background coming out). It’s too involved and to be honest with you, no matter how set up a person is (truly set up) there is someone else who thinks more needs to take place. I’ve spent my professional career planning for retirement and it still freaks me out but you have to also live in the moment. What gives me pause though is my fairly wide spectrum of “stuff” I can do after retirement. If this wasn’t the case I’d stay where I’m at. I want to do something I “want” to do. So, enough of that in this one.
Not a lot of talk about delivery crewing, lessons and other topics I thought would have been popular

 

[MikeHoncho]

One of very pleasant experiences of being retired is no rushing, no deadlines. Want to drink another cup of coffee in the AM, go ahead. See a cool YouTube video, the lawn can wait.

One of the hardest adjustments in retirement is knowing that is OK to spend some of the money I had been saving since I was 16. And feeling guilty that after saving money for 50 years, I wasn't saving money.

I feel I would spend a bunch at first fixing all the stuff that needs fixing.

 

[Jim26m]

Dab nabit! Being the OP and inquiring about sail specific side hustles, I’ll allow the engineering banter because I always thought I would have made a good one but I’m throwing out the retirement planning (my LE background coming out). It’s too involved and to be honest with you, no matter how set up a person is (truly set up) there is someone else who thinks more needs to take place. I’ve spent my professional career planning for retirement and it still freaks me out but you have to also live in the moment. What gives me pause though is my fairly wide spectrum of “stuff” I can do after retirement. If this wasn’t the case I’d stay where I’m at. I want to do something I “want” to do. So, enough of that in this one.
Not a lot of talk about delivery crewing, lessons and other topics I thought would have been popular

Sorry about drifting.

I knew a guy that did delivery crewing when he was young. He's got some great stories - some of which I would rather not live. Many, though, sound like the best time ever.

If I could only do it in winter, any sort of marine electrical or mechanical system repair work would be good. Troubleshooting and repair are very rewarding. Just don't want to do it in the heat down south. I work on my own boat in a conditioned garage for that very reason.

Delivery duty can morph into repair work, particularly delivering used boats - if my buddy's stories are any indication. This might present some unique opportunities/challenges for problem solving.

Small fiberglass repair would be good. Don't want to do really large stuff though.

I'm seriously considering getting a good sewing machine and doing canvas/upholstery work.

I am still too newly retired to be schedule or budget driven. I've only had a couple of projects that were more outcome driven than driven by schedule and budget. They were always the most fun.

 

[dlochner]

I feel I would spend a bunch at first fixing all the stuff that needs fixing.

Probably, and then you will realize that all the things that need fixing have babies that require more fixing. And then you have to fix the things you already fixed because, well, just because you thought of better way.

The paid boat delivery business is hard to break into. Potential customers will prefer those who have licenses, like 100 ton Masters and the license may be required in order to be paid legally. Boat owners are going to prefer someone with experience and you can't get experience with deliveries until you actually make deliveries. Sort of a catch 22. You may find a delivery captain who needs crew and that may work out.

 

[MikeHoncho]

Sorry about drifting.

I knew a guy that did delivery crewing when he was young. He's got some great stories - some of which I would rather not live. Many, though, sound like the best time ever.

If I could only do it in winter, any sort of marine electrical or mechanical system repair work would be good. Troubleshooting and repair are very rewarding. Just don't want to do it in the heat down south. I work on my own boat in a conditioned garage for that very reason.

Delivery duty can morph into repair work, particularly delivering used boats - if my buddy's stories are any indication. This might present some unique opportunities/challenges for problem solving.

Small fiberglass repair would be good. Don't want to do really large stuff though.

I'm seriously considering getting a good sewing machine and doing canvas/upholstery work.

I am still too newly retired to be schedule or budget driven. I've only had a couple of projects that were more outcome driven than driven by schedule and budget. They were always the most fun.

We’re good. There was a little tongue and cheek in there....I have a Sailrite and accessories. I really like canvas work as woodworking translates to it a lot without having to do the finishing. I need the knowledge now. Next project is a tow cover for my dad’s Bayliner.

 

[Dr. D]

I agree. I was able to retire at 63 1/2 only because I could go on my company's COBRA plan for insurance and had budgeted to pay for it until I reached 65 and Medicare kicked in.
I could only do this because my wife was already on Medicare.
Without COBRA I would have been working until 65.

We retired using COBRA a few months ago. The great thing is with the same insurance means we use the same medical care providers. As my wife has a few issues and seeing several specialists so this was a big benefit.

Sailing related gig? How is this: Boat evaluator. (I don’t mean surveyor.) You meet with a guy who just bought a boat, new or used. You find out what he is planning to do with the boat. You review the survey, then undertake a thorough inventory of the boat, including condition of all systems and equipment. You take all that data and develop a plan for turning the “as is” boat into the boat the new owner wants. Hey, it’s an idea......

 

[MikeHoncho]

We retired using COBRA a few months ago. The great thing is with the same insurance means we use the same medical care providers. As my wife has a few issues and seeing several specialists so this was a big benefit.

Sailing related gig? How is this: Boat evaluator. (I don’t mean surveyor.) You meet with a guy who just bought a boat, new or used. You find out what he is planning to do with the boat. You review the survey, then undertake a thorough inventory of the boat, including condition of all systems and equipment. You take all that data and develop a plan for turning the “as is” boat into the boat the new owner wants. Hey, it’s an idea......

Ahh.......spend other people’s money.. I like the cut of your jib.

 

[Davidasailor26]

I knew a guy that did delivery crewing when he was young. He's got some great stories - some of which I would rather not live. Many, though, sound like the best time ever.

I know a guy like that too. The stories he accumulated are pretty fun to hear. But he's happy working a 9-5 desk job now and has no plans to retire. He says he "front-loaded his life" with all of the fun / dangerous / stupid stuff early before he went and got a degree and a "real" job. It does seem alluring to get paid to be out on the water moving boats around. Still, some of his stories are good reminders that when you're getting paid to move boats for someone else you don't always have the liberty of waiting for safe or comfortable processes and weather windows.

 

[Sailm8]

I read about someone who cut and styled hair for other cruisers. Not a living but pocket change at least.

 

[NotCook]

We retired at 65, sold everything that wouldn't fit on or in the boat, sailed it the Caribbean and now bought a house. My job now, it seems, is working on the boat. I also cook breakfast 4 days a week for the local Lighthouse Mission. There doesn't really seem to be time for anything else. What I've said a lot, and other retirees around here seem to agree, is "I'm so busy in retirement, I don't know how I ever had time to work!".