Retirement "What If"

Dec 28, 2015
1,837
Laser, Hunter H30 Cherubini Tacoma
Generalized question.....If you could or could have retired at the age of 53 what would you do for a side hustle that involves sailing? You wouldn't be dependent on the income but some income is needed for the long term plan. It would be icing on the cake.
Now.....you have seven years before 53, what would you do to meet that goal?
 

JRT

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Feb 14, 2017
2,037
Catalina 310 211 Lake Guntersville, AL
Hull cleaning! I'm aiming for 55 with a company pension plan right now so I have 10 years!
 
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Jan 22, 2008
296
Islander Freeport, 41 Ketch Longmont, CO
Do you want to work on boats or around boats
- become a certified marine surveyor
- learn to sew and make/repair sails or marine canvas
- boat mechanic
- Fiberglass work
- Captains license - deliveries, run a small charter boat, dive boat
- Sales - marine related - boats, gear, etc.
- Marina operations - port captain, etc.

Lots to do, just have to decide are you tied down to a single location or wandering and will pull in and setup shop when needed to green up the money tree. How much $$ is needed during each top off and how hard do you want to work?

It will be interesting to see the answers
 
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Jul 7, 2004
8,402
Hunter 30T Cheney, KS
Medical insurance keeps a lot of people from retiring early. It's not smart to ignore it. Medicare doesn't kick in for many more years.
 
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SFS

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Aug 18, 2015
2,066
Currently Boatless Okinawa
victor gave you a good list above. I would add 12V electrical repair/service. You can keep a good amount of "parts", supplies, and tools in a relatively small volume on your boat, and the work is not difficult. Many people just don't want to mess with it.
 
Mar 26, 2011
3,401
Corsair F-24 MK I Deale, MD
Medical insurance keeps a lot of people from retiring early. It's not smart to ignore it. Medicare doesn't kick in for many more years.
This. I had done just that, and had some small sailing and consulting things going on, but the collapse of the Affordable Health Care system and changes in the tax code forced me to get a regular job. If it wasn't for that I had a semi-retired plan that was really working. But that killed it.

Unless you are sure about health care, keep the job. Fortunately, I got a job I like.
 

Ward H

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Nov 7, 2011
3,645
Catalina 30 Mk II Barnegat, NJ
Unless you are sure about health care, keep the job.
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.
 

capta

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Jun 4, 2009
4,766
Pearson 530 Admiralty Bay, Bequia SVG
All the suggestions about becoming a tech of some sort are great if you are in the US, but very few countries will let you work without a work permit, which can be very expensive and time-consuming, and those who try to fly under the radar can lose their boat and their freedom.
Also, keep in mind that being a great tech isn't all that important if you have no reputation, which rarely proceeds us as we travel.
 
Jan 11, 2014
11,323
Sabre 362 113 Fair Haven, NY
Interesting question.

I think the key is to do something that is not "work" but something you enjoy. If you are always fixing other people's boats, how likely are you to spend time fixing your own? It's the old saying, the cobbler's kids are unshod. If you went into the marine tech area are you willing to get ABYC certifications or enroll in a training program?

At one point I had a retirement plan that included working at a BoatUS store, and then WM, then WM closed its doors. So much for that plan.

Teaching sailing would be a lot less work like, might be fun, and would generate some income.

Since I retired 5 years ago, I've done a little writing and been paid for it. I also had the opportunity to return part-time to my old profession. That's worked out well, as I mostly do the parts of the job I liked and not do the parts I didn't like while setting my own hours.

Health insurance is a major concern. Fortunately, my employment contract provided for health insurance coverage from my retirement until Medicare kicked in. They also covered my wife's insurance, one of the reasons we got married before I retired.
 
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May 24, 2004
7,129
CC 30 South Florida
The only job I would consider would be one where I could control the schedule, a job where I could work as much or as little as I wanted. A service that is in demand, with little competition and requires very little investment in equipment is "fuel polishing". Give out business cards at marinas, take calls on your cell and give appointments according to personal schedule. In and out in a couple of hours with check in hand.
 
Apr 19, 2012
1,043
O'Day Daysailor 17 Nevis MN
I retired at 57 and purchased a 17 foot daysailer so that I could give private sailing lessons.
 
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Mar 20, 2011
623
Hunter 31_83-87 New Orleans
I retired at 63 and before I retired I got my OUPV license and then ASA certifications for certain courses. I wanted something to do besides house/home related items. If I’m home then I’m driving the admiral crazy. I typically teach on weekends and occasionally during the week. When not teaching or assisting on boat deliveries I’m working or hanging out on my boat at the marina with a lot of other retirees or live aboard. I don’t get paid a lot but it does cover slip expenses and a few boat toys. Basically I wanted to keep busy doing something I enjoy, get a little comp, and enjoy time on the water. I can’t see retiring without a plan to keep busy doing things you enjoy.
 
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Dec 28, 2015
1,837
Laser, Hunter H30 Cherubini Tacoma
Medical insurance keeps a lot of people from retiring early. It's not smart to ignore it. Medicare doesn't kick in for many more years.
I'll have full coverage until medicare. Perk of the business but you can't overlook the costs for sure.
 
May 2, 2019
136
Hunter 38 Annapolis, MD
Generalized question.....If you could or could have retired at the age of 53 what would you do for a side hustle that involves sailing? You wouldn't be dependent on the income but some income is needed for the long term plan. It would be icing on the cake.
Now.....you have seven years before 53, what would you do to meet that goal?

Better yet purchase 1 BTC or Bitcoin sit on it for 5 years and your going to become a millionaire or close to it!
 
Dec 28, 2015
1,837
Laser, Hunter H30 Cherubini Tacoma
I've thought canvas work. I have a Sailrite and really enjoy the challenge. I've restitched a bunch of stuff, made winch, hatch and solar panel covers.

I was thinking more on the likes of actual sailing.
 
Dec 28, 2015
1,837
Laser, Hunter H30 Cherubini Tacoma
I retired at 63 and before I retired I got my OUPV license and then ASA certifications for certain courses. I wanted something to do besides house/home related items. If I’m home then I’m driving the admiral crazy. I typically teach on weekends and occasionally during the week. When not teaching or assisting on boat deliveries I’m working or hanging out on my boat at the marina with a lot of other retirees or live aboard. I don’t get paid a lot but it does cover slip expenses and a few boat toys. Basically I wanted to keep busy doing something I enjoy, get a little comp, and enjoy time on the water. I can’t see retiring without a plan to keep busy doing things you enjoy.
What's your recommendation for getting into deliveries? Assuming it would be assisting and getting paid?
 
Dec 28, 2015
1,837
Laser, Hunter H30 Cherubini Tacoma
I'm a woodworker. Thoughts on woodworking/boat repair/finish work?
 

FDL S2

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Jun 29, 2014
469
S2 7.3 Fond du Lac
Do you want to work on boats or around boats
- become a certified marine surveyor
- learn to sew and make/repair sails or marine canvas
- boat mechanic
- Fiberglass work
- Captains license - deliveries, run a small charter boat, dive boat
- Sales - marine related - boats, gear, etc.
- Marina operations - port captain, etc.

Lots to do, just have to decide are you tied down to a single location or wandering and will pull in and setup shop when needed to green up the money tree. How much $$ is needed during each top off and how hard do you want to work?

It will be interesting to see the answers
@MikeHoncho I like where your head is at!

I've always thought getting into a "support" business for your hobbies is a sure fire way to not get to enjoy your hobbies.

A personal example is several years ago the owner of a local sporting goods (hunting and shooting) shop was trying to get me to take it over when he retired. I was seriously considering it until I realized that the busy season for the shop was during hunting season- when I wanted to not be working. So my suggestion is to get into a business that is busy during the non-sailing season, but relatively quiet during it, like snowmobile sales.:) Now teaching sailing or running charters combines your hobby with an income, but those have direct involvement with sailing and aren't support.

I plan on retiring in 14 years at 61-when I can get my full pension, COBRA until 65 and I've been working, saving and planning for this for a long time. Not sure what I will do then, but it will involve sailing, hunting and probably an off season job or I'll just be a live aboard bum on a (decent) budget who actually sails.