Good idea/bad idea?

As I interpret what you've said, you're currently in accounting and finance and are talking about getting a job as a deckhand to prepare for sailing 15 years from now.

You mention no problem checking your ego, but you don't discuss the loss of income going from an accounting job to a deckhand.

I would suggest continuing to earn what you can in your occupation while taking lessons available to you in either sailing schools or by using vacation to charter and get training from captains. Then when you reach retirement you can get more training. If it means using a captain or some crew on your boat initially, then do that. While the deckhand detour has some logic and I have no concern about you being able to do the job, I just can't see it being worth the sacrifice in income. Save the money, use some of it for training along the way or later.

I am trying to figure out if you want to have a boat with your wife and sail in the Med or work on a boat.
Work on one if that is what you want to do, but you don't need to do that to gain experience and proficiency for sailing and cruising a catamaran in the Med.
40 years old is just right, 15 years from now you will be almost ready to start life
You have a 26 foot boat on a lake, you know more than you seem to think.
Get some wind in the sails at the local sailing club/yacht club. Find out when the weekly fun races are and get on the crew list. Heck, start windsurfing ( I know it's now called sailboarding) get to know the wind and foil and vessel. I can't imagine you can't find a Sunfish on sale and get started.

So again, depends on what you are trying to do. If you want a job on a boat that is different than wanting to learn to sail.

Gotcha. Then do it I really don't know what type of work you are anticipating or envisioning. TN doesn't strike me as a place where yachts need deckhands. Are you moving to FL too?

I think it could be a good idea to answer your original question. You have to figure out what the goal is and work toward it.

Well, you don't need 15 years experience working on other's boats in order to run your own boat, unless you're wanting to turn it into a charter boat. Then you'll need enough to qualify for a license.

Are you having a midlife crisis? I'm still struggling to understand as now you're saying you want to change professions and spend the next 15 years away from your wife. When do you plan the divorce?

You sound like me when I was 38 and burned out in a finance business. You've got no kids, so why not? I came into the business with an idea what I wanted to do in it, then learned the difference between fantasy and reality. But if you're a thinker. a worker and someone who's open to plans B, C, D,... you can make a living. I did for 30 years. In that time there's not much in the field I didn't do from teaching, transporting, tours and private captaining to yard work, managing marinas and cleaning oil spills. Ego is a mark of an in charge person, just be able to park it when necessary.

I'd been on boats since age 6, was addicted to salt water and figured I'd see if a living could be made there. I accumulated my sea time on my own and friend's boats. After selling my business I went to work in an old boat yard to gain mechanical and maintenance experience while studying for my CG exam. Once I got my 50GT I got a job running an LCM cleaning oil spills in NY Harbor. By then I'd decided to buy a boat and do charters. After examining that business I realized that most of the boats doing charters do it as a write-off, so scratch that since I'm not wealthy. By then I knew I needed a lot more experience and moved the Ft. Lauderdale where I took whatever job on boats I could get while accumulating sea time to increase my license: charter fishing, para-sail, dinner yachts, etc. That led to a few transports (as crew), but when summer came the jobs there dry up. So I started my own business, a tour/sport boat. After a few years we got bored with So. Florida and moved back to NY where I ran a couple of marinas while I made connections and developed a reputation. That led to jobs teaching people how to run their boats, day captaining, and the rest is history. My last run before I retired was from NY to Charleston to the Erie Canal, the Great Lakes and Georgian Bay to Michigan over about 2 years. Over the years I've run boats up to 140', but boats under 80' were my bread and butter. I split my business between private and commercial work and stayed independent. I looked on locking up with one boat as career ending as you lose your connections and get in a rut always working with the same equipment and electronics. Staying independent made every day a learning experience.

Sitting on a dock in the bay, anchored out in the bay or wondering where the next bay may be, in pouring rain, high winds and with gear that you can't understand or fix...then tell yourself or spouse that laundry needs to done, the hatches leak and your collective skills of ship husbandry are wanting, will take the gloss off the aquatic lily. To take the jump into maritime living/adventure takes months if not years of preparation, experience and scared-to death happenings to be successful with even the most forgiving partner. Charter with an understanding/qualified Captain in a couple of different vessel types and not be deterred if the wind and waves pick up....go with a guy or gal who has lived the maritime life. Cheers and good luck. "Go" is the operative word but please be realistic. Cheers, R.

Fantastic concise and specific report for the topic at hand.

I believe that the independent contractor in the marine industry is doable. Reputation can be created. Sometime as simple as answering the phone and responding to emails and text. Not next week, right now. I find people are always amazed when they get a reply that answers their questions right away. Amazing.

There's a bit of a catch 22 here. Every year a lot of people follow their dream of working on yachts to Ft. Lauderdale. When you need an entry level "body" and there's bodies standing in front of you now why even look at CVs from a distance? However most people in the industry in Ft. Lauderdale know that the vast majority of those who show up there each winter will be gone as soon as their money runs out. So they're not taken seriously. Had a local once put it well when he told me that when he sees a tourist his goal is to figure out how much money he has and how to get that money into his pocket. I'd recommend building your reputation till you're a big fish in a small pond then riding that into the big pond if that's your goal. Personally I found it a lot more profitable in the small ponds.

I'm going to address this just as one employer now. I recognize many others would respond differently and might jump at the chance to hire you.

I wouldn't consider you today as you've done nothing to show you intend working on a boat to be a career. (First step to address that, STCW Basic Training, Medical, etc. so you're able to go today. Better would be extra courses). I'd want to see a resume at least reflecting training.

I would need a far greater understanding through an interview of this move. You're going to take a job that takes you away from your wife for an extended time and potentially for years. I would fear you get away for a couple of months and will be heading home. I asked the question here, which you danced around and I understand doing so here, but in an interview I wouldn't allow you to do so.

I wouldn't hire you for a full time job on a boat until you at least did some day work. I want to see one or more boats and captains listed.

I would value your overall work experience and see the potential value of that but you'd have to overcome these obstacles to get in the door. I've seen it too many times, not just with those switching from other careers, but those who come to Fort Lauderdale to get yacht jobs after working on a fishing boat in Maine for a few years or after some commercial work in the gulf. You have to convince an employer that you're ready and willing to give up your white collar job and world for a very low paying job as the lowest deck hand on a boat, that you're willing to go from 9 to 5 work to potentially long hours and overnight watches, you'd have to show that you're willing to go from sleeping in a nice comfortable bed in a nice comfortable home to a bunk where you're sharing a cabin with an immature 20 year old.

I have a phrase I use "logical career move." You would need to convince me this was one for you. Until you convince me that you're sensibly running toward a new career, all I see is you're running away from something and I'm not sure what. Do you hate your current job? Your life? Your wife? You also would need to make clear what your long term goals are and that you really understand the steps to get there.

There are hundreds of other candidates and you must show you're a better hire than they are. Part of that is preparation and being legally ready to go on the day you meet them. The other part is sheer luck, being in the right place at the right time, but that luck happens out of effort. You're not the lucky guy on that dock in Fort Lauderdale without the effort to be there.

You might be able to convince me, but you haven't yet. Best of luck in whatever you pursue.

Olderboater you make the job look very unattractive. Good, because it is. It's long hours of hard work for little money, and don't forget putting your ego in your back pocket. Then there's the crew quarters. Your last paragraph reminds me of how I got my first job in Ft. Lauderdale. I met the owner of a dinner yacht at FLBS, and asked for a job. We talked and he asked me how much I was looking for. So I told him I was making $15 an hour in NY with a ton of OT at time and a half. We concluded our discussion with him saying he'd call me. Of course he didn't. A month or so later while pounding the dock at Bahia Mar I ran into him again. He was about to go out and needed another body. He asked me how much I wanted. So I told him I'd work for free and then he could decide how much I was worth based on my work. He said he'd pay me $7 an hour. I ended up with a job for the season, and every few days he'd slip me an extra $100 or so cause I worked like a NY'er.