“Feeding the kitty” is a common point of discussion among full-time and part-time cruising folk. Maintaining the boat, adding or replacing equipment, living expenses, fuel, travel expenses … everything adds up and without a solid plan and/or regular income source, cruising can quickly become a memory instead of a way of life.
If you plan to remain in your home country, working is easy. Some folks we know maintain regular jobs, live aboard in a marina and sail away on weekends, holidays and vacations This is very restrictive, but they're still living on a boat. Others pick up casual work in the different ports they visit. If they have a specific skill, canvas work or rigging, for instance, they can usually pick up some work easily. Otherwise, a local chandlery or West Marine is usually hiring.
Sailing out of your home country, however, poses a whole other set of issues if you plan to work. First of all, unless you have a work visa, it's usually against the law to work in other countries. Again, if you have a specific trade you can sometimes offer it to other yachties. We've met dentists, barbers, vets, and riggers who sell their services to other cruisers. Some artists create jewelry and artwork to sell along the way. We've met some consultants and full-time writers who work from their boats. Communication is sometimes an issue, but with a little foresight, they manage. Some cruisers have found casual work in foreign ports and get paid “under the table”, but it's not something you can rely on.
That said, seasonal work, like fruit picking for instance, can provide a short-term, legal influx of cash if you're physically willing and able. Teaching English might also be a valid alternative, although when I taught English in Ecuador, it was gratis.
A growing number of folks we've met, cruise for half a year, leave their boats in a local marina and go home to work. After all, there's usually a good season for sailing and a bad season, no matter where we go. Go home for hurricane/cyclone/rainy season and work. Come back when the weather is fair, the sailing is good and the kitty has been replenished.
As an electrical engineer, David has helped innumerable other boats with electrical problems, but he's never felt comfortable charging people for his services. Cruisers help other cruisers. There's not usually any financial remuneration involved. Any work he's done ashore fixing generators and solar panels is all gratis to the local community. We get paid in friendship, fresh fruits and veggies and sometimes lobsters. These feed us, but not the kitty. Don't count on other cruisers as a good income source. We're a rather parsimonious lot by nature.
We do write articles for several sailing magazines and get paid for them. Marcie sells photographs once in awhile. Neither of these provide enough to live on. So... do we work along the way. No. We bought our boat outright, paid off all debt before leaving to cruise, had adequate savings and stick to a reasonable budget. Recently, we've started collecting Social Security. It's not much, but the kitty loves it.