So when Picard says to Lily in First Contact, "the economics of the twenty fourth century are a little different". Were you hoping the rest of the film was going to Picard and Lily sat in the Jeffries tube going through economic policy?
Mighta been nice...
One thing that makes its way into the better prelim models I've seen for how it could possibly work is derived from pilot projects on basic-income programs. Prior to all the ones scheduled to roll out in the US in coming months, the last big one was in a town outside of Toronto. After two years, the only people who worked less were adolescents and pregnant women. People want more than the basics and are willing to work for it -- when the playing field is somewhat leveled and they don't have to worry about making the rent or whether they're going to be able to eat after paying the bills.
Other studies have shown that people like to do things, be useful. What Picard described as "enriching and improving oneself". It's no shocker that many people, when the pressure of living expenses is removed, work on becoming artists or writers or musicians or chefs. And yes, there are even people who get their biggest charge out of being of service to others. Especially if that's become a societally-inculcated thing, I can see that expanding, given the opportunity. One thing that was discovered early on after the introduction of the mandatory retirement age was that a lot of men didn't live a whole lot past it. Once deprived of a main element of their self-identity, they just kinda languished and faded. People like purpose, and I can see an evolved society being better at helping people generate purpose from within themselves, rather than having it have to be imparted from without, as through a job or the like. A lot of the rise in the '50s of civic organizations like the modern Freemasons, Rotary, Toastmasters, Kiwanis, and the like was because retired men found purpose there after they were put out to pasture.
There are, here, today, people who pay money to go pick grapes, press them, and make wine, even though they don't work at the vineyard. There are people who pay to go to dude ranches and participate in cattle drives, rather than being employed by the ranching company. I know tollbooth attendants, ferry deckhands, garbage collectors, postal delivery people, grocery clerks -- all manner of folks to take great pleasure in their work and being of service. There's a flourish in how they do what they do. Most I've asked have said they'd absolutely be doing it (maybe with different hours) without getting paid if their expenses and needs were covered.
Earth and whatever Human colonies are part of the same umbrella -- and, for that matter, other equivalent worlds like Vulcan or Andor or Betazed -- have "money", though not cash, derived from the fungible arts and ideas and such generated. All citizens have a nominal stipend that never obtrudes on their day. They just get the thing and the computers keep track invisibly behind the scenes. Most needs are so negligible it doesn't make a dent and is offset by their self-enrichment activities, as it contributes to the whole planet's future-GDP. 23rd/24th century economists and government accountants can likely attach a figure to Starfleet service for Earth and other non-cash-using worlds' citizens, that they can draw on at need -- like Crusher getting the bolt of fabric in "Encounter at Farpoint" or Troi buying the drinks at the Blue Parrot Café.
There's commentary in TOS about the nature of their work being why they get the big bucks, but Kirk doesn't know how to use money in TVH. It tracks if his (and everyone else onboard the
Enterprise) has a background grasp of money and relative value, but there hasn't been an outward method of transacting in any of their lifetimes. Someone gives him a bill, he doesn't know what to do with it. It's normally just taken care of with biometrics, speech-recognition, and logic subroutines without him actively having to do more than order the thing.
There's also another factor Gene had in mind in the '60s and '70s, that people like the Orion Syndicate and Ralph Offenhouse in the TNG/DS9 era carry on. Gene, through Kirk, muses in the introduction to the TMP novelization that the people who join Starfleet are "throwbacks" -- less evolved than the Evolved Human of the day. Just like how, in the 19th century, Westward expansion was fueled in large part by people who didn't "fit" in civilization leaving it to strike out into the wilderness, so too the people who chafe in the utopian world of the day find they can contribute to it by leaving it. They go out and do all the scary stuff 23rd/24th century civilians would balk at. So there is value to their homeworlds and the Federation in their work. Like the Pony Express riders (but for longer). They are drawn to the danger because civilization holds little allure for them. Same with the Humans we see in DS9 who have "opted out", preferring to be part of something less utopian, but more -- for them -- real. They're the ex-pats of the day.
So yeah, I am willing to bet Robert Picard could put out a notice that it was coming up on harvest time, and have several dozen respondents eager to help, just for the experience and to be of service, a break in routine before going back to whatever they were doing before. Heck, some people probably spend a good chunk of their year transporting from region to region, Northern to Southern hemisphere, helping with the harvest and pressing just because they love the work and find it meditative and take pride in the result. It's not unimaginable at all.