Or choose to be a barkeep/ waiter on the Federation flagship instead of just magically opening his own place...
*Cough Lower Decks*
He likes being out in space doing routine diplomatic missions and visiting Starbases for crew transfers, ahem, "exploring the vast reaches of space!!!"
Let's just say the economic of the future can't make sense to us because it's so out of our understanding and how we think things have to work
for them to work. The nice thing, for me, about the future in Trek shown in TNG is just that humanity just got its shit figured out and somehow it all just works. Everyone has a home, everyone has food, everyone has medical care available to them, yet at the same time we still need to have waiters in restaurants, or people in the alley behind the restaurant shucking oysters, and you've got to somehow "work" for
get that restaurant you own beyond there just needing to be space available. You can be that restaurant owner who has a popular, well visited, restaurant or you can be that famous author who wrote like 3 books who has a large, nice, house and got to attend the Acacdemy when he was in his 50s.
Somehow it works.
Let's equate it to going back in time to 1720 and trying to explain Bitcoin to someone. Something you can hardly explain to people
today. (And in this analogy Bitcoin being a currency that's used by everyone/everywhere like any other currency.)
"Well you see, we have these things called computers, and then they use video cards and with them we "mine" through data to get us to a currency one of which is worth thousands of dollars..."
Humanity got its shit together. And that's supposed to be a future we want to see happening.
But, no, lets have this thing with people forced to work on holidays and using food-processing machines that can only make crummy generic-brand TV-dinner like meals when people in ships above you can ask the same device for any meal whatsoever. You get this because you're a lowly blue-collar
peon and you deserve it! Be glad healthcare is free! ... Or is it?