Funny

It works if you can build up the relationships and reputation, which will depend heavily on the industry and the job.

I know two people who do this, and they have jobs that allow them to.

One is an emergency room physician. His shifts are staffed through a middleman at 3 different local hospitals, and the nature of the work is that he just does work during the shift and doesn't bring any home with him or continuing onto the next shift he works. He gets paid very well when he's working (average annual salary of an emergency physician in the U.S. is about $375,000 per year). And occasionally just lines up a long sabbatical, does volunteer work overseas (Doctors Without Borders/MSF), and takes time off for himself and his family. He basically budgets a $200k lifestyle and takes unpaid time off. But his pathway basically required him to just dominate school, from kindergarten through a bachelor's degree and 4 years of medical school, and then put in his time as a resident.

Another friend of mine works as an electrician and lighting crew member on TV shows and movies. He always has to line up his next project after the current one ends, but occasionally can line something up in the future so that he can take a calculated 3-6 months between projects. He's got a good working relationship with some producers and directors, so he basically knows he can find a job anytime with whatever production those people happen to be working on. Whenever he has enough cash, he can go and travel, timed out to where he's not paying rent for an unoccupied apartment. Then he lines up another gig, signs a new lease, and then continues working. I think he lives very frugally on the job (I think stuff like food is covered when filming on location, so not a lot of out of pocket expenses for food/drink while working), and saves money that way.

With that, I think there are a few opportunities to think through which careers might actually allow for this.

Project-based jobs, where people work for a few months or a year towards a particular project completion, might be good for intentionally taking gaps between projects. I wonder if construction and similar industries would allow for this. Academia often has formal sabbatical policies, too, but that's relatively late career.

Personal independent gigs can do this, if you can earn enough money doing it (so, like, not Uber and Doordash). Some people do contract design work, create independent art, write essays and op eds for different publications, etc. If you're paid by the job, taking a break doesn't really hurt your "resume," so to speak. Even some who are expected to publish on a defined schedule can get ahead of the curve by producing a bunch of work for publication on that schedule (some webcomic authors and social media influencers are known to do this).

Jobs where you are employed by some firm but actually work for a client that hired your firm might also be a good candidate, if you have the seniority and flexibility and credibility to just take unpaid time off while still being on the books and website as an employee. I know people who took off a year of parental leave as lawyers, but it really depends on practice area and firm culture whether that will permanently hold them back on career growth.

Jobs that are basically shift work are designed so that no one person is totally indispensable or non replaceable, which gives the worker the flexibility to leave without hard feelings, and come back whenever they're ready. My emergency medicine friend probably fits in this category. But also, maybe any kind of 24/7 coverage job sorta fits this category, too, in health care, IT, critical infrastructure, etc.