It took about six years of annual asset reviews with my financial planner, Joe Mackey, to confront a big question. After I spent my entire adult life trying to save enough to quit working by 65, Mr. Mackey wanted to know what my rush was.

“Do you even think you’ll want to retire?” I’m a 42-year-old writer with a job offering travel, intellectual grist and social connection. With few hobbies and an allergy for sitting still, it’s fair to assume my view of a comfortable retirement includes more work than quit. Maybe I’ll deliver the mail, write books or teach.

People spend a lot of time wondering if they’ll have the means to retire, often ignoring the equally important calculation: Do they have the will to retire? A job, historically seen as simply a way to make money, is increasingly the source of the types of friendship and stimulation that are hard to find in bingo halls, on beaches or riding a golf cart.

“When my friends and I talk about our futures none of us says, ‘When I’m 65 I’m going to retire and live on a farm and do nothing,’ ” says Kevin Frazier, a former legal assistant at Google who is now pursuing joint law and public-policy degrees at Harvard and the University of California, Berkeley. Mr. Frazier, age 26, watched his dad work a 30-year career at AT&T , but the one-employer tenure is no longer status quo.

Mr. Frazier is representative of the way many entering the workforce today think. Routinely told they won’t have the cash to retire and can expect to live longer and healthier lives than their parents, Gen-Z workers have plenty of motivation to pursue employment even after they become eligible for Social Security.