There are two broad ways of thinking about these questions. The first is the ‘grin and bear it’ approach. This is the view that we should get our expectations under control and recognize that work, for the vast majority of humanity — including ourselves — is mostly drudgery and always will be. Forget the heady dream of fulfillment and remember Mark Twain’s maxim. “Work is a necessary evil to be avoided.” … The history is captured in the word itself. The Latin labor means drudgery or toil, while the French travail derives from the tripalium, an ancient Roman instrument of torture made of three sticks. … The message of the ‘grin and bear it’ school of thought is that we need to accept the inevitable and put up with whatever job we can get, as long as it meets our financial needs and leaves us enough time to pursue our ‘real life’ outside office hours. The best way to protect ourselves from all the optimistic pundits pedaling fulfillment is to develop a hardy philosophy of acceptance, even resignation, and not set our hearts on finding a meaningful career.
I am more hopeful than this, and subscribe to a different approach, which is that it is possible to find work that is life-enhancing, that broadens our horizons and makes us feel more human.
Beginning guitar students are taught to always start below the desired note and tune up to pitch, never down, to prevent the string from going flat. I'm going to repurpose that bit of knowledge for metaphorical use here: if you approach work with an image of your ideal, there's almost nowhere to go but down into flat disappointment. Very few things live up to your highest hopes, but modest expectations going in can leave more room for pleasant surprises along the way. And as Abraham Maslow said, it isn't normal to know what we want. It's a rare and difficult psychological achievement. Our consciously articulated desires are often incoherent or limited; we figure out what makes us content by process of elimination, by trying a lot of different things.
Augusten Burroughs and John Gray, among others, have said that being interested is a more worthwhile goal than being happy. I tend to agree. And as someone who's had to build new careers from scratch after the loss of a family business, let me assure you that having your financial needs met with plenty of free time left over is nothing to sigh about.