In July 2010, amidst con­tin­ued fall-out from the Great Reces­sion, the New York Times pub­lished a front-page story about an unem­ployed col­lege grad­u­ate liv­ing with his par­ents in a Boston sub­urb who’d just turned down a $40,000-a-year job as an insur­ance claims adjustor.

“I am absolutely cer­tain that my job hunt will even­tu­ally pay off,” said 24-year-old Scott Nichol­son, a Col­gate Uni­ver­sity hon­ors grad­u­ate with a degree in polit­i­cal sci­ence, explain­ing his deci­sion to hold out for some­thing bet­ter even after two years of fruit­less searching.

The piece quickly became noto­ri­ous, set­ting off a tsunami of online comments—1,487 at last count—the vast major­ity express­ing out­rage at what read­ers per­ceived as an absurd sense of enti­tle­ment enabled by a too-indulgent family.

“Turn­ing down a job for $40,000 a year after grad­u­at­ing from a sec­ond tier (at best) school because he is too good for the posi­tion? The kid deserves what­ever hard­ship he endures,” was one typ­i­cally harsh response.

I recently thought back to this article—and the heated debate that ensued—when I got a call from a friend who heads up a big depart­ment of a big orga­ni­za­tion. She’d read some of my posts about the chal­lenges of look­ing for work after the Great Reces­sion and wanted to share her own quite dif­fer­ent perspective.

“I can’t give jobs away!” he (or she—I promised anonymity) insisted. “Nobody knows how to work any­more. They’ll say ‘I might have to miss yoga today, and that’s not okay.’”

I have to say I found this fas­ci­nat­ing. And while it was (and is) hard for me to believe that the sit­u­a­tion for employ­ers is really quite so bleak, I did start to notice other signs of sim­i­lar frus­tra­tion. For exam­ple this plain­tive tweet from a local tech entre­pre­neur, for­merly of Microsoft: “Why do so few job appli­cants bother to fol­low up? And some of the best cover let­ters don’t even show up for interviews.”

The more I thought about it, the more con­vinced I became that such behav­iors, along with the result­ing frus­tra­tion, can be traced to a pro­found con­fu­sion about what work is and is not, as well as what it should be—a con­fu­sion now thrown into relief by the stres­sor of hard times.

It’s not news that the so-called millennials—the cohort now enter­ing the workforce—grew up with extra­or­di­nary expec­ta­tions fueled by Baby Boomer par­ents who encour­aged them to dream big. Fur­ther feed­ing such atti­tudes was the Oprah-fication of Amer­i­can pop­u­lar cul­ture along with self-help clas­sics such as Do What You Love and the Money Will Fol­low and the mega-bestseller The Secret, which posits a “law of attrac­tion” that allows each of us to “man­i­fest” our desires. Even the pop­u­lar maxim that “any­one can be pres­i­dent” (never mind the nation’s declin­ing place on social mobil­ity mea­sures) can be traced to this cul­tural strand.

At the same time, our nation is deeply rooted in the Puri­tan work ethic, with its empha­sis on fru­gal­ity, dis­ci­pline, and self-reliance. Such teach­ings have been with us from early days, find­ing expres­sion in the best-selling writ­ings of Ben­jamin Franklin up on through present-day polit­i­cal rhetoric. (Think Mitt Romney’s tire­less if prob­lem­atic claims of being a self-made man.)

Fol­low your dreams, what­ever it takes.  Pay your own way, what­ever it takes.

That mil­len­ni­als are strug­gling should come as no sur­prise, given these exact­ing and often con­flict­ing cul­tural expec­ta­tions. Those of us who came of age in the Boom Years may have man­aged to bridge the two. But when money is scarce and jobs are few (Hello, New Nor­mal!), this is no easy feat.

So what’s a mil­len­nial sup­posed to do? Pre­sented with con­flict­ing absolutes, how are they sup­posed to choose?

This is pre­cisely the sort of dilemma con­sid­ered by Har­vard psy­chol­o­gist Robert Kegan in In Over Our Heads: The Men­tal Demands of Mod­ern Life. As Kegan sees it, we live in an age where demands are many and often at odds, and guide­lines for choos­ing between them are scarce. At the same time, rel­a­tively few of us are suf­fi­ciently grounded in our own beliefs to stand up to social pres­sures and chart an inde­pen­dent course—to be what Kegan calls “self author­ing.” That’s not such a big prob­lem when society’s expec­ta­tions are con­sis­tent. But when a cul­ture makes the sort of con­flict­ing demands that ours rou­tinely does, things can turn ugly very quickly.

Which is where many mil­len­ni­als find them­selves right now: Want­ing to do the Right Thing but with­out a way to decide what that right thing is. Where is the line between self-confidence and enti­tle­ment? Where is the line between admirable risk-taking and fool­ish behav­ior? Where is the line between being respon­si­ble and giv­ing up?

Depend­ing on whom a mil­len­nial asks, they’re likely to get dif­fer­ent answers, and regard­less of which one they choose, they’re likely to find them­selves at odds with some­one whose opin­ion they value. There may not be much that we can do right now to change this cul­tural con­text. What we can do is to acknowl­edge that Scott Nichol­son and other mil­len­ni­als have good rea­son to feel dazed and confused.

Edited 3/15/12: Var­i­ous non-substantive revi­sions for style and clarification.