Editorial Note: Unlike most of the other essays published here, this piece was not written for Work Stew. Amy Gutman wrote this as a post for her blog Plan B Nation, and it debuted there earlier this week. Amy’s observations struck me as excellent fuel for the ‘Follow Your Heart vs. Do the Math’ debate unfolding here, so—when asked—Amy graciously gave me permission to re-publish her post for Work Stew’s readers.

By Amy Gutman

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.

Amy Gutman is a writer and lawyer with eclectic interests and a resume to match. Her work has appeared in the New York Times, Salon, and the Chicago Tribune, among other venues. She is also the author of two suspense novels, both published by Little, Brown. She lives and looks for work in Plan B Nation.