Game Plan

For the person stuck in an unsatisfying career, changing course can seem almost impossible. We're told to follow our dreams, as if that will somehow lead to success and happiness. If only it were that easy. For most of us, following a "passion" is straight-up bad advice: Not everyone can succeed, or even earn a paycheck, as an artist, musician or basketball player. But many of us don't have a singular passion. In that case, how do we pivot out of an ill-fitting career? Where do we even start? Sam and Rebecca, still toiling away in their own first careers, turned for advice to Francesca Hogi. She's a successful matchmaker and dating coach who began her career as a corporate lawyer. "We do have this conversation around passion in our culture," Francesca says. "That puts a lot of pressure on people to feel like, `I've got to quit my job, burn that bridge, go follow my heart and then I'll be a billionaire.' It doesn't work that way most of the time and that's okay."

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Keith Olbermann has a habit of abrupt exits from some pretty high-profile professional gigs. "He didn't burn bridges here, he napalmed them," Mike Soltys, an ESPN executive, said after the commentator left the network for the first time back in 1997. Even so, despite leaving on atrocious terms, Olbermann returned to ESPN not just once, but twice. That's what's so remarkable about his career: Olberman manages to get hired back by the very places he publicly pilloried. How does he do it? This week, Olbermann joins Sam and Rebecca to talk about how he succeeds on his own terms. Olbermann, who left ESPN for the second time last year is back again, this time with a new web series, "The Closer," over at GQ. He talks with Sam and Rebecca about his workplace philosophies and how they've served him through what many would consider an extremely successful career.

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There are a series of practical reasons that losing a job hurts: It cuts you off from a source of income, it interrupts your work history, and then you have to go on a soul crushing job hunt. But, getting laid off also has an emotional sting that can color the rest of your career.\u0010\u0010This week Sam and Rebecca talk about why getting let go from a job often feels like a break-up, especially as the workplace becomes the center of our social lives. They're joined by Brittany Ashley, who this summer had a very public firing from Buzzfeed, where she wrote and starred in some of the company's popular videos. She talks us through the day she got canned, not only from a job that she liked, but from a place around which she had built her social life. The experience has changed the way she views the employer-employee relationship, she says.\u0010\u0010But, maybe leaving a job doesn't have to be that painful. To make the process of getting fired less emotionally shocking, Sam and Rebecca suggest building up a "F*ck Off Fund" for your heart. In addition to having cash saved off for when times get tough, workers can build up an emotional nest egg. Keep in mind: Companies, ultimately, don't actually care about you.

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Listening to this show will not help you make a million dollars or retire early. We don't have 10 easy tricks for how to climb the corporate ladder. Instead, it will probably make you question your career aspirations. Doesn't that sound fun?\u0010\u0010This week, Sam and Rebecca get angsty and talk about what success means to them. Is it money? Fame? Happiness? To do some good in this world? It's a complicated question into which this week's guest, Chris Gethard gives us some insight. Gethard, an actor, comedian, and writer, whom you may recognize from his roles on Broad City and The Office has made a career out of failing. As friends and fellow comedians moved to Los Angeles to find success, Gethard stayed in New York to work on a public access TV show and remain relatively unknown. Decades later, he is finally finding success on his own terms. Gethard starred in this summer's critical darling, Don't Think Twice and has a new show opening off-Broadway this October.\u0010\u0010Gethard has mixed feelings on success. As he puts it, "success oftentimes is a headache that brings pressures with it."

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Job-hunting is a horrible process that no one much likes, except perhaps the headhunters. Applying for a job can feel as if you're sending a message in a bottle into a black hole. Even if your application makes its way to a human being, it might warrant just a five-second glimpse. The tiniest detail (or a spilled cup of coffee) can disqualify you entirely. The view from the other side isn't much better. Hiring managers say that many applications are garbage and employers are having a hard time finding the right people.

It's a broken system that Kieran Snyder, this week's guest, is trying to fix. A linguist by training, Snyder runs Textio, a company that uses machine learning to create better job listings for companies. Snyder talks about common mistakes employers are making, and how a few tweaks to a job listing can result in better and more diverse hires.

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Friends and business don't mix: A Harvard Business School study found that pals make the most unstable founding teams. There's no better example than Facebook. Two college buddies start a website, and then, millions of dollars and users later, they hate each other and get entangled in a nasty lawsuit. Facebook ended up thriving, and we got an entertaining movie about the juicy drama, but a friendship was sacrificed.

It doesn't have to be end that way. Claire Mazur and Erica Cerulo were best friends when they started the online retailer "Of a Kind" in 2010. Six years later, the friendship and company are both intact. Bed Bath and Beyond acquired the shopping site last summer and Claire and Erica still see each other almost every day. How do they do it? It's work. They share the secrets with Rebecca and Sam on this week's show.

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There's a lot of talk about balancing kids and work, but what about the nine months before the baby comes? This week, Francesca and Rebecca talk about going on maternity leave. That's something Francesca has some expertise in because. . . She's pregnant! In her last episode before heading out on leave, Francesca talks about the career anxieties and excitement that she's had for the better part of a year, as she prepares to leave her job until December. She also admits something semi-scandalous: That being pregnant has affected her job performance. Doctors' appointments and the sheer biology of gestation, she admits, can get in the way of office life.Jordan Salcito, the beverage director at Momofuku, joins the show to talk more about how work and pregnancy can be almost diametrically opposed. Not only does Jordan's job involve a fair amount of alcohol, but in the middle of studying to become a master sommelier found out she was pregnant. She talks about the challenges of balancing her career and the realities of pregnancy.

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Remember back when people would stay at a company long enough to get a gold watch, a time before entitled millennials decided they didn't feel like working at the same boring job for their entire career? Those were the good old days, right? Wrong. This week, Francesca and Rebecca challenge the conventional wisdom that America's favorite generation doesn't have its life on track. The demise of the traditional career path might have more to do with student debt and the changing corporate priorities than a personality trait of an entire generation of workers. Plus, older folks have also taken circuitous routes to career success. This week's guest, Mary Norris, has the resume of a hipster: Milk truck driver, costume shop clerk, cheese factory worker and web series hostess with a cult following. But she's no millennial. Since 1978, Norris has been with the New Yorker magazine, where she's a respected copy editor and host of the web series Comma Queen. While she eventually settled down, she took her own sweet, not always logical time getting to where she is today.

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Just about everyone has fantasized about quitting a job in grand style -- telling off a boss, for example, or tearing up a work nemesis's cubicle. Mostly, we hold the urge in check because we don't want to offend people from whom we might need stuff in the future. This week, Francesca and Rebecca tell a tale of bridge-burning that took place close to home. At a previous job, Rebecca very publicly insulted someone who later became an important figure in her work life. Did it hurt her career? She confronts the very man she insulted: This week's guest, Bloomberg's own Joe Weisenthal.

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Don't know what Slack is? Then you probably don't work in an office. The communication tool is like e-mail, but better -- and it's taking over workplaces across America. In this week's episode, Francesca and Rebecca break down the enterprise software phenomenon: How it works, who uses it, and why people are so obsessed with it. Dayna Evans, a writer for New York magazine, who has written about her complicated relationship with Slack, joins them to also discuss some potential downsides of chatting with coworkers all day.

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