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Two Emmys and $57,000 in Debt

‘They don’t teach us about money in high school.’

Today’s video pick is Modern Comedian’s short documentary on comedian Sara Schaefer, who fell deep into debt even while she was pursuing her dream career and earning two Emmys as a writer for Jimmy Fallon. (Schaefer now co-hosts the MTV series Nikki & Sara LIVE, which has its second season premiere on July 30.)

For further reading on debt from the Longreads archive:

“Why I’m Grateful I Got Sued by American Express and What you Can Learn From My Experience” (Nathan Rabin, June 2013)

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A writer-comedian reviews his successes and failures, realizing there’s not much difference between the two:

You might be thinking to yourself, ‘How do you know the fear never goes away?’ It could just be me. It could just be pessimism, or cynicism. The realization hit me like a ton of bricks a few years back after witnessing an eye opening conversation in the green room of the UCB Theater. I saw two very accomplished comedians talking in one of the side rooms. One of these people was a cast member on SNL. The other was a correspondent for The Daily Show. (Luckily being at UCB there are multiple people who have passed through that have gone on to those illustrious jobs and I can use those specific examples without outing anyone. Please don’t ask who they were. It’s not important.) Person one said something along the lines of ‘I’m just not sure what I’m going to do.’ Person two said, ‘Yeah, things have been so fucking dry lately. I’m really, really worried.’ The conversation proceeded from there and sounded like the exact type of conversation I was having with my own friends who were in the trenches performing all around NYC with me. (To give you the context of where I was at, this was around 2008 or 2009, before the Comedy Central show, before my book, when I really was just a guy who was known on stages throughout NYC but could not catch a break for the life of me and was kind of becoming sadly infamous for it.)
These were two people who both had careers I would kill for. Being on SNL! Being on The Daily Show! I think for any of us whose dream it is to do comedy, those would be two crown jewel jobs. Those would be two jobs that most of us would think feel like a life-altering accomplishment. Getting those gigs would feel like grabbing on to the brass ring we’ve been chasing. Those are the types of gigs that you imagine lead to the validation, wealth, and fame that we chase so hard. You have to imagine that’s true, right? Those jobs? You will feel like you did it. You made it. Your life can have a movie ending where the sun rises and the credits roll and the hard times are over, you’ve done it. You’ve won.
But I eavesdropped on those two individuals, and realized – the fear is inside us. It’s part of why we do what we do.

"The Chase Is the Thing and the Thing Is the Chase: Learning to Love Failure." — Chris Gethard, Splitsider

A writer-comedian reviews his successes and failures, realizing there’s not much difference between the two:

You might be thinking to yourself, ‘How do you know the fear never goes away?’ It could just be me. It could just be pessimism, or cynicism. The realization hit me like a ton of bricks a few years back after witnessing an eye opening conversation in the green room of the UCB Theater. I saw two very accomplished comedians talking in one of the side rooms. One of these people was a cast member on SNL. The other was a correspondent for The Daily Show. (Luckily being at UCB there are multiple people who have passed through that have gone on to those illustrious jobs and I can use those specific examples without outing anyone. Please don’t ask who they were. It’s not important.) Person one said something along the lines of ‘I’m just not sure what I’m going to do.’ Person two said, ‘Yeah, things have been so fucking dry lately. I’m really, really worried.’ The conversation proceeded from there and sounded like the exact type of conversation I was having with my own friends who were in the trenches performing all around NYC with me. (To give you the context of where I was at, this was around 2008 or 2009, before the Comedy Central show, before my book, when I really was just a guy who was known on stages throughout NYC but could not catch a break for the life of me and was kind of becoming sadly infamous for it.)

These were two people who both had careers I would kill for. Being on SNL! Being on The Daily Show! I think for any of us whose dream it is to do comedy, those would be two crown jewel jobs. Those would be two jobs that most of us would think feel like a life-altering accomplishment. Getting those gigs would feel like grabbing on to the brass ring we’ve been chasing. Those are the types of gigs that you imagine lead to the validation, wealth, and fame that we chase so hard. You have to imagine that’s true, right? Those jobs? You will feel like you did it. You made it. Your life can have a movie ending where the sun rises and the credits roll and the hard times are over, you’ve done it. You’ve won.

But I eavesdropped on those two individuals, and realized – the fear is inside us. It’s part of why we do what we do.

"The Chase Is the Thing and the Thing Is the Chase: Learning to Love Failure." — Chris Gethard, Splitsider


Comedy is also an industry of paying dues: Many long-time performers regard their first ten years as a kind of clueless wandering, and veteran comics tend to treat newbies like replacement troops: They are young, dumb, and could be gone soon, so it’s best to wait till they survive a while before learning their names. This is all to say that the term “comic” is subjective and nebulous, and even geographically variable: larger cities, with their heightened competition for stage time, are famous for relegating working comics from smaller markets like the Midwest or Florida back to open-mic status, causing many visitors to experience a kind of outraged existential crisis. When two comics meet for the first time, they act like dogs sniffing each other’s butts, asking loaded questions like, “You been doing it long?” or “You been busy?”

"Standup Comity." — Steve Macone, The Morning News
See more comedy #longreads

Comedy is also an industry of paying dues: Many long-time performers regard their first ten years as a kind of clueless wandering, and veteran comics tend to treat newbies like replacement troops: They are young, dumb, and could be gone soon, so it’s best to wait till they survive a while before learning their names. This is all to say that the term “comic” is subjective and nebulous, and even geographically variable: larger cities, with their heightened competition for stage time, are famous for relegating working comics from smaller markets like the Midwest or Florida back to open-mic status, causing many visitors to experience a kind of outraged existential crisis. When two comics meet for the first time, they act like dogs sniffing each other’s butts, asking loaded questions like, “You been doing it long?” or “You been busy?”

"Standup Comity." — Steve Macone, The Morning News

See more comedy #longreads