Careers rarely go according to plan. In Job Hacks, we shake down experts for the insights they cultivated on their way to the top of their field.

Name: Chris Kelly

Original Hometown: Montreal

Job: Kelly is a television writer who has done everything from late talks shows like Late Night With David Letterman to sitcoms like Grounded for Life. Most recently, he writes for Real Time with Bill Maher.

How did you get into television writing?

My father is a comedy writer. He was an editor at the National Lampoon and then he wrote children’s television. So that’s what I wanted to do.

Since Bill Maher and David Letterman are obviously very different from sitcoms, what’s the most challenging part about going between different styles?

10 or 20 years ago, if you worked in late night, everyone wrote spec scripts to get into sitcoms. What your agent wanted you to do was get out of late night and get into this other job. It wasn’t anything anyone questioned back then: You wanted to be in LA and you wanted to write sitcoms. I’m not sure that’s true anymore. But that was the pattern I followed.

Which one is more rewarding, late night or sitcoms?

I go back and forth. When you’re writing late night you’re really only writing one voice — your host’s voice. When you’re writing sitcoms, you’re working with a bunch of different voices. When I’m not doing it, I miss it, and when I’m doing it it’s exhausting.

Since Bill Maher has a particularly distinctive voice, do you find it challenging to write in?

Bill will confess that his monologue is like Johnny Carson’s. Bill did The Tonight Show I think more than 30 times. When Bill was a young man, he used to watch the Tonight Show with a tape recorder and then write the monologue out by hand to get a feeling for the rhythm of it. I was also watching Late Night and I know other people who’ve done the same thing. You really do follow a voice like that until you internalize it.

We’re a tiny staff, so we all do everything. I really enjoy the monologue, just because I’ve been doing it for so long now that it’s like an exercise. It’s funny to get up and go, “Okay I have two hours, I’m going to write 25 jokes.”

Where do you find news for the monologues? Do you have preferred sources?

Back at Letterman, everyone’s office had the assistants going around at the beginning of the day and by the time you got in, there was a New York Times, a Daily News, and the New York Post at your door, and you would go through those. But that’s changed so much now.

Our show is different, because we do have to follow politics, but there are a bunch of sites where you just read the story and say, “oh good that’s the monologue tonight. Someone got arrested in a fast food restaurant, having sex with a quarter pounder.” You try to work around those stories, but you see it in the same way. I’m not sure what others use, but I go the The Week for short monologue premises, and Slate. The Daily Beast is good for quickly going, “those are the ten stories.”

When there’s a guest who you know is going to tangle with him, how do you handle that?

You don’t want Bill to be surprised. The producers are proud of it not being like putting bugs in a jar, but you do want to have two different sides. We bend over backwards to try to get conservative guests. Two years ago, Ben Affleck wanted to come on because he wanted to challenge Bill about generalizations about muslims. So we knew something was going to happen.

So what’s a typical writing cycle like? How long do you spend on a script?

We’re in the office every day. It’s a weekly show, which is much easier than when it was a nightly show. We work on editorial in the beginning of the week, our middle of the show desk piece in the middle of the week, and we concentrate on new things and the monologue at the end of the week. All that time, Bill is editing it, assembling it, and calling on more things.

What’s the most challenging part of your job?

With a daily show, it’s the grind of it. With a weekly show, you want it to be really good. It’s the difference between a monologue and weekend update. That’s changed, too — there are so many late night shows and political shows that you look at Weekend Update now and you go, “you’ve had all week, every single one of your jokes should be good.” Whereas if you watch a nightly show and the monologue has two great jokes in it, you think that’s a successful monologue.

Was working at Letterman very different from Bill Maher?

The Letterman room was different from any other show on TV. There really wasn’t a room, everyone was in their own offices. You were given your assignments and you turned them in. In the general, there was very little collaboration.

I like both things. In a sitcom room, you might write a script a year — two if you’re lucky — and the rest of it is sitting in a room. It can be really fun and exhausting.

What advice would you give a young writer?

Right now, it’s a terrific time to be starting out because if you want to write topical jokes, just tweet them. It used to be difficult. One of the most frustrating things is getting in if you didn’t happen to be smart enough to be related to someone. You would have to write submissions and drop them off, and it was legally tricky for people to read them. Now if you write humor, you can tweet it and it will get seen. The nature of Twitter too, is you can show very clearly not only that you can write jokes, but that you can write a lot of jokes.

Are you working on anything besides Bill Maher at the moment?

I just finished up on this sitcom called The Soul Man that I enjoyed a lot. I was working with some guys who I’ve worked with for decades, and we had a terrifically talented cast. There are times when you write a joke for an actor and you watch them perform it and you go, ‘I guess I’m some sort of god!’ I guess there are people who see that and they want to be super gods and they also want to have everyone do everything they say. There’s this actress on The Soul Man named Niecey Nash. Did you ever see Getting On on HBO?

I saw her in Scream Queens, she was hilarious.

She’s extraordinary! So is the idea that you’re writing things that Niecy Nash might say. And there are all these other good things about the project. I wrote on a sitcom called Cavemen and people didn’t like it very much.

When you’re part of a show that’s not received well, how do you keep that from getting to you?

The stages of grief when your show is dying are the same everywhere. The first stage is you tell yourself that your ratings are really good in certain categories. Someone will come in the room and will come in and tell everyone else it doesn’t matter, we’re killing with men 18-25, as opposed to the show that was in the tie slot last year.

Then your next stage of grief is the network doesn’t have anything else. So it doesn’t matter how badly you’re doing, they’re going to stay with you. Then the next stage is there’s an executive at the network who loves you, so it doesn’t matter that the ratings are bad, they still love you. Then the fourth stage is that you believe some other network is going to pick you up.

Has your style changed at all over the course of your career?

I do get lost in the house style. I think everyone does wherever they’re working. Especially when they’re in a late night show writing for one person, you’ll run into Letterman writers and they’ll all say certain things alike. I think that’s true in any show, especially where you’re writing for one host.

Is there a particular joke that you wrote recently that it’s one of your favorites? Or do you write so many that they’re not fresh in your mind?

They really aren’t. My problem right now is looking at them and going, “I like this one so much — did I write it before?”

It must be hard with topics you return to so regularly.

You write them until they’re exhausted. We do a lot of Trump these days, Ted Cruz and Marco Rubio —an election year is always the most fun and the easiest. It’s between those when you can find yourself taking in the wind a little bit and you can open up a day of jokes you wrote five years ago and read them and think “I sort of think I can remember what we were mad about.”

What are you watching right now?

Right now my favorite show would have to be Crazy Ex Girlfriend, but you know, Game of Thrones isn’t on right now. Getting On was great and Veep. Consumer Reports right now says that when you go out and buy a car now, they’re all pretty good. It’s the same thing. You’re going to be more surprised turning on the TV and seeing something really shitty. I don’t think that was true even 10 years ago.

Has it surprised you? Or did you see it happening?

It was gradually and then it was all of a sudden. I remember the first time I was working on a lot and someone brought over a tape of another show that some guys I knew were working on and it was called Freaks and Geeks. We watched that show and went, “Wow. That’s pretty good.” The description made it sound like any other show, but when you saw it the levels and subtlety and darkness and doing that in 21 minutes. Whenever someone does something like that and it’s even a little bit successful, it’s a challenge for everyone else.