So who knew Goliath threw the fight for cash?

Simon Rich had a two-book contract from Random House by the time he graduated from Harvard in 2007. Since then, he has written for “Saturday Night Live,” been a showrunner for the cable TV comedy “Man Seeking Woman” (based on his collection “The Last Girlfriend on Earth”), wrote the screenplay for the Seth Rogen film “An American Pickle,” and published numerous pieces in publications such as The New Yorker, Vanity Fair, and McSweeney’s.

 His latest collection of short stories (his seventh), “Glory Days,” follows a hilarious cast of characters, including an old man who tells his great-grandson about romance in the age before post-climate change dystopia, a nostalgic participation trophy buried in a landfill under “four hundred tons of Wow potato chips,” and David and Goliath (who, as it turns out, threw the fight).

Rich spoke to the Gazette about his latest work and offered some insight into his creative process — with some tips for young writers. This interview has been edited for length and clarity.

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What approach did you take to “Glory Days” and did you feel like it was similar or different than some of your past work?

I would say it’s embarrassingly identical to my last four books, which were all collections of short stories. But thematically, it’s a little bit new for me. The characters are a little older and grappling with higher-stakes dilemmas than some of the protagonists of my previous collections.

When you say, “embarrassingly identical,” what do you mean?

When I was starting out as a writer, I was a lot more experimental in my approach to books. I was still trying to figure out my style and my own sensibility and taste. Around my late 20s, I hit upon a style that I liked, and I think I haven’t creatively grown or changed. It’s safe to say, whatever people thought of the last four books, I imagine they’ll feel very similarly about this one.

You mentioned your protagonists face higher stakes in this collection. A lot of the themes touch on family, parenting, or the pains of getting older. Did you lean into your own experiences to reflect the type of angst your characters encounter?

I think all of my books are really autobiographical, which you wouldn’t necessarily know by reading them. The premises are so surreal; the characters are ridiculous; and their life experiences don’t actually match my own. But on an emotional level, I’m always trying to write stories that that are authentic to what I’m actually experiencing on earth.

My last collection, “New Teeth,” was very much stories about becoming a parent and having children. And this collection is about turning 40 and entering midlife. There are a lot of characters in the book who are grappling with a sense of obsolescence and trying to adapt to a world in which they’re no longer the youngest generation. There are stories about characters who are used to winning, have to come to grips with their own frailty, and hopefully gained a bit of humility.

Let’s talk a little about process. You approach your stories from surprising angles. For example, you’ll take a well-known plot or character and add an unexpected twist, like Mario (from Super Mario Brothers) going through a midlife crisis or the Tooth Fairy being hounded by what sounds like an illegal tooth smuggling ring. When or how do these ideas occur to you?

Since College, I’ve had a family encyclopedia that I’ll flip through for ideas. The one I use now, the Oxford Family Encyclopedia, I’ve owned literally since school, and I would go to Lamont Library and flip through their encyclopedias, magazine collections, and search for evergreen topics that might yield comedic premises.

I avoided newspapers because I didn’t want to do anything too topical; topics were often fraught and had too many satirical associations. I looked at magazines, but eventually landed on children’s encyclopedias because every page is filled with common reference points. So many of my stories have come from just flipping through the pages and being struck by a topic or reference that could be humorously inverted.

Where did you come across this strategy?

It was early freshman year when I was trying out for the Lampoon. I had read an article about The Onion and knew that the way they generated material was by reading the news and taking that day’s headlines and attempting to subvert them. But I knew I didn’t want to do satire. I wanted to pursue more absurdist humor, but at the same time, I didn’t want to be too untethered or unhinged. I was looking for that sweet spot where I could meet the reader in an accessible place but then take them on an interesting journey.

When do you know you’ve landed on something?

The first step is me thinking the concept is funny, but then the second bar it has to clear is: Do I have a funny idea for how to execute it? There are hundreds of premises on my computer that I that I think are intriguing, funny, or interesting, but I don’t actually know how to write them. I don’t know what perspective they should be written from. I don’t have a story. I don’t know who the protagonist ought to be. A lot of times an idea will sit on my computer for many years before I come up with the right narrator, the right point of view, or the right plot.

Was your time at Harvard and writing for the Lampoon a formative time for your development as a writer?

Totally. I wrote my first book in College, and my process was exactly what I just described. I would take my encyclopedia and go to Peet’s Coffee every night and sit at the glass-walled ledge. In longhand, I would write down any premises that occurred to me and then in the mornings go to the Lampoon and write up the ones that felt the most promising.

 I basically wrote that first book at the Lampoon and in the computer room in Adams House. I never took any creative writing classes, but there were writers at the Lampoon that I really looked up to.

My favorite was the recently graduated Danny Chun, who would come back and visit. I read everything he wrote for the Lampoon, including stuff that didn’t get into the magazine. He was probably my biggest comedic influence at the time.

Colin Jost was also really encouraging and supportive of younger writers and would always take the time to read what I was working on and give me feedback.

And to be totally honest, I took a lot of classes for materials, specifically subjects that I thought might yield premises. I was so single-minded in my pursuit of original comedic premises that I would take courses purely for that reason. I remember thinking, “If I get a piece out of this, it’s worth it.’

Do you have any advice for other young writers?

I remember when I was at Harvard, I fell in love with the writer William Somerset Maugham. I just absolutely flipped for “Of Human Bondage” and “The Razor’s Edge,” which I found at The Coop.

So I went to Lamont and realized he’d written about 100 books. I picked a couple off the shelf at random and found they weren’t as strong as the ones that had been consistently in print for 100 years or so.

I had this epiphany: Nobody remembers your bad stuff. Even if it’s egregiously bad, it just kind of evaporates, like it never existed. People only remember your absolute best stuff.

Realizing that set me free to take a lot of risks and try a lot of different genres and mediums because I knew that nobody was really watching. Even if I put terrible stuff into the world, it would be forgotten. That was a real comfort to me as an undergraduate. I took a lot of risks with my writing. In those early days, I wrote in a lot of genres that I had no business writing in and learned a lot from doing it.

What’s next for you?

I’m doing a show on Broadway in December called “All In: Comedy About Love” directed by Alex Timbers and featuring a rotating cast of actors and comedians — like John Mulaney, Andrew Rannells, Richard Kind, and Chloe Fineman — reading my work. It’s a lot of really funny, talented people and the score is by the Magnetic Fields, who were a big influence on my writing. I’m really excited about it.