So who would have thought that Goliath had given up the fight for money? —Harvard Gazette

Simon Rich had a two-book contract with Random House when he graduated from Harvard in 2007. Since then, he has written for “Saturday Night Live” and was showrunner on the cable television 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 telling his great-grandson about romance in the pre-dystopia, post-climate change era, and a nostalgic participation trophy buried on one Landfill under “four hundred tons of wow potato chips” and David and Goliath (who, as it turns out, lost the battle).

Rich spoke to the Gazette about his latest work and gave an 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 to some of your previous work?

I'd say it's embarrassingly identical to my last four books, which were all short story collections. But thematically it's a bit new for me. The characters are slightly older and struggle with bigger dilemmas than some of the protagonists in my previous collections.

What do you mean when you say “embarrassingly identical”?

When I first started out as a writer, I was much more experimental in my approach to books. I was still trying to figure out my style and my own sensibility and my own taste. Around my late 20s I found a style that I liked and I don't think I developed or changed creatively. It's safe to say that whatever people thought about the last four books, I imagine they'll feel very similar about this one.

You mentioned that the stakes are higher for your protagonists in this collection. Many of the themes touch on family, parenthood or the pain of growing older. Did you draw on your own experiences to reflect the type of fear your characters face?

I think all of my books are truly autobiographical, which you wouldn't necessarily realize from reading them. The spaces are so surreal; the characters are ridiculous; and their life experiences actually don't match my own. But on an emotional level, I always try to write stories that are authentic to what I actually experience on Earth.

My last collection, “New Teeth,” was mostly about stories about becoming parents and having children. And this collection is about turning 40 and reaching midlife. There are many characters in the book who struggle with feelings of obsolescence and try to adapt to a world in which they are no longer the youngest generation. There are stories about characters who are used to winning, have to deal with their own weakness, and hopefully have achieved a little humility.

Let's talk a little about the process. You approach your stories from surprising angles. For example, they take a familiar plot or character and add an unexpected twist, such as Mario (from Super Mario Brothers) having a mid-life crisis or the Tooth Fairy being pursued by what sounds like an illegal tooth smuggling ring. When or how do these ideas come to you?

Since college, I've had a family encyclopedia that I flip through for ideas. The one I use now, the Oxford Family Encyclopedia, I've had literally since school, and I would go to the Lamont Library and look through their encyclopedias and periodical collections, looking for recurring themes that might lead to comedic premises.

I avoided newspapers because I didn't want to do anything too current; The topics were often sensitive and had too many satirical associations. I looked at magazines but ended up with children's encyclopedias because every page is filled with general reference points. So many of my stories have come from simply flipping through the pages and coming across a theme or reference that can be twisted in a humorous way.

Where did you come across this strategy?

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

When do you realize you've landed on something?

The first step is that I think the concept is funny, but then the second point needs to be clarified: Do I have a funny idea how to implement it? There are hundreds of premises on my computer that I think are fascinating, funny, or interesting, but I actually don't know how to write them. I don't know from what perspective they should be written. I don't have a story. I don't know who the protagonist should be. Often an idea sits 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 in your development as a writer?

Fully. I wrote my first book in college and my process was exactly what I just described. I took my encyclopedia, went to Peet's Coffee every night and sat against the glass wall. I wrote down by hand all the premises that came to mind, and then went to the Lampoon in the morning and wrote down the ones that seemed most promising.

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

My favorite was the newly minted Danny Chun, who kept coming to visit. I read everything he wrote for the Lampoon, including things that didn't make it into the magazine. He was probably my biggest comedic influence at the time.

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

And to be completely honest, I took a lot of courses for materials, especially on topics that I thought could provide premises. I was so single-minded in my pursuit of original comedic premises that I took courses for that reason alone. I remember thinking, “If I get a piece of this, it’s worth it.”

Do you have any advice for other young writers?

I remember falling in love with the writer William Somerset Maugham at Harvard. I just chose “Of Human Bondage” and “The Razor's Edge” which I found at The Coop.

So I went to Lamont and found that he had written about 100 books. I happened to pick a few off the shelf and noticed that they weren't as strong as the ones that had been printed regularly for about 100 years.

I had this epiphany: Nobody remembers your bad stuff. Even if it is monstrously bad, it simply evaporates as if it never existed. People only remember your absolute best stuff.

Once I realized that, I was able to take a lot of risks and try out a lot of different genres and mediums because I knew no one was really watching. Even if I brought terrible things into the world, I would forget them. That was a real comfort for me as a student. I took a lot of risks while writing. In those early days I wrote in many genres I had no business being in, and learned a lot along the way.

What's next for you?

In December I'm doing a show on Broadway called All In: Comedy About Love, directed by Alex Timbers and featuring a rotating cast of actors and comedians – including John Mulaney, Andrew Rannells, Richard Kind and Chloe Fineman – which read my work. There's a lot of really fun, talented people there and the music is by the Magnetic Fields, who were a big influence on my writing. I'm really excited about it.