Josh Gondelman's got me thinking. Am I a terrible person? The answer might shock me: it's yes.
As I'm reading through his new book, You Blew It!, I've come to the realization that just because I perceive myself as being highly self-aware, OTHER people might not get the same sense. For example, just yesterday I asked my husband to pause Homeland no less than 97 times because "who's the guy in the red?!" and "why do they talk so fast?!" and "does Clare Danes' hair look yellower this season? It's definitely yellower". Basically, I realized I am the person I hate most, all thanks to Josh.
If you'd like to get a solid read on your own personal shortcomings and learn more about how to do life better, I'd suggest you pick up Josh's book on Amazon and see for yourself. All proceeds go toward people hating you less.
You can also catch Josh's work on Last Week Tonight with John Oliver which airs Sundays at 11pm on HBO.
Josh! Thank you for joining my circus. It’s a pleasure to be here!
First of all, congrats on the book! Thanks! I’m so delighted it’s out in the world for people to read and (ideally) enjoy now.
Have you read it yet? Several times! I’m fairly familiar with the contents at this point.
You co-wrote the book with Joe Berkowitz who is a fellow writer friend and staff editor for Fast Company. What made you want to write a book together? The two of us have very similar senses of humor, and it seemed like a natural fit. We had a really good time working on the proposal, which seemed like a good sign.
Explain your relationship with Joe in five words or less. We’re good collaborators and pals.
Tell us how you came up with the premise. We’d pitched a fake pickup artist guide called Getting It Wet: The Nice Guy’s Guide To Tricking Women From Friendzone To Bonezone, and we met an editor who liked our writing but thought that book was too niche, so we tried to find a fun project that would be slightly less obscure.
I know it’s a humor book, but I’m hoping this is also the precursor to a larger social movement for heightened self-awareness. We can come up with a hashtag later. Haha, I like your style. But also I’m so jealous of people who aren’t self-aware and just amble through life blissfully ruining other people’s days.
How long did the book take to write? It took about nine months for the first draft and another three or four going back and forth with notes and everything.
What was the writing process like? It was terrific. We’d meet up and brainstorm and outline. Then we’d write and edit separately. Then we’d meet up and eat pizza and more outlining. Then came the doubting everything and more re-writing.
What were some of the biggest challenges you experienced in the process? Joe and I both became increasingly busy as the writing process went along, so it was harder and harder to make time to meet up in person!
Can we expect another literary piece from you in the future? I’d love to do one if someone will let me!
Let’s backtrack a bit because I want to know more about how Josh Gondelman came to be. Where are you from? I grew up in the suburbs of Boston, but I say “Boston” and then people ask me to be more specific, and then they don’t recognize the name of my town, which is why I didn’t say it (Stoneham, MA) in the first place.
Never heard of it. What led you to a career in writing? I’ve always loved to smash words together. In high school and college I had writing projects even outside of school, which looking back was not like…what everyone did, but it felt fun and natural so I kept doing it and now I’m technically a professional.
Did you know you were funny early on? I think so? I mean, I thought I was funny early on, but others would argue that it took me a while to actually get there.
In 2012 you and writer Jack Moore created the Twitter account @SeinfeldToday which gives a glimpse into what it would be like if Seinfeld were still on the air today. You have nearly 1 million followers. What will you do to celebrate the milestone? We should go out for soup from the most disagreeable vendor in the city!
Are you and Jack still the only writers for the account, or have you enlisted help? It’s just the two of us.
What other shows besides Seinfeld have inspired your writing style? I think years of watching and loving The Daily Show and The Colbert Report helped prepare me for my job now. Other than that, I don’t know about shows that inspired my style, although I really love the tone of The Simpsons, Arrested Development, and lately Bob’s Burgers and Brooklyn Nine-Nine.
You currently write for Last Week Tonight with John Oliver. How did you land the gig? It’s a very boring story! I submitted some sample materials, then some more. Last year I was hired to create all the digital content, and this year I’m writing for the show itself.
Describe a typical day at the office. It varies. But my main tasks are reading the news, pitching stories, writing up stories I’m assigned, pitching jokes with the other writers, and eating salads.
Sounds rigorous! No one understands how hard it is to eat a salad. How does writing for ‘Last Week’ differ from other projects you’ve worked on? Mostly it has to be about topical things. So when I do stand-up or write freelance pieces, it can be about any nonsense I’ve been thinking about that day, but the show has a tighter focus. I couldn’t come in and be like "what about we do a five minute piece on why bagels have holes in the middle?".
What’s your personal writing process like? Any rituals or special requirements before you get to work on a project? I usually get an iced coffee before I sit down to write, year round. It’s not even for being awake or focusing. It’s more like: “Now it’s time to work. You have no excuses.”
I need a prompt like that. I tried listening to music for awhile, but I get distracted and start looking up "how to dance like Bruno Mars" videos on YouTube. What do you do when you’re struggling to come up with ideas? I nap.
What’s next for you? Gosh, yikes. That’s very grandmotherly of you. “You’ve just written a book and are coming to the end of the season of the tv show you work on, but what do you DO?” There are a few more Last Week Tonight episodes this year, so I’m excited for those. Plus I’m going to do a little standup around the country in November and December. But mostly I think I’m going to lie on the couch and catch up on Veep and rub my dog’s belly.
To close, I’d love for you to write a haiku pitching You Blew It!
Don’t ruin your life.
Joe and I can improve it.
Well, I mean, maybe?