Josh Gondelman is a comedian, writer, and co-creator of Modern Seinfeld on Twitter.
ZAK: Josh Gondelman is one of the funniest people on the internet and in real life. He's a stand-up. He writes on the TV show, Desus and Mero and his coolest credit, in my opinion, is that he co-created the now inactive but deeply beloved Modern Seinfeld twitter feed, which launched the characters into contemporary, internet era situations, like this one..."Jerry meets a woman on JDate but when he begins to suspect she's faking her Judaism, Kramer volunteers to investigate." Ok, why am I telling you all this? I guess it's because, if Seinfeld resonates with you, I think today's advice will too.
JOSH: So, my advice is for over-thinkers and it's to just ask yourself, like, 'What would a person do under these circumstances?" Like, if you're up against a dilemma where you're like, oh...do I do this or that, not one where you're weighing huge, qualitative differences or like, big choices you're weighing against each other, but if you're like, 'Do I do this? Is this a violation of etiquette and norms' or whatever then it's always like, 'What would a person a do?
ZAK: Can you think of a recent example?
JOSH: I recently got to work with somebody on a recording that I'm a big fan of and I was like, I had such a good time, should I email and say 'I'm a big fan. This was cool. I appreciate it.' And then I was like, 'Is that like a dork thing to do? Then I was like, no, I'm gonna do that because, like, a person would do that and a person on the other side as long as I'm like pleasant and respectful and don't ask anything of this other person, like, they would probably be happy to hear it...ranging from neutral to happy to hear it.
ZAK: It seems like in a lot of these examples, you weight the decision and then you go ahead with it because you're thinking like, yes this is a normal thing to do. Are you ever in the position where the normal thing to do is, oh I better not do that?
JOSH: Oh, that's a great question. I think it depends on what your inclination is. I think if you're a person who tends to overthink things, it's like a nice little nudge to be like, this is not an unreasonable thing you're considering doing. But, if you're the kind of person who maybe is sometimes extra assertive...if you're like, you know what I'm just gonna call this person up and tell them to give me a job...you go ok, like, how would they react to that? Do they want to hear that from me? Is that something that you feel like your relationship has space for?
ZAK: Right. So how often do you find yourself asking this question, what would a person do?
JOSH: I think I ask myself a lot. But it's diminished over time because I think it's now hardwired a little bit with me which is nice. Like it feels like I've rewired the way that I maneuver.
ZAK: Isn't that such an amazing thing?
JOSH: Totally. I think it's awesome. It's like one of the coolest things about being a human is that you can, like, see results and I think there are probably people, I imagine, who live with depression and other kinds of mental illness might have a harder time feeling clear about, like, what they deserve or what they're capable of asking for and so I don't want to be like, this is easy for everyone to do. But if it's something that you can apply, that you feel able to apply, comfortable to apply...and also, I think this is...my friend Sarah Haji, I believe it was Sarah Haji that coined the slogan that became a pretty popular meme for awhile of, "Grant me the confidence of a mediocre white man." So I understand the gender and sexuality and racial privilege at play too which is why I'm not like, "Be demanding! Throw your weight around!" But I do think that being polite and courteous and asking for the thing you want once, like, you so rarely get what you want if you don't ask and people are so rarely mad if you ask for something politely once and if they are, they are being unreasonable not you.