You’re seeing this too, right?
5 questions for comedian, podcast host, and author Chris Duffy
When I was a little girl if you’d told me, “Someday you will have a job where people send you free books and you get to read them and talk to the authors, and also sometimes you get to write your own,” my big blue-green eyes would have bugged out and I would fallen back onto my ruffly canopy bed with absolute ecstasy and told my stuffed animals— “Everything is going to work out perfectly, you guys!” Thank you for subscribing and sharing this content, and generally being the best commenting community ever. If you aren’t a paid subscriber, and enjoy the essays and interviews I publish here, you would probably also really enjoy the Sunday 5—five endorsements I send every Sunday morning with the best stuff I’ve read, listened to, or watched. Thank you thank you, always, and on to the main event…
Sometimes it takes a friend asking you a bunch of questions to hear your own wisdom out loud, and that’s what I experienced while recording a recent conversation with Chris Duffy. I’ve been a fan of his podcast for awhile and was very honored when he asked me to be on, but I didn’t expect the depth at which he would see me (he said he prepped for the interview by searching in his email inbox for all the times he’d sent this newsletter to friends over the last few years 😭), but also the depth at which he would help me see myself. When I re-listened, which I don’t always do, I actually appreciated what I was able to articulate here—about the ways in which caregiving has been a portal to meaning for me, and how much helping and being helped are an energetic loop one must not muck up with your own arrogance and ego—among much else. Take a listen:
And then…speaking of energetic loops…check out this awesome interview I did with Chris about his new-ish book, Humor Me: How Laughing More Can Make You Present, Creative, Connected, and Happy. You are really, really going to love this book, which is less a “how to be funny” tome and more a “let me make you LOL while helping you be more present and alive to your own hilarious and very human life” tome. Trust me, you’ll love it. And him. Meet Chris…
Courtney Martin: You say it’s a misconception that people are either born with a sense of humor or not. Are you sure? I feel like my youngest kid was delivering perfectly timed punchlines on like day 12 and I know a lot of really boring kids.
Christ Duffy: It’s a fair point! Definitely some people have more of a natural ease with humor than others. But I will say that I don’t think I’ve ever met a genuinely boring kid! Quiet? Yes. Shy? Certainly. Extremely specific and odd? Without a doubt. But truly boring? I think that’s something it takes you years of corporate training to learn. When I say people aren’t born with or without a sense of humor, I am mainly trying to push back on the idea that laughter and humor are only for some people and that others are destined to live without them. I think it’s something anyone can build more into their lives. I think of it more like there’s no way I was ever going to become as good a swimmer as Katie Ledecky, but that doesn’t mean I couldn’t learn how to be comfortable and have fun in a pool.

You say the three pillars of humor are being present, laughing at yourself, and taking social risks. Such a helpful breakdown! It strikes me that the first one is just sort of the answer to everything these days, but I’ve never heard such a joyful motivation to do so. Rather than saying “get off your phone, you’ll be a better parent,” you’re saying “get off your phone, life will be more fun!” Who could argue with that? On the other hand, being on our phones is sometimes where we find the funny stuff, right? How do you strike the right balance?
I do think being present and paying attention is at the root of everything these days! It’s simple but not easy. But what a gift when you interact with someone who is paying close attention and really there with you! That’s my favorite part about laughing so hard I cry with a friend. We are totally, fully, completely present in that moment together. To be clear though, I’m not anti-technology when it comes to laughter! There’s so much hilarious stuff that you can find online and I think that’s great. I love a good meme or a blooper reel from The Office. I think the balance for me is in trying to appreciate that funny stuff that I always have at my fingertips and use it as a way of bringing some laughter into my week (especially if I can share it with my wife or a friend, so we get to laugh together). But then also trying to cultivate my own ability to notice the odd, delightful, and absurd by deliberately walking away from all the tech and just spending some time noticing.
I’m not a birder, but I think there’s a similar thing where I could easily find photos or videos of every bird imaginable online. But it’s way more satisfying to spot them myself out in the real world. I watched one documentary on birding and the next time I went outside, I was shocked by how many birds I heard and saw. They had always been there but I’d never noticed them before. I think the same is true for funny, delightful, weird stuff. It’s out there but if you don’t try to train yourself to spot it, you’ll just walk right by unaware of all the laughs you’re missing.
There were so many studies in the book that absolutely delighted me. Can you tell folks about the one where the guy most likely to get a job actually spills coffee on himself!?
This is my favorite too! It’s known in psychology as “the pratfall effect.” Long story short, when people were asked to rate job candidates, the candidate they rated the highest was the one who did well in the interview but also had just spilled a cup of coffee all over themselves. The coffee spillers were even rated more highly than the people who answered the questions correctly but hadn’t spilled a piping hot cup of joe onto their work clothes. I love it because it’s such a funny and beautiful way of proving that we don’t have to be perfect to have people like us and be impressed by us. In fact, they like us more if we’re relatable and a bit of a mess.
Some of the funniest people I know are the most anxious, and your book helped me realize that--in part--their humor is a bid for safety and connection - like, “if we all think this is funny, then we’re a crew.” In that way, some of the funniest people are the bravest, but the most genuinely scared, right?
You hit the nail on the head. When we’re laughing together, we’re connected and we know we’re not alone. “You’re seeing this too, right?” That desire to make sure we’re together and seeing the same thing often comes from both courage and fear. I think that’s a big reason why people in the most stressful, scary professions (think ER nurses, social workers, firefighters, etc.) often laugh the most. It’s not a coincidence! It’s how they’re able to do their job and transform the stress and fear into laughter and connection so they can keep going.
You talk about the importance of keeping track of what makes us laugh by creating a file of some kind and throwing stuff in there. What is the last thing you threw into your “things that made me laugh” file?
One is this clip from the comedian Maggie Winters’ upcoming special where she’s talking about the experience of sitting in the waiting room of a hospital ER. Describing the performance of trying to get them to let you in sooner really made me laugh. Another thing I recently put on my list because it made me laugh was a photo my friend sent me of a product he saw at a liquor store that promised it would help you “Make a mimosa in 3 simple steps.” We both thought that was great because, as far as I know, without using their product, a mimosa is already only 2 steps! Orange juice and sparkling wine!
Buy Chris’ book here, check out his Substack here, and tell us in comments, what is in your “things that made me laugh” file this week?




Fascinating idea that when we're laughing with others, we're TOGETHER, "like a crew."
It's related to the positive outcomes of doing things in community, like singing in a choir, or dancing in a group....some of the things that maybe aren't as mainstream as they used to be, and definitely have nothing to do with being on our phones.
Humor’s three pillars:
be present, laugh at yourself,
take social risks. Hmm...
...
When world worries us,
humor superpower trust
shields, sustains, supports!