
Show overview
Tricky Thoughts: Encountering Photography In New York City Podcast launched in 2025 and has put out 18 episodes in the time since. That works out to roughly 6 hours of audio in total. Releases follow a monthly cadence.
Episodes typically run twenty to thirty-five minutes — most land between 16 min and 26 min — though episode length varies meaningfully from one episode to the next. Roughly 39% of episodes carry an explicit flag from the publisher. It is catalogued as a EN-language Arts show.
The show is actively publishing — the most recent episode landed 4 weeks ago, with 3 episodes already out so far this year. The busiest year was 2025, with 15 episodes published. Published by Jim McDermott.
From the publisher
A photographer's adventure unfolding in the streets of New York City thetrickness.substack.com
Latest Episodes
I Froze My Leica!

Shooting Street Portraits on Film at New York Fashion Week PLUS an interview with photographer Paul Reid
New York Fashion Week 2026 was COLD - maybe that's why it was so sleepy? I got some great photos anyway, which I share in this video - 35mm and 120 Medium format film only! Plus, I've got a special guest, the incredible Scottish photographer Paul Reid. Check out Paul Reid's work and photography classes at his website https://www.paulreidphotography.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

Shooting 35mm film in a NYC snowstorm
What's it like to shoot 35mm film in a massive snowstorm in New York City? Watch this video and find out! We had a massive snowstorm in late January in NYC. I met up with some friends and we walked through Chinatown, the Lower East Side, and Soho and dealt with the freezing cold, camera issues, wet foggy eyeglasses, and general misery. I share the photos and talk about the experience. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

S1 Ep 15Under The Bridge, Episode 15: Baby, Don't Ever Change
EIn this episode, recorded at the Guggenheim Museum (and the streets of NYC) on Robert Rauschenberg’s 100th birthday, I was thinking a lot about growth. Not the kind that makes our pants tighter, which is really easy, but artistic growth. Is creative growth something you think about? Give this a listen and let’s get into it.Artists mentioned on this podcast:Rauschenberg Guggenheim show: https://www.guggenheim.org/exhibition/collection-in-focus-robert-rauschenberg-life-cant-be-stoppedChaz Neill: https://www.instagram.com/reddotjournals/Paolo Roversi at Pace: https://www.pacegallery.com/exhibitions/paolo-roversi-2025/Robert Longo at Pace: https://www.pacegallery.com/exhibitions/robert-longo-the-weight-of-hope/Don McCullin at Hauser & Wirth: https://www.hauserwirth.com/hauser-wirth-exhibitions/don-mccullin-a-desecrated-serenity/Thanks for reading Tricky Thoughts: Encountering Photography In New York City! Subscribe for free to receive new posts and support my work.(More pictures from Robert Rauschenberg: Life Can’t Be Stopped) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

S1 Ep 14Under The Bridge Episode 14: What Kind Of Photographer Are We?
Hello! I’m back with another episode, it’s been a while and I’m sorry about that. Had lots of family obligations in August, and when I wasn’t herding kids I was taking pictures like a fiend.I’ve run through dozens of rolls of film this summer, shooting all kinds of different subject matter. The work is so varied, I don’t think any algorithm would be able to make sense of it all. And that’s ok with me! In this episode, I talk about the labels that we, other photographers, and social media platforms put on us. Am I a street photographer? A portrait photographer? Documentary photographer? Fashion photographer? A “visual storyteller” (oh FFS please, anything but that…..)I don’t think about any of this while I’m taking pictures, but when we show our work to the outside world, they kind of want it packaged up nicely, consistently, they want to know what they’re looking at. And you need to decide if you’re going to give it to them that way, or not. I’ve always appreciated artists who stick their middle finger up to the establishment, to societal norms, and do their own thing. Doing things that way is never an easy path - but who wants it easy, anyway?So this…..is about that. And I had to edit this one a bit because the trains passing over the bridge were hella loud and frequent. Figures the MTA would pick the exact 15 minutes this week I was recording to make the subway trains come fast and frequent. Anyway….thanks for listening and if you have any questions, comments or thoughts, please share them!JimThanks for reading Tricky Thoughts: Encountering Photography In New York City! Subscribe for free to receive new posts and support my work. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

S1 Ep 13Under The Bridge Episode 13: The Big Bang of Diane Arbus' Constellation
EEveryone is entitled to their own opinion, no matter how myopic it may be - here’s mine!This is a podcast about Diane Arbus “Constellation” show at Park Avenue Armory, which closed August 17th. This show has been fairly controversial, because of the way the work is presented (for example, read this post by photographer Dita Livotsky or this particularly soggy review of the show (Arbus’ work is no longer relevant because “social media shows me world is bad place so don’t need 60 year old picture” and “I confused because mirror and pictures no context so hard to critic”)Spoiler alert: I loved the show. I’ve seen hundreds of photography exhibits and they’ve mostly been done the same way: perfectly hung right on the sight line, usually with little cards giving context for each image, pictures grouped together by subject matter or project or time period. It’s always very linear. Constellation, however, does none of that. Some pictures are on the walls, but the majority are hung on lattices. Photographs are down near your ankles, some require you to get on your tiptoe to see them. They are not organized in any discernible or traditional manner - there is no beginning or end of the exhibition, so wherever you start viewing seems arbitrary. The sense of spacial disorientation is compounded by a mirror that acts as the rear wall of the exhibition, which makes the show seem almost endless. It’s as though there was a “big bang” beneath a pile of Arbus’ work, and Constellation freezes a moment in time as it expands through the universe. And this is wonderful. Constellation was an experience - an entirely non-traditional one - which I suspect the artist would have loved. Anyway, give a listen and if you have thoughts, please share them.(Note: while at the show, I bumped into the noted photographer Dona Ann McAdams and we talked about our Leica M’s, Kodak Tri-X, and of course our impressions of Constellation. We had a wonderful chat. I was on the steps of the Armory when she came out, and she was curious about my digital recorder, which had a dead cat windscreen on it. She thought the dead cat (which looks like what it is named) was hilarious and wanted to photograph me with it; of course I agreed and kept the recorder rolling. I was wearing a bright white t-shirt and standing against kind of a dark background, so the meter in her M was jumping all over the place, over then underexposed. The M has this kind of kooky circular meter thing, no spot metering option, so it can be tricky to get a correct reading in high contrast, wider shots. So I completely embarrassed myself and mansplained to a brilliant photographer who has been shown at MOMA, The Whitney and ICP how an M light meter works. I swear it was with the best of intentions! And we got it figured out. I still haven’t seen the picture though…..)Best, Jim (and by the way, Happy World Photography Day!)Thanks for reading Tricky Thoughts: Encountering Photography In New York City! Subscribe for free to receive new posts and support my work. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

Under The Bridge Episode 12: Growth and The Real Gold
Hello there! Thanks for looking and listening. For this episode, I’m in Queens (the borough with the best food in NYC) - sitting on the bank of the East River and talking about growth - all the work we do to build our social profiles and community, and whether or not it is worth all the effort. In a way, this is the complete opposite of one of those posts that are so pervasive on Substack which provide methodologies for growth - for once, I think it’s important to stop and look at what we’ve been doing on social media for all these years and get some perspective.If you are a creative and you sometimes ask yourself what the point is, I think you’ll find some good thoughts to unpack here. Hope you enjoy it, thanks for listening and please comment if you have thoughts!JimThe Substack article that inspired this post: https://substack.com/home/post/p-167179451Daniel Ek ist ein fickgesicht: https://fortune.com/2024/06/03/spotify-ceo-daniel-ek-content-cost-close-to-zero-stearming-subscription-fee-hike/Obscure 80’s new wave song by Peter Godwin that I like and you might too and is kind of adjacent to this discussion because it deals with the illusion of the ideal and also its just super good:Thanks for reading Tricky Thoughts: Encountering Photography In New York City! Subscribe for free to receive new posts and support my work. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

S1 Ep 11Under The Bridge Episode 11: Embracing Mistakes and the Roll Of Life
Hello everyone! Back at you from NYC and this time I’m walking ACROSS a bridge and talking about why mistakes and failure are good things. This is a bit of a noisy podcast as I’m walking right next to speeding cars and subway trains - so you’ll get some real NYC vibes on this one!Some things I refer to in this episode:Queensboro Bridge Pedestrian Path: https://qns.com/2025/05/queensboro-bridge-pedestrian-path-opens/Lomography 100: https://shop.lomography.com/us/lomography-color-negative-35-mm-iso-100The Highlander/Silvercup Studios: Embraced Mistakes:Thanks as always for listening! If you have any comments or questions, please share them with me.Best,Jim This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

S1 Ep 10Under The Bridge Episode 10: From A Parisian Graveyard (A Little Too Much F#$king Perspective)
ESorry it’s been a couple weeks since I posted an audio note, but I did have an excuse: I went on a family vacation to Paris. I used to go to the City Of Lights about 5 or 6 times a year for work and fun, starting in the late 90’s, but I haven’t been since around 2005 - TOO LONG. Paris really is my favorite city in the world - no place is perfect but Parisians really seem to have a better grip on what’s important in life than the average New Yorker.My initial thought was to record this episode under a bridge on the Seine, but then I realized that the Cemetiere Montmartre had a bridge going over part of the grounds, so I stood amongst the graves and hit the record button. If I sound a little subdued, well, chalk that up as me being respectful to the residents. Walking around in a graveyard can sure give you some perspective on things, and that’s what this episode is mostly about: perspective. Hope you enjoy it.Music from a couple of the residents below. If you want to see the photos from my Paris trip, I’m posting them on my IG here: https://www.instagram.com/thetrickness/ Thanks as always for listening (and enjoy the special treat at the end!)JimDalida: Dick Rivers: This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

S1 Ep 10Under The Bridge Episode 9: What About The Leica M?
ESo - I don’t really do deep dive explorations of camera gear here, there are plenty of people doing that on YouTube, especially for Leica cameras and accessories. I’ve been using the Leica M camera system on and off for about 30 years, so it is a photographic tool I know quite well. Leica is celebrating their 100th Anniversary in 2025, and the M turned 70 years old last years, I thought I’d talk about the actual experience of using the M (I use a Leica MP film camera in my work, alongside other camera systems.)I’m allergic to all the cliquey fetish/worship of the M, so you aren’t going to hear any of that out of my mouth. I’m much more interested in talking about what makes this camera unique, in use more so than in appearance. Hope you enjoy it and thanks for listening! JimCouple of things I mention in this podcast -Magnum: Fifty Years at the Front Line of History by Russell MillerJoel Meyerowitz talking about the M and rangefinder system: This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

Under The Bridge Episode 8: To Have Ambitions Was My Ambition
This episode comes on a very heavy week (aren’t they all heavy these days?) and I’m under the Queensboro Bridge thinking about creative motivation because I saw someone pissing against a trashcan as I was walking my kid to camp this morning. No, really! If you’re bummed out, pissed off, depressed, can’t bother to create - give this one a listen, it might make you feel better. Thanks for listening and if you have any comments or thoughts, please share them. Jim(Oh, and listen to Gang of Four too): This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

S1 Ep 7Under The Bridge Episode 7: Self-Flagellation with The Mermaids
EHello again! In this episode I discuss choosing the more difficult option creatively - and then finding out what the up and downsides of that are, with the backdrop of the absolutely wonderful 2025 Coney Island Mermaid Parade. This episode is kind of gear oriented, but not the typical YouTube style fetish crap. If you’re curious about TLR cameras, medium format photography, drug-addled opossums, monks hitting themselves in the head, and CONEY ISLAND, join me for this episode, won’t you?Thanks to everyone who listens and comments - and shout out to all the pals who I saw in Coney this past weekend, love you all.Jim This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

S1 Ep 6Under The Bridge Episode 6: Unboxing the NYC BILD expo
EWelcome to episode six of Under The Bridge, recorded on June 18th under the Queensboro Bridge, the day after I attended the Bild expo at the Javitz Center - which organizer B&H Photo calls “NYC’s largest gathering of video/photo storytellers”. In this episode, you’ll hear about:* The last thoughts that will rush through my mind as I am dying* Photographer Mark Mann* Human Connection* And of course, the Bild expoThere’s a short clip of Bill Hicks speaking at the beginning, from his album Revelations: Live In London - very NSFW. I first heard Bill Hicks’ comedy about 30 years ago, and I think of his perspective on things on almost a daily basis (especially these days). Highly recommended stuff.As always, I want to thank anyone who listens to my ramblings, posts comments or questions, and finds what I’m doing here of value or helpful. Your support and encouragement is greatly appreciated.Enjoy! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

Under The Bridge Episode 5: Coney Island Blues
Happy Father’s Day 2025! OK first off: this episode was NOT recorded under a bridge, it was recorded under a boardwalk - and on a boardwalk - at Coney Island, on June 14th, which was just crappy, cold rainy day. Hardly anyone was out. I knew this before I even got on the Q train - but I wanted to get some photos of the Coney Island Sideshow (the photo above was taken on a much nicer day in Coney!) This episode isn’t really about anything other than getting out there, even when we don’t feel like it. ALSO: I mention a group of beautifully dressed people playing drums and dancing in an African style - after the recording, I went back to watch more and a young woman named Elaine explained that the group was gathered in remembrance of their ancestors, for whom the ocean was a burial ground - people taken as slaves by Europeans and brought to America by ship, many of whom died or were killed on the brutal journey and were thrown overboard. She mentioned they gather annually on the 2nd Saturday of June to pay respects, in advance of Juneteenth. It’s a privilege to live in New York City and have the opportunity to be educated socially.Some of the things you’ll hear about in this recording (as usual, recorded with no edits, audio verite style):RAIN!The Warriors movie: TrailerThe Coney Island Sideshow At Coney Island USAThe Coney Island Mermaid ParadeDJ Ray VazquezAnd mentions of some photographers:Brian DembyPurcell NurseReuben RaddingLarry FinkPaul ReidThanks as always for listening- I appreciate your time, encouragement and comments! Jim This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

Under The Bridge Episode 4: What Not To Photograph
In this episode, I talk about Dave Chappelle (thought he did the bit in DC, it was actually Detroit), Fan Ho, Evel Knievel, The Girl In The Coffee Shop Window, and Colon Blow. And believe it or not, this all has something to do with photography. Recorded as per usual, under a bridge (this time the Queensboro Bridge), with no edits, audio verite. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

Under The Bridge Episode 3: Visual Signature Is Everything
What is visual signature and why is it important for photographers, or really any creative, to make the pursuit of visual signature a maxim? Join me in the latest episode of my unedited audio chats recorded beneath the Manhattan Bridge in NYC for some fragmented thoughts and foul language about the ultimate goal for any artist. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

S1 Ep 2Under The Bridge Episode 2: Film Photography As An Act Of Rebellion
EA brief chat about film photography, consumerism, the digital economy, Wim Wenders and enjoying one raisin. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com

Under The Bridge Episode 1: Shut down imposter syndrome
Join me under the Manhattan Bridge, and listen to the trains booming overhead while I talk about silencing the inner voice that makes artists doubt ourselves. Recorded in one take with no edits on the streets of NYC.. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thetrickness.substack.com