Apple Event in Chicago 2026



As I work backwards through shoots in August, I place them into my little workspace of task-master lists if they still have outstanding invoices. And then my blog post task scheduler comes alive and tells me to Create a Blog Post for this Apple Wallet Event in Chicago that I took photos for, and so, I do not know how much is under an NDA (I did not sign any). I can post what I shot on my phone, I guess. 

Andrew and I flew to Chicago in August for this influencer event. We shot on iPhones. “Shot on iPhone” was the goal, and oh boy, what a bad idea that is (in case Apple reads this: this is merely a bug report/feature request. Or it was all user-error that we problem-solved through, which makes good blog-post plot). I mean, we got the job done. The job was wonderful. The staff were wonderful. Influencers are wonderful. iPhone is wonderful. At the queer wedding (mentioned in the last blog post, but not yet blogged about, for the automatic task scheduler has new demands on me), Andrew and I met an Apple Employee who said, “shot on iPhone? Hm....” and she intuited the experience we went through. Here’s the deal.

I, as a professional photographer, like many (but not all) professional photographers, have specific software to cull my photos. Culling photos means selecting the best ones. So I can shoot a million photos in a day and then only select the ones I like to edit, and only import those into the editing software. The rest basically do not exist. (One time another professional photographer told me to use AI to cull my photos, and I said, “absolutely not,” because so much of what makes a good photographer, to me, is the ability to cull well. I’ve learned this recently. As a tangent to this tangent, I’ve shot for other photographers, who have not invested as much time into practicing culling as others might, and these photogs not only take years to deliver the photos, but include the bad photos and do not include the good ones. I could show you but I will not: I do not want to spread shade. So when the other photographer suggested I use AI, I sat there and said “no,” and he saw me quickly zoom through my pictures, selecting the good ones, and said, “I think you’re faster than AI is,” and I said, “yeah.” The length of time it takes to choose a photo does not make the choice more intentional. The “intention” is just hidden, baked in, buried beneath series of snap-judgements that are intentionally-cultivated.) 

So of course I shot a lot of photos at the Apple Influencer Event in Chicago. I wanted the phone to overheat in my hand. And I knew I could cull the bad and blurry ones out. It was no big deal that the employees that contracted me wanted the photos by that night. 

So the day went well and I took photos and charged the phone and took more photos. Two rounds of influencer events occurred. And at the end of the day, the Apple Employee in charge said, “we need the phone that we lent you back, so could you transfer the photos before our flight at 5:00?” It was 4:00. Andrew plugged the phone into his computer. And none of the photos loaded. The transfer was too bulky. The phone froze. The computer did not transfer the photos. So we said, “uh oh!” and they said, “ship us the phone when you get back home,” and so we had another day before needing to pawn the phone off the to agency that hired us, so they could cover the cost of shipping the phone. I spent the afternoon finding techniques for fast file transfers from the iPhone. 
   
So we stayed up late, visiting Betsy’s old apartment (she passed away in December last year). Andrew pointed to one or two apartments in the building. One had no lights on. The other may have had lights on. One of those was her’s. Andrew spoke of how the American Health Care system may have failed her. But she did not take very good care of herself. So her death is complicated: I said it would be just like Betsy to go and die like that (I am not heartless. I am saying this to cope); it was not out of character; and we were shocked at the lack of friends she made in her years in Chicago. Maybe that would have prevented her dying. If she went on more dates, and had someone to care for her...we walked by a gay bar. It was 5 minutes from her apartment. We had gone to a gay bar with a Glee night the night before; Andrew stole my phone and texted my boyfriend at another gay bar about the Chicago Cubs; my boyfriend told us to stay for the drag show, but we did not because we had to be up for the shoot...but this is all to say that options were available to Betsy. I had even pressured her to go on an online date. Once. She was not impressed. And now I wish I could send her Romy to listen to, but she can’t really listen to Romy right now. That’s how things are. 

Here is an iPhone photo of Betsy’s apartment building. I got the photo off of my iPhone.


We walked back to the hotel to transfer the photos. And the photos transfered quickly, but only half of them showed up. Which means that some of them transferred infintely slowly. Half the photos showed up and the rest were missing. And each method for grabbing the photos off the phone repeated this result. I wanted to scream (in case Apple is still reading: I have good professional equanimity and did not scream). It was midnight and our flight was at six in the morning. So I transferred the photos again, by getting them into the downloads folder somehow, and waited. I just gave up and leaned into the wait. And somehow all of the photos appeared, or promised to appear. I double checked through my culling program. Every photo that appeared in the iPhone photos app appeared on the computer as well. That was it: I went to bed. 

So on the airplane I culled all of the photos. I edited the ones I took on my camera (oh yes, Apple wanted real camera photos, not-shot-on-iPhone, as well). And I airdropped them on the airplane to Andrew sitting seven or eight or nine rows in front of me. How mystical modern technology is: airdropped on the airplane. 

The mysticism of technology, depending on how you define mysticism, appeared in a statement an influencer made. She responded to a new feature of the Apple Wallet, which “splits the bill” according to an image of the receipt: the iPhone camera reads each item in the receipt, puts a list of the items on a screen, and you can select which item in the receipt was yours to pay. The iPhone will add up the total for the items that you have selected, and add, proportionally, tax and tip. And then you can opt to send that total, through Apple Pay, to the person who put their card down and paid for everyone. So the influencer responded to this, saying, “why doesn’t Siri know which items are mine already?” Oh Rachel (this was not her name), how would Siri know that you ate half of the pizza ordered? Do you want it to watch you? Somehow it must know, but that knowledge, like much of technology, is a mystical knowledge: it is a mystery beyond reach, “unknowable” to those who aren’t specialists. “AI,” so people call it, embodies a new form of faith in probability algorithms, a new form of modern mysticism. A faith against reason; a faith against decision.

 (There is a 2005 essay about this that I told my pastor about when he began to talk about AI, which I can cite here: Thomas Carlson’s “Modernity and the Mystical: Science, Technology, and the Task of Human Self-Creation,” in James Proctor, ed., Science, Religion, and the Human Experience. Oxford: Oxford U. Press, 2005.”)

This is all to say, I do not think this influencer would like culling very much at all.



Anyways, that is the blog post. Stay tuned for more, and hire me for photography (email blake.a.williams@live.com).

-Blake