My 2.5 year-old didn’t have school over the February break. This was somewhat of a calamity. Her school provides a welcome respite from the chaos of caring for two girls 20 months apart, and my mental well being somewhat depends on it.

This was also not a calamity at all because school is only two mornings per week. And between snow days, holidays, conferences, sicknesses, and the moon being in waxing gibbous, two days is more like 1.7 days.

During one of those mornings, we decided to take a trip to our town’s bookstore. As I’ve written about before, the bookstore has become a go-to of mine when in need of a low-cost indoor activity. It’s been incredibly rewarding to see my older daughter develop a strong affinity for books, and she’s starting to approach her browsing experience like a pro. She’ll weigh the merits of several titles while methodically combing through shelves, eventually settling on the day’s selection. Usually, one with Sesame Street characters on the cover.

We spent about 20 minutes in the children’s section. This was about the limit for younger daughter, who is starting to behave like an upbeat realtor who instead of admiring a house’s details with enthusiastic persuasion, longs to eat them. Left to her own devices, she would’ve ripped pages out of every book she encountered before chowing them down as a mid-morning snack.

Now slightly hurrying Older Daughter, we confirmed her new Sesame Street title and went to check out. I did that thing where I feel around my jeans pockets to find my wallet.

Immediately, I realized we had a problem. What I thought was my wallet was actually a pocket-sized notebook, which I had recently bought as part of an ongoing practice to reduce dependency on my phone. My wallet was at home, and so was my ability to pay for my daughter’s books.

I went up to the checkout counter to explain the situation. We had an account at the bookstore, I pleaded. Would it be possible to add the book to the account and somehow pay later?

“Sorry, the account is just to track orders,” the clerk said. “Do you have Apple Pay?”

I did not have Apple Pay.

One of the reasons I did not have Apple Pay was the same reason that I bought a pocket sized notebook. After living in smartphone world for 15 years now, I’ve concluded that having “everything” on one device is definitely not for me. I don’t need to pay for a book, and then simultaneously see that I got 10 notifications re: some thread I’ve been avoiding, or find out that there was a shooting at a charity event. I just want to pay for a book without also playing mental health Russian Roulette.

I began to tell my older daughter that I left our “money” (a concept she is in the nascent stage of understanding) at home, and that we had to go home to get it. Then, we could come back and “pay for” the book.

I watched as she worked out this new information, her face wracked with an expression that reminded me of a middle schooler trying to comprehend the quadratic equation.

“We’ll come back later!” she began repeating, her way of processing the unpleasant news.

**

I was immensely proud that she was not having a meltdown. But I am afflicted with never-let-my-daughter-down-itis, so seeing her have to struggle this way physically pained me. I also started doing the mental gymnastics in my head of what it would entail to get the book later.

The prognosis wasn’t great. We needed to get back home, eat lunch, change diapers, do a feed, and come back. There’s no way we’d make it before younger daughter needed to nap again. And as I’ve learned from my new job, if you decide to put off something for later there’s a good chance it’ll never happen. It took my wife and I two years to properly organize our utensil drawer.

So naturally, the voice of inevitable compromise grew louder. Why don’t you just get over yourself and set up Apple Pay?

**

Up to this point, I had resisted Apple Pay for two reasons.

One, as stated above: I think single use technologies are the way to go. Cash or cards are used for paying. My phone has enough power over me, and doesn't need more ammunition to be indispensable.

Secondly. I generally believe that further we get away from the original embodiment or intent of something, the worse off we all are. Three examples:

There is a technological sweet spot where convenience aligns with utility and still requires human physical or cognitive participation. A vacuum enables you to clean a space in way less time, but you are still the one calling the shots on where and how diligently to clean. You are controlling the vacuum rather than the vacuum dictating what constitutes the space being acceptably spotless. But technological progress seems to be moving this past this sweet spot more and more, as we sacrifice our sense of self worth on the Altman altar of making things easier.

The quest to remove “friction” from our lives often starts with noble intentions. But its unquestioned momentum seems increasingly hellbent on decimating any ability for humans to develop competence in virtually all arenas, as there is always a shortcut, cheat code, or means of outsourcing. Resisting this momentum requires constant intentionality.

Which is why I’m especially concerned about this phenomenon for my children. Already, I get a little bit ill-at-ease when my daughter demands that I play a song, and two seconds later it’s blaring on the speaker. When you could listen to any song at will, order food (or anything) at the press of a button, and get an entire essay written with one or two prompts, it feels like you’re fighting a losing battle. Or at the very least an exhaustingly uphill one.

**

But I live in 2026 and have a daughter who I didn’t want to let down, so there was only ever one solution.

I proceeded to try and set up Apple Pay only to be initially stymied. I didn’t know the CVV of the credit card that is hooked up to my Apple ID. Taking a deep breath, I mentally prepared for the toddler fury I was about to withstand.

But then I remembered that I had a phone-a-wife lifeline—she was working from home. So I called her, got the 3 digit CVV code, and officially joined the 2020s.

I returned back to the checkout counter, proud of myself in the way a GenX parent probably feels when they finally use “mid” correctly in a sentence. The GenZ bookstore employee didn’t appear to share any enthusiasm for my corny accomplishment. Having barked on Greenwich Village street corners for years trying to get people into comedy shows, I can intuitively sense when people sweetly think you’re kind of pathetic.

We walked home. My older daughter occupied herself in the stroller, poring through her new book. In the immediate term, I was relieved that the walk home didn’t consist of me playacting the role of infinitely patient parent while his child has an embarrassingly loud tantrum.

But in the long-term, I questioned the efficacy of what I just did. Would it have been better for my daughter to experience the disappointment of not getting the book so that she could experience (and overcome) a setback? Are these sorts of low-stakes, character-building snafus a thing of the past? What is going to happen to these kids?

Or, is she two-and-half years old, and was I being completely absurd?

**

Later that day I realized that due to a scheduling conflict, I needed to change an upcoming appointment with my primary care doctor. My doctor is an incredible doctor and it’s often very difficult to find appointments. I generally need to book out six months at a time.

Usually I do this sort of thing on my laptop while my younger daughter is napping, or when both of them are sleeping. But this was a mini-crisis I wanted to address ASAP. So I whipped out my phone.

Logging into the frictionless, never frustrating utopia that is MyChart, I was prompted to pay an outstanding balance. While I was here, I figured I might as well get this done.

Once on the payment screen, I remembered that I didn’t have my credit card on me. I resigned to take care of the payment later that night. But then I saw there was another payment option. I pressed two buttons, and my bill was settled.

I don’t think I need to tell you what that option was.