I do believe the number of headphones Jasper says I need

Jasper says, You’re not going to believe the number of headphones I think you should have.

Except, I have more than that (not all in active use) and a different set of preferences. So I thought I’d write about the headphones I use and why and in what order.

1. AirPods Pro 2 (soon 3)– these are my “everyday carry” literally 100% of the time in my pocket, and in my ears for hours every day. If I’m anywhere except at my desk or driving, as long as I’m not actively engaging with someone, these are probably in my ears. 90% of my listening is podcasts, not music, because music is rarely something I listen to passively.
2. Beyerdynamic DT770s – close-backed headphones that replaced (mostly) my open-backed Philips Fidelio X2s. I love open-backed headphones, but I needed close-backed headphones for monitoring while recording tracks for/with my band. The Beyerdynamic headphones are so comfortable, they work fine at my desk too. So that’s what I use for music during work, Zoom calls, and recording/mixing/mastering.
3. Sony WH-1000XM5 noise cancelling headphones. Over ear, active noise cancelling is a requirement for travel. AirPods are just not as good and not as comfortable (to date) for cross country or international flights. While I use my AirPods all the time, I need them out for a few minutes at least every few hours and you can overdo it. These headphones can be worn essentially endlessly.

I don’t think you need IEMs– but I do have a pair of audiologist custom fit ear plugs, which I require for hearing protection at concerts and when playing with the band. If you ever see live performed music, wear earplugs. And if you do it all the time or perform, spend the money to get proper, custom fitted ear plugs. Your future self with thank you.

Wow – Chase app just straight up doesn’t work on iOS 26. When I try and log in, it just refreshes the log in page. And I can’t log in on my computer, because it wants to send a push notification to my old, wiped phone.

Today is, “Jason’s individual YouTube Premium Membership annual payment ended” which means after 4 years of asking, it’s also “Jason begrudgingly pays for YouTube Premium Family” which is so expensive and not at all a deal. But Elsa needs/deserves the ad-free life, too.

A non-obvious thing about this process– you have to make a Google Family before they’ll show you the YouTube Premium Family option, unlike every other service in the world where you can invite people after the fact.